Butyryl chloride

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

Butyryl chloride
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
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
Main hazards Reacts violently with water, flammable, corrosive
GHS pictograms
GHS Signal word Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501
NFPA 704 (fire diamond)
Flammability code 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. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 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 [77 °F], 100 kPa).
N verify (what is YN ?)
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. http://chemicalland21.com/specialtychem/perchem/N-BUTYRYL%20CHLORIDE.htm
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