583-75-5

Basic information

• Product Name: 4-BROMO-2-METHYLANILINE
• Synonyms: LABOTEST-BB LT02085203;5-BROMO-2-AMINOTOLUENE;4-BROMO-2-METHYLANILINE;4-BROMO-O-TOLUIDINE;AKOS BBS-00004345;2-AMINO-5-BROMOTOLUENE;2-METHYL-4-BROMOANILINE;1-AMINO-4-BROMO-2-METHYLBENZENE
• CAS NO: 583-75-5
• Molecular Formula: C₇H₈BrN
• Molecular Weight: 186.05
• EINECS: 209-519-9
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Anilines, Amides & Amines;Bromine Compounds;Thiazines ,Benzothiazoles,Thiazoles
• Mol File: 583-75-5.mol
• Article Data: 36

Chemical Properties

• Melting Point: 57-59 °C(lit.)
• Boiling Point: 240 °C(lit.)
• Flash Point: >230 °F
• Appearance: white to light yellow crystal powder
• Density: 1.4700 (rough estimate)
• Vapor Pressure: 0.0337mmHg at 25°C
• Refractive Index: 1.6190 (estimate)
• Storage Temp.: 0-10°C
• PKA: 3.75±0.10(Predicted)
• BRN: 636521
• CAS DataBase Reference: 4-BROMO-2-METHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-METHYLANILINE(583-75-5)
• EPA Substance Registry System: 4-BROMO-2-METHYLANILINE(583-75-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-33
• Safety Statements: 26-37/39-24/25
• RIDADR: UN2811
• WGK Germany: 3
• RTECS: XU4250000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 583-75-5(Hazardous Substances Data)

Usage

Chemical Properties

whitetolightyellowcrystalpowde

Uses

4-Bromo-2-methylaniline was used in the preparation of 4-Bromo-2-methylphenol.

Purification Methods

Steam distil the aniline and recrystallise it from EtOH. UV: max 292.5nm (H2O). [Beilstein 12 H 838, 12 I 389, 12 II 456, 12 IV 1804.]

InChI:InChI=1/C7H8BrN/c1-5-4-6(8)2-3-7(5)9/h2-4H,9H2,1H3

Upstream product

• 330832-49-0 toluene-4-sulfonic acid-(4-bromo-2-methyl-anilide) 
• 611-23-4 2-nitrosotoluene 
• 95-53-4 o-toluidine 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 82185-43-1 N-(trimethylsilyl)-o-toluidine 
• 958990-53-9 6-amino-5-bromo-toluene-3-sulfonic acid 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 52414-98-9 5-bromo-2-nitrotoluene 
• 56056-25-8 (4-bromo-2-methylphenyl)hydrazine 
• 10035-10-6 hydrogen bromide 
• 611-22-3 N-(o-tolyl)hydroxylamine 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 

Downstream Products

• 330832-49-0 toluene-4-sulfonic acid-(4-bromo-2-methyl-anilide) 
• 178396-31-1 6-bromo-8-methylquinoline 
• 10443-94-4 N-(4-Brom-2-methyl-phenyl)-benzolsulfonamid 
• 122212-34-4 4-bromo-2-methyl-N,N-bis(trimethylsilyl)benzeneamine 
• 99465-17-5 trans-N-(4-bromo-2-methylphenyl)-3-ethoxy-2-propenamide 
• 77067-93-7 4'-bromo-5-chloro-2'-methylsalicylanilide 
• 77067-95-9 4'-bromo-5-iodo-2'-methylsalicylanilide 
• 77068-04-3 4'-bromo-5-fluoro-2'-methylsalicylanilide 
• 77067-99-3 4',5-dibromo-2'-methylsalicylanilide 
• 79402-03-2 N-(4-Bromo-2-methyl-phenyl)-3,5-dichloro-2-hydroxy-benzamide 
• 90425-99-3 3,5-Dibromo-N-(4-bromo-2-methyl-phenyl)-2-hydroxy-benzamide 
• 50638-49-8 2-methyl-4-bromo-N,N-dimethylaniline 
• 429627-41-8 naphthalene-2-carboxylic acid (4-bromo-2-methyl-phenyl)-amide 
• 922170-67-0 4-bromo-2-iodo-6-methylaniline 

Relevant articles and documents

A metal-free aerobic oxidative bromination of anilines and aryl ketones with 2-methylpyridinium nitrate as a reusable ionic liquid

An aerobic oxidative bromination of anilines and aryl ketones catalyzed by recyclable 2-methylpyridinium nitrate ionic liquid is achieved in water using hydrobromic acid as the bromine source and molecular oxygen as the oxidant. The catalytic system shows good efficiency and atom economy.

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.

Preparation method of SGLT2 inhibitor-empagliflozin

The invention relates to a preparation method of a SGLT2 inhibitor-empagliflozin. The preparation method includes: using 2-methylaniline as a starting raw material, subjecting the starting raw material to bromination, diazotization, chlorination and bromination, and enabling the starting raw material to be in friedel-crafts alkylation reaction with (S)-3-phenoxy tetrahydrofuran to obtain an intermediate-(S)-3-(4-(5-bromo-2-chlorobenzyl)phenoxy) tetrahydrofuran; subjecting the intermediate and 2, 3, 4, 6-tetra-O-trimethylsilyl-D-glucolactone to condensation, etherification and methoxy removal.The preparation method has the advantages that compared with existing synthetic methods, 2-methylaniline is used as the starting raw material, so that the raw material is low in cost and easy to get,the process is easy for industrialization, and a synthetic route is short and easy to operate; in the process of preparation, temperature conditions are easy to control, reaction conversion rate is high, and total yield is up to higher than 75%. In addition, through the preparation method, the inhibitor is less prone to isomerization, impurities are few, and purity of the inhibitor can be improvedto higher than 99%.