Month: November 2022

Cooperstein, S. J.; Lazarow, A.; Patterson, J. W. published an article in 1953, the title of the article was The mechanism of Janus Green B staining of mitochondria. II. Reactions and properties of Janus Green B and its derivatives.Application of 4569-86-2 And the article contains the following content:

The absorption spectra are reported of Janus Green B(I) and G(II) and their derivatives, diethylsafranine, leucosafranine, and dimethylsafranine. I was readily reduced by cysteine (III) and glutathione whereas II was not significantly reduced by III. At pH 7.48 I showed 2 reduction steps upon polarographic analysis, one at a potential of -0.001 v. and the other at -0.188 v. II had only one reduction step at -0.214 v. The experimental process involved the reaction of 3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas: 4569-86-2).Application of 4569-86-2

3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas:4569-86-2) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Application of 4569-86-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Hideo, Endo; Tada, Masao; Katagiri, Ken published an article in 1965, the title of the article was Antitumor activity of phenazine derivatives against S 180 and C 63 in mice I.SDS of cas: 4569-86-2 And the article contains the following content:

Phenazine and 68 derivatives of phenazine were screened for their antitumor activity against Sarcoma 180 and Carcinoma 63, transplanted in mice. The ratio of the average weights of tumors in the treated and the controls, and the ratio of body weight changes in the 2 groups were recorded for each compound 2-Methoxyphenazine, 3,7-diamino-2-methylphenazine and 3-morpholino-1,2-benzophenazine at doses of 50 mg./kg.-body weight/day, brought down the tumor weight to less than half in the carcinoma infected mice and 3-acetamido-7-amino-5-phenylphenazonium chloride at the same dosage caused a similar effect in the sarcoma-infected animals. No correlation was observed between tumor weight change and the change in body weight in the treated animals. The experimental process involved the reaction of 3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas: 4569-86-2).SDS of cas: 4569-86-2

3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas:4569-86-2) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. SDS of cas: 4569-86-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Hodgson, Herbert H.; Batty, Walter E. published an article in 1934, the title of the article was Direct nitration of 5-chloro-3-hydroxy- and of 5-chloro-3-nitroanisole.Quality Control of 1,5-Dichloro-3-methoxy-2-nitrobenzene And the article contains the following content:

5-Chloro-3-hydroxyanisole (I), NaNO3, H2SO4 and H2O give a mixture of the 4-NO2 derivative, m. 106° (volatile with steam), and the 4,6-di-NO2 derivative (II), m. 126°. I and Me2SO4 give 5-chlororesorcinol di-Me ether, m. 38°; HNO3 in Ac2O at room temperature gives the 4-NO2 derivative, m. 123°; twice the quantity of HNO3 gives the 4,6-di-NO2 derivative (III), m. 216°, also obtained from II and Me2SO4. 2,4,6-Cl3C6H2NO2 and MeONa-MeOH, refluxed 4 hrs., give 3,5,2-Cl2(O2N)C6H2OMe, m. 75°; heating at 120° for 1.5 hrs. gives 5-chloro-2-nitroresorcinol di-Me ether (IV), m. 184°; heating 5 hrs. at 150° gives nitrophloroglucinol tri-Me ether, m. 153°; HNO3 gives the di-NO2 derivative (V), m. 166°. IV, HNO3 and Ac2O give the 2,4-di-NO2 derivative, m. 110°. 1,3,5,2,4-Cl3C6H(NO2)2 and MeONa at room temperature for 10 days give III and V. 5-Chloro-3-nitroanisole and HNO3 in H2SO4 give the 3,4,6-tri-NO2 derivative, orange-yellow, m. 128°; with MeONa on the water bath for 10 min. there results III. 3,5-Dichloro-2-nitroanisole and 20% EtOH-KOH, 2 hrs. at 130°, give 5-chloro-2-nitro-3-hydroxyanisole, m. 88°. 5-Chloro-3-hydroxyanisole and HNO3 give the 2,4,6-tri-NO2 derivative, m. 147°. The experimental process involved the reaction of 1,5-Dichloro-3-methoxy-2-nitrobenzene(cas: 74672-01-8).Quality Control of 1,5-Dichloro-3-methoxy-2-nitrobenzene

1,5-Dichloro-3-methoxy-2-nitrobenzene(cas:74672-01-8) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Quality Control of 1,5-Dichloro-3-methoxy-2-nitrobenzene

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Izzo, Patrick T. published an article in 1963, the title of the article was Preparation of 1-aryl-1,2-cyclopropanedicarboximides. An application of dimethylsulfoxonium methylide.Related Products of 5034-06-0 And the article contains the following content:

1-Aryl-1,2-cyclopropanedicarboximides (I) were prepared in the presence of dimethylsulfoxonium methylide (II). Trimethylsulfoxonium chloride (III) was prepared by the method of Kuhn and Trischmann (CA 52, 14523g),m. 215-16°. III(1.5g.) added to a suspension of 0.29 g. NaH in 150 ml. tetrahydrofuran (THF), the mixture refluxed with evolution of H, stirred under reflux 45-60 min., and 0.012 mole N-methyl-2-arylmaleimide added to the solution (containing II), the mixture refluxed 2 hrs., cooled, alc. added, solvent removed in vacuo, the residue taken up in CH2Cl2, and the solution washed, dried, and evaporated gave I (R, R1, m.p., % yield given): Ph, H, 55-7°, 21; Ph, Et, 113-146deg;, 81; 3,4,5-trimethoxyphenyl, H, 136-86°, 21. The structure of I was supported by infrared and ultraviolet spectra, elementary analyses, and unsaturation tests. N-Methyl-2-phenylsuccinimide (37.8 g.), 39.2 g. N-bromosuccinimide, 0.4 g. Bz2O2, and 800 ml. CCl4 refluxed 24 hrs., stored 16 hrs. at room temperature, the succinimide removed, and the filtrate evaporated gave 49.2 g. 2-bromo-N-methyl2-phenylsuccinimide (IV), m. 110.5-12°. IV (7.5 g.) in 75 ml. C6H6 and 3 g. NEt3 kept 1 hr. at room temperature and the product separated gave 3.7 g. N-methyl-2-phenylmaleimide (V), m. 147-8°. Arylation of maleimide with 3,4,5-trimethoxyphenyldiazonium chloride gave 27% 2-chloro-3-(3,4,5-trimethoxyphenyl)succinimide (VI), m. 207-8° (decomposition). VI (2 g.) heated 0.5 hr. with 8 ml. 2,6-lutidine gave 1.5 g. 2-(3,4,5-trimethoxyphenyl)maleimide (VII), m. 211-13°. VII (2.8 g.) in 75 ml. THF brought to reflux with 0.24 g. NaH, then treated in 45 min. under reflux with 7 g. MeI in 10 ml. THF, the mixture refluxed 1.75 hrs., evaporated, and the residue taken up in CHCl8 gave 2 g. N-methyl-2-(3,4,5-trimethoxyphenyl)maleimide, m. 155-66deg;. V (8.9 g.) in 150 ml. CH2Cl2 treated in one lot with 0.054 mole MeCHN2 in Et2O gave 11.6 g. N,5-dimethyl-3-phenyl-1-pyrazoline-3,4-dicarboximide (VIII), m. 106-76deg; (decomposition). VIII (5.1 g.) in 50 ml. alc. was heated 0.5 hr., evapd, in vacuo, and the 4.4 g. of oil subjected to partition chromatography. Evaporation of material from the first peak gave 5% N-methyl-2-ethyl-3phenylmaleimide, m. 69-70°. The 2nd and slower moving component was obtained as the chief yield, 4 g., of N,3-dimethyl-1-phenyl-1,2-cyclopropanedicarboximide. The experimental process involved the reaction of trimethyloxosulphonium chloride(cas: 5034-06-0).Related Products of 5034-06-0

trimethyloxosulphonium chloride(cas:5034-06-0) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Related Products of 5034-06-0

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Holleman, A. F.; van Haeften, F. H. published an article in 1921, the title of the article was Replacement of substituents in the benzene ring. V. The six trichloronitrobenzenes and the three trinitrobenzenes; their reaction with sodium methylate.Computed Properties of 74672-01-8 And the article contains the following content:

Preparation of the 6 trinitrobenzenes. The 6 isomers are already described in the literature but the method of preparation was improved in several instances and the details are here given. Qualitative results on the action of NaOMe on the trichloronitrobenzenes. The methods used in this reaction were described previously (C. A. 15, 65). In this case the reaction is much slower than with the dichlorodinitrobenzenes so that heating some hrs. on the H2O bath is necessary. 15 g. 2,3,4-Cl3C6H2NO2 (A) after heating with 105 cc. 0 4755 N NaOMe solution 5 hrs. in an autoclave at 110° were poured into H2O and filtered. The product was distilled with steam and on crystallization from EtOH gave 3,4,2-Cl2(O2N)C6H6OMe, silky needles, m. 72.5°, identical with that obtained by d. Hollander (C. A. 15, 65). 5 g. 3,4,5-Cl3C6H2NO2 (B) heated 6 hrs. under a condenser on the H2O bath with 52 cc. NaOMe (0.47 N) gave after evaporating most of the MeOH and pouring into H2O a solid which from EtOH gave silky needles with a green reflex, m. 98°, identical with the Cl2(O2N)C6H2OMe obtained by d. H. (l. c.) from 1,3,2,5-C6H2Cl2(NO2)2. 20 g. 2,5,6-C3C6H2NO2 (C) were heated with 210 cc. NaOMe (0.47 N) 24 hrs. on a H2O bath under a condenser and after evaporating most of the MeOH the mixture was poured into H2O and filtered. The oil separated was distilled with steam and gave colorless crystals of 3,4,2-Cl2(O2N)COH2OMe, m. 128°. The main portion gave crystals of 2,5,6-Cl3C6H2OMe, m. 42.8°. 5 g. 2,4,5-Cl3C6H2NO2 (D) were heated with 52 g. NaOMe (0.47 N) for 6 hrs. on the H2O bath and gave a 2,5,4- Cl2(O2N)C6H2OMe, m. 101°, identical with that obtained from 1,4,2,5-C6H2Cl2(NO2)2. Beilstein and Kurbatow (Ann. 192, 23(1878)) found that with NH3 the Cl ortho to the NO2 group is replaced. 2,3,5-Cl3C6H2NO2 (E) with NaOMe gave the same anisole, m. 44°, obtained by d. H. from 1,3 5,6-C6H2Cl2(NO2)2. 6 g. 2,4,6-Cl3C6N2O2 (F) heated 6 hrs. with 65 cc. NaOMe on the H2O bath gave an anisole, m. 72.5°, which by arguments based on analogy is said to be 2,4,6-Cl2(MeO)C6H2NO2. Quantitative researches. The methods used were the same as those used by d. H. (l. c.) and the numerical results are given in table. Discussion of results. The numerical results are summarized in several tables. The reaction constants at 0 ° of chloronitrobenzenes, dichloronitrobenzenes, trichloronitrobenzenes and chlorodinitrobenzenes increase in the same order. The Cl atom which leaves the ring is always o- or P- with respect to the NO2 group. In each group of isomers the largest constant of reaction is obtained for that compound in which the Cl atom which leaves is in the P-position with respect to the NO2 group which it renders mobile. When another Cl atom is placed o- or p- to the Cl atom which leaves the mobility of the latter is increased. The conclusion of d. H. (l. c.) that in m-C6H4(NO2)2, m-ClC6H4NO2 and sym-Cl2C6H3NO2, which are inert toward NaOMe, any of the substituents is rendered mobile by the introduction of a NO2 group or a Cl atom, was fully confirmed. When one introduces a substituent it is always this which reacts with NaOMe. C and F showed the smallest velocity of reaction. The same is true of 2,6-Cl2C6H3NO2, showing that a NO2 group placed between 2 adjacent Cl atoms determines a very slow velocity of substitution. The fact that the velocity with C is less than with F shows that the presence of 3 Cl atoms adjacent diminishes the liberating activity of a NO2 group. The examination of the products of the transformation of C with NaOMe shows that in this isomer the NO2 group is changed in character. Comparison of the results for isomers of Cl2C6H3NO2 and Cl3C6H2NO2 shows that the latter behave more like Cl2C6H3NO2 derivatives than like Cl3C6H2NO2 derivatives The quant. conclusions are among the parts of the paper that cannot be adequately abstracted. Preparation of isomeric trinitrobenzenes. The details of the preparation of the 1,2,4-(G), 1,2,3- (H), and 1,3,5-trinitrobenzenes (I) are given here, although all were previously known. 5 g. H with 55 cc. 0.47 N NaOMe reacted at room temperature and after 0. 5 hr. on the H2O bath and after standing 24 hrs. separated 2,6-(O2N)2C6H8OMe, m. 118°. 5 g. G treated similarly gave 2,4-(O2N)2C6H8OMe, m. 88°. 5 g. I treated similarly gave 3,5-(O2N)2C63OMe, m. 105°. Data on quant. measurements of the same reactions are given. The experimental process involved the reaction of 1,5-Dichloro-3-methoxy-2-nitrobenzene(cas: 74672-01-8).Computed Properties of 74672-01-8

1,5-Dichloro-3-methoxy-2-nitrobenzene(cas:74672-01-8) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Computed Properties of 74672-01-8

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On March 7, 1951, Hayden, John J. published a patent.Recommanded Product: 4569-86-2 The title of the patent was Azo safranine leather dyes. And the patent contained the following:

Azo dyes (I) of the safranine series for dyeing leather, particularly chrometanned leather, are obtained by coupling a monodiazo safranine compound with an N-(hydroxyalkyl)arylamine in which the N-hydroxyalkyl group contains at least 2 C atoms and which is unsubstituted in the 4-position. Thus, Methylene Violet 3RA diethyl analog paste 30 (containing 80% 3-amino-7-diethylamino-5-phenylphenazinium chloride) in concentrated H2SO4 16 is diazotized and coupled with PhN(CH2CH2OH)2 11 at pH 2.5-3.0 to give II (R and R’ = H), soluble in H2O, dyes chrome leather in bright greenish black shades. Similarly are obtained the following II (R and R’ given): Me, H, dyes brilliant dark green shades; AcNH, H, dyes brilliant dark green shades; N(CH2CH2OH)2, H, dyes brilliant, slightly reddish black shades; AcNH, MeO, dyes black shades; and 7-diethylamino-3-[4-(ethylhydroxyethylamino)phenylazo]-5-phenylphenazinium chloride. The experimental process involved the reaction of 3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas: 4569-86-2).Recommanded Product: 4569-86-2

3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas:4569-86-2) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Recommanded Product: 4569-86-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On May 22, 1951, Hayden, John J. published a patent.HPLC of Formula: 4569-86-2 The title of the patent was Azo safranine leather dyes. And the patent contained the following:

Azo dyes (I) of the safranine series for dyeing leather, particularly chrometanned leather, are obtained by coupling a monodiazo safranine compound with an N-(hydroxyalkyl)arylamine in which the N-hydroxyalkyl group contains at least 2 C atoms and which is unsubstituted in the 4-position. Thus, Methylene Violet 3RA diethyl analog paste 30 (containing 80% 3-amino-7-diethylamino-5-phenylphenazinium chloride) in concentrated H2SO4 16 is diazotized and coupled with PhN(CH2CH2OH)2 11 at pH 2.5-3.0 to give II (R and R’ = H), soluble in H2O, dyes chrome leather in bright greenish black shades. Similarly are obtained the following II (R and R’ given): Me, H, dyes brilliant dark green shades; AcNH, H, dyes brilliant dark green shades; N(CH2CH2OH)2, H, dyes brilliant, slightly reddish black shades; AcNH, MeO, dyes black shades; and 7-diethylamino-3-[4-(ethylhydroxyethylamino)phenylazo]-5-phenylphenazinium chloride. The experimental process involved the reaction of 3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas: 4569-86-2).HPLC of Formula: 4569-86-2

3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride(cas:4569-86-2) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. HPLC of Formula: 4569-86-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Hodgson, H. H.; Wignall, J. S. published an article in 1927, the title of the article was Nitrosation of phenols. IV. 3,5-Dichlorophenol.COA of Formula: C7H5Cl2NO3 And the article contains the following content:

cf. C. A. 20, 3449. Nitration of 16 g. 3,5-Cl2C6H3OH with NaNO3 and dilute H2SO4 gives 5 g. 3,5-dichloro-2-nitrophenol (I), lemon-yellow, m. 51°, volatile with steam, does not give a solid Ac derivative, and 6 g. 3,5,4-Cl2(O2N)C6H2OH (II), m. 150°, whose acetate, m. 99°. The action of HNO2 on 3,5-Cl2C6H3OH gives II. Reduction of I gives the 2-amino derivative, m. 132°; the 4-amino derivative; m. 154°; the 2 isomers give reddish brown and violet colors with FeCl3. I or II, with Me2SO4, gives 70% of the corresponding anisoles, m. 75° and 70°, resp. 3,5-Dicloro-4-aminoanisole, m. 71°. 3,5-Dichloro-4-nitrosoanisole, m. 125°, results by oxidation of the NH2 derivative with Caro’s acid; it turns green on melting but becomes colorless on cooling; heating with concentrated H2SO on the H2O bath for 0.5 hr. gives 3,5-dichloro-4-nitrosophenol [quinone-4-oxime (?) ], decomposes 165°; boiling acids decompose it. Reduction of 3,4-Cl(O2N)C6H3OMe with Sn and HCl gives 3,5,4-Cl2(H2N)C5H2OMe. 3-Chloro-4-nitrosoanisole, deep green, m. 59°, results when the HCl salt of the 4-NH2 derivative is oxidized with K2S2O5 in AcONa solution 3,5-Dichloro-4-nitrodimethylaniline, golden, m. 142°, results from NaNO2 in HCO2H or from HNO3-H2SO4 at 0°. The experimental process involved the reaction of 1,5-Dichloro-3-methoxy-2-nitrobenzene(cas: 74672-01-8).COA of Formula: C7H5Cl2NO3

1,5-Dichloro-3-methoxy-2-nitrobenzene(cas:74672-01-8) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. COA of Formula: C7H5Cl2NO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Favini, Giorgio published an article in 1957, the title of the article was Electronic absorption spectra of the chloronitrotoluenes and chloronitroanisoles.HPLC of Formula: 38939-88-7 And the article contains the following content:

cf. C.A. 51, 15271c; Simonetta, et al., C.A. 52, 11771f. The absorption spectra in the near ultraviolet from 3500 to 2200 A. of the 10 possible isomeric nitrochlorotoluenes and nitrochloroanisoles in MeOH and cyclohexane solution are examined The spectra of PhNO2 are compared with the isomeric nitrotoluenes and chloronitrotoluenes, especially in regard to the primary band. For the Me substituent passing from ο- to m- and p-position relative to -NO2 there results, resp., a light hypsochromic, a light bathochromic, and a bathochromic effect, and for Cl substituent, resp., hypsochromic, light hypsochromic, and bathochromic effect. Similar results are obtained for the MeO substituent. Besides considering the absorption intensities and the solvent influence on the λ of absorption maximum, and following McConnel’s methodology (C.A. 46, 10875i), it is possible to assign every observed band to π → π* electronic transitions. 15 references. The experimental process involved the reaction of 2-Chloro-4-methyl-1-nitrobenzene(cas: 38939-88-7).HPLC of Formula: 38939-88-7

2-Chloro-4-methyl-1-nitrobenzene(cas:38939-88-7) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. HPLC of Formula: 38939-88-7

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Kruber, Otto; Raeithel, Armin published an article in 1954, the title of the article was Coal-tar anthracene oil.Computed Properties of 93012-36-3 And the article contains the following content:

The following new components were found in coal tar anthracene oil: 1-methylfluorene (I), diphenylsuccindan (C.A. 4b,5,9b,10-tetrahydroindeno[2,1-a]indene) (II), 2-methylphenanthrene (III), 3,6-dimethylphenanthrene (IV), and 1,8-dimethylbiphenylene sulfide (V) of which V was unknown. I was obtained from the anthracene oil fraction, b. 316.5-18° (cf. C.A. 47, 1701d) by fractional distillation, freezing out, and Na fusion. The unreacted oil was sulfonated at room temperature with 10% by weight portions of 92% H2SO4 (2 times), 95% (4 times), and 97% (to completion). The crude crystalline sulfonic acids obtained upon cooling from sulfonation fractions 3-7 were desulfonated with 50% H2SO4. Distilling up to 115° gave a noncrystg. oil, from 115-30° an oil which partly crystallized upon cooling to give I, white needles from MeOH, m. 86-7° (identified by oxidation to 1-methylfluorenone, yellow needles from petroleum ether, m. 98-9°) and fluorenone-1-carboxylic acid, yellow needles by sublimation, m. 195-6°. II was obtained from the anthracene oil fraction, b. 333-5° (C.A. 49, 7575a). Fractions 8-14 of the yellow oil (loc. cit.) (640 g.) were treated with 50 g. of 100% H2SO4 in presence of Ac2O at 15°, the unreacted oil (485 g.) was agitated with 160 g. 100% H2SO4 for 3 h. at 70°. The sulfonic acid layer was repeatedly extracted with benzene, and the combined extract and unsulfonated oil, after washing to neutrality and evaporating the benzene, was distilled in vacuo. After separating 55 g. biphenylene sulfide crystallizing from 285 g. distillate, the remaining 181 g. oil was again treated with 150 g. 100% H2SO4 at 70-5°, the sulfonated product worked up as above gave 20.5 g. of a dark oil from which crystallized 6.6 g. of crude II (4.7 g. of white needles from EtOH, m. 104-4.5°), identified by the mixed m.p. with the synthetic product [cf. Ann. 247, 157(1888)]. The UV spectrum of II in EtOH closely resembles that of hydrindene. III was isolated from the heavy ends of the anthracene oil fraction, b. 350-70°, which was dissolved in an equal amount of PhMe. The filtrate, after evaporating the solvent, was fused with KOH to remove carbazoles, extracted with dilute acid then alkali to remove bases and phenols, resp., and treated with Na at 190-200° to remove most of the 4,5-methylene-phenanthrene. From the remaining oil a 3.5 kg. fraction, b. 350-60°, was redistilled at 30 mm. Hg in an adiabatic column of about 28 theor. plates at a reflux ratio of 30:1 to fractions of 100 g. each. The crystalline portion of fractions 11-16 was distilled over Na and recrystallized from EtOH to give 150 g. III, colorless leaflets, m. 56°, b760 354.8°. III was further purified by dissolving in a little PhMe and sulfonated at 40-5° with concentrated H2SO4, recrystallized from 33% H2SO4, and desulfonated with 33% H2SO4 at 125-30° to give III, m. 57-7.5°; picrate, orange needles, m. 120-1°. Oxidation of III gave 2-methylphenanthrenequinone (VI), orange leaflets, m. 155-6°; condensation of VI with o-C6H4(NH2)2 gave the corresponding quinoxaline, pale yellow needles, m. 196-7°. The solution obtained upon treating 2 g. VI with 10 cc. 30% H2O2 and 18 cc. of 2N NaOH at room temperature for 1.5 h., when diluted with H2O, kept overnight, and filtered gave upon acidification of the filtrate 4-methyldiphenic acid, colorless needles from very dilute EtOH, m. 246-7°. The latter can be obtained directly from III by refluxing with 30% H2O2 in AcOH for 2.5 h. and converted to 2-methylfluorenone by dry distillation over CaO. IV was obtained from the heavy ends of the anthracene oil fraction, b. 355-60°, after pretreatment as described for the preparation of III, by distilling 7 kg. in an adiabatic column of about 18 theor. plates at a reflux ratio of 20:1 at 30 mm. Hg to fractions of about 120 g. each. Fractions 6-10, upon redistillation, served as starting material for the isolation of V. The 4 penultimate fractions obtained upon redistillation of fractions 20-32 in the same column gave 45 g. IV, colorless needles, m. 141° (from EtOH), b760 363.2°; picrate, orange needles, m. 172-3°; oxidation gave 3,6-dimethylphenanthrenequinone, orange needles, m. 221-2° (from EtOH), which condensed with o-C6H4(NH2)2 to the corresponding quinoxaline, pale yellow needles, m. 266-7° (from EtOH). Heating 4 g. IV in 30 cc. of AcOH to boiling and gradually adding 24 cc. 30% H2O2 gave 2.2 g. 5,5′-dimethyldiphenic acid, pale yellow leaflets, m. 268-70° (from H2O) which upon dry distillation with CaO gave 3,6-dimethylfluorenone, orange leaflets, m. 116-17° (from petroleum ether). The filtrate obtained from the above mentioned crude starting material for V was sulfonated with 92% H2SO4 at room temperature, and the unsulfonated oil adsorbed on Al2O3 and eluted first with petroleum benzin and then with a mixture of benzene and EtOH. The colorless oily eluate, nD20 1.669, crystallized on standing V, white needles, m. 154-5° (from EtOH); picrate, yellow needles, m. 130-1°. Heating 0.2 g. V in 5 cc. of glacial AcOH with 0.5 cc. 30% H2O2 on the water bath gave 0.2 g. 1,8-dimethyldiphenylenesulfone, white needles, m. 293-4° (from EtOH or glacial AcOH), heating 10 g. 2,2′-dihydroxy-3,3′-dimethylbiphenyl with 5 g. P2S5 in an Anschütz distillation flask over 15 min. from 140 to 410° gives 0.38 g. V after recrystallizing the crude distillate from EtOH. The experimental process involved the reaction of 5,5′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic acid(cas: 93012-36-3).Computed Properties of 93012-36-3

5,5′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic acid(cas:93012-36-3) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Computed Properties of 93012-36-3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics