591-80-0 Usage
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
Different sources of media describe the Chemical Properties of 591-80-0 differently. You can refer to the following data:
1. clear colorless to light yellow liquid
2. 4-Pentenoic acid has a sour, caramellic flavor with sweet aftertaste. It has an acrid flavor and odor at high levels.
Uses
Different sources of media describe the Uses of 591-80-0 differently. You can refer to the following data:
1. Sulfonation yields the corresponding γ-lactone.1
2. 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.
3. 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.
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.
Exploring the physicochemical and antiproliferative properties of biaryl-linked [13]-macrodilactones
Chen, Chengsheng,Bosko, Cristin,McGeough, Catherine P.,McLean, Ryan,Zaino, Angela M.,Kyle Hadden,Peczuh, Mark W.
, (2020/08/19)
A macrocyclic motif fosters productive protein-small molecule interactions. There are numerous examples of both natural product and designed, synthetic macrocycles that modulate the immune system, slow microbial infection, or kill eukaryotic cells. Reported here are the synthesis, physicochemical characterization, and antiproliferative activity of a group of [13]-macrodilactones decorated with a pendant biaryl moiety. Biaryl analogs were prepared by Suzuki reactions conducted on a common intermediate that contained a bromophenyl unit alpha to one of the carbonyls of the [13]-macrodilactone. Principal component analysis placed the new compounds in physicochemical context relative to a variety of pharmaceuticals and natural products. Modest inhibition of proliferation was observed in ASZ cells, a murine basal cell carcinoma line. This work underscores the value of an approach toward the identification of bioactive compounds that places the evaluation of physicochemical parameters early in the search process.
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.
