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160210

Sigma-Aldrich

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
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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.[1]

Application

4-Nitrophenyl chloroformate is used as:
  • A coupling agent to link the drug molecule with the polyrotaxane carrier molecule[2]
  • As an activated ester reagent that enables the covalent coupling of a peptide onto a macromer, such as oligo(poly(ethylene glycol) fumarate) (OPF)[3]

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
HMBK4857
HMBK4859
HMBK4858
HMBK2223
HMBK1665

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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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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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