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384321

Sigma-Aldrich

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
Beilstein:
506005
MDL number:
MFCD00000980
UNSPSC Code:
12352100
PubChem Substance ID:
24863662
NACRES:
NA.22

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. 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.

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.

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

66.2 °F

Flash Point(C)

19 °C

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

384321-BULK:
384321-500ML:4548173263823
384321-100ML:4548173142180
384321-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK8698
MKCK0671
MKCH7956
MKCH1152
MKBZ9212V

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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)
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)
Selective synthesis of optically active allenic and homopropargylic alcohols from propargyl chloride.
Nakajima M, et al.
Tetrahedron Asymmetry, 12(22), 2449-2452 (2002)
Trimethylsilylation of Propargyl Chloride and Propargyl Bromide.
Verkruijsse HD and Brandsma L.
Synthetic Communications, 20(21), 3375-3378 (1990)
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