77811-44-0

Basic information

• Product Name: 4-Bromo-2-methyl-6-nitroaniline
• Synonyms: 4-BROMO-6-NITRO-O-TOLUIDINE;4-BROMO-2-METHYL-6-NITROANILINE;4-BROMO-2-METHYL-6-NITRO-PHENYLAMINE;2-Nitro-4-bromo-6-methylaniline;4-Bromo-2-methyl-6-nitrobenzenamine;4-broMo-2-Methyl-6-nitroanilin;2-Amino-5-bromo-3-nitrotoluene, 2-Amino-5-bromo-3-methylnitrobenzene, 4-Bromo-6-nitro-o-toulidine;BenzenaMine, 4-broMo-2-Methyl-6-nitro-
• CAS NO: 77811-44-0
• Molecular Formula: C₇H₇BrN₂O₂
• Molecular Weight: 231.05
• EINECS: 615-013-2
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Anilines, Amides & Amines;Bromine Compounds;Nitro Compounds;Amines;C7;Nitrogen Compounds
• Mol File: 77811-44-0.mol

Chemical Properties

• Melting Point: 143-147 °C
• Boiling Point: 326.8 °C at 760 mmHg
• Flash Point: 151.4 °C
• Appearance: orange to orange-brown glistening crystals
• Density: 1.7207 (rough estimate)
• Vapor Pressure: 0.000211mmHg at 25°C
• Refractive Index: 1.5150 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -1.23±0.25(Predicted)
• Water Solubility: Slightly soluble in water and soluble in hot methanol.
• BRN: 3530524
• CAS DataBase Reference: 4-Bromo-2-methyl-6-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-methyl-6-nitroaniline(77811-44-0)
• EPA Substance Registry System: 4-Bromo-2-methyl-6-nitroaniline(77811-44-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 77811-44-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-methyl-6-nitroaniline is used as a key intermediate in the design and synthesis of CK2 inhibitors. These inhibitors are important for the development of drugs targeting protein kinase CK2, which plays a crucial role in various cellular processes and is implicated in numerous diseases, including cancer and inflammatory disorders.
Used in Medicinal Chemistry Research:
4-Bromo-2-methyl-6-nitroaniline is also used in the docking studies of novel telmisartan-glitazone hybrid analogs for the treatment of metabolic syndrome. These hybrid analogs are designed to combine the beneficial effects of both telmisartan, an angiotensin II receptor antagonist, and glitazone, a peroxisome proliferator-activated receptor gamma agonist, to provide a more effective treatment for metabolic syndrome and its associated complications.

InChI:InChI=1/C7H7BrN2O2/c1-4-2-5(8)3-6(7(4)9)10(11)12/h2-3H,9H2,1H3

Upstream product

• 24106-05-6 4'-bromo-2'-methylacetanilide 
• 583-75-5 4-Bromo-2-methylaniline 
• 95-53-4 o-toluidine 
• 570-24-1 2-Methyl-6-nitroaniline 
• 120-66-1 N-(2-methylphenyl)acetamide 

Downstream Products

• 929194-28-5 7-phenyl-5-methyl-1,2,4-benzotriazine-3-ylamine 
• 867333-31-1 7-(2,6-dichlorophenyl)-5-methyl-1,2,4-benzotriazine-3-ylamine 
• 867333-12-8 7-(5-chloro-2-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine 
• 867332-72-7 7-(2-chloro-6-methoxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-amine 
• 867330-72-1 7-(2-chloro-5-methoxyphenyl)-5-methyl-1,2,4-benzotriazine-3-ylamine 
• 929194-29-6 7-(2,6-difluoro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine 
• 1007224-64-7 2-(3-amino-5-methyl-benzo[1,2,4]triazin-7-yl)-3-chloro-phenol 
• 1007224-62-5 7-(5-amino-2-chloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine 
• 867333-25-3 3-(3-amino-5-methyl-benzo[1,2,4]triazin-7-yl)-4-methyl-benzonitrile 
• 867331-23-5 N-[3-(3-amino-5-methyl-benzo[1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide 
• 867330-68-5 TG 100435 
• 867331-63-3 7-(2-chloro-5-methoxyphenyl)-5-methyl-N-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1,2,4-benzotriazin-3-ylamine 

Relevant articles and documents

2-(HETERO)ARYL-BENZIMIDAZOLE AND IMIDAZOPYRIDINE DERIVATIVES AS INHIBITORS OF ASPARAGIME EMETHYL TRANSFERASE

Substituted benzimidazole and 3H-imidazo[4,5-b]pyridines or formula I: where X and Y respectively are selected from: (i) N and N; and (ii) N and CR4; A2 is selected from:, a C5 heteroarylene group, containing 2 or 3 ring heteroatoms, where the bonds to L1 and the core are β to one another; L1 is selected from: (i)A1-O-CH2-A2; (ii)A1-CH2-O-A2; (iii)A1-C(=O)-NH-A2; (iv)A1-CH(OH)-A2; (v)A1-CH2-NH-C(=O)-A2; (vi) A1-S-CH2-A2; (vii)A1- CH2-S-A2; (viii)A1-CH2-A2; and (ix)A1-CH(CH3)-O-A2; A1 is phenyl, optionally substituted by F or CF3; their use as pharmaceuticals, and in particular, in treating cancer and hemoglobinopathies.

TRICYCLIC COMPOUND

Provided is a tricyclic compound having a PPAR γ agonist activity, which is represented by the general formula (I) wherein Z represents a single bond or the like, Y represents a hydrogen atom, lower alkyl optionally having substituent(s) or the like, X represents a hydrogen atom or the like, A represents aryl or the like, B and C are the same or different and each represents an aromatic carbocycle or the like, R4 - R9 are the same or different and each represents hydrogen or the like, V represents a single bond or the like, R10 and R11 are the same or different and each represents hydrogen or the like, or a pharmaceutically acceptable salt thereof or the like:

PROCESS FOR THE PREPARATION OF BENZIMIDAZOLES

The invention provides a process for the preparation of compounds of formula (I) wherein wherein R1 is C1-6-alkyl or C3-6-cycloalkyl, R2 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl, and Q1 is selected from the group consisting of halogen, cyano and -CO-R3, wherein R3 is selected from hydrogen, hydroxy, C1-6-alkoxy, C3-8-cycloalkyloxy, aryloxy, C1-6-alkylamino, aryl-(C1-6-alkyl)amino and di-C1-6-alkylamino, comprising the step of reacting a corresponding o-nitroaniline with an aldehyde R2-CH0 or an equivalent thereof in the presence of a reducing agent.

The nitration of 8-methylquinoxalines in mixed acid

8-Methylquinoxalines are nitrated surprisingly efficiently at C-5 following a simple nitration protocol with mixed acid at 40-50°C. The implications of halogen functionalisation at C-6 and modification of the mixed acid conditions on the relative rates of conversion and process safety are discussed. Competing side reactions for 6-halo-8-methylquinoxalines involve hydrolysis at C-6 and halogenation at C-7 or C-5.

Research in 7-aminoindazole series: Synthesis of new halo-7H-4-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-6-ones and 5H-9-halo-6-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-4-ones

A new class of 7-aminohaloindazoles has been synthesized. Reactivity of the amino groups of these bicyclic systems has been investigated. The halogenated pyrazolo-1,5-benzodiazepinones have been synthesized by the condensation of 7-aminoindazoles with ethyl acetoacetate.

Oxidative Bromination of Aromatic Amides using Sodium Perborate as Oxidant

Sodium perborate in glacial acetic acid-acetic anhydride with potassium bromide and sodium tungstate as a catalyst, provides a novel system for the bromination of aromatic amides.

Catalysts for the Oxidative Bromination of Aromatic Amines and their N-Acetyl Derivatives

In the nuclear bromination of aromatic amines by bromide and hydrogen peroxide in acetic acid, sodium tungstate has been compared with ammonium molybdate and ammonium vanadate, and found to be an effective catalyst.

Heterocyclic Systems Containing Bridgehead Nitrogen Atom : Part XXXVIII- Reaction of 6-Bromo-2-mercapto-4-methylbenzimidazole with Chloroacetic Acid, α-Halogenoketones and 1,2-Dibromoethane

6-Bromo-8-methylthiazolobenzimidazol-3(2H)-one (IV), 3-substituted-6-bromo-8-methylthiazolobenzimidazoles (VII) and 2,3-dihydro-6-bromo-8-methylthiazolobenzimidazole (VIII) have been synthesized starting from 6-bromo-2-mercapto-4-methylbenzimidazole (II), prepared by the treatment of 5-bromo-3-methyl-1,2-diaminobenzene (I) with carbon disulphide.II on condensation with chloroacetic acid gives 6-bromo-4-methyl-2-benzimidazothiolacetic acid (III) which on cyclization with acetic anhydride furnishes IV and not the other isomer (V).Condensation of II with α-halogenoketones followed by PPA cyclization of the intermediate ketones (VI) yields 3-aryl-6-bromo-8-methylthiazolobenzimidazoles (VII).A similar reaction of II with 1,2-dibromoethane gives VIII.