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P51559

Sigma-Aldrich

Propionyl chloride

98%

Synonym(s):

Chloro ethyl ketone, Ethyl chloroform, Propionic acid chloride, Prorionyl chloride

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About This Item

Linear Formula:
CH3CH2COCl
CAS Number:
79-03-8
Molecular Weight:
92.52
Beilstein:
385632
EC Number:
201-170-0
MDL number:
MFCD00000745
UNSPSC Code:
12352100
PubChem Substance ID:
24898602
NACRES:
NA.22

vapor density

3.2 (vs air)

Assay

98%

refractive index

n20/D 1.404 (lit.)

bp

77-79 °C (lit.)

mp

−94 °C

density

1.059 g/mL at 25 °C (lit.)

SMILES string

CCC(Cl)=O

InChI

1S/C3H5ClO/c1-2-3(4)5/h2H2,1H3

InChI key

RZWZRACFZGVKFM-UHFFFAOYSA-N

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General description

Propionyl chloride is an important chemical intermediate used to synthesize various propionic acid derivatives.

Application

Propionyl chloride can be used as an acylating agent:
  • To convert anisole to 4-methoxypropiophenone and 2-methoxynaphthalene to 1-propio-2-methoxynaphthalene in the presence of Indium(III) chloride (InCl3) impregnated mesoporous Si-MCM-41 catalyst.

It can also be used:
  • For chlorination in the presence of sulfuryl chloride and peroxides to form α-chloropropionyl chloride and β-chloropropionyl chloride.
  • In reaction with (hydroxypropyl)cellulose to form the propanoate ester, [(propionyloxy)propyl]cellulose.

Signal Word

Danger

Hazard Statements

H225,H302,H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

42.8 °F - closed cup

Flash Point(C)

6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Acylation of aromatic compounds using moisture insensitive InCl3 impregnated mesoporous Si-MCM-41 catalyst
Choudhary VR, et al.
Tetrahedron Letters, 43(6), 1105-1107 (2002)
Joanna Kurczewska et al.
International journal of pharmaceutics, 486(1-2), 226-231 (2015-04-07)
Vancomycin was immobilized on three different organically functionalized silicas. The materials obtained were used for a controlled release of the antibiotic. The influence of the type of chemical bond on the in vitro drug release was investigated. A weak ionic
Douglas T Durig et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 60(7), 1481-1504 (2004-05-19)
Variable temperature (-60 to -100 degrees C) studies of the infrared spectra (3500-400 cm(-1)) of propionyl fluoride (CH3CH2CFO) and 2-methylpropionyl fluoride ((CH3)2CHCFO), dissolved in liquid xenon have been recorded. From these data, the enthalpy difference has been determined to be
The propanoate ester of (2-hydroxypropyl) cellulose: a thermotropic cholesteric polymer that reflects visible light at ambient temperatures
Tseng SL, et L.
Macromolecules, 15(5), 1262-1264 (1982)
Chlorinations with Sulfuryl Chloride. III.(a) The Peroxide-Catalyzed Chlorination of Aliphatic Acids and Acid Chlorides.(b) The Photochemical Sulfonation of Aliphatic Acids
Kharasch MS and Brown HC
Journal of the American Chemical Society, 62(4), 925-929 (1940)
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