76639-93-5

Basic information

• Product Name: Sch 40458
• Synonyms: Sch 40458;florfenicol amine;(αR)-α-[(1S)-1-Amino-2-fluoroethyl]-4-(methylsulfonyl)benzenemethanol;D-(?)-threo-2-Amino-3-fluoro-1-[4-(methylsulfonyl)phenyl]-1-propanol
• CAS NO: 76639-93-5
• Molecular Formula: C10H14FNO3S
• Molecular Weight: 247.2864632
• Mol File: 76639-93-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 654.3°C at 760 mmHg
• Flash Point: 349.5°C
• Appearance: /
• Density: 1.313±0.06 g/cm3(Predicted)
• Vapor Pressure: 5.17E-18mmHg at 25°C
• PKA: 10.90±0.45(Predicted)
• CAS DataBase Reference: Sch 40458(CAS DataBase Reference)
• NIST Chemistry Reference: Sch 40458(76639-93-5)
• EPA Substance Registry System: Sch 40458(76639-93-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 76639-93-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 76639-93-5 differently. You can refer to the following data:
1. Florfenicol amine is the 4-methylsulphonophenylpropylamine parent compound formed by hydrolysing the dichloroacetamide of florfenicol. Florfenicol amine is a metabolite and degradation product of flofenicol. Florfenicol amine has no antibiotic activity but is an important standard for monitoring animal and environmental residues of florfenicol.
2. Florfenicol Amine is a metabolite of Florfenicol; Florfenicol is an antibacterial agent. It is also used in the treatment of respiratory diseases in cattles.

InChI:InChI=1/C12H14Cl2FNO4S.H3N/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14;/h2-5,9-11,17H,6H2,1H3,(H,16,18);1H3/t9-,10-;/m1./s1

Upstream product

• 126428-97-5 D-(-)-threo-2-phenyl-4-(fluoromethyl)-5-(4-(methylsulfonyl)phenyl)-2-oxazoline 
• 23150-35-8 (R*,R*)-(+)-thiomicamine 
• 51458-28-7 (1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol 
• 96795-00-5 D-threo-4,5-dihydro-5-(4-methylsulphonylphenyl)-2-phenyl-4-oxazolemethanol 
• 73231-34-2 Florfenicol 
• 849419-84-7 (4S,5R)-3-acetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine 
• 929115-19-5 (4S,5R)-3-propionyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine 
• 1284258-89-4 (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate 
• 1284258-90-7 ((2S,3S)-1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridin-2-yl)methanol 
• 1308663-57-1 (2S,3S)-1-benzhydryl-2-(fluoromethyl)-3-(4-(methylsulfonyl)phenyl)aziridine 
• 1308663-62-8 (1R,2S)-2-(benzhydrylamino)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propan-1-ol 
• 1284258-88-3 N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine 
• 5398-77-6 para-methanesulfonylbenzaldehyde 
• 1373543-41-9 ethyl (2S,3S)-3-hydroxy-2-[(4-methoxybenzoyl)amino]-3-[4-(methylsulfonyl)phenyl]propanoate 

Downstream Products

• 864527-07-1 C₁₀H₁₂FN₃O₃S 
• 73231-34-2 Florfenicol 
• 1431545-23-1 C₁₇H₁₈FNO₆S 
• 138872-74-9 C₁₄H₂₀FNO₄S 

Relevant articles and documents

Method for synthesis of florfenicol

The invention discloses a method for synthesis of florfenicol and belongs to the technical field of medicine synthesis. 1-R1-2-(R)-4- methylsulfino phenyl formyl aziridine is dissolved in solvent to react with sterically hindered reductant to form chiral alkamine compound 1 with a single configuration; compound 1 is heated and reacts with triethylamine hydrofluoride in the solvent to form (1R, 2S)-3-fluoride-1-4-(methylsulfino phenyl)-2-(R1-amido)-1-propyl alcohol; (1R, 2S)-3-fluoride-1-4-(methylsulfino phenyl)-2-(R1-amido)-1-propyl alcohol has the blocking group taken away in the solvent to form (1R 2S)-2-amido-3-fluoride-1-4-methylsulfino phenyl-1-propyl alcohol; florfenicol can then be obtained through dichloro-acetylation reaction of (1R, 2S)-2-amido-3-fluoride-1-4-methylsulfino phenyl-1-propyl alcohol.

FLORFENICOL SYNTHESIZING METHOD

The present invention discloses a new florfenicol synthesizing method. The method synthesizes florfenicol products meeting requirements of the Drug Administration by a series of combinations of cyclization, selective reduction, fluorinated open ring, deprotection and acylation, hydroxyl sulfoacid esterified configuration converting reaction, hydrolysis reaction and the like. The synthesizing method of the present invention utilizing chiral amine closed-ring aziridine three-membered ring uses a physical separation method to repeatedly purify chiral aminoketone of high yield obtaining single R configuration, and uses selective reduction and converts the configuration to obtain florfenicol, greatly improving atom economy, while avoiding waste water pollution caused by the existing process, and greatly reducing costs for treating waste water and reducing pollution to the environment, thus lowering costs and simplifying the process. In addition, the present invention uses triethylamine hydrofluoride as a fluorinated open-ring reagent, to improve safety of a liquid reaction compared to a gas reaction and reduce corrosion of equipment, facilitating industrial production.

Chlorination of florfenicol (FF): reaction kinetics, influencing factors and by-products formation

Florfenicol (FF) is a widely used antibiotic, which is commonly found in natural waters. In this study, we investigated the removal fate of FF in two different drinking water treatment plants (DWTPs), which suggest that FF was easily transformed by free available chlorine (FAC) and the potential reactions of FF with FAC was the focus of this study. The oxidation kinetics of FF by FAC (7 × 10?4 mol) are very rapid with large pseudo-first-order rate constants kobs = 0.31 min?1, while FF (5 mg L?1) can be completely transformed in 30 min. The results showed that high Cl? (the dominant seawater constituent), Br?, and lower humic acid (HA, main constituents in freshwater) favor the FF oxidation. 21 degradation products were identified by liquid chromatography-tandems mass spectrometry (LC-MS/MS) and the possible routes for FF chlorination were proposed. These results are of importance toward the goal of assessing the persistence of FF in water chlorination.