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MilliporeSigma

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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$56.30

25 ML

$193.00

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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

refractive index

n20/D 1.435 (lit.)

bp

118-122 °C (lit.)

density

1.215 g/mL at 25 °C (lit.)

functional group

chloro

storage temp.

2-8°C

Quality Level

100

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1 of 4

This Item
460931237906143995
Propargyl chloroformate 96%

Sigma-Aldrich

460923

Propargyl chloroformate

Neopentyl chloroformate 97%

Sigma-Aldrich

460931

Neopentyl chloroformate

Phenyl chloroformate 97%

Sigma-Aldrich

237906

Phenyl chloroformate

Propargyl chloride 98%

Sigma-Aldrich

143995

Propargyl chloride

assay

96%

assay

97%

assay

97%

assay

98%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

reaction suitability

reaction type: click chemistry

reaction suitability

-

reaction suitability

-

reaction suitability

-

refractive index

n20/D 1.435 (lit.)

refractive index

n20/D 1.410 (lit.)

refractive index

n20/D 1.511 (lit.)

refractive index

n20/D 1.435 (lit.)

bp

118-122 °C (lit.)

bp

55 °C/36 mmHg (lit.)

bp

74-75 °C/13 mmHg (lit.)

bp

58 °C (lit.)

density

1.215 g/mL at 25 °C (lit.)

density

1.003 g/mL at 25 °C (lit.)

density

1.248 g/mL at 25 °C (lit.)

density

1.03 g/mL at 25 °C (lit.)

General description

Propargyl chloroformate is a propargyl ester. It serves as a protecting group for the hydroxy and amino functional group.[1] 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.[2]

Application

Propargyl chloroformate may be used for the preparation of the following:
  • binaphthol-diacetylene derivatives[3]
  • propargyl pentafluorophenyl carbonate[4]
  • N-Poc protected amino acids (Poc = propargyloxycarbonyl)[5]

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

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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)
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)
Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions.
Fukase Y, et al.
Tetrahedron Letters, 40(6), 1169-1170 (1999)
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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