6933-10-4

Basic information

• Product Name: 4-Bromo-3-methylaniline
• Synonyms: 3-Methyl-4-bromoaniline;4-Bromo-3-methylbenzenamine;m-Toluidine, 4-bromo-;AKOS BBS-00003654;5-AMINO-2-BROMOTOLUENE;4-BROMO-3-METHYLANILINE;4-BROMO-3-METHYL-PHENYLAMINE;4-BROMO-M-TOLUIDINE
• CAS NO: 6933-10-4
• Molecular Formula: C₇H₈BrN
• Molecular Weight: 186.05
• EINECS: 230-056-3
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Miscellaneous;Anilines, Amides & Amines;Bromine Compounds
• Mol File: 6933-10-4.mol

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: 240 °C(lit.)
• Flash Point: 239-241°C
• Appearance: Off-white to beige to light brown/Powder
• Density: 1.4700 (rough estimate)
• Vapor Pressure: 0.0389mmHg at 25°C
• Refractive Index: 1.6190 (estimate)
• Storage Temp.: Room temperature.
• PKA: 4.02±0.10(Predicted)
• BRN: 2689600
• CAS DataBase Reference: 4-Bromo-3-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-3-methylaniline(6933-10-4)
• EPA Substance Registry System: 4-Bromo-3-methylaniline(6933-10-4)

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
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6933-10-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-3-methylaniline is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
4-Bromo-3-methylaniline is used as a starting material in the preparation of various organic compounds, such as 1-(4-bromo-3-methylphenyl)pyrrolidin-2-one. 4-Bromo-3-methylaniline can be further modified or used as a precursor for the synthesis of other complex organic molecules with specific properties and applications.

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

Upstream product

• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 7149-70-4 2-bromo-5-nitrotoluene 
• 537-92-8 3-Methylacetanilide 
• 90151-49-8 2-bromo-5,5-dimethyl-2-nitro-cyclohexane-1,3-dione 
• 108-44-1 1-amino-3-methylbenzene 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 582-77-4 3'-methylbenzanilide 
• 615-59-8 1,4-dibromo-2-methylbenzene 
• 1097885-39-6 4-azido-1-bromo-2-methylbenzene 

Downstream Products

• 28170-76-5 3-(4-bromo-3-methylphenyl)-1,1-dimethylurea 
• 445008-79-7 N-(4-bromo-3-methyl-phenyl)-N'-(4-chloro-phenyl)-urea 
• 78508-46-0 (4-bromo-3-methyl-phenyl)-urea 
• 14472-14-1 4-bromo-3-methylphenol 
• 615-59-8 1,4-dibromo-2-methylbenzene 
• 95-46-5 2-methylphenyl bromide 
• 14395-52-9 3-methyl-4-bromothiophenol 
• 41963-20-6 4-bromo-3-methylbenzonirtile 
• 92022-07-6 1-bromo-2-methyl-4-phenylbenzene 
• 92022-23-6 (4-bromo-3-methyl-phenyl)-phenyl-diazene 
• 57730-26-4 (4-Bromo-3-methyl-phenyl)-(2,4-dinitro-6-trifluoromethyl-phenyl)-amine 
• 7697-28-1 4-bromo-3-methylbenzoic acid 
• 73206-54-9 2,4-Dibrom-5-methylbenzonitril 

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.

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones

The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.

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.

o-xylylene bis(triethyl ammonium tribromide) as a mild and recyclable reagent for rapid and regioselective bromination of anilines and phenols

Background: o-Xylylene bis(triethyl ammonium tribromide) (OXBTEATB) as a recyclable and high bromine containing di-(tribromide) reagent has been employed for the bromination of various organic substrates such as phenol and aniline or its derivatives. This catalyst can be recovered and reused several times. Methods: Aryl bromides shown in Table 1, were easily produced from bromination of aromatic compounds by OXBTEATB. This high-yield process lets the reagents to be recycled and reused. Results: As shown in Table 1, substituted anilines, phenols and β-naphthol were found to be the most reactive and immediately converted to the corresponding mono-brominated products by OXBTEATB. Conclusion: OXBTEATB can be considered a solidified bromine. This novel reagent has variable solubility in different polar protic and aprotic solvents but insoluble in non-polar aprotic solvent. Subsequently, OXBTEATB can be recognized as a more useful brominating and regioselective catalyst than the liquid bromine.

Green synthesis method of bromoaromatic amine and alpha-bromoaromatic ketone

The invention discloses a green synthesis method of bromoaromatic amine and alpha-bromoaromatic ketone. The synthesis method comprises: adopting hydrobromic acid as a brominating agent, adopting 2-methylpyridine nitrate as a catalyst, and adopting molecular oxygen as an oxidizing agent, brominating an aromatic compound with a structure shown in formula (1) or aromatic ketone with a structure shown in formula (2) or (3), and preparing corresponding bromoaromatic amine or alpha-bromoaromatic ketone. The synthesis method is wide in substrate application reaction, high in atom utilization rate, capable of avoiding the application of the transitional metal element and volatile organic solvent and has the characteristics of economical efficiency and environmental protection. (Shown in the description).

Method for synthesizing monobrominated aniline compound

The invention discloses a method for synthesizing a monobrominated aniline compound. The method comprises the following steps: by taking an aniline compound as a raw material, and taking zinc aluminum hydrotalcite ZnAl-BrO3-LDHs with a bromate inserted layer and an alkali metal bromide as bromine sources in a mixed solvent of water and an organic solvent, reacting for 1-3h at 10-50 DEG C; after ending the reaction, extracting a reaction mixed solution A by using dichloromethane; adding a column chromatography silica gel into dichloromethane phase; removing the solvent in the manner of reduced pressure distillation; and acquiring a mono-bromination objective product in the manner of column chromatography separation by using an eluent composed of petroleum ether and ethyl acetate at the ratio of 10:1. The invention realizes a high-selectivity oxidative bromination method by adopting an aniline compound under the effects of ZnAl-BrO3-LDHs and potassium bromide; the monobrominated aniline compound is prepared; the reaction popularity is high and the raw material is low in cost and is easily acquired; the reaction condition is mild; the reaction yield is high; the atom utilization ratio is high; and the chemical selectivity is excellent and the environment is protected.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

Selective reduction of halogenated nitroarenes with hydrazine hydrate in the presence of Pd/C

A large variety of halogenated nitroarenes have been selectively reduced with hydrazine hydrate in the presence of Pd/C to give the corresponding (halogenated) anilines in good yield.

Selective bromination of pyrrole derivatives, carbazole and aromatic amines with DMSO/HBr under mild conditions

Bromination of pyrrole derivatives, carbazole and aromatic amines using the DMSO/HBr system affords high yields of the corresponding bromo compounds. Temperature control used in the bromination of anilines helped to promote selective formation of mono- or di-brominated products. Simple operation, low toxicity and high selectivity make this a promising new procedure for the bromination of aromatic compounds.

Preparation of carbazole and dibenzofuran derivatives by selective bromination on aromatic rings or benzylic groups with N-bromosuccinimide

N-Bromosuccinimide (NBS), a bromine source, has been used to study the bromination of toluidine and cresols systematically to clarify the underlying mechanism and the orientation effect. It has been found that bromination of toluidine and cresols which possess electron-donating NH2/OH with NBS gives electrophilic aromatic substitution products quickly instead of the desired benzylic bromination products. In contrast, when the electronic effect of the substituted groups is reversed, only the benzylic bromination products are gained. Based on this methodology, several potential AChE inhibitors, such as 2-methoxy-5-(benzylamino)methyl-dibenzofuran, 3-bromo-2-methoxy-5-methyl-9H- carbazole, 3,6-dibromo-2-methoxy-5-methyl-9H-carbazole, and 5-(bromomethyl)-2- methoxy-9H-(phenylsulfonyl)-carbazole have been synthesized.