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Sigma-Aldrich

4-Bromo-2-nitrotoluene

97%

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About This Item

Linear Formula:
CH3C6H3(NO2)Br
CAS Number:
60956-26-5
Molecular Weight:
216.03
EC Number:
262-536-3
MDL number:
MFCD00041243
UNSPSC Code:
12352100
PubChem Substance ID:
24866621
NACRES:
NA.22

assay

97%

form

solid

bp

130 °C/12 mmHg (lit.)

mp

45-48 °C (lit.)

solubility

water: insoluble(lit.)

functional group

bromo
nitro

SMILES string

Cc1ccc(Br)cc1[N+]([O-])=O

InChI

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

InChI key

KZNXALJXBRSMFL-UHFFFAOYSA-N

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General description

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

Application

4-Bromo-2-nitrotoluene may be used as a starting material in the synthesis of the following:
  • 4-bromo-2-nitrobenzylidene
  • 4-bromo-2-nitrobenzaldehyde
  • 4-bromo-2-chlorotoluene
  • 4-bromo-2-nitrobenzoic acid by oxidation
  • 6-bromoindole by Batcho-Leimgruber indole synthesis
  • 3-(4-bromo-2-nitrophenyl)-2-[2-(tert-butyldimethylsilanyloxy)ethyl]-N-(2,4-dichloro-6-iodophenyl)-N-methoxymethylacrylamide

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ5782
MKBS8677V
MKBL6142V
MKBG6609V
MKBC5776

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A Simple, Safe and Efficient Synthesis of Tyrian Purple (6, 6'-Dibromoindigo).
Wolk JL and Frimer AA.
Molecules (Basel), 15(8), 5561-5580 (2010)
The bromo-2-nitrobenzoic acids.
Erickson JLE, et al.
Journal of the American Chemical Society, 74(22), 5621-5623 (1952)
Jae Hong Seo et al.
The Journal of organic chemistry, 71(23), 8891-8900 (2006-11-04)
An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on
Olga V Barykina et al.
Organic letters, 12(11), 2664-2667 (2010-05-08)
The synthesis of (+/-)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the alpha-ketoamide proceeded efficiently
Tyrian purple: 6, 6'-dibromoindigo and related compounds.
Cooksey CJ.
Molecules (Basel), 6(9), 736-769 (2001)
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