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160210

Sigma-Aldrich

4-Nitrophenyl chloroformate

96%

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Synonym(s):
Chloroformic acid 4-nitrophenyl ester
Linear Formula:
ClCO2C6H4NO2
CAS Number:
Molecular Weight:
201.56
Beilstein/REAXYS Number:
518127
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

form

powder

reaction suitability

reaction type: Carbonylations

bp

159-162 °C/19 mmHg (lit.)

mp

77-79 °C (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

[O-][N+](=O)c1ccc(OC(Cl)=O)cc1

InChI

1S/C7H4ClNO4/c8-7(10)13-6-3-1-5(2-4-6)9(11)12/h1-4H

InChI key

NXLNNXIXOYSCMB-UHFFFAOYSA-N

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1 of 4

This Item
N3627N0252N8130
vibrant-m

160210

4-Nitrophenyl chloroformate

vibrant-m

N3627

4-Nitrophenyl stearate

vibrant-m

N0252

4-Nitrophenyl decanoate

vibrant-m

N8130

4-Nitrophenyl acetate

assay

96%

assay

≥90% (TLC)

assay

≥98% (TLC)

assay

≥98% (TLC)

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

mp

77-79 °C (lit.)

mp

-

mp

-

mp

75-77 °C (lit.)

reaction suitability

reaction type: Carbonylations

reaction suitability

-

reaction suitability

-

reaction suitability

-

General description

4-Nitrophenyl chloroformate, also known as p-nitrophenyl chloroformate, is a coupling agent used in the synthesis of ureas, carbamates, and carbonates. It is also used as a building block in solid-phase peptide synthesis (SPPS) to obtain altered side chain functionalities in peptides.

Application

4-Nitrophenyl chloroformate is used as:
  • A coupling agent to link the drug molecule with the polyrotaxane carrier molecule
  • As an activated ester reagent that enables the covalent coupling of a peptide onto a macromer, such as oligo(poly(ethylene glycol) fumarate) (OPF)

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

230.0 °F

flash_point_c

> 110 °C

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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4-Nitrophenyl chloroformate: A versatile coupling reagent.
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