Allyl acetoacetate

Base Information

• Chemical Name: Allyl acetoacetate
• CAS No.: 1118-84-9
• Molecular Formula: C7H10O3
• Molecular Weight: 142.155
• Hs Code.: 29183000
• European Community (EC) Number: 214-269-9
• NSC Number: 24280
• UNII: 8HX066J62P
• DSSTox Substance ID: DTXSID40149740
• Nikkaji Number: J101.267C
• Wikidata: Q27270546
• Mol file: 1118-84-9.mol

Synonyms:Allyl acetoacetate;1118-84-9;Allyl 3-oxobutanoate;Allylacetoacetate;(2-Propenyl) 3-oxobutanoate;Allyl acetylacetate;Acetoacetic acid, allyl ester;Butanoic acid, 3-oxo-, 2-propenyl ester;prop-2-en-1-yl 3-oxobutanoate;prop-2-enyl 3-oxobutanoate;Acetoacetic Acid Allyl Ester;(2-Propenyl)3-oxobutanoate;UNII-8HX066J62P;AI3-04977;8HX066J62P;EINECS 214-269-9;NSC-24280;EC 214-269-9;2-propenyl acetoacetate;allyl aceto-acetate;Actoactate d'allyle;Allyl 3-oxobutanoate #;Allyl acetoacetate, 97%;Allyl acetoacetate, 98%;ACETOACETATE, ALLYL;SCHEMBL9513;Acetylacetic acid, allyl ester;3-oxo-butyric acid allyl ester;DTXSID40149740;BCP12037;NSC24280;BBL011433;MFCD00009811;NSC 24280;STL146541;AKOS000120505;CS-W018294;VS-02949;FT-0621771;EN300-20951;E75749;J-002655;J-519551;Q27270546;F0001-0255

Chemical Property of Allyl acetoacetate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.501mmHg at 25°C
• Melting Point: -70 °C
• Refractive Index: n20/D 1.439(lit.)
• Boiling Point: 191.958 °C at 760 mmHg
• PKA: 10.53±0.46(Predicted)
• Flash Point: 75.556 °C
• PSA: 43.37000
• Density: 1.017 g/cm³
• LogP: 0.69470
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: 48g/l
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

Allyl Acetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 22-24-38
• Safety Statements: 36/37-45-36/37/39-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC(=O)CC(=O)OCC=C

Technology Process of Allyl acetoacetate

There total 15 articles about Allyl acetoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

acetoacetic acid methyl ester (105-45-3) + allyl alcohol (107-18-6) → allyl acetoacetate (1118-84-9)

Guidance literature:

With dmap; 3 A molecular sieve; In toluene; Heating;

DOI:10.1021/jo00237a049

Reference yield: 90.0%

acetoacetic acid methyl ester (105-45-3) → allyl acetoacetate (1118-84-9)

Guidance literature:

sulfated tin oxide; In ethyl acetate; toluene; Petroleum ether;

Reference yield: 90.0%

5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (85920-63-4) + allyl alcohol (107-18-6) → allyl acetoacetate (1118-84-9)

Guidance literature:

In tetrahydrofuran; for 4h; Heating;

upstream raw materials:

4-methyleneoxetan-2-one

allyl alcohol

acetoacetic acid methyl ester

3-chloroprop-1-ene

Downstream raw materials:

5-hydroxy-1-(4-methoxy-benzyl)-2-methyl-1H-indole-3-carboxylic acid allyl ester

2-((R)-methoxycarbonylamino-m-tolyl-methyl)-3-oxo-butyric acid allyl ester

2-[(R)-(3-fluoro-phenyl)-methoxycarbonylamino-methyl]-3-oxo-butyric acid allyl ester

2-[(R)-(4-fluoro-phenyl)-methoxycarbonylamino-methyl]-3-oxo-butyric acid allyl ester

Refernces

• 1、 Srinivas,Rajanna,Krishnaiah,Kumar, M. Satish,Reddy, J. Narender. "Prussian blue as an efficient catalyst for rate accelerations in the transesterification of β-ketoesters". . p. 1212 - 1220. Retrieved 2014.
• 2、 Kondaiah,Reddy, L. Amarnath,Babu, K. Srihari,Gurav,Huge,Bandichhor,Reddy, P. Pratap,Bhattacharya,Anand, R. Vijaya. "Boric acid: an efficient and environmentally benign catalyst for transesterification of ethyl acetoacetate". . p. 106 - 109. Retrieved 2008.
• 3、 Bowie,J.H. et al.. "-". . p. 689 - 697. Retrieved 1967.
• 4、 Gilbert, John C.,Kelly, Terence A.. "Transesterification of 3-Oxo Esters with Allylic Alcohols". . p. 449 - 450. Retrieved 1988.
• 5、 Zhang, Mei-Na,Zhao, Mi-Na,Chen, Ming,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui. "Copper-catalyzed radical coupling of 1,3-dicarbonyl compounds with terminal alkenes for the synthesis of tetracarbonyl compounds". . p. 6127 - 6130. Retrieved 2016.
• 6、 Chavan, Subhash P.,Zubaidha,Dantale, Shubhada W.,Keshavaraja,Ramaswamy,Ravindranathan. "Use of solid superacid (sulphated SnO2) as efficient catalyst in facile transesterification of ketoesters". . p. 233 - 236. Retrieved 1996.
• 7、 Chityala, Yadaiah,Duguta, Govardhan,Kamatala, Chinna Rajanna,Muddam, Bhooshan,Mukka, Satish Kumar. "N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack adducts with 1,3,5-triazine compounds as efficient catalysts for the transesterification of β-ketoesters". supporting information. p. 1641 - 1655. Retrieved 2020/05/25.