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Merck
CN

460923

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24869771
MDL number:
MFCD00270127
Beilstein/REAXYS Number:
1745399
Assay:
96%

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InChI

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

SMILES string

ClC(=O)OCC#C

InChI key

RAMTXCRMKBFPRG-UHFFFAOYSA-N

vapor pressure

0.65 psi ( 20 °C)

assay

96%

reaction suitability

reaction type: click chemistry

Quality Level

100

bp

118-122 °C (lit.)

density

1.215 g/mL at 25 °C (lit.)

functional group

chloro

storage temp.

2-8°C

Related Categories

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)

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

86.0 °F - closed cup

flash_point_c

30 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX3215
MKCW9941
MKCS9080
MKCS5228
MKCQ0623

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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)
Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis.
Bhat RG, et al.
Tetrahedron Letters, 43(13), 2467-2469 (2002)
Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions.
Fukase Y, et al.
Tetrahedron Letters, 40(6), 1169-1170 (1999)
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)
Daria Lipowska-Kur et al.
Polymers, 12(8) (2020-07-30)
A series of copolymers of di(ethylene glycol) methyl ether methacrylate (D) and 2-aminoethyl methacrylate (A) (P(D-co-A)) with variable ratios of comonomers were synthesized using atom transfer radical polymerization. Then, the amino groups of obtained copolymers were modified to clickable azide
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