Allylacetic acid Chemical Properties

Melting point:

-22.5 °C (lit.)

Boiling point:

83-84 °C/12 mmHg (lit.)

Density 

0.981 g/mL at 25 °C (lit.)

vapor density 

>1 (vs air)

refractive index 

n20/D 1.428(lit.)

FEMA 

2843 | 4-PENTENOIC ACID

Flash point:

193 °F

storage temp. 

2-8°C

solubility 

soluble in Chloroform, Methanol

pka

pK1:4.677 (25°C)

form 

Liquid

Specific Gravity

0.981

color 

Clear colorless to light yellow

Odor

at 0.10 % in propylene glycol. cheese parmesan romano ricotta

Odor Type

cheesy

explosive limit

1.58%(V)

Water Solubility 

Soluble in alcohol, Slightly soluble in water

JECFA Number

314

BRN 

1633696

InChIKey

HVAMZGADVCBITI-UHFFFAOYSA-N

LogP

0.99

CAS DataBase Reference

591-80-0(CAS DataBase Reference)

NIST Chemistry Reference

4-Pentenoic acid(591-80-0)

EPA Substance Registry System

4-Pentenoic acid (591-80-0)

Safety Information

Hazard Codes 

C,T

Risk Statements 

34-22

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

RTECS 

SC4751000

F 

8-10-23

TSCA 

T

HazardClass 

8

PackingGroup 

III

HS Code 

29161980

Toxicity

LD50 oral in rat: 470mg/kg

MSDS

• Language:English Provider:Pent-4-enoic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Allylacetic acid Usage And Synthesis

Description

Allylacetic acid (allyl acetate) is a derivative of acetate. It is the acetate ester of allyl alcohol. It is useful industrial intermediate. It is the precursor of some special polymer such as drying oils. It can also be used as a useful allylating reagent for catalyzing the allylation of aldehydes, and also allylation of aryl bromides in the palladium-catalyzed cross-coupling reaction. It has also demonstrated that it is a potential fumigant against grain beetle pests; study has shown that doses of 50–150 mg litre?1 with 24–120-h exposures are necessary to achieve 100% mortality of all life stages against grain beetle pests. Study has also shown that ally acetate is an effective oxidants during the Palladium— Iminophosphine-Catalyzed Homocoupling of Alkynylstannanes and Other Organostannanes

References

Denmark, S. E., and S. T. Nguyen. "Catalytic, nucleophilic allylation of aldehydes with allyl acetate. " Organic Letters 11.3 (2009):781-4.
Yokoyama, Y., et al. "ChemInform Abstract: Palladium- Catalyzed Cross-Coupling Reaction: Direct Allylation of Aryl Bromides with Allyl Acetate."Chemischer Informationsdienst 26.52 (1986):6457-6460.
Rajendran, Dr Somiahnadar, and N. Muralidharan. "Effectiveness of allyl acetate as a fumigant against five stored grain beetle pests." Pest Management Science 61.1(2005):97-101.
Shirakawa, Eiji, et al. "Palladium—Iminophosphine-Catalyzed Homocoupling of Alkynylstannanes and Other Organostannanes Using Allyl Acetate or Air as an Oxidant." Journal of Organometallic Chemistry670.1(2003):132-136.

Chemical Properties

clear colorless to light yellow liquid

Chemical Properties

4-Pentenoic acid has a sour, caramellic flavor with sweet aftertaste. It has an acrid flavor and odor at high levels.

Uses

Sulfonation yields the corresponding γ-lactone.1

Uses

The sulfonation of 4-pentenoic acid (Allylacetic acid) yields the corresponding γ-lactone. It was used to inhibit fatty acid oxidation in rat heart mitochondria.

Uses

4-Pentenoic acid (Allylacetic acid) was used to inhibit fatty acid oxidation in rat heart mitochondria.

Definition

ChEBI: A pentenoic acid having the double bond at position 4.

Preparation

By decarboxylation via heating allylmalonic acid; from the corresponding ethyl ester prepared by boiling ethyl 4-chloron- valerate in quinoline.

Synthesis Reference(s)

Synthetic Communications, 13, p. 889, 1983 DOI: 10.1080/00397918308059542

General Description

4-Pentenoic acid is a volatile acid reported to be found in tobacco.

Safety Profile

Poison by subcutaneous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Allylacetic acid (591-80-0)Related Product Information

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• Sodium allylsulfonate
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• Ethyl 2-(Chlorosulfonyl)acetate
• Allyl bromide
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• 4-tert-Butylphenylhydrazine hydrochloride