4-Nitrophenyl carbonochloridate, CAS No. 7693-46-1

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7693-46-1

Catalog No. EBD14326

CAS 7693-46-1

Name 4-Nitrophenyl carbonochloridate

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Basic Information

Synonyms: Chloroformicacid4-nitrophenylester 4-Nitrophenylchloridocarbonate Formicacid,chloro-,p-nitrophenylester p-Nitrophenoxycarbonylchloride carbonochloridicacid,4-nitrophenylester ChloroformicacidP-nitrophenylester 4-nitrophenylchlorocarbonate 4-nitrophenylcarbonochloridate 4-Nitrophenyl chloroformate 4-Nitrophenylchloroformate

Molecular Formula: C7H4ClNO4

Molecular Weight: 201.56

MDL Number: MFCD00007321

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Protecting and Deprotecting Reagents

Product Description:

4-Nitrophenyl carbonochloridate is a reactive acylating agent featuring a carbonochloridate (chloroformate) group attached to a 4-nitrophenyl ester moiety. The electron-withdrawing nitro group significantly activates the carbonyl carbon, making it highly susceptible to nucleophilic attack. This compound is typically a crystalline solid and is moisture-sensitive, requiring storage under inert conditions. Its primary application is as a versatile reagent for introducing the 4-nitrophenyloxycarbonyl (Noc) protecting group for amines in peptide and organic synthesis. It is also widely used to activate carboxylic acids via mixed anhydride formation, facilitating amide bond formation under mild conditions. In medicinal chemistry, it serves as a key building block for synthesizing carbamate-linked prodrugs and various pharmaceutical intermediates, particularly those requiring a stable yet activatable carbonyl linkage. Due to its high reactivity, it is a standard laboratory reagent for preparing activated carbonates and carbamates. It is also employed in polymer chemistry for end-group functionalization and in the synthesis of crosslinkers. Safety precautions are necessary as it is a lachrymator and corrosive agent.

Physical Properties

Melting Point: 77-79 °C(lit.)

Boiling Point: 159-162 °C/19 mmHg(lit.)

Flash Point: >110°C

Density: 1.506 g/cm3

Solubility: decomposes

Storage: 2-8°C

Safety Information

Packing Level: II

Hazard Category: 8

Transport Codes: 3261

Analytical Data

Appearance: cream solid