16854-32-3

Basic information

• Product Name: (1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL
• Synonyms: 2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol;L-THIOMICAMINE;(1S,2S)-(+)-THIOMICAMINE;(1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL;[S(R*,R*)]-2-amino-1-[p-(methylthio)phenyl]propane-1,3-diol;thiomicamine;(1S,2S)-1-[4-(Methylthio)phenyl]-2-amino-1,3-propanediol;(1S,2S)-1-[4-(Methylthio)phenyl]-2-aminopropane-1,3-diol
• CAS NO: 16854-32-3
• Molecular Formula: C₁₀H₁₅NO₂S
• Molecular Weight: 213.3
• EINECS: 240-878-4
• Mol File: 16854-32-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 151-154 °C(lit.)
• Boiling Point: 428.2°Cat760mmHg
• Flash Point: 212.8°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 4.29E-08mmHg at 25°C
• Refractive Index: 1.624
• PKA: 11.75±0.45(Predicted)
• CAS DataBase Reference: (1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL(16854-32-3)
• EPA Substance Registry System: (1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL(16854-32-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 16854-32-3(Hazardous Substances Data)

Usage

Description

(1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL, also known as (1S,2S)-(+)-Thiomicamine, is an organic compound with a unique structure that features a chiral center and a methylthio group. It is characterized by its optical activity and is a valuable building block in the synthesis of various biologically active molecules.

Uses

(1S,2S)-(+)-Thiomicamine is used as a starting material in the synthesis of 3,4-dihydroisoquinolinium salts, which are employed as promoters in asymmetric epoxidation and oxidation reactions. These reactions are crucial in the production of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of drugs with specific therapeutic effects.
Used in Pharmaceutical Industry:
(1S,2S)-(+)-Thiomicamine is used as a starting material in the synthesis of an α-amino acid named (3R,4R)-4-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. This α-amino acid is used to prepare modified peptides of biological importance, which can have potential applications in the development of new drugs and therapies.
Used in Chiral Resolution:
(1S,2S)-(+)-Thiomicamine is used as a chiral base in the resolution of an angiotensin II type 2 receptor (AT2R) antagonist named EMA401. The resolution of chiral compounds is an important process in the pharmaceutical industry, as it allows for the separation of enantiomers with different biological activities, leading to more effective and safer drugs.

InChI:InChI=1/C10H15NO2S/c1-14-8-4-2-7(3-5-8)10(13)9(11)6-12/h2-5,9-10,12-13H,6,11H2,1H3/t9-,10-/m0/s1

Upstream product

• 14172-52-2 (1RS,2RS)-2-amino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 14052-59-6 D-threo-1-p-methylmercaptophenyl-2-dichloroacetamidopropane-1,3-diol 
• 119293-92-4 (+/-)-2-dichloroacetamido-β-hydroxy-4-methylmercaptopropiophenone 
• 23150-33-6 (1RS,2RS)-2-acetylamino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 38423-42-6 N-[1-hydroxymethyl-2-(4-methylsulfanyl-phenyl)-2-oxo-ethyl]-acetamide 
• 135266-97-6 (2RS,3SR)-2-amino-3-hydroxy-3-(4-methylsulfanyl-phenyl)-propionic acid ethyl ester 
• 122934-51-4 (4-Methylsulfanyl-phenyl)-(2-phenyl-4,5-dihydro-oxazol-4-yl)-methanone 
• 122934-50-3 (S)-(4-Methylsulfanyl-phenyl)-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methanol 
• 122934-50-3 (S)-(4-Methylsulfanyl-phenyl)-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methanol 
• 95448-24-1 (1S,2S)-threo-2-benzamido-1-(4-methylthiophenyl)-1,3-propanediol 

Downstream Products

• 4302-89-0 (1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 23150-35-8 (R*,R*)-(+)-thiomicamine 
• 71830-03-0 (1S,2S)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 122934-50-3 (R)-(4-Methylsulfanyl-phenyl)-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methanol 
• 95448-24-1 (1S,2S)-threo-2-benzamido-1-(4-methylthiophenyl)-1,3-propanediol 
• 135204-38-5 (4S,5S)-5-(4-methylthiophenyl)-4-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine 
• 210292-02-7 [(4S,5S)-5-(4-Methylsulfanyl-phenyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-methanol 
• 696659-62-8 (1S,2S)-2-o-toluamide-1-[4-(methylthio)phenyl]-1,3-propanediol 
• 203576-39-0 (4S,5S)-4-hydroxymethyl-2-methyl-5-[4-(methylthio)phenyl]-2-oxazoline 
• 906548-44-5 (1S,2S)-(+)-2-(dimethylamino)-1-[4-(methylthio)phenyl]propane-1,3-diol 
• 914477-56-8 (4S,5S)-4-hydroxymethyl-5-(4-methylsulfanylphenyl)-2-tert-butyl-oxazoline 
• 914477-57-9 (4S,5S)-2-methyl-4-mesyloxymethyl-5-(4-methylsulfanylphenyl)-oxazoline 

Relevant articles and documents

NEW STRATEGY FOR RACEMIZATION OF 2-AMINO-1,3-PROPANEDIOLS, KEY INTERMEDIATES FOR THE SYNTHESIS OF ANTIBIOTIC DRUGS

A new strategy for racemization of the 2-amino-1,3-propanediol 2b, based on a chemoselective oxazoline ring formation and a highly diastereoselective reduction of the ketone 4 is reported.