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Sigma-Aldrich

2,4-Difluoronitrobenzene

99%

Synonym(s):

2,4-Difluoro-1-nitrobenzene

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About This Item

Linear Formula:
F2C6H3NO2
CAS Number:
446-35-5
Molecular Weight:
159.09
EC Number:
207-167-0
MDL number:
MFCD00007050
UNSPSC Code:
12352100
PubChem Substance ID:
24853961
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

100

assay

99%

form

liquid

refractive index

n20/D 1.511 (lit.)

bp

203-204 °C (lit.)

mp

9-10 °C (lit.)

density

1.451 g/mL at 25 °C (lit.)

SMILES string

[O-][N+](=O)c1ccc(F)cc1F

InChI

1S/C6H3F2NO2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H

InChI key

RJXOVESYJFXCGI-UHFFFAOYSA-N

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General description

Nucleophilic aromatic substitution of 2,4-difluoronitrobenzene with morpholine has been investigated using flow reactor with simulated moving bed (SMB) chromatography module.

Application

2,4-Difluoronitrobenzene has been used in the synthesis of:
  • 2,4-difluoro-5-nitrobenzenesulfonic acid via sulfonation reaction
  • (±)-horsfiline
  • resin-bound 2-arylaminobenzimidazoles

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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A direct synthesis of 2-arylpropenoic acid esters having nitro groups in the aromatic ring: a short synthesis of (?)-coerulescine and (?)-horsfiline.
Selvakumar N, et al.
Tetrahedron Letters, 43(50), 9175-9178 (2002)
Alexander G O'Brien et al.
Angewandte Chemie (International ed. in English), 51(28), 7028-7030 (2012-06-08)
Continuous synthesis meets continuous purification to produce pure products from crude reaction mixtures. In the nucleophilic aromatic substitution of 2,4-difluoronitrobenzene with morpholine the desired monosubstituted product can be continuously separated from the byproducts in a purity of over 99 %
U M Kremer
Biological chemistry Hoppe-Seyler, 371(9), 861-864 (1990-09-01)
2,4-Difluoro-5-nitrobenzenesulfonic acid has been synthesized by the sulfonation of 2,4-difluoronitrobenzene, and precipitated with KCl as the potassium sulfonate. The structure was confirmed by chemical and spectroscopic methods (IR, 1H-NMR, 13C-NMR, 19F-NMR, UV, MS and ultimate organic analysis). Lysozyme was cross-linked
A solid phase traceless synthesis of 2-arylaminobenzimidazoles.
Krchnak V, et al.
Tetrahedron Letters, 42(9), 1627-1630 (2001)

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