5326-34-1

Basic information

• Product Name: 4-Bromo-3-nitrotoluene
• Synonyms: 1-Bromo-4-methyl-2-nitrobenzene;Benzene, 1-bromo-4-methyl-2-nitro-;4-BROMO-3-NITROTOLUENE;BROMONITROTOLUENE-4;4-BROMO-3-NITROTOLUENE, TECH., 90%;4-BROMO-3-NITROTOLUENE 99%;1-Nitro-2-bromo-5-methylbenzene;4-Bromo-3-nitrotoluene,99%
• CAS NO: 5326-34-1
• Molecular Formula: C₇H₆BrNO₂
• Molecular Weight: 216.03
• EINECS: 226-203-6
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Bromine Compounds;Nitro Compounds;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 5326-34-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 31-33 °C(lit.)
• Boiling Point: 151.5-152.5 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: almost colorless crystalline powder
• Density: 1.578 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0312mmHg at 25°C
• Refractive Index: 1.5930 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive: Light Sensitive
• BRN: 1945925
• CAS DataBase Reference: 4-Bromo-3-nitrotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-3-nitrotoluene(5326-34-1)
• EPA Substance Registry System: 4-Bromo-3-nitrotoluene(5326-34-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-20/21/22
• Safety Statements: 26-36-36/37-36/37/39-22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5326-34-1(Hazardous Substances Data)

Usage

Chemical Properties

Low melting solid

Uses

4-Bromo-3-nitrotoluene may be used as a starting material in the synthesis of 2-bromo-5-methylaniline and as a reagent in the synthesis of 2-nitro-4:4′-dimethyl-diphenyl by reacting with p-iodotoluene.

General Description

4-Bromo-3-nitrotoluene (2-bromo-5-methylnitrobenzene, 1-bromo-4-methyl-2-nitrobenzene) is a halonitrobenzene. It has been synthesized from 4-methyl-2-nitroaniline and confirmed by 1H NMR. The crystal structure of 1-bromo-4-methyl-2-nitrobenzene is found to be orthorhombic in the Pna21 space group. Its enthalpy of vaporization at boiling point has been determined.

InChI:InChI=1/C7H6BrNO2/c1-5-2-3-6(8)7(4-5)9(10)11/h2-4H,1H3

Upstream product

• 106-38-7 para-bromotoluene 
• 99-08-1 1-methyl-3-nitrobenzene 
• 108-24-7 acetic anhydride 
• 7697-37-2 nitric acid 
• 27329-27-7 4-methyl-2-nitrobenzoic acid 
• 612-45-3 4-methyl-2-nitroacetanilide 
• 7726-95-6 bromine 
• 89-62-3 4-methyl-2-nitroaniline 

Downstream Products

• 35883-87-5 4,4'-dimethyl-2,2'-dinitrobiphenyl 
• 2236-38-6 4-Methyl-1-(4-methylphenoxy)-2-nitrobenzene 
• 6319-40-0 4-bromo-3-nitrobenzoic acid 
• 53078-85-6 2-bromo-5-methylaniline 
• 857001-06-0 4-bromo-3,5-dinitro-toluene 
• 101936-32-7 9-(4-methyl-2-nitro-phenyl)-carbazole 
• 4600-08-2 4,N-dimethyl-2-nitroaniline 
• 2172-90-9 4-Methyl-2-nitro-1-phenoxybenzene 
• 59504-34-6 4-(N-pyrrolidino)-5-nitrotoluene 
• 581-46-4 3,3'-bipyridine 
• 4373-73-3 3-(4-methyl-2-nitro-phenyl)-pyridine 
• 106851-21-2 4-methyl-2-nitro-1-[2-(trimethylsilyl)ethynyl]benzene 
• 81157-23-5 bis-(4-methyl-2-nitro-phenyl)-diselenide 
• 588-04-5 3,3'-dimethylazobenzene 

Relevant articles and documents

Nitration of deactivated aromatic compounds via mechanochemical reaction

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions

Versatile and practical Ag/Cu-mediated decarboxylative halogenation between readily available aryl carboxylic acids and abundant NaX (X = I, Br, Cl) has been achieved under aerobic conditions in moderate to good yields. The halodecarboxylation is shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib have been performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicates that Cu plays a vital role and a radical pathway is involved in the transformation.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.