(S)-Guaifenesin

Base Information

• Chemical Name: (S)-Guaifenesin
• CAS No.: 61248-76-8
• Molecular Formula: C10H14O4
• Molecular Weight: 198.219
• Mol file: 61248-76-8.mol

Synonyms:(S)-3-(2-Methoxyphenoxy)-1,2-propanediol;(S)-Guaifenesin;1,2-Propanediol, 3-(2-methoxyphenoxy)-, (2S)-;1,2-Propanediol, 3-(2-methoxyphenoxy)-, (S)-

Chemical Property of (S)-Guaifenesin

Chemical Property:

• Melting Point: 97 - 99 °C
• PSA: 58.92000
• LogP: 0.42720

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-Guaifenesin

There total 21 articles about (S)-Guaifenesin 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: 97.0%

2-methoxy-phenol (90-05-1) + (S)-oxiranemethanol (60456-23-7) → (S)-guaifenesin (61248-76-8)

Guidance literature:

With triethylamine; In ethanol; acetone;

Reference yield: 91.0%

(S)-1-hydroxy-3-(2-methoxyphenoxy)propan-2-yl acetate → (S)-guaifenesin (61248-76-8)

Guidance literature:

With water; potassium carbonate; In methanol; at 25 - 30 ℃; for 2h;

DOI:10.1002/chir.22574

Reference yield: 90.0%

3-(2-methoxyphenoxy)-1-O-(β-D-glucopyranosyl)propane-1,2-diol → (R)-guaifenesin (61248-75-7) + (S)-guaifenesin (61248-76-8)

Guidance literature:

With sulfuric acid; at 90 ℃; for 3h;

DOI:10.1055/s-2003-42437

upstream raw materials:

O-allyl guaiacol

1,2-di-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol

1-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol

acetic anhydride

Downstream raw materials:

(R)-(+)-Methylsulfamic acid 3-(2-methoxyphenoxy)-2-[[(methylamino)sulfonyl]-oxy]propyl ester

(R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2-oxide

(2S)-1-(isopropylamino)-3-(2-methoxyphenoxy)propan-2-ol

(R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2,2-dioxide

Refernces

• 1、 Ghosh, Saptarshi,Bhaumik, Jayeeta,Banoth, Linga,Banesh, Sooram,Banerjee, Uttam Chand. "Chemoenzymatic Route for the Synthesis of (S)-Moprolol, a Potential β-Blocker". . p. 313 - 318. Retrieved 2016/03/19.
• 2、 Hadimani, Mallinath B.,Purohit, Meena K.,Vanampally, Chandrashaker,Van Der Ploeg, Randy,Arballo, Victor,Morrow, Dwane,Frizzi, Katie E.,Calcutt, Nigel A.,Fernyhough, Paul,Kotra, Lakshmi P.. "Guaifenesin derivatives promote neurite outgrowth and protect diabetic mice from neuropathy". . p. 5071 - 5078. Retrieved 2013/07/26.