(E)-2-Butenoyl chloride Chemical Properties

Melting point:

72-74 °C

Boiling point:

120-123 °C(lit.)

Density 

1.091 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.459(lit.)

Flash point:

95 °F

storage temp. 

2-8°C

form 

Liquid

color 

Clear colorless to brown

Water Solubility 

Reacts with water.

Sensitive 

Moisture Sensitive

BRN 

506118

InChI

InChI=1S/C4H5ClO/c1-2-3-4(5)6/h2-3H,1H3/b3-2+

InChIKey

RJUIDDKTATZJFE-NSCUHMNNSA-N

SMILES

C(Cl)(=O)/C=C/C

CAS DataBase Reference

625-35-4(CAS DataBase Reference)

NIST Chemistry Reference

2-Butenoyl chloride, (E)-(625-35-4)

Safety Information

Hazard Codes 

C

Risk Statements 

10-34-36/37-37

Safety Statements 

16-26-27-36/37/39-45-28A-24/25

RIDADR 

UN 2920 8/PG 2

WGK Germany 

3

F 

13-19-21

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29161900

MSDS

• Language:English Provider:(E)-2-Butenoyl chloride
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(E)-2-Butenoyl chloride Usage And Synthesis

Chemical Properties

clear colourless to brown liquid

Uses

Crotonyl chloride is used in agrochemical, pharmaceutical and dyestuff field. Crotonoyl chloride was used in the synthesis of α,β-unsaturated ester.

Synthesis

Preparation of Raw Materials; 1-1 :(Preparation of Crotonyl chloride) Firstly, 1kg of crotonic acid was added to a 5L three-necked reaction flask fitted with a condenser and gas absorption device. Under slow stirring, 1650 mL (1.5 mol) of thionyl chloride was slowly added through a constant pressure dropping funnel, and a large amount of hydrogen chloride gas was released during the reaction. Stirring was continued at room temperature until the gas release slowed down significantly. Subsequently, the reaction mixture was slowly heated to reflux. Upon completion of the reaction, the unit was changed to a distillation unit for atmospheric pressure distillation and the 116-124 °C fraction was collected to give 871 g of crotonyl chloride in 72% yield.

Purification Methods

If the IR of a film has no OH bands, then fractionally distil it, taking the middle fraction and redistilling it. If OH bands are present, then add excess of oxalyl chloride, reflux for 3hours, then distil off the reagent and fractionally distil the crotonoyl chloride as before. Stabilise the distillate with 160ppm of hydroquinone. The amide forms needles m 158o from aqueous ammonia, and the anilide also forms needles but with m 115-118o from H2O. [Beilstein 2 H 411, 2 I 188, 2 II 392, 2 III 1265, 2 IV 1506.]

References

[1] Journal of Organometallic Chemistry, 1987, vol. 322, p. 131 - 140
[2] Journal of Organic Chemistry, 2009, vol. 74, # 22, p. 8739 - 8753
[3] Patent: US2012/165532, 2012, A1. Location in patent: Page/Page column 3
[4] Helvetica Chimica Acta, 1985, vol. 68, p. 1406 - 1426
[5] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 11, p. 2072 - 2075

(E)-2-Butenoyl chloride(625-35-4)Related Product Information

• SULFOXIDE
• Isobutylene
• Octanoyl chloride
• Crotonic acid
• Crotonyl chloride 2-Butenoyl chloride -Methacryloyl chloride
• CROTONYL CHLORIDE,E-CROTONYL CHLORIDE
• Methacryloyl chloride