racefenicol

Base Information

• Chemical Name: racefenicol
• CAS No.: 847-25-6
• Molecular Formula: C₁₂H₁₅Cl₂NO₅S
• Molecular Weight: 356.227
• Mol file: 847-25-6.mol

Synonyms:Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-,(R*,R*)-(?à)-; Acetamide, 2,2-dichloro-N-[b-hydroxy-a-(hydroxymethyl)-p-(methylsulfonyl)phenethyl]-,threo-(?à)- (8CI); (?à)-Thiamphenicol; (?à)-threo-2,2-Dichloro-N-[b-hydroxy-a-(hydroxymethyl)-p-(methylsulfonyl)phenethyl]acetamide;Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-,(R*,R*)-; Dexawin; Racefenicol; Raceophenidol; Racephenicol; dl-Thiamphenicol;dl-threo-2-Dichloroacetamido-1-(4-methylsulfonyl-phenyl)-1-3-propanediol

Chemical Property of racefenicol

Chemical Property:

• Vapor Pressure: 2.5E-20mmHg at 25°C
• Boiling Point: 695.9°C at 760 mmHg
• Flash Point: 374.7°C
• PSA: 112.08000
• Density: 1.491g/cm³
• LogP: 1.87600

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Antibacterial.

Technology Process of racefenicol

There total 15 articles about racefenicol 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:

(1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol (4302-89-0,6631-50-1,13185-24-5,14052-59-6,27348-37-4,27348-49-8,27348-50-1,71830-03-0) → (+/-)-Thiamphenicol (847-25-6,7780-07-6,15318-45-3,19934-71-5,21079-44-7,27348-38-5,27348-52-3,90-91-5)

Guidance literature:

With peracetic acid;

DOI:10.1021/ja01141a074

Reference yield:

→ (+/-)-Thiamphenicol (847-25-6,7780-07-6,15318-45-3,19934-71-5,21079-44-7,27348-38-5,27348-52-3,90-91-5)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01113a057

Reference yield:

N-(4-methanesulfonyl-phenacyl)-acetamide (56739-66-3) → (+/-)-Thiamphenicol (847-25-6,7780-07-6,15318-45-3,19934-71-5,21079-44-7,27348-38-5,27348-52-3,90-91-5)

Guidance literature:

Multi-step reaction with 4 steps

1: aq.-ethanolic NaHCO₃

2: aluminium isopropylate; isopropyl alcohol

3: aqueous HCl

With hydrogenchloride; aluminum isopropoxide; sodium hydrogencarbonate; isopropyl alcohol;

DOI:10.1021/ja01113a057

upstream raw materials:

dichloroacetic acid methyl ester

(1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol

pentachloroacetone

dichloroacetyl-phosphorous acid diethyl ester

Downstream raw materials:

(1S,2S)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol

(1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol

Refernces