4-Chlorobutyryl chloride Chemical Properties

Melting point:

-47 °C

Boiling point:

173-174 °C(lit.)

Density 

1.26 g/mL at 25 °C(lit.)

vapor pressure 

3 mm Hg ( 20 °C)

refractive index 

n20/D 1.461(lit.)

Flash point:

163 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform, DMSO (Sparingly), Ethyl Acetate (Slightly)

form 

Liquid

color 

Clear colorless to yellow

explosive limit

5.5-11.7%(V)

Water Solubility 

soluble in diethyl ether, ethanol, slightly soluble in water.

Sensitive 

Moisture Sensitive

BRN 

773860

Stability:

Hygroscopic, Moisture Sensitive

InChIKey

CDIIZULDSLKBKV-UHFFFAOYSA-N

CAS DataBase Reference

4635-59-0(CAS DataBase Reference)

NIST Chemistry Reference

Butanoyl chloride, 4-chloro-(4635-59-0)

EPA Substance Registry System

Butanoyl chloride, 4-chloro- (4635-59-0)

Safety Information

Hazard Codes 

T,C

Risk Statements 

22-23-35

Safety Statements 

26-28-36/37/39-45-28A

RIDADR 

UN 3390 6.1/PG 1

WGK Germany 

1

RTECS 

EM1406000

Autoignition Temperature

824 °F

Hazard Note 

Toxic/Corrosive/Moisture Sensitive

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29159080

Hazardous Substances Data

4635-59-0(Hazardous Substances Data)

MSDS

• Language:English Provider:4-CBC
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Chlorobutyryl chloride Usage And Synthesis

Chemical Properties

Clear colorless to yellow liquid

Uses

4-Chlorobutyryl chloride (4-CBCl) is mainly used in the production of pharmaceuticals and agrochemicals. It is used as pyrazinamide intermediate.

Uses

4-Chlorobutyroyl Chloride is used in the preparation of mitosene and mitosane analogs of Mitomycin C (M371900), an antitumor antibiotic. .

Synthesis Reference(s)

Synthesis, p. 538, 1973 DOI: 10.1055/s-1973-22254

Flammability and Explosibility

Non flammable

Synthesis

1. γ-Butyrolactone (7.7 mL, 0.1 mol) was added one time under stirring conditions to a mixed solution containing thionyl chloride (8 mL, 0.11 mol) and anhydrous zinc chloride (0.6 g, 4.4 mmol). 2. The reaction mixture was heated at 55 °C with continuous stirring for 12 hours. 3. Upon completion of the reaction, the reaction product was purified by fractional distillation at a pressure of 15-30 mmHg, and fractions with boiling points in the range of 110-125 °C were collected to afford the intermediate 4-chlorobutanoyl chloride (10.4 g, 74 mmol, 74% yield). 4. The resulting intermediate 4-chlorobutanoyl chloride was slowly (over 15 min) added dropwise to a mixed solution of pyridine (6 mL, 74 mmol) and tert-butanol (8.75 mL, 92 mmol) cooled to 0 °C. The solution was then added dropwise to a mixture of pyridine (6 mL, 74 mmol) and tert-butanol (8.75 mL, 92 mmol). 5. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 4 hours. 6. After completion of the reaction, the mixture was partitioned between water and ether, and the aqueous layer was acidified with concentrated sulfuric acid and extracted with ether (3 x 50 mL). 7. The organic layers were combined and washed sequentially with 1N HCl solution (3 x 100 mL), water (100 mL) and saturated NaCl solution (100 mL). 8. Collect the organic layer, dry with anhydrous Na2SO4, filter and remove the solvent in vacuum. 9. Purification by silica gel column chromatography using 100% dichloromethane as eluent (Rf = 0.9) gave the target product 9a as a clear oil in 25% yield (3.28 g, 18.35 mmol). 10. The structure of the product was confirmed by 1H NMR (CDCl3): δ 3.59 (t, 2H, CH2), 2.41 (t, 2H, CH2), 2.05 (t, 2H, CH2), 1.45 (s, 9H, CH3).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1124 - 1130
[2] Patent: WO2005/40109, 2005, A1. Location in patent: Page/Page column 66
[3] Russian Journal of Organic Chemistry, 1996, vol. 32, # 1, p. 21 - 24
[4] Canadian Journal of Chemistry, 1993, vol. 71, # 8, p. 1152 - 1168
[5] Journal of the American Chemical Society, 1957, vol. 79, p. 1455,1457

4-Chlorobutyryl chloride(4635-59-0)Related Product Information

• Calcium chloride
• Polychloroprene
• Benzoyl chloride
• Sulfuryl chloride
• Butyryl chloride
• Zinc chloride
• Sodium chloride
• Choline chloride
• Oxalyl chloride
• Thionyl chloride
• Tosyl chloride
• Ammonium chloride
• Pivaloyl chloride
• Chloroacetyl chloride
• Potassium chloride
• H-NVA-NH2 HCL
• 1-Pyrrolidineaceticacid,alpha-ethylidene-2-oxo-,(alphaZ)-(9CI)
• 2-aminobutanenitrile