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 Butanoyl chloride
Identifiers
CAS Number	141-75-3 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1300263
ChemSpider	8523 Y
ECHA InfoCard	100.004.999
EC Number	205-498-5
PubChem CID	8855
UNII	2XVM8E16IR
UN number	2353
CompTox Dashboard (EPA)	DTXSID5024710
InChI InChI=1S/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3 Y Key: DVECBJCOGJRVPX-UHFFFAOYSA-N Y InChI=1/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3 Key: DVECBJCOGJRVPX-UHFFFAOYAA
SMILES ClC(=O)CCC
Properties
Chemical formula	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)
Solubility in water	decomposition
Solubility	miscible with ether
Magnetic susceptibility (χ)	−62.1·10−6 cm3/mol
Refractive index (nD)	1.412
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Reacts violently with water, flammable, corrosive
GHS labelling:
Pictograms
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)	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.