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A11871 1-Fluoro-2,4-dinitrobenzene, 99%

CAS Number
70-34-8
Synonyms
2,4-Dinitrofluorobenzene
Sanger's Reagent

Stock No. Size Price ($) Quantity Availability
A11871-06 5g 29.80
A11871-14 25g 77.50
A11871-22 100g 207.00
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1-Fluoro-2,4-dinitrobenzene, 99%

MDL
MFCD00007056
EINECS
200-734-3

Chemical Properties

Formula
C6H3FN2O4
Formula Weight
186.10
Melting point
24-30°
Boiling Point
296°
Flash Point
>110°(230°F)
Density
1.482
Refractive Index
1.5690
Storage & Sensitivity
Ambient temperatures.
Solubility
Soluble in chloroform, benzene, ether and propylene glycol.

Applications

1-Fluoro-2,4-dinitrobenzene is used to identify the amino acid sequence. It reacts with amino group of amino acids to yield dinitrophenyl-amino acids. It is also used in chromatographic methods. Further, it acts as an alkylating agent used in elucidating amino acid sequence in proteins.

Notes

Moisture sensitive. Store in a cool place. Incompatible with strong oxidizing agents and strong bases.

Literature References

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).

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.

Harifi-Mood, A. R.; Faramarzi, F.; Mehrabi, Y. Investigation of solvent effects on the reaction of 1-fluoro-2,4-dinitrobenzene with aniline in molecular-molecular and ionic liquid-molecular solvent mixtures. Prog. React. Kinet. Mec. 2015, 40 (1), 35-47.

Jalalizadeh, H.; Raei, M.; Tafti, R. F.; Farsam, H.; Kebriaeezadeh, A.; Souri, E. A Stability-Indicating HPLC Method for the Determination of Memantine Hydrochloride in Dosage Forms through Derivatization with 1-Fluoro-2,4-dinitrobenzene. Sci. Pharm. 2014, 82 (2), 265-279.

GHS Hazard and Precautionary Statements

Hazard Statements: H301+H311+H331-H315-H317-H320-H335-H336-H373

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. May cause an allergic skin reaction. Causes eye irritation. May cause respiratory irritation. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P260-P262-P264b-P270-P271-P272-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P311-P312-P314-P330-P333+P313-P362-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Get medical advice/attention if you feel unwell. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,4172
Beilstein
398632
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2904.99
TSCA
Yes
RTECS
CZ7800000

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