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Butyryl chloride

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Butyryl chloride
Ball-and-stick model
Names
Preferred IUPAC name Butanoyl chloride
Other names Butyryl chloride
n-Butyryl chloride
Butanoyl chloride
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.999 Edit this at Wikidata
EC Number
  • 205-498-5
PubChem CID
UNII
UN number 2353
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3Key: DVECBJCOGJRVPX-UHFFFAOYSA-N
  • InChI=1/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3Key: DVECBJCOGJRVPX-UHFFFAOYAA
SMILES
  • ClC(=O)CCC
Properties
Chemical formula C4H7ClO
Molar mass 106.55 g·mol
Appearance colorless liquid
Odor pungent
Density 1.033 g/cm
Melting point −89 °C (−128 °F; 184 K)
Boiling point 102 °C (216 °F; 375 K)
Solubility in water decomposition
Solubility miscible with ether
Magnetic susceptibility (χ) -62.1·10 cm/mol
Refractive index (nD) 1.412
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Reacts violently with water, flammable, corrosive
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
Signal word Danger
Hazard statements H225, H314
Precautionary statements 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 diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

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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