(S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate

Base Information

• Chemical Name: (S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate
• CAS No.: 40435-14-1
• Molecular Formula: C15H16O4S
• Molecular Weight: 292.356
• Hs Code.: 29062990
• DSSTox Substance ID: DTXSID30427145
• Nikkaji Number: J998.815G
• Wikidata: Q72501759
• Mol file: 40435-14-1.mol

Synonyms:40435-14-1;(S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate;(S)-2-Hydroxy-2-phenylethyl 4-methylbenzenesulfonate;[(2S)-2-hydroxy-2-phenylethyl] 4-methylbenzenesulfonate;(s)-(+)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate;(2S)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate;SCHEMBL1206501;DTXSID30427145;IOTJIFRGXYQHAQ-OAHLLOKOSA-N;(S)-2-(Tosyloxy)-1-phenylethanol;MFCD00013428;AKOS015889475;CS-W012179;DS-13645;(S)-1-phenyl-1,2-ethanediol 2-tosylate;(s)-1-phenyl-2-(p-tolylsulfonyloxy)ethanol;(s)-2-phenyl-2-hydroxyethyl p-toluenesulfonate;(S)-(+)-1-Phenyl-1,2-ethanediol 2 -tosylate;A873340;(S)-2-Hydroxy-2-phenylethyl4-methylbenzenesulfonate;(S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate, 98%

Chemical Property of (S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate

Chemical Property:

• Vapor Pressure: 4.77E-10mmHg at 25°C
• Melting Point: 74-76 °C(lit.)
• Refractive Index: 1.59
• Boiling Point: 480.6°Cat760mmHg
• PKA: 12.95±0.20(Predicted)
• Flash Point: 244.5°C
• PSA: 71.98000
• Density: 1.274g/cm³
• LogP: 3.51470
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 292.07693016
• Heavy Atom Count: 20
• Complexity: 373

Purity/Quality:

99% ^*data from raw suppliers

(S)-(+)-1-Phenylethane-1,2-diol2-tosylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC(C2=CC=CC=C2)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H](C2=CC=CC=C2)O
• Uses: (S)-(+)-1-Phenylethane-1,2-diol 2-tosylate is an intermediate in the synthesis of (S)-Mirabegron (M364895), which is an impurity of Mirabegron (M364900). Mirabegron is a potent bladder relaxant and reagent for diabetes remedy.

Technology Process of (S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate

There total 35 articles about (S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate 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: 99.0%

phenylethane 1,2-diol (93-56-1) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 2-hydroxy-2-phenylethyl ester (40434-87-5,40435-14-1,127911-68-6,40348-74-1)

Guidance literature:

With triethylamine; di(n-butyl)tin oxide; In dichloromethane; at 20 ℃; for 0.833333h;

DOI:10.1021/ja016031r

Reference yield: 99.0%

1-phenyl-2-(p-tolylsulfonyloxy)ethanone (7257-94-5) → (S)-1-phenyl-2-(tosyloxy)ethanol (40435-14-1)

Guidance literature:

With borane N-ethyl-N-isopropylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 25 ℃; for 0.166667h;

DOI:10.1039/b010155i

Reference yield: 99.0%

(S)-1-phenyl-1,2-ethanediol (25779-13-9) + p-toluenesulfonyl chloride (98-59-9) → (S)-1-phenyl-2-(tosyloxy)ethanol (40435-14-1)

Guidance literature:

With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1016/j.tetasy.2004.11.005

upstream raw materials:

styrene oxide

toluene-4-sulfonic acid

phenylethane 1,2-diol

p-toluenesulfonyl chloride

Downstream raw materials:

Acetic acid (S)-1-phenyl-2-(toluene-4-sulfonyloxy)-ethyl ester

(S)-2-azido-1-phenylethanol

(S)-1-phenylethanol

(R)-1-phenylethanol

Refernces

• 1、 Dong, Hai,Liu, Yu,Lv, Jian,Zhu, Jia-Jia. "Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study". . p. 3307 - 3319. Retrieved 2020/03/25.
• 2、 Pasquinucci, Lorella,Turnaturi, Rita,Prezzavento, Orazio,Arena, Emanuela,Aricò, Giuseppina,Georgoussi, Zafiroula,Parenti, Rosalba,Cantarella, Giuseppina,Parenti, Carmela. "Development of novel LP1-based analogues with enhanced delta opioid receptor profile". . p. 4745 - 4752. Retrieved 2017/10/05.