Florfenicol

Base Information

• Chemical Name: Florfenicol
• CAS No.: 73231-34-2
• Deprecated CAS: 76639-94-6,81588-76-3
• Molecular Formula: C12H14Cl2FNO4S
• Molecular Weight: 358.218
• Hs Code.: 29419090
• European Community (EC) Number: 620-107-1,642-986-0
• UNII: 9J97307Y1H
• DSSTox Substance ID: DTXSID9045500
• Nikkaji Number: J128.612I
• Wikipedia: Florfenicol
• Wikidata: Q408400
• NCI Thesaurus Code: C75146
• RXCUI: 25086
• Metabolomics Workbench ID: 152615
• ChEMBL ID: CHEMBL1241590
• Mol file: 73231-34-2.mol

Synonyms:3-fluorothiamphenicol;chloramphen;florfenicol;florphenicol;Sch 25298;Sch-25298;thiamphenicol, 3-fluoro

Chemical Property of Florfenicol

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 4.05E-12mmHg at 25°C
• Melting Point: 153 °C
• Refractive Index: 1.575
• Boiling Point: 617.5 °C at 760 mmHg
• PKA: 10.73±0.46(Predicted)
• Flash Point: 327.3 °C
• PSA: 91.85000
• Density: 1.451 g/cm³
• LogP: 2.70550
• Storage Temp.: 0-6°C
• Solubility.: Soluble in ethanol to 25mM and in DMSO to 100mM
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 357.0004627
• Heavy Atom Count: 21
• Complexity: 447

Purity/Quality:

99%min ^*data from raw suppliers

Florfenicol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CS(=O)(=O)C1=CC=C(C=C1)C(C(CF)NC(=O)C(Cl)Cl)O
• Isomeric SMILES: CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CF)NC(=O)C(Cl)Cl)O
• Indications: Florfenicol can strongly interfere with the bacterial protein synthesis. It has a rapid absorption rate and is widely distributed in the body; it has long half-life without side effects such as aplastic anemia; not easy for bacteria to evolve drug resistance, and has no cross-resistance. Florfenicol can be used for the treatment of the systemic infection of livestock and aquatic animals, and has significant efficacy on treating respiratory infections and intestinal infections. Poultry: Escherichia coli disease, salmonellosis, infectious rhinitis, chronic respiratory disease, duck plague and other kinds of mixed infections caused by susceptible strains. Animals: Mixed infections such as infectious pleurisy, asthma, streptococcal disease, Escherichia coli disease, salmonellosis, contagious pleuropneumonia, enzootic pneumonia, paratyphoid piglets yellow white diarrhea, edema disease, atrophic rhinitis, lung epidemic, red white diarrhea piglets, and agalactia syndrome occurred in animals such as pigs, cows, and sheep. Crab: appendages ulcer disease, yellow gills, rotten gill, red legs and red fluorescent body inflammatory disease syndrome. Turtle: red neck disease, furunculosis, shot-hole disease, skin fester disease, inflammatory bowel disease, mumps, and bacterial sepsis. Frogs: cataract syndrome, ascites disease, sepsis, enteritis. Fish: enteritis disease, ascites disease, vibriosis, Edward coli disease. Eel: debonding septicemia (unique effect), Edward coli disease, red skin disease, inflammatory bowel disease.
• Uses: It is a kind of antibacterial drug. It is used as the veterinary antimicrobial drugs for treating bacterial diseases of pigs, chickens and fish. It has good efficacy in treating the infection disease of pigs, chickens and fish induced by sensitive bacteria, especially for treating respiratory infections and intestinal infections. Florfenicol is a fluorinated derivative of thiamphenicol. It is a protein synthesis inhibitor that inhibits bacterial protein synthesis by binding to ribosome 50S and 70S subunits. Florfenicol is used as an antibacterial.
• Description: Florfenicol is a broad-spectrum fluorinated antibiotic and a derivative of thiamphenicol . It is active against human clinical isolates of enteric bacteria, including E. coli, Klebsiella, Enterobacter, Citrobacter, P. mirabilis, and Salmonella (MIC50s = 6.3-12.5 μg/ml). Florfenicol is also active against clinical isolates of various bovine and porcine respiratory tract pathogens, including P. multocida, A. pleuropneumoniae, and B. bronchiseptica (MIC50s = 0.25-4 μg/ml). It inhibits peptidyl transferase activity in 70S ribosomes isolated from E. coli when used at a concentration of 1 mM. Formulations containing florfenicol have been used in the treatment of infectious respiratory disease in cattle.

Technology Process of Florfenicol

There total 127 articles about Florfenicol 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: 96.0%

dichloroacetic acid methyl ester (116-54-1) + (1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol (76639-93-5,105182-37-4,118015-48-8) → Florfenicol (73231-34-2)

Guidance literature:

With triethylamine; In methanol; at 20 ℃;

Reference yield: 96.0%

(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol (895571-10-5) + ethyl 1,1-dichloroacetate (535-15-9) → Florfenicol (73231-34-2)

Guidance literature:

(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol; With sulfuric acid; hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 2h;

ethyl 1,1-dichloroacetate; With triethylamine; In methanol; at 30 ℃; for 6h; Further stages.;

DOI:10.1016/j.tet.2008.05.113

Reference yield: 95.0%

C12H12Cl2FNO3S → Florfenicol (73231-34-2)

Guidance literature:

With methanol; sodium acetate; at 60 ℃; for 1h; Reagent/catalyst;

upstream raw materials:

dichloroacetic acid methyl ester

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

(1R,2S)-2-(2,3-dimethylbenzoyl)amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

Downstream raw materials:

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

C₁₂H₁₃BrCl₂FNO₃S

sodium 4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoate

methanesulfonic acid

Refernces

• 1、 -. "METHODS FOR PREPARING FLORFENIOL AND INTERMEDIATE THEREOF". . . Retrieved 2021/07/02.
• 2、 -. "Method for continuously preparing florfenicol based on micro-reaction system". Paragraph 0053-0054; 0057-0061; 0065-0068; 0072-0075; .... . Retrieved 2021/07/24.