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196622

Sigma-Aldrich

2,5-Difluoronitrobenzene

97%

Synonym(s):

1,4-Difluoro-2-nitrobenzene

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About This Item

Linear Formula:
F2C6H3NO2
CAS Number:
364-74-9
Molecular Weight:
159.09
EC Number:
206-663-4
MDL number:
MFCD00007054
UNSPSC Code:
12352100
PubChem Substance ID:
24851776
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.509 (lit.)

bp

206.5 °C (lit.)

mp

−11.7 °C (lit.)

density

1.467 g/mL at 25 °C (lit.)

SMILES string

[O-][N+](=O)c1cc(F)ccc1F

InChI

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

InChI key

XNJAYQHWXYJBBD-UHFFFAOYSA-N

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Application

2,5-Difluoronitrobenzene was used in the synthesis of :
  • N-alkylated 2-arylaminobenzimidazoles
  • quinoxalinones
  • N-(2-nitro-4-fluorophenyl)-l,2,3,4-tetrahydroisoquinoline

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

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

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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H E Haenen et al.
Chemico-biological interactions, 98(2), 97-112 (1995-11-17)
Proximal tubular biotransformation of the glutathionyl (GSH) conjugate derived from 2,5-difluoronitrobenzene (5-fluoro-2-glutathionyl-nitrobenzene) was studied by means of 19F-NMR. This method allows a direct and specific detection of the fluorinated metabolites formed, at a detection limit of 1 microM for an
A solid phase traceless synthesis of quinoxalinones.
Krchnak V, et al.
Tetrahedron Letters, 41(16), 2835-2838 (2000)
Ring-opening reactions of N-aryl-, 1, 2, 3, 4-tetrahydroisoquinoline derivatives.
Andrew HK and Stanforth SP.
Tetrahedron, 48(4), 743-750 (1992)
Manuel A V Ribeiro da Silva et al.
The journal of physical chemistry. B, 114(40), 12914-12925 (2010-09-24)
This work reports the experimental and computational thermochemical study performed on three difluorinated nitrobenzene isomers: 2,4-difluoronitrobenzene (2,4-DFNB), 2,5-difluoronitrobenzene (2,5-DFNB), and 3,4-difluoronitrobenzene (3,4-DFNB). The standard (p° = 0.1 MPa) molar enthalpies of formation in the liquid phase of these compounds were
I M Rietjens et al.
Chemico-biological interactions, 94(1), 49-72 (1995-01-01)
The in vivo metabolite patterns of 2,5-difluoroaminobenzene and of its nitrobenzene analogue, 2,5-difluoronitrobenzene, were determined using 19F NMR analysis of urine samples. Results obtained demonstrate significant differences between the biotransformation patterns of these two analogues. For the aminobenzene, cytochrome P450
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