84272-19-5

Basic information

• Product Name: (4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98
• Synonyms: (4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98;4-Isopropyl-1,3-oxazolidine-2-thione;(4S)-4-Isopropyloxazolidine-2-thione;[4S,(-)]-4-Isopropyloxazolidine-2-thione;4β-Isopropyloxazolidine-2-thione
• CAS NO: 84272-19-5
• Molecular Formula: C₆H₁₁NOS
• Molecular Weight: 145.22264
• Mol File: 84272-19-5.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98(84272-19-5)
• EPA Substance Registry System: (4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98(84272-19-5)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 84272-19-5(Hazardous Substances Data)

Usage

Description

(4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98 is a chiral chemical compound that is widely utilized in the organic synthesis and pharmaceutical industry. It features a thione and oxazolidine functional groups and exists as a clear liquid at room temperature. Known for its role as a chiral building block in asymmetric synthesis, this compound is frequently employed in the production of pharmaceutical drugs. It has also garnered interest for its potential antiviral and antibacterial properties, making it a significant compound in medicinal chemistry research. However, it is crucial to handle this chemical with caution, as it is classified as hazardous and should only be used by trained professionals in a controlled environment.

Uses

Used in Pharmaceutical Industry:
(4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98 is used as a chiral building block for the asymmetric synthesis of pharmaceutical drugs. Its unique structure allows for the creation of various drug candidates with improved efficacy and selectivity.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98 is used for studying its potential antiviral and antibacterial properties. This research could lead to the development of new treatments for various infectious diseases.
Used in Organic Synthesis:
(4S)-(-)-4-ISOPROPYL-1,3-OXAZOLIDINE-2-THIONE, 98 is employed as a key intermediate in organic synthesis, enabling the production of a range of complex molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 75-15-0 carbon disulfide 
• 2026-48-4 (S)-valinol 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 750647-29-1 (S)-N-[3-phenyl-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-46-2 (S)-N-[(3R)-3-phenyl-3-mercaptobutanoyl]-4-isopropyloxazolidin-2-one 
• 750647-32-6 (S)-N-[3-(4-bromophenyl)-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-49-5 (S)-N-[(3R)-3-(4-bromophenyl)-3-mercaptobutanoyl]-4-isopropyloxazolidin-2-one 
• 350611-02-8 (S)-N-[2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 350611-03-9 (S)-N-[2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 350611-04-0 (S)-N-[4-methyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 599164-44-0 (S)-N-[(3R)-3-mercaptobutanoyl]-4-isopropyloxazolidin-2-one 
• 350611-17-5 (S)-N-[(3R)-3-mercaptopentanoyl]-4-isopropyloxazolidin-2-one 
• 350611-18-6 (S)-N-[(3S)-3-mercapto-4-methyl-pentanoyl]-4-isopropyloxazolidin-2-one 
• 463-71-8 thiophosgene 

Downstream Products

• 104499-12-9 (R)-3,3,3-Trifluoro-1-((R)-4-isopropyl-2-thioxo-oxazolidin-3-yl)-2-methoxy-2-phenyl-propan-1-one 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 113023-57-7 (S)-1-(4-isopropyl-2-thioxooxazolidin-3-yl)propan-1-one 
• 750647-29-1 (S)-N-[3-phenyl-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-37-1 (S)-N-[3-phenyl-2-(E)-pentenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-31-5 (S)-N-[3-(4-chlorophenyl)-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-33-7 (S)-N-[3-(4-methoxyphenyl)-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-34-8 (S)-N-[3-(3-methoxyphenyl)-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-32-6 (S)-N-[3-(4-bromophenyl)-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-35-9 (S)-N-[3-(4-cyanophenyl)-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-36-0 (S)-N-[3-(4-nitrophenyl)-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 918287-61-3 (S)-N-[3-phenyl-2-(Z)-heptenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 750647-38-2 (S)-N-[3-phenyl-2-(E)-heptenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 350611-05-1 (S)-N-[3-(4-chloro)phenyl-2-(E)-propenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 

Relevant articles and documents

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.

Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction

An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.

N-(diazoacetyl)oxazolidin-2-thiones as sulfur-donor reagents: Asymmetric synthesis of thiiranes from aldehydes

Sulfur tyranny: Thiiranes, instead of oxiranes, can be obtained in a highly stereoselective manner through the cycloaddition reaction of N-acyl oxazolidine tethered diazo thione compounds with aldehydes catalyzed by RhII. Thus, this reaction provides versatile adducts S functionalized at both the α and β position, with concomitant generation of two contiguous stereocenters. Copyright