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Sigma-Aldrich

2-Fluoro-6-nitrotoluene

98%

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Linear Formula:
CH3C6H3(NO2)F
CAS Number:
Molecular Weight:
155.13
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.523 (lit.)

bp

97 °C/11 mmHg (lit.)

mp

6.5-7 °C (lit.)

density

1.27 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C7H6FNO2/c1-5-6(8)3-2-4-7(5)9(10)11/h2-4H,1H3

InChI key

GXPIVRKDWZKIKZ-UHFFFAOYSA-N

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General description

2-Fluoro-6-nitrotoluene undergoes reduction in the presence of stannous chloride, followed by benzoylation to yield N-(3-fluoro-o-tolyl)benzamide. 2-Fluoro-6-nitrotoluene undergoes reaction with concentrated nitric acid at 100°C to yield 2-fluoro-6-nitrobenzoic acid.

Application

2-Fluoro-6-nitrotoluene has been used in the preparation of 4-fluoroindole via Leimgruber-Batcho procedure.

Regulatory Information

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139. Heterocyclic fluorine compounds. Part IV. Monofluoroindazoles.
Barben IK and Suschitzky H.
Journal of the Chemical Society, 672-676 (1960)
A synthesis of (-)-indolactam V.
Semmelhack MF and Rhee H.
Tetrahedron Letters, 34(9), 1395-1398 (1993)
359. Preparation of some fluoronitro-and aminofluoro-benzoic acids, and of fluoronitro-benzenes,-toluenes, and-xylenes.
Valkanas G and Hopff H.
Journal of the Chemical Society, 1925-1927 (1963)

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