1-fluoro-2,4-dinitrobenzene

• ChemBase ID: 95166
• Molecular Formular: C6H3FN2O4
• Molecular Mass: 186.0974232
• Monoisotopic Mass: 186.00768481
• SMILES: Fc1c(cc(cc1)[N+](=O)[O-])[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)c1ccc(c(c1)[N+](=O)[O-])F
• InChI: InChI=1S/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
• InChIKey: LOTKRQAVGJMPNV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-fluoro-2,4-dinitrobenzene
• IUPAC Traditional name: dinitrofluorobenzene
• Synonyms: Sanger's Reagent; 2,4-Dinitro-1-fluorobenzene 99%; 2,4-dinitro-1-fluorobenzene; DNFB; DNPF; FDNB; 1-Fluoro-2,4-dinitrobenzene; 2,4-DINITROFLUOROBENZENE; Sanger reagent; 1-Fluoro-2,4-dinitrobenzene; 1-FLUORO-2,4-DINITROBENZENE; Dinitrofluorobenzene; 2,4-Dinitrofluorobenzene; 2,4-二硝基-1-氟苯; 桑格试剂; 2,4-二硝基氟苯; 2,4-二硝基-1-氟苯

Database IDs

• CAS Number: 70-34-8
• EC Number: 200-734-3
• MDL Number: MFCD00007056
• Beilstein Number: 398632
• Merck Index: 144172
• PubChem SID: 24893470; 24866357; 162081816
• PubChem CID: 6264
• CHEBI ID: 53049
• CHEMBL: 167423
• Chemspider ID: 21106037
• Unique Ingredient Identifier: D241E059U6
• Wikipedia Title: 1-Fluoro-2,4-dinitrobenzene

CALCULATED PROPERTIES

• Acid pKa: 18.12873
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.9959161
• LogD (pH = 7.4): 1.9959161
• Log P: 1.9959161
• Molar Refractivity: 38.9154 cm^3
• Polarizability: 14.10993 Å^3
• Polar Surface Area: 86.28 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble0.1 g/mL, clear
• Apperance: yellow crystals
• Melting Point: 24-30°C; 25.8 °C; 25-27 °C; 25-27 °C(lit.); 28-30°C
• Boiling Point: 178 °C/25 mmHg(lit.); 178°C; 296 °C; 296°C
• Flash Point: >110°C; >110°C(230°F); 164 °C; 327.2 °F
• Density: 1.4718 g·cm^-3 (54 °C); 1.482; 1.482 g/ml; 1.482 g/mL at 25 °C(lit.)
• Refractive Index: 1.569; 1.5690; n20/D 1.569(lit.); n20/D 1.570

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Toxic/Irritant/Moisture Sensitive/Store under Argon/Keep Cold
• RTECS: CZ7800000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2810; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 22-33-36/37/38-43; 23/24/25-38-41-43-68; R:22
• Safety Statements: 24-26-36/37/39-45; 26-36/37; S:36/37/39
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H311-H331-H315-H317-H318-H341; H302-H315-H317-H319-H335-H373
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P361-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~97%; ~98-99%; ≥98.0% (GC); ≥99%; ≥99.0% (GC); 98%; 99%
• Grade: purum p.a.
• Cation Traces: Ca: ≤50 mg/kg; Cd: ≤50 mg/kg; Co: ≤50 mg/kg; Cu: ≤50 mg/kg; Fe: ≤50 mg/kg; K: ≤100 mg/kg; Na: ≤100 mg/kg; Ni: ≤50 mg/kg; Pb: ≤50 mg/kg; Zn: ≤50 mg/kg
• Linear Formula: (O2N)2C6H3F

DETAILS

MP Biomedicals - 02101604

Purity: ~98-99%
Reagent for labeling terminal amino acid groups.

MP Biomedicals - 05202495

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150964

Purity: ~97%
Reagent for labeling terminal amino acid groups.

Apollo Scientific Ltd - PC3040

Nucleophiles can displace the activated fluorine atom.Reagent for labelling of terminal amino acid groups.

Sigma Aldrich - 42080

Other Notes
For the modification and determination of amino acids, peptides and phenols 1,2; As a probe for the presence of hydrodisulfide groups in proteins3, For the detection of amphetamine enantiomers by circular dichroism spectroscopy4.

Sigma Aldrich - D1529

包装
10, 25, 100 mL in glass bottle

Sigma Aldrich - D196800

Packaging
100 g in glass bottle
Application
Reagent for labeling terminal amino acid groups.1 Used in the detection of phenols.2 Suppresses the action potential in nerves.3 Induces contact hypersensitivity.4

Sigma Aldrich - 42085

Packaging
50, 250 g in glass bottle

REFERENCES

• Biochem. J. , 45 : 563 (1949).
• Has been used as a means of protection for the thiol group. The resulting thioether can be cleaved quantitatively with 2-mercaptoethanol: Biochem. Biophys. Res. Commun., 29, 178 (1967).
• Can also be used for the masking of the imidazole ring in histidine as the 2,4-dinitrophenyl derivative during peptide synthesis, introduced in the presence of, e.g. K₂CO₃: Biochem. Biophys. Acta., 82, 412 (1964). The group can be cleaved by treatment with thioglycolic acid, mercaptoethanol, dithiothreitol or thiophenol: Biochem. Biophys. Res. Commun., 29, 178 (1967); Biochemistry, 9, 5122 (1970). The electron withdrawing character of the group has been shown to reduce racemization promoted by the imidazole function: J. Biol. Chem., 247, 4768 (1972). See Appendix 6.
• The activated fluoro-substituent is readily displaced by nucleophiles under mild conditions. The anomeric center of a carbohydrate has been protected as the 2,4-dinitrophenyl ether in the presence of DABCO in DMF: Rec. Trav. Chim., 99, 355 (1980).
• Used for labelling terminal amino acids in peptides: Biochem. J., 45, 563 (1949); Biochemistry, 20, 512 (1981).