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Merck
CN

384321

Propargyl chloride solution

70 wt. % in toluene

Synonym(s):

3-Chloro-1-propyne

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About This Item

Linear Formula:
HC≡CCH2Cl
CAS Number:
624-65-7
Molecular Weight:
74.51
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863662
MDL number:
MFCD00000980
Beilstein/REAXYS Number:
506005
Form:
liquid

Key Documents

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Product Name

Propargyl chloride solution, 70 wt. % in toluene

InChI

1S/C3H3Cl/c1-2-3-4/h1H,3H2

SMILES string

ClCC#C

InChI key

LJZPPWWHKPGCHS-UHFFFAOYSA-N

form

liquid

concentration

70 wt. % in toluene

refractive index

n20/D 1.456

density

0.963 g/mL at 25 °C

functional group

alkyl halide
chloro

storage temp.

2-8°C

Application

Propargyl chloride may be used as propargylating agent in the preparation of arabinogalactan propargyl ethers with degree of substitution up to 1.8. It may be used for the in situ preparation of propargyltrichlorosilane and allenyltrichlorosilane, required for the synthesis of optically active allenic and homopropargylic alcohols.
Propargyl chloride solution may be used for the enantioselective synthesis of enantiomerically enriched homopropargyl alcohols.

General description

Product is the 70wt.% solution of propargyl chloride in toluene. Propargyl chloride is a propargyl halide. Its trimethylsilylation reaction has been reported. Liquid-phase Raman spectra, and vapor-phase and solution-phase infrared spectra of propargyl chloride has been studied at 100-3400cm-1 and 300-3800cm-1, respectively. It participates in the addition reaction with acyclic 1,3-dienes (at -78°C) in the presence of zinc chloride.

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Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

target_organs

Central nervous system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

66.2 °F

flash_point_c

19 °C

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK8698
MKCK0671
MKCH7956
MKCH1152
MKBZ9212V

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Selective synthesis of optically active allenic and homopropargylic alcohols from propargyl chloride.
Nakajima M, et al.
Tetrahedron Asymmetry, 12(22), 2449-2452 (2002)
Zinc chloride catalyzed addition reactions of propargyl chlorides with acyclic 1, 3-dienes.
Mayr H and Klein H.
The Journal of Organic Chemistry, 46(20), 4097-4100 (1981)
Chemo-and enantioselective catalytic addition of propargyl chloride to aldehydes promoted by [Cr (Salen)] complexes.
Bandini M, et al.
Tetrahedron Asymmetry, 12(7), 1063-1069 (2001)
The vibrational spectra and vibrational assignments of the propargyl halides.
Evans JC and Nyquist RA.
Spectrochimica Acta Part A: Molecular Spectroscopy, 19(7), 1153-1163 (1963)
Trimethylsilylation of Propargyl Chloride and Propargyl Bromide.
Verkruijsse HD and Brandsma L.
Synthetic Communications, 20(21), 3375-3378 (1990)
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