1003-10-7

Basic information

• Product Name: 4-BUTYROTHIOLACTONE
• Synonyms: 2(3H)-dihydrothiophenone;2(3H)-Thiophenone, dihydro-;2-Oxothiolane;2-Thiophenone, tetrahydro-;4-Thiobutyrolactone;gaMMa-Thiobutyrolactone 98%;dihydro-2(3h)-thiophenon;dihydro-2(3h)-thiophenone
• CAS NO: 1003-10-7
• Molecular Formula: C₄H₆OS
• Molecular Weight: 102.15
• EINECS: 213-700-8
• Product Categories: Heterocyclic Compounds
• Mol File: 1003-10-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 138 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 39-40 °C1 mm Hg(lit.)
• Flash Point: 186 °F
• Appearance: /
• Density: 1.18 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.38mmHg at 25°C
• Refractive Index: n20/D 1.523(lit.)
• Solubility: THF: soluble
• CAS DataBase Reference: 4-BUTYROTHIOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BUTYROTHIOLACTONE(1003-10-7)
• EPA Substance Registry System: 4-BUTYROTHIOLACTONE(1003-10-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• RIDADR: UN 3334
• WGK Germany: 3
• RTECS: XN1930000
• Hazardous Substances Data: 1003-10-7(Hazardous Substances Data)

Usage

Description

4-Butyrothiolactone, also known as γ-thiobutyrolactone, is a heterocyclic compound with a sulfur-containing ring structure. It is characterized by its ability to undergo copolymerization with other compounds, such as glycidyl phenyl ether, to form poly(ester-alt-sulfide). This unique property makes it a versatile compound with potential applications in various industries.

Uses

Used in Polymer Synthesis:
4-Butyrothiolactone is used as a monomer in the synthesis of difunctional polyesters. It is particularly useful in the ring-opening polymerization of ω-pentadecalactone, where it serves as a terminator to control the molecular weight and functionality of the resulting polymers.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-Butyrothiolactone is used as a tool to study the metabolism of sulfur-containing heterocyclic compounds. It has been utilized in research involving lignin-degrading basidiomycete Coriolus versicolor to better understand the metabolic pathways and potential applications of these compounds in drug development.
Used in Material Science:
4-Butyrothiolactone is used as a comonomer in the copolymerization process with glycidyl phenyl ether. The resulting poly(ester-alt-sulfide) materials exhibit unique properties, such as improved thermal stability and chemical resistance, making them suitable for various applications in the material science field.

InChI:InChI=1/C4H6OS/c5-4-2-1-3-6-4/h1-3H2

Upstream product

• 96-48-0 4-butanolide 
• 75-15-0 carbon disulfide 
• 13095-73-3 4-mercaptobutyric acid 
• 110-01-0 thiophene 
• 3354-35-6 dihydro-2(3H)-thiophenethione 
• 201230-82-2 carbon monoxide 
• 88738-51-6 3-benzylmercaptopropyl bromide 
• 927-58-2 4-bromobutyroyl chloride 
• 7647-01-0 hydrogenchloride 
• 359865-01-3 (E)-1-((1RS,2SR)-2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one 
• 54634-49-0 N-nitroso-dihydro-2(3H)-pyrrolidinone 
• 287-27-4 trimethylene sulphide 
• 119549-23-4 3-bromopropyl 1,1-dimethylethyl sulfide 
• 927-59-3 4-iodobutanoyl chloride 

Downstream Products

• 39257-91-5 methyl 4-mercaptobutanoate 
• 65286-54-6 2-Oxo-3-acetyl-tetrahydrothiophen 
• 2906-60-7 5,6-dithia-decanedioic acid 
• 99060-83-0 4-((4-nitrophenyl)thio)butanoic acid 
• 41108-57-0 cis-3-(3'-Carboxypropylthio)acrylsaeure 
• 41108-59-2 cis-3-(3'-Carboxypropylthio)acrylsaeureethylester 
• 41108-60-5 trans-3-(3'-Carboxypropylthio)acrylsaeureethylester 
• 13095-73-3 4-mercaptobutyric acid 
• 14970-83-3 4-Mercapto-1-butanol 
• 222046-78-8 2-oxotetrahydrothiophene-3-carboxylic acid 

Relevant articles and documents

N-NITROSAMINES AS REAGENTS FOR THE =C=S=C=O TRANSFORMATION

N-nitrosopiperidine and N-nitroso-N-methylaniline react in acidic solution with thiocarbonyl compounds to give the corresponding carbonyl analogues.Secondary- and tertiary thioamides, xanthione, thio- and dithiobutyrolactone, thiocoumarin, certain thiourea derivatives, dithio-O,O-thiocarbonic, S,S-trithiocarbonic- and N,N disubstituted thiocarbamic esters are all converted into the corresponding O-analogues.Thiobenzamide and N-phenylthiourea yield 1,2,4-thiadiazoles.All the reactions are run with iodide (I-) as NO+-carrier.The kinetics of the reaction have been studied under pseudo-first order conditions, and the reaction rate is proportional to the Pearson's nucleophilicity parameter of ions.The =C=S =C=O transformation is also found to take place in gastric juice.

-

-

Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere

A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.

-

-

Indium-catalyzed direct conversion of lactones into thiolactones using a disilathiane as a sulfur source

An indium-catalyzed reaction of lactones and a disilathiane leading to thiolactones is described. The direct synthesis of thiolactones from lactones with an appropriate sulfur source is one of the most attractive approaches in organic and pharmaceutical chemistry. In this context, we found an indium-catalyzed direct conversion of lactones into thiolactones in the presence of elemental sulfur and a hydrosilane via formation of the disilathiane in situ. On the basis of the previous reaction, the application utilizing the disilathiane as a sulfur source was performed herein for the efficient synthesis of a variety of thiolactone derivatives from lactones by an indium catalyst.

Catalytic synthesis of thiobutyrolactones via CO insertion into the C-S bond of thietanes in the presence of a heterodinuclear organoplatinum-cobalt complex

Heterodinuclear organoplatinum-cobalt complex having a 1,2-bis(diphenylphosphino)ethane ligand (dppe)MePt-Co(CO)4 catalyzes CO insertion into the C-S bond of thietanes in THF at 100°C under 1.0 MPa of CO for 2 h to give γ-thiobutyrolactone in q