BenzenaMine,3-broMo-4-chloro-
3-bromo-4-chloroaniline
CAS: 823-54-1
Molecular Formula: C6H5BrClN
BenzenaMine,3-broMo-4-chloro- - Names and Identifiers
| Name | 3-bromo-4-chloroaniline |
| Synonyms | 3-BROMO-4-CHLOROANILINE 3-bromo-4-chloroaniline 3-Bromo-4-chlorophenylamine 3-Bromo-4-chlorobenzenamine BenzenaMine,3-broMo-4-chloro- benzenamine, 3-bromo-4-chloro |
| CAS | 823-54-1 |
| InChI | InChI=1/C6H5BrClN/c7-5-3-4(9)1-2-6(5)8/h1-3H,9H2 |
BenzenaMine,3-broMo-4-chloro- - Physico-chemical Properties
| Molecular Formula | C6H5BrClN |
| Molar Mass | 206.47 |
| Density | 1.722±0.06 g/cm3 (20 ºC 760 Torr) |
| Melting Point | 82°C |
| Boling Point | 290.6±20.0℃ (760 Torr) |
| Flash Point | 129.5±21.8℃ |
| Vapor Presure | 0.002mmHg at 25°C |
| Appearance | Solid |
| pKa | 2.89±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.638 |
| MDL | MFCD00173905 |
| Use | Uses 3-bromo 4-chloroaniline is an amine derivative, which can be used as an organic reagent. |
BenzenaMine,3-broMo-4-chloro- - Risk and Safety
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R33 - Danger of cumulative effects |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | 2811 |
| HS Code | 29214200 |
| Hazard Class | 6.1 |
| Packing Group | Ⅲ |
BenzenaMine,3-broMo-4-chloro- - Upstream Downstream Industry
BenzenaMine,3-broMo-4-chloro- - Uses and synthesis methods
Introduction
3-Bromo-4-chloroaniline can be used as an intermediate in pharmaceutical synthesis. For example, it can be used to prepare vimodini (Vismodegib), the trade name is Erivedge, and the chemical name is 2-chloro-N-(4-Chloro-3-(pyridine-2-yl) phenyl)-4-(methylsulfonyl) benzamide, which is jointly developed by Curis, Genentech and Evotec, it was approved by the U.S. Food and Drug Administration (FDA) on January 30, 2012 as a small molecule targeted inhibitor of Hedgehog pathway for the treatment of basal cell carcinoma.
Preparation
1) add p-chloronitrobenzene (157.5g,1mol) into a 3L three-mouth bottle, add 2L sulfuric acid aqueous solution (mass fraction 80%) to dissolve, heat to 80 ℃ to dissolve, wait for the solid to dissolve completely, then slowly add 1.5mol of brominating reagent (bromine or potassium bromate) to the above reaction solution, add the heat preservation reaction for 3 hours, and cool the reaction solution after the reaction is complete, and slowly pour into 10kg of crushed ice, stir with a large amount of solid precipitation, filtration, filter cake with a large amount of water washing, drying, to obtain intermediate 2, yellow solid 217.5g, yield: 92%.
2) add intermediate 2(217.5g,0.92mol) obtained in step 1) into a 3L three-mouth bottle, add 1300ml of ethanol and reduced iron powder (103g,1.84mol), and slowly heat to 78 ℃ for reflux reaction for 3 hours. after the reaction is complete, the reaction liquid is cooled, filtered and concentrated to obtain 3-bromo 4-chloroaniline yellow solid 180.5g with a yield of 95%.
Last Update：2024-04-09 01:59:50
BenzenaMine,3-broMo-4-chloro- - Reference Information
| Introduction | 3-bromo-4-chloroaniline can be used as an intermediate in pharmaceutical synthesis, such as It can be used to prepare Vimodini (Vismodegib), the trade name is Erivedge, the chemical name is 2-chloro-N-(4-chloro-3-(pyridine-2-yl) phenyl)-4-(methylsulfonyl) benzamide, which was developed by Curis, Genentech and Evotec. It was approved by the U.S. Food and Drug Administration (FDA) on January 30, 2012 as a small molecule targeted inhibitor of Hedgehog pathway for the treatment of basal cell carcinoma. |
| use | 3-bromo 4-chloroaniline is an amine derivative and can be used as an organic reagent. |
| preparation | 1) add p-chloronitrobenzene (157.5g,1mol) into a 3L three-mouth bottle, add 2L sulfuric acid aqueous solution (mass fraction 80%) to dissolve, and heat to 80 ℃ to dissolve until the solid is completely dissolved, then 1.5mol of brominating reagent (bromine or potassium bromate) is slowly added to the above reaction solution, and the heat preservation reaction is completed for 3 hours. After the reaction is complete, the reaction solution is cooled and slowly poured into 10kg of crushed ice. A large amount of solid is stirred for precipitation, filtered, the filter cake is washed with a large amount of water and dried to obtain intermediate 2, 217.5g of yellow solid, and the yield is 92%. 2) Add intermediate 2(217.5g,0.92mol) obtained in step 1) into a 3L three-mouth bottle, add 1300ml of ethanol and reduced iron powder (103g,1.84mol), and slowly heat to 78 ℃ for reflux reaction for 3 hours. After the reaction is complete, the reaction liquid is cooled, filtered and concentrated to obtain 3-bromo 4-chloroaniline solid 180.5g, and the yield is 95%. |
Last Update：2024-04-09 01:59:58
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View History
Raw Materials for BenzenaMine,3-broMo-4-chloro-
Benzenamine, 2,3,4-tribromo-
2,3-Dibromoaniline
3'-BROMOACETANILIDE
3,4-DIBROMOANILINE
N-(3-bromo-4-chlorophenyl)acetamide(WS205137)
3-BROMO-4-CHLORONITROBENZENE
2,3-Dibromoaniline
3'-BROMOACETANILIDE
3,4-DIBROMOANILINE
N-(3-bromo-4-chlorophenyl)acetamide(WS205137)
3-BROMO-4-CHLORONITROBENZENE
Downstream Products for BenzenaMine,3-broMo-4-chloro-
Acetamide, N-(3-bromophenyl)-N-hydroxy-
2-BROMO-1,4-BENZOQUINONE
2-BROMO-1-CHLORO-4-IODOBENZENE
4-AMINO-2-BROMOPHENOL
5-BROMO-2-CHLOROANILINE
2-BROMO-1,4-BENZOQUINONE
2-BROMO-1-CHLORO-4-IODOBENZENE
4-AMINO-2-BROMOPHENOL
5-BROMO-2-CHLOROANILINE