Author: Jessica.F

Some common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: O-Phenyl carbonochloridothioate

6a (100 mg, 0.30 mmol) was dissolved in 5 mL of acetonitrile,4-Dimethylaminopyridine (162 mg,1.33 mmol) andPhenylchloroformate (0.1 mL)After stirring at 0-60 C for 2-12 hours, the reaction solution was filtered, concentrated and separated by column(N-hexane / ethyl acetate: 20/1) gave a colorless oil 8 (128 mg, 0.27 mmol, 90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1005-56-7, its application will become more common.

Reference:
Patent; China Pharmaceutical University; Xie Weijia; Zhang Chenxi; Wang Zihao; Wu Xiaoming; Xu Jinyi; Yao Hequan; Lin Aijun; (12 pag.)CN107043403; (2017); A;,
Chloride – Wikipedia,
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Electric Literature of 928783-85-1, These common heterocyclic compound, 928783-85-1, name is 1-Bromo-3-chloro-5-(trifluoromethyl)benzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a 25 mL sealed tube, sodium 2-methylpropan-2-olate (62.7 mg, 653 muetaiotaomicron, Eq: 1.20), bis(dibenzylideneacetone)palladium (31.3 mg, 54.4 muetaiotaomicron, Eq: 0.1) and 2-di-tert-butyl(2′,4′,6′- triisopropylbiphenyl-2-yl)phosphine (23.1 mg, 54.4 muetaiotaomicron, Eq: 0.1) were combined with toluene (5.00 mL) to give a dark brown suspension. N5,N5,l-tris(4-methoxybenzyl)-lH-l,2,4-triazole- 3,5-diamine (250 mg, 544 muetaiotaomicron, Eq: 1.00) and l-bromo-3-chloro-5-(trifluoromethyl)benzene (141 mg, 544 muetaiotaomicron, Eq: 1.00) were added. The reaction mixture was degassed with argon for 15 min, and then heated to 110C for 3 hours. The reaction mixture was cooled and diluted with EtOAc (50 mL), washed with H20 (25 mL) and brine (25 mL). The organic layer was dried over anhydrous MgS04, filtered and volatiles were removed under reduced pressure to yield an oil from which the compound was isolated by column chromatography (Hexanes/EtOAc = 70/30) to give an off-white solid 40 mg (12%). MH+ 638.4

Statistics shows that 1-Bromo-3-chloro-5-(trifluoromethyl)benzene is playing an increasingly important role. we look forward to future research findings about 928783-85-1.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); A1;,
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Synthetic Route of 33786-89-9,Some common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, molecular formula is C6H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[3]: 1.1-(4-Methoxyphenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (500 mg, 1.75 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere with HATU (732 mg, 1.93 mmol, 1.1 equiv). While stirring, DIPEA (1.8 g, 14 mmol, 8 equiv) was added drop wise at 0 C. When all the DIPEA was added, it was allowed to sit for 15 minutes. After this, 5-chloro-m-phenylenediamine (996 mg, 7.0 mmol, 4 equiv) was added. The reaction was allowed to warm up to R.T. over the course of 2 hrs and was monitored by TLC and LC/MS. When complete, 5 mL of H2O and 5 mL of EtOAc were added and the mixture transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford the coupled intermediate as a clear oil (410.78 g/mol, 245 mg, 34% yield).2. A portion of the purified product from step one (100 mg, .22 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere. Dry TEA (90 mg, .85 mmole, 4 equiv) was added via syringe at 0 C.20 mL of acryloyl chloride was transferred via syringe to the reaction vial (22 mg, .242 mmol, 1.1 equiv) at 0 C. The reaction was allowed to warm up to R. T. and was monitored by TLC and LC/MS. Once complete, 1 mL of saturated NaHCO3 solution was added and allowed to mix for 15 minutes to quench the reaction. To this, 5 mL of EtOAc was added and the mixture was transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford compound 3 as a clear oil (464.78 g/mol, 48 mg, 47% yield).1H (500 MHz, (CD3)2SO) d: 10.71 (s, 1H), 10.41 (s, 1H), 8.05 (m, 1H), 7.69 (m, 1H), 7.49 (m, 1H), 8.29 (s, 1H), 7.46 (m, 2H), 7.12 (m, 2H), 6.44(dd, J1 = 17.00Hz, J2= 10.08 Hz, 1H), 6.30(dd, J1 = 17.00 Hz, J2= 1.76Hz, 1H), 5.80(dd, J1 = 10.08 Hz, J2= 1.76Hz, 1H), 3.85(s, 3H).13C (125 MHz, (CD3)2SO) d: 163.47, 160.15, 159.32, 140.64, 140.25, 139.55, 133.08, 131.51, 131.46, 127.64, 127.47 (2C), 120.74, 120.38, 118.22, 114.40 (2C), 114.28, 114.26, 108.83, 55.60.; [4]: 1. Please refer to step one of the synthesis of compound 3 above.2. A portion of the purified coupled intermediate from step one compound 3?s synthesis (100 mg, .22 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere. Dry TEA (90 mg, .85 mmole, 4 equiv) was added via syringe at 00C.20 mL of propionyl chloride was transferred via syringe to the reaction vial (22 mg, .242 mmol, 1.1 equiv) at 00C. The reaction was allowed to warm up to R. T. and was monitored by TLC and LC/MS. Once complete, 1 mL of saturated NaHCO3 solution was added and allowed to mix for 15 minutes to quench the reaction. To this, 5 mL of EtOAc was added and the mixture was transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford compound 4 as a clear oil (466.8 g/mol, 74 mg, 72% yield).1H (500 MHz, (CD3)2SO) d: 10.66 (s, 1H), 10.12 (s, 1H), 8.28, (s, 1H), 7.97 (m, 1H), 7.58 (m, 1H), 7.46 (m, 3H), 7.12 (m, 2H), 3.85 (s, 3H), 2.33 (q, J = 7.6 Hz, 2H), 1.08 (t, J = 7.6 Hz, 3H).13C (125 MHz, (CD3)2SO) d: 172.47, 160.13, 159.29, 140.96, 140.16, 139.54, 132.96, 131.47, 127.47 (2C), 120.78, 120.39, 118.22, 114.40 (2C), 113.97, 113.73, 108.52, 55.60, 29.56, 9.53.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-m-phenylenediamine, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHOKAT, Kevan, M.; GENTILE, Daniel; MOSS, Steven; (380 pag.)WO2018/112420; (2018); A1;,
Chloride – Wikipedia,
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Related Products of 14862-52-3, The chemical industry reduces the impact on the environment during synthesis 14862-52-3, name is 3,5-Dibromochlorobenzene, I believe this compound will play a more active role in future production and life.

A solution of 1,3-dibromo-5-chlorobenzene (10 mmol, 3.2 g)Diphenylamine (40 mmol, 6.7 g) was added to a 100 mL three-necked flask,A cuprous iodide (4 mmol, 0.8 g) was added under nitrogen,Potassium carbonate (40 mmol, 2.8 g),Phenanthroline (4 mmol, 0.8 g),50 mL of DMF,The reaction was carried out at 155 C for 3 days,The resulting reaction product is subjected to extraction,The extracted organic phase was evaporated to dryness with ethanol,And then recrystallized from ethyl acetate and petroleum ether to give 3.57 g of intermediate A-4,

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3,5-Dibromochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jilin Aolai De Optoelectronic Materials Co., Ltd.; Gao, Chunji; Cui, Dunzhu; Sun, Yi; Zhang, Chengcheng; (52 pag.)CN104892434; (2017); B;,
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Application of 108-37-2, A common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

This example illustrates the tandem Ir-catalyzed borylation and catalytic amination process. [0064] 3-Aminoboronic acids and esters as shown below are of interest as evidenced by the large number of derivatives synthesized, and by several patents, which note their activity as O-lactamase inhibitors (See, for example, Shoichet et al., WO0035905). Few in number, however, are 1, 3, 5-aminoboronic acids and esters (about 25 compounds by SCIFINDER SCHOLAR). Such substrates may prove useful for further derivatization as they can possess three unique sites for diversity. Furthermore, these compounds may prove ideal as scaffolds for combinatorial libraries. The boronic acid or ester can be transformed into a myriad of functionalities including aryl or vinyl via the Suzuki-Miyuara coupling (Miyaura and Suzuki, Chem. Rev. 95: 2457-2483 (1995); Suzuki, J. Organomet. Chem. 576: 147-168 (1999); Miyaura, In Advances in Metal-Organic Chemistry: Liebeskind, Ed.: JAI: London,; Vol. 6, pp. 187-243 (1998)). If R is a halogen, then there exists a multitude of coupling opportunities (See, for examples, Metal-catalyzed Cross-coupling Reactions; Diederich and Stang, eds.: Wiley: Wienheim, 1998). [0066] Recently, a catalytic aromatic C-H activation/borylation reaction utilizing Ir- or Rh-catalysts was developed. The process is high yielding, functional group tolerant (alkyl, halo, carboxy, alkoxy, and protected amino), chemoselective (1,3-substited arenes give only the 5-boryl product), and efficient (Iverson and Smith, J. Am. Chem. Soc. 121: 7696-7697 (1999); Cho et al., J. Am. Chem. Soc. 122: 12868-12869 (2000); Tse et al., Org. Lett. 3: 2831 (2001); Chao et al., Science 295: 305-308 (2002)). Furthermore, the process allows for the direct construction of aryl boronic esters from hydrocarbon feedstocks without going through an aryl halide. Scheme 2 depicts a prototypical borylation reaction: borylation of benzene using (Ind)Ir(COD)(2 mol %), dppe (2 mol %). The borane of choice is pinacolborane (HBPin). A variety of Ir(I) catalysts can be used, including [Ir(COD)Cl]2, Ir(Indenyl)(C2H4)2, Ir(Indenyl)dppe, and (Indenyl)Ir(COD), in the presence of 2 mol equivalents of PMe3 or 1 mol equivalent of a bidentate ligand like dmpe or dppe. The catalyst system of choice is (Indenyl)Ir(COD), dppe or dmpe (2 mol % each) because of it’s cleanness of reaction and efficient TOF (24 h-1 with benzene). The reaction can be run in the neat arene or in inert solvents (e.g. cyclohexane). During our studies into tandem borylation/Suzuki coupling, we noted difficulties with the hydrolysis of the boronic ester functionality (Bpin). The robustness of the BPin group suggested that, perhaps, the pinacol might serve as a protecting group for the boron. Thus, it was deemed of interest to explore other catalytic transformations in the presence of the BPin group. One such transformation is the Buchwald-Hartwig amination of aryl halides (See, for example; Wolfe et al.,. J. Org. Chem. 65: 1158 (2000); Hartwig et al., J. Org. Chem. 64: 5575 (1999); Wolfe and Buchwald, Angew. Chem. Int. Ed. 38: 2413 (1999)). Initially, the reaction was attempted on pure 1-chloro-3-methylphenyl-5-BPin. As shown in Scheme 3 (Buchwald-Hartwig coupling of 1-chloro-3-methylphenyl-5-BPin with aniline), application of Buchwalds protocol proceeded cleanly to give the desired cross-coupling product in 64.7% and 63.8% yield. The use of PtBu3 improved the yield to 78.8%. Unfortunately, initial attempts to perform the reaction in the ?one-pot? protocol were unsuccessful. Table 1 summarizes the results. In all cases where K3PO4.nH2O was used, a significant amount of pinacol was observed by GC-FID (Entries 1-5). While this is indicative of reaction of the BPin group and is most likely a by-product of Suzuki coupling (in this case, dimerization or oligiomerization of the starting material), no dimers or oligiomers were isolated. Noteworthy, is the formation of the desired product, albeit in low yield (10% GC-FID ratio), using K3PO4.nH2O and PtBu3 when all other attempts using the base failed. With anhydrous K3PO4, results were better (Entries 6-9). Most importantly, no pinacol was formed in these reactions. Changing the base or increasing catalyst loading did not improve the results. The use of PtBu3 led to the best results and after 4 days at 100 C., 34.4% of the desired product was isolated (Entry 10). This result, however, falls short of the reaction performed on pure material and shows that the by-products from the Ir-catalyzed borylation are not completely innocuous. As was previously mentioned, a potential source of concern is the presence of free bidentate phosphines after the borylation, which may interfere with subsequent reactions. In the tandem Suzuki reactions, an aryl chloride was successfully coupled only when dmpe was used as the Ir ligand. Thus, the tandem borylation/Buchwald-Hartwig amination reaction of the present invention was attempted using the (Ind)Ir(COD)/dmpe precatalyst….

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Board of Trustees of Michigan State University; US2004/24237; (2004); A1;,
Chloride – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1005-56-7, name is O-Phenyl carbonochloridothioate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5ClOS

194.2 mg (1.0 mmol) of methyl alpha-D-glucopyranoside, 41.6 mg (0.10 mmol) of dioctyl dichloro tin, tetrabutylammonium iodide36.9 mg (0.10 mmol) and 10 ml of tetrahydrofuran were added and stirred. To this mixed solution, 0.175 ml (1.3 mmol) of phenyl chlorothionoformate was added, then 0.271 ml (1.5 mmol) of 1,2,2,6,6-pentamethylpiperidine was added and the mixture was stirred at 20 C. for 6 hours.After completion of the reaction, 20 ml of a saturated aqueous solution of ammonium chloride was added to the reaction solution, and extraction operation was carried out three times with 20 ml of ethyl acetate. The organic phase (ethyl acetate phase) was washed with 20 ml of water and 20 ml of an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the solvent (ethyl acetate) was distilled off under reduced pressure. The residue was purified by silica gel chromatography (developing solvent n-hexane: ethyl acetate = 5:: 1), 319.5 mg (yield: 97%) of methyl 2-O-phenoxythiocarbonyl-alpha-D-glucopyranoside was obtained.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1005-56-7.

Reference:
Patent; NAGASAKI UNIVERSITY; TOKUYAMA CORPORATION; ONOMURA, OSAMU; MURAMATSU, WATARU; TANIGAWA, SATOKO; IWASAKI, FUMIAKI; (19 pag.)JP5669637; (2015); B2;,
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Application of 7149-75-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 7149-75-9 as follows.

Step 1 (0415) To a mixture of 4-chloro-3-methylphenylamine (300 mg), acetone (0.19 mL) and methanol (10 mL) was added decaborane (130 mg), and the mixture was stirred at room temperature for 6 hours. After the mixture was diluted with ethyl acetate, to the resulting mixture was added aminopropyl silica gel powder (3 g). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to give (4-chloro-3-methylphenyl)(isopropyl)amine (390 mg).

According to the analysis of related databases, 7149-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); A1;,
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Some common heterocyclic compound, 699-89-8, name is 4,7-Dichlorothieno[2,3-d]pyridazine, molecular formula is C6H2Cl2N2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C6H2Cl2N2S

A 250 mL, round-bottomed flask was equipped with a stir bar and reflux condenser. To the flask was added the product of step 4 (7.65 g, 37.3 mmol), 4-chloroaniline (4.76, 37.3 mmol) in EtOH (75 mL). The mixture was refluxed for 3 h. An orange solid precipitated from the reaction after 3 h. The reaction was cooled to rt and the solid was collected by filtration and washed with hexane. The desired 7-chloro-4-(4-chlorophenylamino)thieno[2,3-d]pyridazine was obtained (6.5 g, 21.9 mmol; 60% yield); mp=139-142 C.; ES MS (M+H)+=297; TLC (Hexane-EtOAc, 60:40); Rf=0.48.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 699-89-8, its application will become more common.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US6689883; (2004); B1;,
Chloride – Wikipedia,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H4Cl3NO

General procedure: The thiol was placed in a dry round bottom flask and dissolved in anhydrous THF (or toluene) to a concentration of 0.2 M. The trichloroacetimidate (1.2 equiv) was then added and the reaction was warmed to reflux. After 18 hours the reaction was cooled to room temperature and concentrated under reduced pressure. The residue was then pre-adsorbed on silica gel and purified by column chromatography. Alternatively, the residue can be dissolved in ethyl acetate, washed with 2M aq. NaOH(3x), dried (Na2SO4) and concentrated (this workup removes the trichloroacetamide byproduct). Forsome sulfides this workup provided analytically pure material, in others the residue is purified by silicagel chromatography to provide the pure sulfide product.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Duffy, Brian C.; Howard, Kyle T.; Chisholm, John D.; Tetrahedron Letters; vol. 56; 23; (2015); p. 3301 – 3305;,
Chloride – Wikipedia,
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These common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C7H5ClOS

A suspension of activated zinc dust (98.5 mg, 1.51 mmol) and ethyl bromodifluoroacetate (0.19 mL, 1.51 mmol) in THF (5 mL) was refluxed for 20 min and then cooled to 00C. To this, the solution of the aldehyde (+)- 39 (100 mg, 0.30 mmol) in THF (5 mL) was added. The reaction mixture was warmed to15 room temperature, followed by refluxing for 20 min, and then cooled to room temperature. The reaction mixture was poured into 1 M KHSO4 and extracted with EtOAc (3x 20 mL), washed with brine, dried over MgSO4, concentrated in vacuo, and then purified by column chromatography (10% EtOAc/hexanes) to give 84.5 mg (62%) of a 1:1 mixture of diastereomers of the desired alcohol as a colorless oil. To a solution of ethyl ester (84 mg,20 0.18 mmol) and pyridine (0.066 mL, 0.82 mmol) in CH2Cl2 (5 mL), phenyl chlorothionoformate (0.053 mL, 0.38 mmol) was added. After being stirred at room temperature for 20 hours, the reaction mixture was diluted with water, extracted with ether (3x 20 mL), washed with satd NaHCO3 solution and brine, dried over MgSO4, concentrated in vacuo, and then purified by column chromatography (5% EtOAc/hexanes) to give 97.825 mg (90%) of the desired carbonate as diastereomeric mixtures. To the solution of the resulting phenylthianocarbonate (97.5 mg, 0.16 mmol) in anhydrous benzene (10 mL), 2,2′- azobisisobutyronitrile (AlBN, 5 mg) and tributyltin hydride (0.066 mL, 0.24 mmol) were added at room temperature. After being refluxed for 3 hours, the mixture was cooled to 0 0C, diluted with water, extracted with EtOAc (3x 20 mL), washed with brine, dried over30 MgSO4, concentrated in vacuo, and then purified by column chromatography (3%EtOAc/hexanes) to give 58.2 mg (80%) of the desired difluoro ester 42 as a colorless oil: 1H NMR (400 MHz, CDCl3) delta 4.32 (q, J= 7.2 Hz, 2H), 4.03 (s, IH), 2.14-2.06 (m, IH), 1.98- 1.89 (m, 2H), 1.85-1.75 (m, 2H), 1.69-1.64 (m, IH), 1.61-1.53 (m, 2H), 1.49-1.43 (m, EPO IH), 1.38-1.34 (m, 2H), 1.35 (t, J= 7.2 Hz5 3H), 1.26-1.17 (m, 3H), 1.13-0.99 (m, 2H), 0.94 (t, J= 8.0 Hz, 9H), 0.91 (d, J= 6.0 Hz5 3H), 0.90 (s, 3H), 0.55 (q, J= 8.0 Hz, 6H).

The synthetic route of O-Phenyl carbonochloridothioate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JOHNS HOPKINS UNIVERSITY; WO2006/74227; (2006); A2;,
Chloride – Wikipedia,
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