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:
Molecular Weight:
74.51
Beilstein/REAXYS Number:
506005
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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
SMILES string
ClCC#C
InChI
1S/C3H3Cl/c1-2-3-4/h1H,3H2
InChI key
LJZPPWWHKPGCHS-UHFFFAOYSA-N
General description
Product is the 70wt.% solution of propargyl chloride in toluene. Propargyl chloride is a propargyl halide. Its trimethylsilylation reaction has been reported.[1] 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.[2] It participates in the addition reaction with acyclic 1,3-dienes (at -78°C) in the presence of zinc chloride.[3]
Application
Propargyl chloride may be used as propargylating agent in the preparation of arabinogalactan propargyl ethers with degree of substitution up to 1.8.[4] It may be used for the in situ preparation of propargyltrichlorosilane and allenyltrichlorosilane, required for the synthesis of optically active allenic and homopropargylic alcohols.[5]
Propargyl chloride solution may be used for the enantioselective synthesis of enantiomerically enriched homopropargyl alcohols.[6]
signalword
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_germany
WGK 3
flash_point_f
66.2 °F
flash_point_c
19 °C
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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)
Selective synthesis of optically active allenic and homopropargylic alcohols from propargyl chloride.
Nakajima M, et al.
Tetrahedron Asymmetry, 12(22), 2449-2452 (2002)
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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