Tag: M.W=100-200

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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2106-04-9

Step 6. Preparation of N’-(3-chloro-2-fluoro-phenyl)-N,N-dimethyl-formamidine (compound (XII)).; 3-chloro-2-fluroaniline (5.30 g, 35.29 mmoles) was dissolved in 2- methyltetrahydrofuran (52.94 g). To this N,N-dimethylformamide dimethyl acetal (6.07 g, 49.41 mmoles) and acetic acid (0.11 g, 1.76 mmoles) were added. The resulting reaction mixture was heated, with stirring, to 76 0C for 3 hours. Following this the solvent was removed in vacuo at 400C to give compound (XII) as a yellow oil (6.60 g, 93% yield); IH NMR Spectrum (400 MHz, DMSO-d6) delta ppm 2.74 (s, 0.29H), 2.89 (s, 0.31H), 2.94 (s, 2.75H), 3.03 (s, 2.66H), 3.34 (br s, 0.70H), 5.48 (s, 0.06H) 6.91-7.10 (m, 3H), 7.79 (s, 1 H), 7.96 (s, 1 H). The NMR data above includes signals for N,N-dimethylformamide dimethyl acetal which is present in a 0.06 molar equivalence. The signals pertaining to N5N- dimethylformamide dimethyl acetal are at delta ppm shifts of 3.75, and 6.90-6.95. The signal at delta ppm 3.35 is due to residual water. Mass Spectrum (by LCMS EI): m/z (M+H)+ 201.2.

According to the analysis of related databases, 2106-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BOARDMAN, Kay, Alison; CUNNINGHAM, Oliver, Robert; GOUNDRY, William; LAFFAN, David, Dermot, Patrick; WO2010/122340; (2010); A2;,
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Electric Literature of 2401-24-3,Some common heterocyclic compound, 2401-24-3, name is 2-Chloro-5-methoxyaniline, molecular formula is C7H8ClNO, 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-bromo-2-(trifluoromethyl)pyridine (0.4 g, 1.770 mmol), 2-(Dicyclohexylphosphino)-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (0.063 g, 0.133 mmol), Cesium carbonate (0.692 g, 2.124 mmol) and Palladium (II) Acetate (0.020 g, 0.088 mmol) were added to a microwave vial. Then, 2-chloro-5-methoxyaniline (0.293 g, 1.858 mmol) was added. The vial was purged with argon repeatedly. Dry toluene was added. The reaction was heated to 100 C. for 15 hours. The reaction mixture was filtered through celite, concentrated en vacuo. Normal phase chromatography (ethyl acetate/hexanes) was used to purify the crude material to give N-(2-chloro-5-methoxyphenyl)-2-(trifluoromethyl)pyridin-3-amine (0.376 g, 1.242 mmol, 70.2% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-methoxyaniline, its application will become more common.

Reference:
Patent; OssiFi Inc.; Ellies, Debra; Rey, Jean-Philippe; Kimball, F. Scott; US2014/288068; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 445-13-6, Safety of 3-Chloro-4-(trifluoromethyl)aniline

General procedure: To a solution of ethyl 4-bromo-1H-indole-2-carboxylate in toluene underargon atmosphere was added Pd2(dba)3 (0.1 eq), DavePhos (0.2 eq), K3PO4 (3 eq, 1Maqueous solution) and aryl amine (3 eq), and then the mixture was reacted at 80 Cuntil the starting material disappeared. The mixture was cooled to room temperatureand concentrated. Ethyl acetate was added to dissolve the residue and the mixture waswashed with saturated brine and water, dried over anhydrous Na2SO4, andconcentrated in vacuo. The crude product was purified by column chromatography toafford the target compound. Compounds 8a-8f, 8i-8l, 8a-1, 8a-6 ~ 8a-11, 8a-14 wereprepared with method 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Article; Cui, Guonan; Lai, Fangfang; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 188; (2020);,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4090-55-5, HPLC of Formula: C5H10ClO3P

Synthesis Example 1 (Synthesis of Phosphorus Compound 1) (Reaction); In a four-necked 1-L flask provided with a stirrer, a thermometer, a dropping device, a hydrochloric-acid-absorber device and a condenser, 104.0 g (1 mole) of neopentyl glycol and 114.4 g of chlorobenzene were fed. The resulting mixture was heated at 45 to 55 C while stirring and 153.5 g (1 mole) of phosphorus oxychloride were dropwise added to the mixture in an hour. After addition, the mixture was heated to 75 C in an hour, and then was allowed to react at the same temperature (75 C) for an hour and 65.7 g of generated hydrogen chloride were recovered. Thereafter, the mixture was depressurized at the same temperature (75 C) and 26.6 kPa for 2 hours and remaining hydrogen chloride was absorbed as a gas. As a result, 298.9 g of the reaction mixture were obtained. The purity of the reaction mixture was found to be 95.6 area % by GPC (gel permeation chromatography). The resulting reaction mixture was cooled to room temperature to which 161.5 g (0.95 mole) of 2-phenylphenol (ortho-phenylphenol), 0.9 g of magnesium chloride and 145.6 g of chlorobenzene were added. The mixture was heated at 65 to 75 C while stirring and 106.1 g (1.05 moles) of triethylamine were dropwise added to the mixture in an hour. Thereafter, the mixture was allowed to react at the same temperature (75 C) for an hour and thereby obtaining a mixture of 5, 5-dimethyl-2-(2′-phenylphenoxy)-1, 3, 2-dioxaphosphorinane-2-oxide.(After-treatment) The obtained mixture was neutralized at 85 C by adding hydrochloric acid solution which corresponds to an excess amount of triethylamine and the mixture was allowed to stand to separate an oil phase. Next, the obtained oil phase was washed with approximately 85 C water and then dehydrated. The obtained oil phase was gradually cooled and 259.8 g of white needle-like crystals were crystallized out from the oil phase. The purity of the obtained crystals was found to be 99.0 area % by GPC. Also, if all of the crystals were assumed to be an object compound, the crude yield was 86.0 %. A structure of the obtained crystals was determined according to results of quantitative analysis of phosphorus by elemental analysis and absorption spectrometry using an UV spectrometer, 1H-NMR, 13C-NMR and FT-IR. The crystals were identified as 5, 5-dimethyl-2-(2′-phenylphenoxy)-1, 3, 2-dioxaphosphorinane-2-oxide (phosphorus compound 1) of the below-mentioned constructional formula. Also, a melting point of the crystal was measured by a microdose melting point apparatus (model number: MP-J3, manufactured by Yanaco Co., Ltd.). Quantitative analysis of phosphorus by elemental analysis and absorption spectrometry (theoretical values in parentheses): Carbon: 64.3 % (64.2 %) Hydrogen: 5.9 % (6.0 %) Phosphorus: 9.7 % (9.7 %) Melting point: 127 to 130 CIR (KBr): 2992, 2352, 1584, 1514, 1485, 1430, 1373, 1306, 1251, 1104, 1158, 1120, 1050, 1004, 980, 947, 922, 877, 701, 624 cm-1 2992, 2352, 1584, 1514, 1485, 1430, 1373, 1306, 1251, 1104, 1158, 1120, 1050, 1004, 980, 947, 922, 877, 701, 624 cm-1 NMR: 1H-NMR (CDCl3; 300MHz); delta 7.71 (1H, d, J=8Hz, o-PP), 7.55-7.26 (8H, m, o-PP), 3.62 (1H, d, J=10Hz, POCH2C(CH3)2-), 3.53 (2H, dd, JHH=10Hz, POCH2C(CH3)2-), 3.48 (1H, d, JHH=10Hz, POCH2C(CH3)2-), 1.17 (3H, s, POCH2C(CH3)2-), 0.42 (3H, s, POCH2C(CH3)2-) ppm1H-NMR (CDCl3; 300MHz); delta 7.71 (1H, d, J=8Hz, o-PP), 7.55-7.26 (8H, m, o-PP), 3.62 (1H, d, J=10Hz, POCH2C(CH3)2-), 3.53 (2H, dd, JHH=10Hz, POCH2C(CH3)2-), 3.48 (1H, d, JHH=10Hz, POCH2C(CH3)2-), 1.17 (3H, s, POCH2C(CH3)2-), 0.42 (3H, s, POCH2C(CH3)2-) ppm13C-NMR (CDCl3; 75MHz); delta 146.9 (d, 2JPC=6Hz), 137.3, 132.7 (d, 3JPC=7Hz), 130.9, 129.6, 129.0, 128.2, 127.6, 125.2, 120.4 (d, 3JPC=2Hz) (o-PP), 77.6 (d, 2JPC=7Hz, POCH2C(CH3)2-), 31.5 (d, 2JPC=6Hz, POCH2C (CH3)2-), 21.6, 19.5 ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, and friends who are interested can also refer to it.

Reference:
Patent; DAIHACHI CHEMICAL INDUSTRY CO., LTD.; EP1925622; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 108-37-2

General procedure: The substituted aryl bromide (1.0 mmol), 8-hydroxyquinoline (20 mol%) and KOtBu (2.0 mmol) were loaded into a Schlenk tube equipped with a Teflon-coated magnetic stir bar. The unactivated arene (8.0 mL or 80 equiv) was then added and the mixture was stirred at r.t. for 3-5 min. The Schlenk tube was placed in a preheated oil bath at 80 C and the mixture was stirred for 18 h. After completion of the reaction as judged by GC analysis, the Schlenk tube was allowed to cool to r.t. and the contents quenched with H2O and diluted with EtOAc. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel to afford the desired biaryl product.

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zheng, Xuehua; Wu, Xu-Nian; Chen, Jing-Yi; Luo, Hai-Bin; Wu, Deyan; Wu, Yinuo; Synthesis; vol. 50; 8; (2018); p. 1721 – 1727;,
Chloride – Wikipedia,
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Reference of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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.

[0075] 4-Chloro-3-fluoroaniline (2g, 13.7 mmol) was dissolved in 60 mL of dichloromethane.Under ice bath, saturated sodium bicarbonate solution (60 mL) was added. The mixture wasstirred at 0 C and triphosgene (1.36g, 4.58 mmol) was added. The mixture was stirred at 0 C for1 h and then extracted with dichloromethane and water. The organic layer was dried with sodiumsulfate and filtered. The filtrate solution was concentrated and the residue was treated with 50mL ofhexanes. The hexane solution was concentrated to remove all solvents. The residue wastaken up in 12 mL ofhexanes and filtered. The solution was concentrated and dried to give 1-chloro-2-fluoro-4-isocyanatobenzene as an offwhite solid (1.69 g). 1H NMR (400 MHz,CHLOROFORM-d) 8 ppm 6.82- 6.90 (m, 1 H) 6.93 (dd, J=9.22, 2.65 Hz, 1 H) 7.31 – 7.41 (m, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-fluoroaniline, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine, E.; CHEN, Zhi; ERICKSON, Shawn, David; KIM, Kyungjin; LI, Hongju; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter, Michael; YI, Lin; WO2014/56958; (2014); A1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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: Cinnamyl chloride

General procedure: A representative procedure of skeleton 4 is as follows: K2CO3 (400 mg, 2.9 mmol) was added to a solution of 3 (1.0 mmol) in acetone (10 mL) at rt. The reaction mixture was stirred at rt for 10 min. Cinnamyl chloride (1.05 mmol) was added to the reaction mixture at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled to rt, concentrated, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=6:1 to 1:1) afforded 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2687-12-9, its application will become more common.

Reference:
Article; Chang, Meng-Yang; Lu, Yi-Ju; Cheng, Yu-Chieh; Tetrahedron; vol. 71; 8; (2015); p. 1192 – 1201;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 626-43-7, name is 3,5-Dichloroaniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 626-43-7, Recommanded Product: 3,5-Dichloroaniline

Step 1 Preparation of #-(3,5-dichlorophenyl)-2-hydroxyimino-acetamide To a solution of 3,5-dichloroanilin (10.0 g, 61.7 mmol) in purified water were added conc. hydrochloric acid (12 ml) and 1,4-dioxane (20 ml), and the resulting mixture was heated until it became transparent, followed by the addition of a 50 C. solution of chloral hydrate (10.5 g, 66.9 mmol) and Na2SO4 (66.0 g) in purified water (224 ml) thereto. Then, the resulting mixture was added to a solution of hydroxylamine hydrochloride (13.0 g, 180 mmol) in water (60 ml) and heated for 50 min with flux. After the mixture was cooled to room temperature, the insoluble solid was filtered, washed with distilled water, and dried in a vacuum to afford the title compound as a pale solid (12.8 g, 89%). TLC Rf=0.5 (ethylacetate:n-hexane=1:3); m.p. 196-197 C.; 1H NMR (DMSO-d6) delta 7.39 (t, 1H, J=1.8 Hz, ArH), 7.70 (s, 1H, CHNOH), 7.89 (d, 2H, J=1.8 Hz, ArH), 10.54 (br s, 1H, NH), 12.40 (br s, 1H, NOH); MS (EI) m/e 233 [M+], 216, 202, 189, 161.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Korea Research Institute of Chemical Technology; US2009/203708; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 108-41-8, 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. 108-41-8, name is 1-Chloro-3-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a tube equipped with a magnetic stir bar were added the Pd catalyst 1 (11.2 mg, 0.4 mol% Pd) and 1.0 equiv. of aryl chloride (0.2 mmol) in turn. Subsequently, the solvent (toluene, 2.0 mL) and phenylmagnesium bromide (0.3 mmol, 1.5 equiv) were added under N2 atmosphere, respectively. The reaction was then heated to 140 C and stirred until aryl chloride was completely consumed as determined by TLC. At last, the reaction mixture was purified by silica gel column chromatography to afford the desired pure coupling product.

The chemical industry reduces the impact on the environment during synthesis 1-Chloro-3-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Xing; Zhu, Tingting; Shao, Zhongqi; Li, Yingjun; Chang, Honghong; Gao, Wenchao; Zhang, Yongli; Wei, Wenlong; Tetrahedron; vol. 72; 1; (2016); p. 69 – 75;,
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Synthetic Route of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (5.5 g, 29.3 mmol), morpholine (2.8 mL, 32.2 mmol) and K2C03 (8.0 g, 58.6 mmol) in DCM (50 mL) was stirred at room temperature for 3h. The TLC showed the starting material was completely consumed and H20 (50 mL) was added. The mixture was extracted with DCM (50 mL*2).The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to obtain 6.5 g of compound 2, yield in 93%. ?H NMR (CDC13, 400MHz): oe 7.58-7.57 (m, 1H), 6.74-6.72 (m, 1H), 6.64-6.62 (m, 1H), 4.05 (t, 4H, J =4.8Hz), 3.84 (t, 4H, J = 5.2Hz). ESI-MS (M+H): 239.

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, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUZHOU KINTOR PHARMACEUTICALS, INC.; GUO, Chuangxin; TONG, Youzhi; (160 pag.)WO2017/219800; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics