ChemicalBook Product Catalog Chemical Reagents Organic reagents Acyl halide (E)-2-Butenoyl chloride

(E)-2-Butenoyl chloride

Product Name(E)-2-Butenoyl chloride
CAS625-35-4
MFC4H5ClO
MW104.53
EINECS234-010-3
MOL File625-35-4.mol

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
Storage Class	3 - Flammable liquids
Hazard Classifications	Aquatic Chronic 3 Eye Dam. 1 Flam. Liq. 3 Skin Corr. 1B STOT SE 3

MSDS

Provider	Language
(E)-2-Butenoyl chloride	English
SigmaAldrich	English
ACROS	English
ALFA	English

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

107-93-7

625-35-4

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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