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70-34-8 - 1-Fluoro-2,4-dinitrobenzene, 99% - 2,4-Dinitrofluorobenzene - Sanger's Reagent - A11871 - Alfa Aesar

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

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

Size Price ($) Quantity Availability
5g 26.37
25g 63.68
100g 167.40
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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
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-H318-H341

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage. Suspected of causing genetic defects.

Precautionary Statements: P201-P261-P280-P281-P301+P310-P305+P351+P338-P361-P304+P340-P405-P501a

Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Remove/Take off immediately all contaminated clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,4172
Beilstein
398632
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2904.90
TSCA
Yes
RTECS
CZ7800000

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