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260053

Sigma-Aldrich

2-Bromo-6-nitrotoluene

98%

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About This Item

Linear Formula:
CH3C6H3(NO2)Br
CAS Number:
55289-35-5
Molecular Weight:
216.03
Beilstein/REAXYS Number:
2502581
EC Number:
259-566-4
MDL number:
MFCD00009792
UNSPSC Code:
12352100
PubChem Substance ID:
24855451
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

bp

143 °C/22 mmHg (lit.)

mp

38-40 °C (lit.)

SMILES string

Cc1c(Br)cccc1[N+]([O-])=O

InChI

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

InChI key

LYTNSGFSAXWBCA-UHFFFAOYSA-N

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Application

2-Bromo-6-nitrotoluene has been used:
  • as starting reagent in total synthesis of N-acetyl methyl ester of (±)-clavicipitic acids
  • in synthesis of carbazomadurin A, highly oxygenated neuronal cell protecting carbazole alkaloid

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

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Palladium-catalyzed reactions in the synthesis of 3-and 4-substituted indoles. 2. Total synthesis of the N-acetyl methyl ester of (?)-clavicipitic acids.
Harrington PJ, et al.
Journal of the American Chemical Society, 109(14), 4335-4338 (1987)
Hans-Joachim Knölker et al.
Chemical communications (Cambridge, England), (10)(10), 1170-1171 (2003-06-05)
The highly oxygenated neuronal cell protecting carbazole alkaloid carbazomadurin A was synthesized in nine steps and 11% overall yield from isovanillic acid.

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