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Butyryl chloride

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Butyryl chloride Basic information

Product Name:
Butyryl chloride
Synonyms:
  • BUTYRIC ACID CHLORIDE
  • BUTYROYL CHLORIDE
  • BUTYRYL CHLORIDE
  • BUTANOYL CHLORIDE
  • N-BUTYRIC ACID CHLORIDE
  • N-BUTYROYL CHLORIDE
  • N-BUTYRYL CHLORIDE
  • N-BUTANOYL CHLORIDE
CAS:
141-75-3
MF:
C4H7ClO
MW:
106.55
EINECS:
205-498-5
Product Categories:
  • Pharmaceutical Intermediates
  • Organics
  • Acid Halides
  • Carbonyl Compounds
  • Organic Building Blocks
  • pharmaceutical, pesticide intermediate
Mol File:
141-75-3.mol
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Butyryl chloride Chemical Properties

Melting point:
−89 °C(lit.)
Boiling point:
102 °C(lit.)
Density 
1.026 g/mL at 25 °C(lit.)
vapor density 
3.7 (vs air)
vapor pressure 
39 hPa (20 °C)
refractive index 
n20/D 1.412(lit.)
RTECS 
EM0595000
Flash point:
71 °F
storage temp. 
Store below +30°C.
solubility 
Miscible with ether.
form 
Liquid
color 
Clear slightly yellow
Odor
pungent odor
explosive limit
2.5-7.3%(V)
Water Solubility 
decomposes
FreezingPoint 
-89℃
Sensitive 
Moisture Sensitive
Merck 
14,1598
BRN 
605395
InChIKey
DVECBJCOGJRVPX-UHFFFAOYSA-N
LogP
0.51 at 25℃
CAS DataBase Reference
141-75-3(CAS DataBase Reference)
NIST Chemistry Reference
Butanoyl chloride(141-75-3)
EPA Substance Registry System
Butanoyl chloride (141-75-3)
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Safety Information

Hazard Codes 
F,C
Risk Statements 
11-34
Safety Statements 
16-23-26-36-45
RIDADR 
UN 2353 3/PG 2
WGK Germany 
1
13
Autoignition Temperature
280 °C
TSCA 
Yes
HS Code 
2915 90 70
HazardClass 
3
PackingGroup 
II
Hazardous Substances Data
141-75-3(Hazardous Substances Data)

MSDS

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Butyryl chloride Usage And Synthesis

Chemical Properties

Butyryl chloride is a colorless to light yellow liquid with a strong pungent odor. It undergoes vigorous hydrolysis with water; decomposes in water; soluble in almost aprotic organic solvents. It is used as an intermediate for organic synthesis for the preparation of pharmaceuticals, agrochemicals, dyes, cellulose esters, and peroxide compounds.

Uses

Butyryl chloride is used as an intermediate for the synthesis of active pharmaceutical ingredients benzoyl peroxide, t-butyl perbenzoate, and benzophenone. It is also used as an acylation reagent. Further, it is used in the preparation of peroxides such as benzoyl peroxide, benzophenone and t-butyl perbenzoate. In addition to this, it is involved in the preparation of chromones and antiproliferative agents.
Butyryl chloride has been used to esterify wood meal dissolved in the ionic liquid, 1-butyl-3-methylimidazolium chloride.

General Description

A clear colorless liquid with a sharp odor. Slightly denser than water. Flash point near 20°F. Severely irritates skin, eyes, and mucous membranes. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Fumes in air. Decomposes exothermically in water to give corrosive hydrochloric acid.

Reactivity Profile

Butyryl chloride slowly dissolves in water with decomposition and formation of a weakly acidic solution. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

Extremely destructive to the mucous membranes, upper respiratory tract, eyes, and skin. Inhalation may cause death as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.

Fire Hazard

Special Hazards of Combustion Products: Emits toxic fumes of chlorine gas

Flammability and Explosibility

Flammable

Purification Methods

Check IR to see if there is a significant peak at 3000-3500 cm-1 (br) for OH. If OH is present then reflux with less than one mole equivalent of SOCl2 for 1hour and distil directly. The fraction boiling between 85-100o is then refractionated at atmospheric pressure. Keep all apparatus free from moisture and store the product in sealed glass ampoules under N2. LACHRYMATORY; handle in a good fume hood. [Hefferich & Schaeffer Org Synth Coll Vol I 147 1941, Beilstein 2 IV 803.]

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