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

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

Uses

Used in Chemical Synthesis:
4-BROMO-2-METHYLANILINE is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and agrochemicals. Its unique structural features make it a versatile building block for the development of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-BROMO-2-METHYLANILINE is used as a key intermediate for the synthesis of various drugs. Its reactivity and structural diversity allow for the creation of new drug candidates with improved therapeutic properties.
Used in Dye Manufacturing:
4-BROMO-2-METHYLANILINE is also used in the manufacturing of dyes, particularly those with specific color properties. Its aromatic amine structure contributes to the color intensity and stability of the resulting dyes, making it a valuable component in the dye industry.
Used in Agrochemicals:
In the agrochemical industry, 4-BROMO-2-METHYLANILINE is utilized as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its chemical properties enable the development of effective and targeted agrochemicals for crop protection and management.
Used in the Preparation of 4-Bromo-2-methylphenol:
4-BROMO-2-METHYLANILINE is specifically used in the preparation of 4-Bromo-2-methylphenol, a compound with potential applications in the synthesis of various organic compounds and materials. The conversion of 4-BROMO-2-METHYLANILINE to 4-Bromo-2-methylphenol demonstrates its utility as a versatile intermediate in organic chemistry.

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

• 52414-98-9 5-bromo-2-nitrotoluene 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 95-53-4 o-toluidine 
• 611-22-3 N-(o-tolyl)hydroxylamine 
• 24106-05-6 4'-bromo-2'-methylacetanilide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 10035-10-6 hydrogen bromide 
• 7647-01-0 hydrogenchloride 
• 56056-25-8 (4-bromo-2-methylphenyl)hydrazine 
• 7732-18-5 water 
• 958990-53-9 6-amino-5-bromo-toluene-3-sulfonic acid 
• 82185-43-1 N-(trimethylsilyl)-o-toluidine 
• 611-23-4 2-nitrosotoluene 

Downstream Products

• 116595-38-1 N-(4-bromo-2-methyl-anilinomethyl)-phthalimide 
• 96686-51-0 PCM-0102799 
• 330832-49-0 toluene-4-sulfonic acid-(4-bromo-2-methyl-anilide) 
• 178396-31-1 6-bromo-8-methylquinoline 
• 50638-49-8 2-methyl-4-bromo-N,N-dimethylaniline 
• 116568-38-8 (4-bromo-2-methyl-anilino)-methanesulfonic acid ; sodium-salt 
• 81090-36-0 4-bromo-N-ethyl-2-methylaniline 
• 19241-38-4 4-bromo-2-methylphenyl isothiocyanate 
• 861622-60-8 N,N'-bis-(4-bromo-2-methyl-phenyl)-thiourea 
• 879407-23-5 4'-bromo-2'-methyl-cis-stilbene-carbonitrile-⁽⁴⁾ 
• 153696-64-1 3-hydroxy-[2]naphthoic acid-(4-bromo-2-methyl-anilide) 

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.

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%.

Chemoselective Deprotection of Sulfonamides under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Chemoselective acidic hydrolysis of sulfonamides with trifluoromethanesulfonic acid has been evaluated as a deprotection method and further extended to more complex synthetic applications. In contrast to conventional troublesome sulfonamide hydrolysis, a near-stoichiometric amount of acid was found to be sufficient to bring about efficient deprotection of various neutral or electron-deficient N-arylsulfonamides, whereas electron-rich substrates provided sulfonyl group migration products. The deprotection method developed is fully selective for N-arylsulfonamides, and the possibility to discriminate among various different sulfonamides is demonstrated.

5-bromo-2-chloro -4 the-oxethyl diphenylmothane [...] preparation method

The invention relates to the chemical field and particularly relates to a novel synthesis method for preparing a key intermediate 5-bromine-2-chlorine-4'-ethyoxyl diphenylmethane of a drug dapagliflozin for treating diabetes mellitus II. The preparation method comprises the following steps: enabling a starting raw material ortho-toluidine to firstly perform bromization and then perform chlorination after diazotization on a benzene ring with N-bromo-succinimide; then, in the presence of a halogenating agent, performing halogenating reaction of beta-position; and finally, performing Friedel-Crafts alkylation synthesis with phenetole, thereby obtaining the key intermediate. The preparation method is simple and convenient, economical and relatively high in reaction yield in each step, and suitable for industrial production.

Under the conditions of a solvent-free method of hydrogenation to synthesize haloarylamine

The invention provides a method for synthesising halogenated aromatic amine through hydrogenation in a solvent-free condition. The method comprises the following step of: carrying out a liquid-phase hydrogenation reaction on the halogenated aromatic nitro compound shown in formula (I) under the action of hydrogen, in the absence of a solvent and a dehalogenation inhibitor under the action of a carbon-supported large-particle-size precious metal catalyst to prepare the halogenated aromatic amine shown in formula (II). The method provided by the invention is capable of achieving the effect of inhibiting a hydrogenation dehalogenation side reaction in the case of not adding a dehalogenation inhibitor, is high in target product selectivity, and is capable of remarkably increasing the reaction speed.

New insights into bromination process: Effective preparation of Ambroxol

Ambroxol used as an expectorant in treating respiratory diseases was effectively prepared with a total yield of 62 %, with o-toluidine as the feedstock via successive procedures of electrophilic bromination, acetylation, radical benzylic bromination, N-alkylation and hydrolysis processes. The addition of aqueous hydrogen peroxide could enhance the utilisation of liquid bromine in the electrophilic bromination of o-toluidine, avoiding the hazardous HBr generated as a by-product. In addition, liquid bromine promoted by MnO2 was used efficiently for the radical benzylic bromination of N-acetyl-N-(2,4-dibromo-6-methylphenyl)acetamide under mild conditions.

Para-Selective Halogenation of Nitrosoarenes with Copper(II) Halides

The para-selective direct bromination and chlorination of nitrosoarenes with copper(II) bromide and chloride is reported. Under mild reaction conditions, a range of halogenated arylnitroso compounds are obtained in moderate to good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of a one-pot procedure to obtain the corresponding para-halogenated aniline- and nitrobenzene derivatives.