(S)-(+)-2-(p-toluenesulfonate)-1,2-Propaniol

Base Information

• Chemical Name: (S)-(+)-2-(p-toluenesulfonate)-1,2-Propaniol
• CAS No.: 96882-98-3
• Molecular Formula: C10H14 O4 S
• Molecular Weight: 230.285
• Hs Code.: 2905399090
• DSSTox Substance ID: DTXSID00446883
• Wikidata: Q82265623
• Mol file: 96882-98-3.mol

Synonyms:96882-98-3;(S)-(+)-2-(p-toluenesulfonate)-1,2-Propaniol;[(2S)-1-hydroxypropan-2-yl] 4-methylbenzenesulfonate;SCHEMBL8356278;DTXSID00446883;AKOS015961535;AC-14038;(R)-(-)-2-(p-toluenesulfonate)-1,2-Propaniol;(S)-1-hydroxypropan-2-yl 4-methylbenzenesulfonate;1,2-Propanediol,2-(4-methylbenzenesulfonate),(S)-(9ci)

Chemical Property of (S)-(+)-2-(p-toluenesulfonate)-1,2-Propaniol

Chemical Property:

• Vapor Pressure: 1.95E-06mmHg at 25°C
• Boiling Point: 379.5°Cat760mmHg
• Flash Point: 183.3°C
• PSA: 71.98000
• Density: 1.246g/cm³
• LogP: 2.16190
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 230.06128010
• Heavy Atom Count: 15
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

(S)-(+)-2-(PARA-TOLUENESULFONATE)-1,2-PROPANEDIOL 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC(C)CO
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@@H](C)CO

Technology Process of (S)-(+)-2-(p-toluenesulfonate)-1,2-Propaniol

There total 3 articles about (S)-(+)-2-(p-toluenesulfonate)-1,2-Propaniol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate (57057-80-4) → (S)-1,2-propanediol 2-tosylate (96882-98-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -5 ℃;

DOI:10.1055/s-0028-1088015

Reference yield:

ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate (33798-77-5) → (S)-1,2-propanediol 2-tosylate (96882-98-3)

Guidance literature:

With borane-THF; In tetrahydrofuran; Yield given; 1.) RT, 5 d, 2.) 40 to 50 deg C, 1 d;

DOI:10.1016/S0040-4020(01)96497-X

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (S)-1,2-propanediol 2-tosylate (96882-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95.5 percent / pyridine / 1.) -10 to -5 deg C, 1 h, 2.) 7 deg C

2: BH₃*THF / tetrahydrofuran / 1.) RT, 5 d, 2.) 40 to 50 deg C, 1 d

With pyridine; borane-THF; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)96497-X

upstream raw materials:

ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate

p-toluenesulfonyl chloride

ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate

Downstream raw materials:

(R)-1,2-propylene carbonate

(R)-propylene oxide

2(R)-methyl-3-phenylsulfonyl-1,5(R)-hexanediol-1-THP ether

Refernces

• 1、 Mori, Kenji,Senda, Shuji. "SYNTHESIS OF THE ENANTIOMERS OF CIS-2-METHYL-5-HEXANOLIDE, THE MAJOR COMPONENT OF THE SEX PHEROMONE OF THE CARPENTER BEE". . p. 541 - 546. Retrieved 2007/10/02.