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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

Quality Level

100

Assay

97%

form

solid

bp

130 °C/12 mmHg (lit.)

mp

45-48 °C (lit.)

solubility

water: insoluble(lit.)

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

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tyrian purple: 6, 6'-dibromoindigo and related compounds.
Cooksey CJ.
Molecules (Basel), 6(9), 736-769 (2001)
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
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
The bromo-2-nitrobenzoic acids.
Erickson JLE, et al.
Journal of the American Chemical Society, 74(22), 5621-5623 (1952)
A Simple, Safe and Efficient Synthesis of Tyrian Purple (6, 6'-Dibromoindigo).
Wolk JL and Frimer AA.
Molecules (Basel), 15(8), 5561-5580 (2010)
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