54013-55-7

Basic information

• Product Name: 4,4-DIMETHYLOXAZOLIDINE-2-THIONE
• Synonyms: 4,4-DIMETHYL-1,3-OXAZOLANE-2-THIONE;4,4-DIMETHYL-1,3-OXAZOLIDINE-2-THIONE;4,4-DIMETHYLOXAZOLIDINE-2-THIONE;TIMTEC-BB SBB004220;4,4-dimethyl-2-oxazolidinethion;4,4-dimethyl-oxazolidine-2-thion;4,4-dimethyloxazoline-2-thiol;4,4-DiMethyl-oxazolidin-2-thione
• CAS NO: 54013-55-7
• Molecular Formula: C₅H₉NOS
• Molecular Weight: 131.2
• EINECS: 258-924-7
• Mol File: 54013-55-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 122-124 °C
• Boiling Point: 139.9 °C at 760 mmHg
• Flash Point: 38.4 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 6.28mmHg at 25°C
• Refractive Index: 1.547
• PKA: 13.91±0.40(Predicted)
• CAS DataBase Reference: 4,4-DIMETHYLOXAZOLIDINE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-DIMETHYLOXAZOLIDINE-2-THIONE(54013-55-7)
• EPA Substance Registry System: 4,4-DIMETHYLOXAZOLIDINE-2-THIONE(54013-55-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: RQ2153000
• Hazardous Substances Data: 54013-55-7(Hazardous Substances Data)

Usage

General Description

4,4-DIMETHYLOXAZOLIDINE-2-THIONE is a chemical compound with the molecular formula C5H9NOS. It is a sulfur-containing heterocyclic compound that is commonly used as a reagent in organic synthesis and as a precursor in the manufacturing of pharmaceuticals. 4,4-DIMETHYLOXAZOLIDINE-2-THIONE is known for its ability to react with various nucleophiles, serving as a versatile building block in organic chemistry. Additionally, 4,4-DIMETHYLOXAZOLIDINE-2-THIONE has been studied for its potential biological activities, including antimicrobial and anti-inflammatory properties. However, due to its potential toxicity and environmental impact, the use and handling of this chemical should be carefully regulated and controlled.

InChI:InChI=1/C5H9NOS/c1-5(2)3-7-4(8)6-5/h3H2,1-2H3,(H,6,8)

Upstream product

• 124-68-5 2-Amino-2-methyl-1-propanol 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 75-15-0 carbon disulfide 
• 927-82-2 2-amino-2-methylpropyl hydrogensulfate 

Downstream Products

• 53244-69-2 2-benzylsulfanyl-4,4-dimethyl-4,5-dihydro-oxazole 
• 53244-68-1 2-(methylthio)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 26654-39-7 4,4-dimethyl-1,3-oxazolidin-2-one 
• 86064-95-1 4,4-dimethyl-2-(phenylthio)-4,5-dihydrooxazole 
• 89940-95-4 2-(2-Mercapto-ethylamino)-4,4-dimethyl-2-oxazolin 
• 58396-22-8 2-(2-cyclohexyl-2-trimethylsilanyloxy-ethylsulfanyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 58396-20-6 4,4-dimethyl-2-(1-phenyl-ethylsulfanyl)-4,5-dihydro-oxazole 
• 100253-40-5 benzyl-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-amine 
• 100098-50-8 2-(3-bromobenzylthio)-4,4-dimethyl-2-oxazoline 

Relevant articles and documents

New Synthetic Route to Tucatinib

A new and improved synthetic route to tucatinib is described that involves three key intermediates. The first of these, 4-([1,2,4]triazolo[1,5- a ]pyridin-7-yloxy)-3-methylaniline, was prepared on a 100 g scale in 33percent yield over five steps and 99percent purity. Next, N 4 -(4-([1,2,4]triazolo[1,5- a ]pyridin-7-yloxy)-3-methylphenyl)quinazoline-4,6-diamine was isolated in 67percent yield over three steps and >99percent purity. Then, 4,4-dimethyl-2-(methylthio)-4,5-dihydrooxazole trifluoromethanesulfonate was prepared under mild conditions in 67percent yield over two steps. Finally, tucatinib was obtained in 17percent yield over nine steps and in >99percent purity (HPLC). Purification methods used to isolate the product and the intermediates involved in the route are also reported.

Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones

There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.

Synthesis and use of achiral oxazolidine-2-thiones in selective preparation of trans 2,5-disubstituted tetrahydrofurans

The use of achiral N-acetyloxazolidine-2-thiones in the C-glycosylation of lactol acetates has allowed us to prepare with high diastereoselectivity the expected trans 2,5-disubstituted tetrahydrofurans. A study based on the role of the steric hindrance of the N-acetyloxazolidine-2-thiones is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.