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D1529

Sigma-Aldrich

1-Fluoro-2,4-dinitrobenzene

≥99%

Synonym(s):

2,4-Dinitro-1-fluorobenzene, DNFB, DNPF, FDNB, Sanger reagent

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About This Item

Linear Formula:
(O2N)2C6H3F
CAS Number:
70-34-8
Molecular Weight:
186.10
Beilstein:
398632
EC Number:
200-734-3
MDL number:
MFCD00007056
UNSPSC Code:
12352204
PubChem Substance ID:
24893470
NACRES:
NA.83

Assay

≥99%

form

solid

refractive index

n20/D 1.569 (lit.)

bp

178 °C/25 mmHg (lit.)

mp

25-27 °C (lit.)

density

1.482 g/mL at 25 °C (lit.)

storage temp.

room temp

SMILES string

[O-][N+](=O)c1ccc(F)c(c1)[N+]([O-])=O

InChI

1S/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

InChI key

LOTKRQAVGJMPNV-UHFFFAOYSA-N

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General description

1-Fluoro-2,4-dinitrobenzene (DNFB) is a reagent that modifies the N-terminal amino acids of proteins and peptides. DNFB is also commonly known as Sanger′s Reagent, named after Frederick Sanger, who reported in a classic 1945 paper the use of DNFB for derivatization of proteins and peptides specifically at their N-termini.†

Application

1-Fluoro-2,4-dinitrobenzene has been used to induce severe contact hypersensitivity in mice and to monitor gene expression by in vivo imaging method, and to induce chronic itch as a model for analysing itch-scratching behavior.

Biochem/physiol Actions

1-Fluoro-2,4-dinitrobenzene is a contact-sensitizing hapten, commonly used in experimental studies on contact hypersensitivity, inducing itch model, and atopic dermatitis. Mast cell activation is a key step in the DNFB induced sensitivity. DNFB covalently binds to the N-terminal amino acid of the protein and aids in Sanger sequencing.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

327.2 °F

Flash Point(C)

164 °C

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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Imaging protective mast cells in living mice during severe contact hypersensitivity
Reber LL, et al.
JCI insight, 2(9), e92900-e92900 (2017)
Microbial Genetics (2014)
Bamboo salt suppresses skin inflammation in mice with 2, 4-dinitrofluorobenzene-induced atopic dermatitis
Yoou MS, et al.
Chinese Journal of Natural Medicines, 16(2), 97-104 (2018)
Tac1-Expressing Neurons in the Periaqueductal Gray Facilitate the Itch-Scratching Cycle via Descending Regulation
Gao ZR, et al.
Neuron, 101(9), 45-59 (2018)
Beatrice Parma et al.
Journal of experimental & clinical cancer research : CR, 40(1), 248-248 (2021-08-09)
The identification of novel targets is of paramount importance to develop more effective drugs and improve the treatment of non-small cell lung cancer (NSCLC), the leading cause of cancer-related deaths worldwide. Since cells alter their metabolic rewiring during tumorigenesis and
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