4-Chlorobutanal dimethyl acetal Chemical Properties

Boiling point:

120 °C / 40mmHg

Density 

1.04

refractive index 

1.4270-1.4310

Flash point:

43°C(lit.)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform, Methanol

form 

Oil

color 

Clear Colourless

Stability:

Moisture Sensitive

InChIKey

LTLKJYMNUSSFAH-UHFFFAOYSA-N

CAS DataBase Reference

29882-07-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-36

RIDADR 

1993

HazardClass 

3.2

PackingGroup 

III

HS Code 

2909199090

4-Chlorobutanal dimethyl acetal Usage And Synthesis

Chemical Properties

Colorless Liquid

Uses

4-Chlorobutanal Dimethyl Acetal 90% is a compound useful in organic synthesis and other chemical processes. It is used as an intermediate in the synthesis of aripiprazole, buspirone, and NAN-190 via reductive alkylation of piperazine derivatives with aldehydes

Synthesis

Preparation of 4-chlorobutanal dimethanol: 72 g (0.49 mol) of 4-chloro-1-acetoxy-1-butene was dissolved in 300 mL of anhydrous methanol, to which were added 240 g (7.5 mol) of methanol and 15 g of acidic ion exchange resin catalyst treated with macroporous resin 15. The mixture was stirred overnight under reflux conditions and the complete conversion of the E and Z isomers of 4-chloro-1-acetoxy-1-butene to a single high-boiling product, accompanied by a small number of side reactions, was confirmed by GC analysis. Upon completion of the reaction, the mixture was filtered to recover the catalyst and the filtrate was treated with 5 g of solid sodium bicarbonate. Excess methanol was removed by distillation under reduced pressure until the volume was reduced to about 50 mL. The liquid was decanted from the insoluble sodium bicarbonate and distilled through a 6-inch Vigro fractionating column at 25 mm Hg. A colorless fraction with a boiling range of 83-85 °C was collected to give 55.0 g of product (74.4% of the theoretical yield).NMR analysis confirmed the fraction as pure 4-chlorobutanal dimethyl acetal.

References

[1] Organic Preparations and Procedures International, 2004, vol. 36, # 5, p. 487 - 490
[2] Patent: US2004/192958, 2004, A1. Location in patent: Page 3

4-Chlorobutanal dimethyl acetal(29882-07-3)Related Product Information

• Glyoxal
• Dimethyl fumarate
• Dimethyl sulfoxide
• Glutaraldehyde
• Bromoacetaldehyde dimethyl acetal
• Aminoacetaldehyde dimethyl acetal
• ETHANE
• Epichlorohydrin
• Polychloroprene
• Polyoxymethylene
• Methylglyoxal 1,1-dimethyl acetal
• Dimethyl phthalate
• Dimethyl ether
• Acetal
• Chloroacetic acid
• 5-Chloro-2-pentanone cyclic ethylene ketal
• PHENYLETHYL ACETAL
• Difluorochloromethane