60956-26-5

Basic information

• Product Name: 4-Bromo-2-nitrotoluene
• Synonyms: 4-BROMO-6-NITROTOLUENE;4-BROMO-2-NITROTOLUENE;BROMO(4-)-2-NITROTOLUENE;Benzene, 4-bromo-1-methyl-2-nitro-;4-Bromo-2-nitrotolune;2-nitro-4-bromotoluene;4-Bromo-2-Nitreotoluene;4-Bromo-2-nitrotoluene, 99+%
• CAS NO: 60956-26-5
• Molecular Formula: C₇H₆BrNO₂
• Molecular Weight: 216.03
• EINECS: 262-536-3
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 60956-26-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 45-48 °C(lit.)
• Boiling Point: 130 °C12 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: Yellow to light orange/Crystals or Crystalline Powder
• Density: 1.6841 (rough estimate)
• Vapor Pressure: 0.0246mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: water: insoluble(lit.)
• Water Solubility: insoluble
• BRN: 2328190
• CAS DataBase Reference: 4-Bromo-2-nitrotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-nitrotoluene(60956-26-5)
• EPA Substance Registry System: 4-Bromo-2-nitrotoluene(60956-26-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 3
• Hazardous Substances Data: 60956-26-5(Hazardous Substances Data)

Usage

Chemical Properties

YELLOW TO LIGHT ORANGE CRYSTALS OR CRYST. POWDER

Uses

4-Bromo-2-nitrotoluene may be used as a starting material in the synthesis of the following:4-bromo-2-nitrobenzylidene4-bromo-2-nitrobenzaldehyde4-bromo-2-chlorotoluene4-bromo-2-nitrobenzoic acid by oxidation6-bromoindole by Batcho-Leimgruber indole synthesis3-(4-bromo-2-nitrophenyl)-2-[2-(tert-butyldimethylsilanyloxy)ethyl]-N-(2,4-dichloro-6-iodophenyl)-N-methoxymethylacrylamide

General Description

4-Bromo-2-nitrotoluene is a nitrotoluene derivative. It can be synthesized by the regioselective bromination of o-nitrotoluene.

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

Upstream product

• 106-38-7 para-bromotoluene 
• 108-24-7 acetic anhydride 
• 88-72-2 1-methyl-2-nitrobenzene 
• 7726-95-6 bromine 
• 7647-18-9 antimonypentachloride 
• 10025-91-9 antimony(III) chloride 
• 7553-56-2 iodine 
• 107650-20-4 5-bromo-2-methyl-3-nitro-benzoic acid 
• 1600-27-7 mercury(II) diacetate 
• 64-17-5 ethanol 
• 39478-78-9 5-bromo-2-methylaniline 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 106-49-0 p-toluidine 
• 7697-37-2 nitric acid 

Downstream Products

• 108061-73-0 (E)-4-bromo-2-nitro-β-piperidinostyrene 
• 82420-34-6 4-bromo-1-(bromomethyl)-2-nitrobenzene 
• 6127-11-3 (4-bromo-2-nitrophenyl)acetic acid 
• 53078-85-6 2-bromo-5-methylaniline 
• 4373-62-0 2-nitro-4-(3-pyridyl)toluene 
• 856839-64-0 2-(4-bromo-2-nitrophenyl)ethanol 
• 1269802-80-3 methyl 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate 
• 1303571-74-5 6-(4-fluorophenyl)-1-hydroxy-1H-indole-2-carboxylic acid 
• 929606-22-4 (2E)-3-(4-bromo-2-nitrophenyl)-2-(4-bromophenyl)prop-2-enoic acid 
• 929606-25-7 (2E)-3-(2-amino-4-bromophenyl)-2-(4-bromophenyl)prop-2-enoic acid 
• 929606-23-5 (2E)-3-(4-bromo-2-nitrophenyl)-2-(4-chlorophenyl)prop-2-enoic acid 
• 929606-26-8 (2E)-3-(2-amino-4-bromophenyl)-2-(4-chlorophenyl)prop-2-enoic acid 
• 59278-65-8 2-amino-4-bromobenzaldehyde 
• 5551-12-2 4-bromo-2-nitrobenzaldehyde 

Relevant articles and documents

Concerning the preparation of 6-bromotryptamine

Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.

Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group

A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.