15925-47-0

Basic information

• Product Name: S-TERT-BUTYL ACETOTHIOACETATE
• Synonyms: S-TERT-BUTYL ACETOTHIOACETATE;Acetoacetic acid, 1-thio-, S-tert-butyl ester;S-(tert-Butyl) 3-oxobutanethioate;S-tert-Butyl 3-oxothiobutyrate;tert-Butyl acetothiolacetate;3-Oxo-butanethioic acid S-tert-butyl ester;3-Oxobutanethioic acid S-tert-butyl ester;3-Oxothiobutyric acid S-tert-butyl ester
• CAS NO: 15925-47-0
• Molecular Formula: C₈H₁₄O₂S
• Molecular Weight: 174.26
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiol Esters
• Mol File: 15925-47-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 95-100 °C0.9 mm Hg(lit.)
• Flash Point: 182 °F
• Appearance: /
• Density: 0.994 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00363mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• PKA: 8.90±0.46(Predicted)
• CAS DataBase Reference: S-TERT-BUTYL ACETOTHIOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: S-TERT-BUTYL ACETOTHIOACETATE(15925-47-0)
• EPA Substance Registry System: S-TERT-BUTYL ACETOTHIOACETATE(15925-47-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 15925-47-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 22, p. 2329, 1992 DOI: 10.1080/00397919208019087

InChI:InChI=1/C8H14O2S/c1-6(9)5-7(10)11-8(2,3)4/h5H2,1-4H3

Upstream product

• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 75-66-1 2-methylpropan-2-thiol 
• 674-82-8 4-methyleneoxetan-2-one 
• 29364-29-2 sodium tert-butyl thiolate 
• 999-90-6 S-tert-butyl thioacetate 
• 60-29-7 diethyl ether 
• 920-39-8 isopropylmagnesium bromide 

Downstream Products

• 53544-25-5 1-(2-oxopyrrolidin-1-yl)butane-1,3-dione 
• 1657-28-9 3-oxo-N-(pyrid-2-yl)butyramide 
• 204977-81-1 2-Benzyl-3-oxo-thiobutyric acid S-tert-butyl ester 
• 204977-82-2 3-Oxo-5-phenyl-pentanethioic acid S-tert-butyl ester 
• 339274-36-1 S-tert-butyl cyclohexylcarbamoylthioacetate 
• 1429484-90-1 S-tert-butyl 4-(4-bromophenyl)-2-methyl-6-(4-tolyl)-1,4-dihydropyridine-3-carbothioate 
• 1429484-89-8 S-tert-butyl 4-(4-methoxyphenyl)-2-methyl-6-phenyl-1,4-dihydropyridine-3-carbothioate 
• 1429484-88-7 S-tert-butyl 2-methyl-4,6-diphenyl-1,4-dihydropyridine-3-carbothioate 
• 1355175-72-2 C₂₄H₂₇NOS 
• 1283084-23-0 S-(tert-butyl) 1-benzyl-4-[(dimethylamino)carbonyl]-2,5-dimethyl-1H-pyrrole-3-carbothioate 
• 1071496-46-2 3-oxo-2-(4-pyrazol-1-ylbenzyl)thiobutyric acid S-tert-butyl ester 
• 1068159-50-1 2-(4-cyanobenzyl)-3-oxothiobutyric acid S-tert-butyl ester 
• 128466-41-1 (R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-tert-butylsulfanylcarbonyl-3-dimethylaminomethyl-2-methylene-pyrrolidine-1-carboxylic acid benzyl ester 
• 135246-01-4 benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate 

Relevant articles and documents

Solvent-free microwave-assisted organic reactions prepation of β-keto esters

Microwave technique has been utilised in the preparation of β-keto esters. Two different procedures are described: transesterification of β- keto esters and ring opening of 2,2,6-trimethyl-1,3-dioxin-4-one.

A novel synthesis of β-ketothioesters

-

PREPARATION OF ACYLTETRONIC ACIDS USING t-BUTYL ACETOTHIOACETATE: TOTAL SYNTHESIS OF THE FUNGAL METABOLITES CAROLIC, CARLOSIC, AND CARLIC ACIDS

Dianions generated from S-t-butyl acetothioacetate ( 1 ) were alkylated with a variety of electrophiles at the γ-carbon centre.Treatment of the alkylated products with 2-hydroxy esters in the presence of silver(I) salts gave transesterified acetoacetate derivatives in good yields.These acetoacetates were cyclised efficiently to acyltetronic acid derivatives using tetrabutyl ammonium fluoride in THF solution at room temperature.By an appropriate choice of substituents the total synthesis of the fungal metabolite natural products carlosic, carolic, and carlic acids have been achieved.