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| CAS No.: | 73231-34-2 |
|---|---|
| Name: | Florfenicol |
| Molecular Structure: | |
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|
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| Formula: | C12H14Cl2FNO4S |
| Molecular Weight: | 358.218 |
| Synonyms: | Acetamide,2,2-dichloro-N-[1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]-,[R-(R*,S*)]-;(-)-Florfenicol;Aquafen;Aquaflor;Floron;Nuflor;Sch 25298;Florfeniol; |
| EINECS: | 642-986-0 |
| Density: | 1.451 g/cm3 |
| Melting Point: | 153 °C |
| Boiling Point: | 617.5 °C at 760 mmHg |
| Flash Point: | 327.3 °C |
| Appearance: | White crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 91.85000 |
| LogP: | 2.70550 |
(4S,5R)-2-dichloromethyl-4-fluoromethyl-4,5-dihydro-5-(4-(methylsulfonyl)phenyl)oxazoline
Florfenicol
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; isopropyl alcohol at 70℃; for 5h; pH=6; | 99% |
| With potassium acetate In methanol; water; isopropyl alcohol for 3h; Heating; pH 5; Yield given; | |
| With ammonium hydroxide; water at 25℃; | |
| With sodium acetate In water; isopropyl alcohol for 3h; pH=5; Reflux; | 4.15 g |
| In water; isopropyl alcohol at 80℃; for 1h; | 9.2 g |
dichloroacetic acid methyl ester
(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
Florfenicol
| Conditions | Yield |
|---|---|
| With triethylamine In methanol at 20℃; | 96% |
| With triethylamine In methanol for 18h; Ambient temperature; | 84% |
| With triethylamine for 3.5h; Heating; Yield given; |
(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol
ethyl 1,1-dichloroacetate
Florfenicol
| Conditions | Yield |
|---|---|
| Stage #1: (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; Stage #2: ethyl 1,1-dichloroacetate With triethylamine In methanol at 30℃; for 6h; Further stages.; | 96% |
dichloroacetic acid methyl ester
Florfenicol
| Conditions | Yield |
|---|---|
| With triethylamine In methanol Heating; | 95% |
| With sodium hydrogencarbonate In methanol at 50℃; for 16h; | 5.6 g |
| With triethylamine In methanol at 50℃; for 10h; | 7.1 g |
Florfenicol
| Conditions | Yield |
|---|---|
| With methanol; sodium acetate at 60℃; for 1h; Reagent/catalyst; | 95% |
D-threo-2-(dichloromethyl)-5-(4-methanesulfonylphenyl)-4,5-dihydro-1,3-oxazol-4-yl methanol
Florfenicol
| Conditions | Yield |
|---|---|
| With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃; under 1520.1 - 2280.15 Torr; for 24h; | 93% |
| Multi-step reaction with 2 steps 1: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 2: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme | |
| Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 25 °C 2: triethylamine tris(hydrogen fluoride) / acetonitrile / 10 h / Reflux View Scheme | |
| Multi-step reaction with 3 steps 1: phosgene / dichloromethane / 16 h / 20 - 25 °C / Cooling with ice 2: sodium fluoride / N,N-dimethyl-formamide / 7 h / 80 °C / Inert atmosphere 3: hydrogenchloride / isopropyl alcohol; water / 5 h / 70 °C / pH 6 View Scheme |
dichloroacetic acid methyl ester
Florfenicol
| Conditions | Yield |
|---|---|
| Stage #1: (1R,2S)-3-fluoro-1-(4-(methylsulfonyl)phenyl)-2-nitropropan-1-ol With palladium 10% on activated carbon; hydrogen In methanol Stage #2: dichloroacetic acid methyl ester With triethylamine In methanol at 20℃; for 18h; | 70% |
C13H15Cl2NO6S2
Florfenicol
| Conditions | Yield |
|---|---|
| With triethylamine tris(hydrogen fluoride) In acetonitrile for 10h; Reflux; | 65% |
dichloroacetic acid methyl ester
(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
Florfenicol
| Conditions | Yield |
|---|---|
| Stage #1: (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone With sodium hydroxide In ethanol at 80℃; for 3h; Stage #2: With sodium acetate In tetrahydrofuran at 0℃; for 0.166667h; Stage #3: dichloroacetic acid methyl ester In tetrahydrofuran at 25℃; for 5h; | 56% |
Florfenicol
| Conditions | Yield |
|---|---|
| Stage #1: 2,2-dichloro-N-{(4R,5R)-4-[4-(methylsulfonyl)phenyl]-2,2-dioxido-1,3,2-dioxathian-5-yl}acetamide With triethylamine tris(hydrogen fluoride) In 1,2-dichloro-ethane at 70℃; for 8h; Stage #2: With hydrogenchloride In ethyl acetate at 0℃; for 2h; | 35% |
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Molecular Structure of Florfenicol (CAS NO.73231-34-2):
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IUPAC Name: 2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
Empirical Formula: C12H14Cl2FNO4S
Molecular Weight: 358.21
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 7
Polar Surface Area: 72.06 Å2
Index of Refraction: 1.548
Molar Refractivity: 78.36 cm3
Molar Volume: 246.7 cm3
Surface Tension: 49.1 dyne/cm
Density: 1.451 g/cm3
Flash Point: 327.3 °C
Enthalpy of Vaporization: 96.27 kJ/mol
Boiling Point: 617.5 °C at 760 mmHg
Vapour Pressure: 4.16E-16 mmHg at 25°C
Melting point: 153 °C
Storage temp: 0-6°C
Product Categories: Feed additives; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds
Synonyms 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)ethanamide
InChI
InChI=1/C12H14Cl2FNO4S/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)/t9-,10-/m1/s1
Smiles
c1cc([C@H]([C@@H](CF)NC(C(Cl)Cl)=O)O)ccc1S(C)(=O)=O
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | Drugs of the Future. Vol. 7, Pg. 172, 1982. |
Hazard Codes: 
Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
Florfenicol (CAS NO.73231-34-2) is a fluorinated synthetic analog of thiamphenicol. In the United States, florfenicol is currently indicated for the treatment of bovine respiratory disease . Florfenicol is a bacteriostatic antibiotic that inhibits protein synthesis by binding to ribosomal subunits of susceptible bacteria, leading to the inhibition of peptidyl transferase and thereby preventing the transfer of amino acids to growing peptide chains and subsequent protein formation.
