4-NITROPHENYL CHLOROFORMATE

PRODUCT IDENTIFICATION
CAS NO. 7693-46-1

4-NITROPHENYL CHLOROFORMATE
EINECS NO. 231-706-9
FORMULA ClCO2C6H4NO2
MOL WT. 201.57

H.S. CODE

 2915.13.
SMILES

 

TOXICITY

  
SYNONYMS Carbonochloridic Acid, 4-Nitrophenyl Ester;
Formic acid, chloro-, p-nitrophenyl ester; p-Nitrophenoxycarbonyl chloride; p-Nitrophenyl chlorocarbonate; p-Nitrophenyl chloroformate; Chloroformic acid, p-nitrophenyl ester;

CLASSIFICATION

  

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white to pale yellow crystalline powder
MELTING POINT 77 - 81 C
BOILING POINT 159 - 162 C
SPECIFIC GRAVITY

 
SOLUBILITY IN WATER  
pH  
VAPOR DENSITY

 
AUTOIGNITION  

REFRACTIVE INDEX

 
NFPA RATINGS  
FLASH POINT

 
STABILITY Stable under normal conditions

GENERAL DESCRIPTION & APPLICATIONS
Phosgene (carbonyl dichloride, COCl2) is a very reactive chemical intermediate to prepare isocyanates, chloroformates, isothiocyanates, isonitriles and acid chlorides as well as in the production of polymers including polyurethanes, polycarbonates, and polyureas. Phosgene , however, is extremely toxic gas associated strong safety hazards and handling precautions. It is listed on schedule 3 of the Chemical Weapons Convention. All production sites must be declared to the OPCW. Phosgene is almost entirely in captive consume in the production plant. Chloroformates are relatively less dangerous route to prepare important families of compounds, the carbonates and carbamates. Carbonates are prepared by reaction with alcohol (or phenol) and carbamates are by reaction with an amine ( primary or secondary). Chloroformates are starting materials to prepare carbonate and carbamate derivatives that are used in the pharmaceutical and agrochemical industry.

 
Chloroformates are esters of chloroformic acid, single acyl-halide derivative of carbonic acid (phosgene is the double acyl-halide derivative).  Chloroformic acid itself is too unstable to be handled for chemical reactions. However, many esters of this carboxylic acid are stable and these chloroformates are important reagents in organic chemistry. They are widely used as reagents in organic chemistry. Some important chloroformates are:
  • 4-Nitrophenyl chloroformate (CAS NO. 7693-46-1): a reagent for the synthesis of mixed, activated carbonates and thiocarbonates, activated urethanes, and other compounds. Used to synthesize a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA. Employed in the preparation of poly(oxyethylene) modified dextrans.
  • Fluorenylmethyloxycarbonylchloride (CAS No. 28920-43-6): a reagent for derivatizing amino acids and for introducing N-Fmoc amino acids for solid-phase peptide synthesis and for the synthesis of a bicyclic proline analog. FMOC protection is important in solid phase peptide synthesis because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin. Very stable in acidic condition, and moderately stable in inorganic base.
  • Benzyl chloroformate (CAS No. 501-53-1): a reagent useful for the introduction of the carboxybenzyl (Cbz or Z) protecting group for amines. Easily deprotected under hydrogenation or triethyl silane.
  • Ethyl chloroformate (CAS No. 541-41-3): a reagent for the introduction of the ethyl carbamate protecting group and for the formation of carboxylic anhydrides. Used to convert carboxylic acids to nitriles.
  • Chloroethyl Chloroformate (2-Chloroethyl chloroformate: CAS No. 627-11-2, 1-Chloroethyl chloroformate:CAS No. 50893-53-3): a reagent for the selective N-dealkylation of tertiary amines. and for the synthesis of alkyl 1-chloroethyl carbonates. Useful in the synthesis of pharmaceuticals (e.g.: Cefpodoxime, Candesartan, Ampiroxicam, Bacampicillin)
SALES SPECIFICATION

APPEARANCE

 Cream solid
ASSAY

99.0% min

MELTING POINT

78 C min
TRANSPORTATION
PACKING  
HAZARD CLASS 8 (Packing group:II)
UN NO. 1759
REMARKS