D1529

1-Fluoro-2,4-dinitrobenzene

≥99%

• Synonym(s): 2,4-Dinitro-1-fluorobenzene, DNFB, DNPF, FDNB, Sanger reagent
• Linear Formula: (O₂N)₂C₆H₃F
• CAS Number: 70-34-8
• Molecular Weight: 186.10
• Beilstein/REAXYS Number: 398632
• EC Number: 200-734-3
• MDL number: MFCD00007056
• UNSPSC Code: 12352204
• PubChem Substance ID: 24893470
• NACRES: NA.83

Properties

• 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

Description

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,[1] and to induce chronic itch as a model for analysing itch-scratching behavior.[2]

Biochem/physiol Actions

1-Fluoro-2,4-dinitrobenzene is a contact-sensitizing hapten, commonly used in experimental studies on contact hypersensitivity,[1][3] inducing itch model,[2] and atopic dermatitis.[3] Mast cell activation is a key step in the DNFB induced sensitivity.[1][3] DNFB covalently binds to the N-terminal amino acid of the protein and aids in Sanger sequencing.[4]

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302,H315,H317,H319,H335,H373
• pcodes: P260 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P314
• 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: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 327.2 °F
• flash_point_c: 164 °C
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves