Benzyl acetoacetate

Base Information

• Chemical Name: Benzyl acetoacetate
• CAS No.: 5396-89-4
• Deprecated CAS: 1629358-35-5
• Molecular Formula: C11H12O3
• Molecular Weight: 192.214
• Hs Code.: 29183000
• European Community (EC) Number: 226-416-4
• NSC Number: 4391
• UNII: F9S0XGV18X
• DSSTox Substance ID: DTXSID8063834
• Nikkaji Number: J103.932F
• Wikidata: Q27277858
• Mol file: 5396-89-4.mol

Synonyms:Benzyl acetoacetate;Benzyl 3-oxobutanoate;5396-89-4;Acetoacetic acid benzyl ester;Benzyl acetylacetate;Acetoacetic acid, benzyl ester;Phenylmethyl 3-oxobutanoate;Butanoic acid, 3-oxo-, phenylmethyl ester;Benzyl beta-ketobutyrate;FEMA No. 2136;NSC 4391;MFCD00008785;UNII-F9S0XGV18X;F9S0XGV18X;NSC-4391;EINECS 226-416-4;AI3-06229;BENZYLACETOACETATE;AC-benzyl;38432-58-5;Benzyl acetoacetate, 97%;SCHEMBL26569;DTXSID8063834;FEMA 2136;WOFAGNLBCJWEOE-UHFFFAOYSA-;3-oxo-butanoicaciphenylmethylester;NSC4391;CHEBI:173928;BENZYL ACETOACETATE [FHFI];BCP23315;BBL027729;STL373489;Acetoacetic acid, benzyl ester (8CI);AKOS000119530;3-OXOBUTANOIC ACID BENZYL ESTER;AS-47647;SY015679;3-OXOBUTANOIC ACID PHENYLMETHYL ESTER;A1080;AM20040668;CS-0071955;FT-0621772;EN300-21320;F14832;Benzyl acetoacetate, Lonza quality, >=96.0% (GC);Q-103471;Q27277858;F0001-1407;Z104495340;Benzyl acetoacetate, produced by Wacker Chemie AG, Burghausen, Germany, >=96% (GC);3-Oxobutanoic Acid Benzyl Ester;3-Oxobutanoic Acid Phenylmethyl Este;Benzyl 3-Oxobutanoate;Benzyl 3-Oxobutyrate

Chemical Property of Benzyl acetoacetate

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.00128mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Boiling Point: 298.3 °C at 760 mmHg
• PKA: 10.60±0.46(Predicted)
• Flash Point: 120.7 °C
• PSA: 43.37000
• Density: 1.115 g/cm³
• LogP: 1.70890
• Storage Temp.: Store below +30°C.
• Solubility.: It is soluble in alkali solutions.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 205

Purity/Quality:

98% ^*data from raw suppliers

Benzyl acetoacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)OCC1=CC=CC=C1
• Uses: Benzyl acetoacetate is used as a Pharmaceutical and fine chemical intermediate. Benzyl acetoacetate (AAbenzyl) is chemical intermediate used for the syntheses of different organic chemicals Product Data Sheet

Technology Process of Benzyl acetoacetate

There total 30 articles about Benzyl 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: 100.0%

ethyl acetoacetate (141-97-9) + benzyl alcohol (100-51-6,185532-71-2) → benzyl acetoacetate (5396-89-4)

Guidance literature:

[Cl(C₆F₁₃C₂H₄)2SnOSn(C₂H₄C₆F₁₃)2Cl]2; In toluene; for 6h; Heating;

DOI:10.1002/1615-4169(200201)344:1<84::AID-ADSC84>3.0.CO;2-C

Reference yield: 100.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + benzylamine (100-46-9) → benzyl acetoacetate (5396-89-4)

Guidance literature:

In dichloromethane; at 0 - 20 ℃;

Reference yield: 99.0%

acetoacetic acid methyl ester (105-45-3) + benzyl alcohol (100-51-6,185532-71-2) → benzyl acetoacetate (5396-89-4)

Guidance literature:

yttria-zirconia based Lewis acid catalyst; In toluene; for 14h; Heating;

DOI:10.1055/s-2000-6496

upstream raw materials:

diethyl ether

Benzyl acetate

ethyl acetoacetate

benzyl alcohol

Downstream raw materials:

7-methyl-5,5a,8a,9-tetrahydro-furo[2,3-g]pteridine-8-carboxylic acid benzyl ester

3,3-Bis-(3-tert-butyl-4-hydroxy-phenyl)-butyric acid benzyl ester

2-Methyl-3-(α-benzyloxycarbonyl-acetonyl)-naphthochinon-(1,4)

cis(3a,6a)-3-benzyloxycarbonyl-2-methyl-3a,4,5,6a-tetrahydro-furo<2,3-b>furan

Refernces

• 1、 Daniel Little,Russu. "A facile synthesis of 5-acyl-6-alkyl/aryl-2,2-dimethyl-1,3-dioxin-4-ones". . p. 8096 - 8099. Retrieved 2000.
• 2、 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". . p. 1641 - 1655. Retrieved 2020/05/25.
• 3、 Titova, Yu. A.,Filatova,Fedorova,Rusinov,Charushin. "4-(Het)aryl-4,7-dihydroazolopyrimidines and Their Tuberculostatic Activity". . p. 775 - 781. Retrieved 2019/08/02.