sec-Butyl Acetoacetate

Base Information

• Chemical Name: sec-Butyl Acetoacetate
• CAS No.: 13562-76-0
• Molecular Formula: C8H14O3
• Molecular Weight: 158.19
• Hs Code.: 2918300090
• European Community (EC) Number: 672-729-8
• UNII: UL7357J39W
• DSSTox Substance ID: DTXSID30875763
• Nikkaji Number: J133.519G
• Wikidata: Q27894245
• Mol file: 13562-76-0.mol

Synonyms:sec-Butyl Acetoacetate;13562-76-0;Acetoacetic Acid sec-Butyl Ester;Sec-butyl 3-oxobutanoate;butan-2-yl 3-oxobutanoate;Butanoic acid, 3-oxo-, 1-methylpropyl ester;Acetoacetic acid, sec-butyl ester;UL7357J39W;Aethylacetessigester;sec.-butyl acetoacetate;Sec-butyl3-oxobutanoate;sec-Butyl 3-oxobutanoate #;ethyl-alpha-ethyl acetoacetate;SCHEMBL270301;UNII-UL7357J39W;sec-Butyl acetoacetate;>98%;DTXSID30875763;ACETOACETICACIDSEC-BUTYLESTER;MFCD00059392;Butanoic acid,3-oxo-,1-methylpropyl ester;A0815;CS-0362621;FT-0713367;D88332;Q27894245

Chemical Property of sec-Butyl Acetoacetate

Chemical Property:

• Vapor Pressure: 0.342mmHg at 25°C
• Refractive Index: 1.419
• Boiling Point: 199.4 °C at 760 mmHg
• Flash Point: 75.7 °C
• PSA: 43.37000
• Density: 0.979g/cm³
• LogP: 1.30720
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

98%,99%, ^*data from raw suppliers

Butan-2-yl3-Oxobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)OC(=O)CC(=O)C

Technology Process of sec-Butyl Acetoacetate

There total 6 articles about sec-Butyl 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: 81.0%

acetoacetic acid methyl ester (105-45-3) + iso-butanol (78-92-2,15892-23-6) → sec-butyl acetoacetate (13562-76-0)

Guidance literature:

With boron trifluoride diethyl etherate; In toluene; for 5.5h; Reflux;

DOI:10.1080/00397910903029842

Reference yield: 76.0%

ethyl acetoacetate (141-97-9) + iso-butanol (78-92-2,15892-23-6) → sec-butyl acetoacetate (13562-76-0)

Guidance literature:

With iodine; In toluene; for 6h; Ionic liquid; Reflux;

DOI:10.1080/00397910903161660

Reference yield: 72.0%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + iso-butanol (78-92-2,15892-23-6) → sec-butyl acetoacetate (13562-76-0)

Guidance literature:

With toluene-4-sulfonic acid; Heating;

DOI:10.1016/S0957-4166(97)00050-5

upstream raw materials:

4-methyleneoxetan-2-one

iso-butanol

2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine

2,2,6-trimethyl-4H-1,3-dioxin-4-one

Downstream raw materials:

2,5-di-α-methylpropylformate 1,4-cyclohexanedione

2-(3-Nitrophenylmethylidene)-3-oxobutanoic acid, 1-methylpropyl ester

Refernces

• 1、 Yang, Jinhui,Ji, Congbin,Zhao, Yanmin,Li, Yunfeng,Jiang, Shizhi,Zhang, Zhiwei,Ji, Yongqiang,Liu, Wanyi. "BF3OEt2: An efficient catalyst for transesterification of β-ketoesters". experimental part. p. 957 - 963. Retrieved 2010/06/12.
• 2、 Bo, Wang,Ming, Yang Li,Shuan, Suo Ji. "Ionic liquid-regulated sulfamic acid: Chemoselective catalyst for the transesterification of β-ketoesters". . p. 5037 - 5039. Retrieved 2007/10/03.