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Merck
CN

160210

4-Nitrophenyl chloroformate

96%, for peptide synthesis

Synonym(s):

Chloroformic acid 4-nitrophenyl ester

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About This Item

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

Key Documents

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Product Name

4-Nitrophenyl chloroformate, 96%

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
HMBK7653
HMBK7577
HMBK7350
HMBK6972
HMBK6890

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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)
4-Nitrophenyl chloroformate: A versatile coupling reagent.
Sammet B, et al.
Synlett, 2009(18), 3050-3051 (2009)
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)
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
Synthesis and characterization of poly (oxyethylene) modified dextrans
Hoste K, et al.
Macromolecular Rapid Communications, 15(9), 697-697 (1994)
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