Butyryl chloride

Butyryl chloride is an organic compound with the chemical formula CH3CH2CH2C(O)Cl. It is a colorless liquid with a unpleasant odor. Butyryl chloride is soluble in organic solvents, but it reacts readily with water and alcohols. It is usually produced by chlorination of butyric acid.[1]

Butyryl chloride
Ball-and-stick model
Names
Preferred IUPAC name
Butanoyl chloride
Other names
Butyryl chloride
n-Butyryl chloride
C-4 Acyl halide
butanoyl chloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.999
EC Number
  • 205-498-5
UNII
UN number 2353
  • InChI=1S/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3 checkY
    Key: DVECBJCOGJRVPX-UHFFFAOYSA-N checkY
  • InChI=1/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3
    Key: DVECBJCOGJRVPX-UHFFFAOYAA
  • ClC(=O)CCC
Properties
C4H7ClO
Molar mass 106.55 g·mol−1
Appearance colorless liquid
Odor pungent
Density 1.033 g/cm3
Melting point −89 °C (−128 °F; 184 K)
Boiling point 102 °C (216 °F; 375 K)
decomposition
Solubility miscible with ether
-62.1·10−6 cm3/mol
1.412
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Reacts violently with water, flammable, corrosive
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
3
3
2
Flash point 21.7 °C (71.1 °F; 294.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Reactions

Like related acyl chlorides, butyryl chloride hydrolyzes readily:

CH3CH2CH2C(O)Cl + H2O → CH3CH2CH2CO2H + HCl

Alcohols react to give esters:

CH3CH2CH2C(O)Cl + ROH → CH3CH2CH2CO2R + HCl

Amines react to give amides:

CH3CH2CH2C(O)Cl + R2NH → CH3CH2CH2C(O)NR2 + HCl

Derivatives of butyryl chloride are used in manufacturing pesticides, pharmaceuticals, perfume fixative, polymerization catalyst, and dyestuffs. Butyryl chloride is also commonly used as an intermediate for organic synthesis for the preparation of pharmaceuticals, agrochemicals, dyes, esters, and peroxide compounds.[2]

Safety

Butyryl chloride is flammable and fumes in air, releasing hydrogen chloride.

References
  1. Helferich, B.; Schaefer, W. (1929). "n-Butyryl Chloride". Org. Synth. 9: 32. doi:10.15227/orgsyn.009.0032.
  2. "N-BUTYRYL CHLORIDE (BUTANOYL CHLORIDE)". chemicalland21.com. Retrieved 2023-02-20.
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