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Sigma-Aldrich

4-Nitrophenyl chloroformate

96%, for peptide synthesis

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Synonym(s):
Chloroformic acid 4-nitrophenyl ester
Linear Formula:
ClCO2C6H4NO2
CAS Number:
7693-46-1
Molecular Weight:
201.56
Beilstein:
518127
EC Number:
231-706-9
MDL number:
MFCD00007321
UNSPSC Code:
12352108
PubChem Substance ID:
24849861
NACRES:
NA.22

Quality Level

200

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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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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Modification of oligo (poly (ethylene glycol) fumarate) macromer with a GRGD peptide for the preparation of functionalized polymer networks
S Jo, et al.
Biomacromolecules, 2, 255-261 (2001)
Solid-phase combinatorial synthesis and cytotoxicity of 3-aryl-2, 4-quinazolindiones.
Choo Hea YP, et al.
Bioorganic & Medicinal Chemistry, 10(3), 517-523 (2002)
4-Nitrophenyl chloroformate: A versatile coupling reagent.
Sammet B, et al.
Synlett, 2009(18), 3050-3051 (2009)
Zhuojun Gu et al.
Drug development and industrial pharmacy, 41(5), 812-818 (2014-04-22)
Polyamidoamine (PAMAM) dendrimers have attracted lots of interest as drug carriers. And little study about whether pluronic-attached PAMAM dendrimers could be potential drug delivery systems has been carried on. Pluronic F127 (PF127) attached PAMAM dendrimers were designed as novel drug
Novel and Efficient Synthesis of 4-Substituted-1, 2, 4-triazolidine-3, 5-diones from Anilines.
Mallakpour S and Rafiee Z
Synthetic Communications, 37(11), 1927-1934 (2007)
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