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460923

Sigma-Aldrich

Propargyl chloroformate

96%

Synonym(s):

(Prop-2-ynyloxy)carbonyl chloride, 2-Propyn-1-yl carbonochloridate, 2-Propynyl chloroformate, Prop-2-yn-1-yl carbonochloridate, Propargyloxycarbonyl chloride

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About This Item

Linear Formula:
HC≡CCH2OCOCl
CAS Number:
35718-08-2
Molecular Weight:
118.52
Beilstein:
1745399
MDL number:
MFCD00270127
UNSPSC Code:
12352100
PubChem Substance ID:
24869771
NACRES:
NA.22

vapor pressure

0.65 psi ( 20 °C)

Quality Level

100

Assay

96%

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.435 (lit.)

bp

118-122 °C (lit.)

density

1.215 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC(=O)OCC#C

InChI

1S/C4H3ClO2/c1-2-3-7-4(5)6/h1H,3H2

InChI key

RAMTXCRMKBFPRG-UHFFFAOYSA-N

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General description

Propargyl chloroformate is a propargyl ester. It serves as a protecting group for the hydroxy and amino functional group. Rates of solvolysis of propargyl chloroformate has been analyzed in various solvents of widely varying nucleophilicity and ionizing power values using the extended Grunwald-Winstein equation.

Application

Propargyl chloroformate may be used for the preparation of the following:
  • binaphthol-diacetylene derivatives
  • propargyl pentafluorophenyl carbonate
  • N-Poc protected amino acids (Poc = propargyloxycarbonyl)

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

86.0 °F - closed cup

Flash Point(C)

30 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions.
Fukase Y, et al.
Tetrahedron Letters, 40(6), 1169-1170 (1999)
Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis.
Bhat RG, et al.
Tetrahedron Letters, 43(13), 2467-2469 (2002)
Propargyloxycarbonyl (Poc) amino acid chlorides as efficient coupling reagents for the synthesis of 100% diastereopure peptides and resin bound tetrathiomolybdate as an effective deblocking agent for the Poc group.
Bhat RG, et al.
Chemical Communications (Cambridge, England), 8, 812-813 (2002)
Malcolm J D'Souza et al.
ISRN organic chemistry, 2011 (2011-06-15)
The specific rates of solvolysis of propargyl chloroformate (1) are analyzed in 22 solvents of widely varying nucleophilicity and ionizing power values at 25.0 °C using the extended Grunwald-Winstein equation. Sensitivities to solvent nucleophilicity (l) of 1.37 and to solvent
Organogold (I) complexes of a C 2-symmetric diacetylide ligand derived from 1, 1'-bi-2-naphthol.
Burchell TJ, et al.
Inorgorganica Chimica Acta, 359(9), 2812-2818 (2006)
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