591-80-0 Usage
Description
Allylacetic acid, also known as allyl acetate, is a derivative of acetate and the acetate ester of allyl alcohol. It is a useful industrial intermediate and serves as a precursor for some special polymers, such as drying oils. Additionally, it acts as a valuable allylating reagent for catalyzing the allylation of aldehydes and aryl bromides in palladium-catalyzed cross-coupling reactions. Allylacetic acid has also demonstrated potential as a fumigant against grain beetle pests and is an effective oxidant in palladium-iminophosphine-catalyzed homocoupling of alkynylstannanes and other organostannanes.
Uses
Used in Chemical Synthesis:
Allylacetic acid is used as an industrial intermediate for the synthesis of various chemicals and polymers, such as drying oils.
Used in Organic Chemistry:
Allylacetic acid is used as an allylating reagent for catalyzing the allylation of aldehydes and aryl bromides in palladium-catalyzed cross-coupling reactions.
Used in Pest Control:
Allylacetic acid is used as a potential fumigant against grain beetle pests, with effective doses of 50–150 mg liter-1 and exposure times of 24–120 hours required to achieve 100% mortality of all life stages.
Used in Oxidation Reactions:
Allylacetic acid is used as an effective oxidant in palladium-iminophosphine-catalyzed homocoupling of alkynylstannanes and other organostannanes.
Used in Sulfonation:
Allylacetic acid is used in the sulfonation process to yield the corresponding γ-lactone.
Used in Inhibiting Fatty Acid Oxidation:
Allylacetic acid, specifically as 4-pentenoic acid, is used to inhibit fatty acid oxidation in rat heart mitochondria.
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.
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
Safety Profile
Poison by subcutaneous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 591-80-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 1 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 591-80:
(5*5)+(4*9)+(3*1)+(2*8)+(1*0)=80
80 % 10 = 0
So 591-80-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c1-2-3-4-5(6)7/h2H,1,3-4H2,(H,6,7)/p-1
591-80-0Relevant articles and documents
Selective Ring Transformations of 1-imidazoles
Hirao, Toshikazu,Misu, Daisuke,Agawa, Toshio
, p. 26 - 27 (1986)
The title compounds underwent CsF- or BF3*Et2O-induced selective ring-opening reactions leading to the cyclobutanone derivatives or γ,δ-unsaturated carboxylic acids, respectively.
Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols
Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji
supporting information, p. 20394 - 20398 (2020/09/21)
A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.
Bidentate auxiliary-directed alkenyl C-H allylation: Via exo-palladacycles: Synthesis of branched 1,4-dienes
Shen, Cong,Lu, Xiunan,Zhang, Jian,Ding, Liyuan,Sun, Yaling,Zhong, Guofu
supporting information, p. 13582 - 13585 (2019/11/14)
An alkenyl C-H allylation by an exo-palladacycle intermediate is demonstrated, employing unactivated (Z)-Alkenes and allyl carbonates. With the use of an 8-Aminoquinoline (AQ) derived amide as the directing group, the N,N-bidentate-chelation-Assisted C-H activation protocol proceeded under mild and oxidant-free conditions with excellent selectivity. The utility of this approach is demonstrated by the preparative scale, selective conversion of inseparable Z/E alkenes and ready removal of the amide auxiliary to provide the corresponding ester.