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Methyl 4-(chloroformyl)butyrate

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Methyl 4-(chloroformyl)butyrate Basic information

Product Name:
Methyl 4-(chloroformyl)butyrate
Synonyms:
  • Methyl 4-(chlorocarbonyl)butanoate
  • Methyl 4-(Chlorocarbonyl)butyrate
  • METHYL 4-(CHLOROFORMYL)BUTYRATE
  • METHYL 5-CHLORO-5-OXOVALERATE
  • METHYL GLUTARYL CHLORIDE
  • GLUTARIC ACID MONOMETHYL ESTER CHLORIDE
  • CARBOMETHOXYL BUTYRYL CHLORIDE
  • 5-CHLORO-5-OXOPENTANOIC ACID METHYL ESTER
CAS:
1501-26-4
MF:
C6H9ClO3
MW:
164.59
EINECS:
216-115-6
Product Categories:
  • Acid Halides
  • Building Blocks
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • API intermediates
  • Halogen compounds
Mol File:
1501-26-4.mol
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Methyl 4-(chloroformyl)butyrate Chemical Properties

Boiling point:
110 °C/17 mmHg (lit.)
Density 
1.191 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.445(lit.)
Flash point:
180 °F
storage temp. 
Inert atmosphere,2-8°C
solubility 
Chloroform, Hexane
form 
Oil
color 
Clear Colourless
Water Solubility 
reacts
Sensitive 
Moisture Sensitive
BRN 
1762383
CAS DataBase Reference
1501-26-4(CAS DataBase Reference)
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Safety Information

Hazard Codes 
C
Risk Statements 
34
Safety Statements 
26-36/37/39-45-24/25
RIDADR 
UN 3265 8/PG 2
WGK Germany 
3
10-21
HazardClass 
8
PackingGroup 
II
HS Code 
2918300090

MSDS

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Methyl 4-(chloroformyl)butyrate Usage And Synthesis

Chemical Properties

clear colourless to light yellow liquid

Uses

Methyl 4-(Chloroformyl)butyrate is used in the synthesis of Leukotriene B4, a proinflammatory agent produced from leukocytes.

Synthesis

67-56-1

108-55-4

1501-26-4

1. 100 g (0.878 mol) of glutaric anhydride was dissolved in 50 mL of anhydrous methanol and heated to reflux for 1 h. 2. Upon completion of the reaction, unreacted methanol was removed by distillation under reduced pressure. 3. The reaction mixture was cooled to room temperature, and 200 mL of acetochloride was slowly added. 4. The reaction mixture was heated for 6 h., wherein after 2 h of heating the remaining dichloro sulfoxide.5. Finally, the fractions were dried at 96 °C to 98 °C/10 mmHg to give 124.2 g of methyl 4-chlorocarbonylbutyrate as a light yellow liquid in 86.4% yield.

References

[1] Patent: CN103864658, 2016, B. Location in patent: Paragraph 0056; 0057
[2] Tetrahedron Letters, 1984, vol. 25, # 39, p. 4371 - 4374
[3] Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, # 6, p. 915 - 923

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