CHLORAMPHENICOL

Base Information

• Chemical Name: CHLORAMPHENICOL
• CAS No.: 2787-09-9
• Molecular Formula: C₁₁H₁₂Cl₂N₂O₅
• Molecular Weight: 323.133
• Hs Code.: 2941400000
• Mol file: 2787-09-9.mol

Synonyms:Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, (R*,R*)-(?à)-;Acetamide, 2,2-dichloro-N-[b-hydroxy-a-(hydroxymethyl)-p-nitrophenethyl]-,DL-threo- (8CI);(?à)-Chloramphenicol;Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, (R*,R*)-;DL-Chloramphenicol;DL-trans-1-p-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol;Synthomycin;

Chemical Property of CHLORAMPHENICOL

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 148-150 °C(lit.)
• Boiling Point: 644.913 °C at 760 mmHg
• PKA: 11.03±0.46(Predicted)
• Flash Point: 343.831 °C
• PSA: 115.38000
• Density: 1.547 g/cm³
• LogP: 1.82310
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

DL-Chloramphenicol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: DL-Chloramphenicol is an antibiotic drug.

Technology Process of CHLORAMPHENICOL

There total 65 articles about CHLORAMPHENICOL 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: 79.0%

(2RS,3SR)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (100381-03-1) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/ol901784m

Reference yield:

chloramphenicol (26367-75-9) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01145a523

Reference yield:

(+/-)-threo-2-amino-1-phenyl-1,3-propanediol (3306-06-7,5285-86-9,28143-91-1,36391-67-0,36391-68-1,46032-98-8,55057-81-3,105452-39-9,119364-52-2) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

Multi-step reaction with 5 steps

2: pyridine

3: amidosulfuric acid; nitric acid

4: aqueous hydrochloric acid

With pyridine; hydrogenchloride; aminosulfonic acid; nitric acid;

DOI:10.1021/ja01175a066

upstream raw materials:

3,3,3-trichloro-2-hydroxy-propionitrile

(+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol

dichloroacetic acid methyl ester

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

Downstream raw materials:

chloramphenicol

L-threo-chloramphenicol

dichloroacetic acid-[4t-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide]

dichloroacetic acid-[4c-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide]

Refernces

• 1、 Singjunla, Yuttapong,Baudoux, Jeroime,Rouden, Jacques. "Direct synthesis of β-hydroxy-α-amino acids via diastereoselective decarboxylative aldol reaction". . p. 5770 - 5773. Retrieved 2013/12/04.
• 2、 Hazra, Braja G.,Pore, Vandana S.,Maybhate, Shailaja P.. "Synthesis of chloramphenicol via a new intermediate 4-para-nitrophenyl- 5-formamido-1,3-dioxane". . p. 1857 - 1864. Retrieved 2007/10/03.