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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
NACRES:
NA.22
PubChem Substance ID:
24849861
UNSPSC Code:
12352108
EC Number:
231-706-9
MDL number:
MFCD00007321
Beilstein/REAXYS Number:
518127

Key Documents

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Product Name

4-Nitrophenyl chloroformate, 96%

form

powder

InChI key

NXLNNXIXOYSCMB-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

96%

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

Quality Level

200

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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)

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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H314,H335

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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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Certificates of Analysis (COA)

Lot/Batch Number
HMBK7653
HMBK7577
HMBK7350
HMBK6972
HMBK6890

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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)
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)
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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