Product Name

  • Name

    Florfenicol

  • EINECS 642-986-0
  • CAS No. 73231-34-2
  • Article Data37
  • CAS DataBase
  • Density 1.451 g/cm3
  • Solubility
  • Melting Point 153 °C
  • Formula C12H14Cl2FNO4S
  • Boiling Point 617.5 °C at 760 mmHg
  • Molecular Weight 358.218
  • Flash Point 327.3 °C
  • Transport Information
  • Appearance White crystalline powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 73231-34-2 (Florfenicol)
  • Hazard Symbols IrritantXi
  • 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;
  • PSA 91.85000
  • LogP 2.70550

Synthetic route

(4S,5R)-2-dichloromethyl-4-fluoromethyl-4,5-dihydro-5-(4-(methylsulfonyl)phenyl)oxazoline
143026-79-3

(4S,5R)-2-dichloromethyl-4-fluoromethyl-4,5-dihydro-5-(4-(methylsulfonyl)phenyl)oxazoline

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
76639-93-5, 105182-37-4, 118015-48-8

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

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
895571-10-5

(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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%
(1R,2S)-2-amino-3-fluoro-1-(4-methylsulphonylphenyl)-1-propanol hydrochloride

(1R,2S)-2-amino-3-fluoro-1-(4-methylsulphonylphenyl)-1-propanol hydrochloride

dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
C12H12Cl2FNO3S

C12H12Cl2FNO3S

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
126813-11-4

D-threo-2-(dichloromethyl)-5-(4-methanesulfonylphenyl)-4,5-dihydro-1,3-oxazol-4-yl methanol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-3-fluoro-1-(4-(methylsulfonyl)phenyl)-2-nitropropan-1-ol

(1R,2S)-3-fluoro-1-(4-(methylsulfonyl)phenyl)-2-nitropropan-1-ol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
96795-01-6

C13H15Cl2NO6S2

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
With triethylamine tris(hydrogen fluoride) In acetonitrile for 10h; Reflux;65%
dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
108656-28-6

(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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%
2,2-dichloro-N-{(4R,5R)-4-[4-(methylsulfonyl)phenyl]-2,2-dioxido-1,3,2-dioxathian-5-yl}acetamide

2,2-dichloro-N-{(4R,5R)-4-[4-(methylsulfonyl)phenyl]-2,2-dioxido-1,3,2-dioxathian-5-yl}acetamide

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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%
florfenicol phosphate
857859-74-6

florfenicol phosphate

A

C12H14Cl2NO7PS

C12H14Cl2NO7PS

B

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
With sodium hydroxide In water pH=4.54 - 5.53; Conversion of starting material;A 0.17%
B 0.93%
With ethanolamine In water pH=4.48 - 5.51; Conversion of starting material;A 0.18%
B 0.7%
dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-2-(2,3-dimethylbenzoyl)amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
108656-27-5

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

A

thiamphenicol
15318-45-3

thiamphenicol

B

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
With hydrogenchloride; triethylamine 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;
...Expand
(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol
4302-89-0

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

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multistep reaction;
dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
76639-93-5, 105182-37-4, 118015-48-8

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

A

(1R,2S)-2-Dichloroacetamido-3-Fluoro-1-[4-(Methylsulfonyl)Phenyl]-1-Propanol(Florfenicol)

(1R,2S)-2-Dichloroacetamido-3-Fluoro-1-[4-(Methylsulfonyl)Phenyl]-1-Propanol(Florfenicol)

B

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
In methanol; water; toluene
...Expand
para-methanesulfonylbenzaldehyde
5398-77-6

para-methanesulfonylbenzaldehyde

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 83 percent / piperidine / pyridine / 4 h / 95 - 100 °C
2: 1.) SOCl2, 2.) NaBH4 / 1) reflux, 1 h; 2) CH2Cl2, EtOH, 10 deg C, 1 h
3: 82 percent / 4 Anstroem molecular sieves, diisopropyl L-tartrate, Ti(OPr-i)4, t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C
4: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h
5: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5
6: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C
7: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5
View Scheme
Multi-step reaction with 7 steps
1.1: ethanol / 3 h / Inert atmosphere; Reflux
2.1: (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane / toluene / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere
2.2: 19 h / -10 - 20 °C / Molecular sieve; Inert atmosphere
3.1: lithium borohydride / tetrahydrofuran / 50 °C / Inert atmosphere
3.2: 1 h / 20 °C / Inert atmosphere
4.1: diethylamino-sulfur trifluoride; triethylamine / dichloromethane / 8 h / -40 - 20 °C / Inert atmosphere
5.1: water; toluene-4-sulfonic acid / acetonitrile / 24 h / 40 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water / 6 h / 20 °C / 760.05 Torr
7.1: triethylamine / methanol / 3 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydroxide / dichloromethane; ethanol / 0 - 20 °C
1.2: 1 h / 20 °C / Cooling with ice
2.1: thionyl chloride / 8 h / 0 - 60 °C
2.2: 2 h / 20 - 60 °C
3.1: hydrogenchloride / water; methanol / 6 h / Reflux
3.2: 8 h / 0 - 60 °C
3.3: 6 h / 20 °C
4.1: sodium tetrahydroborate; methanol / 5 h / 0 - 20 °C
5.1: triethylamine; thionyl chloride / dichloromethane / 0 °C
5.2: 20 °C
6.1: triethylamine tris(hydrogen fluoride) / 1,2-dichloro-ethane / 8 h / 70 °C
6.2: 2 h / 0 - 20 °C
7.1: triethylamine / methanol / Heating
View Scheme
3-(4-methanesulfonyl-phenyl)-acrylic acid
5345-30-2, 88899-85-8

3-(4-methanesulfonyl-phenyl)-acrylic acid

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) SOCl2, 2.) NaBH4 / 1) reflux, 1 h; 2) CH2Cl2, EtOH, 10 deg C, 1 h
2: 82 percent / 4 Anstroem molecular sieves, diisopropyl L-tartrate, Ti(OPr-i)4, t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C
3: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h
4: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5
5: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C
6: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5
View Scheme
(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol
51458-28-7

(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88 percent / conc. H2SO4 / propan-2-ol / 1) 70 deg C, 1.5-2 h; 2) 50 deg C, 14 h
2: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C
3: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5
View Scheme
Multi-step reaction with 6 steps
1: K2CO3 / H2O / 1 h / Ambient temperature
2: EtONa / ethanol
3: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
4: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
5: 70 percent / KOH / methanol / 7 h / -30 °C
6: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / K2CO3 / glycerol / 18 h / 115 °C
2: 95 percent Chromat. / (1,1,2,3,3,3-hexafluoropropyl)diethylamine (FPA) / CH2Cl2 / 2 h / 100 °C / 5171.5 Torr
3: 95 percent / 6 N HCl / 12 h / 100 - 105 °C
4: 84 percent / Et3N / methanol / 18 h / Ambient temperature
View Scheme
(E)-3-(4-(methylsulfonyl)phenyl)prop-2-en-1-ol
125872-64-2

(E)-3-(4-(methylsulfonyl)phenyl)prop-2-en-1-ol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 82 percent / 4 Anstroem molecular sieves, diisopropyl L-tartrate, Ti(OPr-i)4, t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C
2: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h
3: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5
4: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C
5: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5
View Scheme
Multi-step reaction with 10 steps
1: tert.-butylhydroperoxide; C3H7O(1-)*C34H32N2O4(2-)*V(3+) / dichloromethane; water / 72 h / 0 °C
2: N,N-dimethyl-formamide / 10 h / 20 °C
3: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C
4: triethylamine / dichloromethane / 2 h / 0 - 20 °C
5: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / 90 °C
6: potassium hydroxide / methanol; water / 1 h / Reflux; Inert atmosphere
7: palladium 10% on activated carbon; formic acid / methanol / 10 h / 20 °C / Inert atmosphere
8: hydrogenchloride / water; isopropyl alcohol / 16 h / 50 - 70 °C
9: Nonafluorobutanesulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine / tetrahydrofuran / 12 h / 20 °C
10: sodium acetate / water; isopropyl alcohol / 3 h / pH 5 / Reflux
View Scheme
(S,S)-3-[4-(methylsulfonyl)phenyl]-2,3-epoxypropyl alcohol

(S,S)-3-[4-(methylsulfonyl)phenyl]-2,3-epoxypropyl alcohol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h
2: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5
3: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C
4: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5
View Scheme
Multi-step reaction with 9 steps
1: N,N-dimethyl-formamide / 10 h / 20 °C
2: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C
3: triethylamine / dichloromethane / 2 h / 0 - 20 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / 90 °C
5: potassium hydroxide / methanol; water / 1 h / Reflux; Inert atmosphere
6: palladium 10% on activated carbon; formic acid / methanol / 10 h / 20 °C / Inert atmosphere
7: hydrogenchloride / water; isopropyl alcohol / 16 h / 50 - 70 °C
8: Nonafluorobutanesulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine / tetrahydrofuran / 12 h / 20 °C
9: sodium acetate / water; isopropyl alcohol / 3 h / pH 5 / Reflux
View Scheme
(3S,4R)-2-(dichloromethyl)-4,5-dihydro-α-[4-(methylsulfonyl)phenyl]oxazole-4-methanol
157142-64-8

(3S,4R)-2-(dichloromethyl)-4,5-dihydro-α-[4-(methylsulfonyl)phenyl]oxazole-4-methanol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5
2: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C
3: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5
View Scheme
(2R,3S,9bRS)-3-(mesyloxymethyl)-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

(2R,3S,9bRS)-3-(mesyloxymethyl)-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 27 percent Chromat. / hexadecyltributylphosphonium chloride, potassium fluoride hydrate / toluene; H2O / 7 h / Heating
2: 2N HCl / 6 h / Heating
3: Et3N / 3.5 h / Heating
View Scheme
(2R,3R,9bRS)-3-hydroxymethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

(2R,3R,9bRS)-3-hydroxymethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92.8 percent / pyridine / 0 °C
2: 27 percent Chromat. / hexadecyltributylphosphonium chloride, potassium fluoride hydrate / toluene; H2O / 7 h / Heating
3: 2N HCl / 6 h / Heating
4: Et3N / 3.5 h / Heating
View Scheme
(2R,3S,9bRS)-3-fluoromethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

(2R,3S,9bRS)-3-fluoromethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2N HCl / 6 h / Heating
2: Et3N / 3.5 h / Heating
View Scheme
(R*,R*)-(+)-thiomicamine
23150-35-8

(R*,R*)-(+)-thiomicamine

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: K2CO3 / H2O / 1 h / Ambient temperature
2: t-BuOK / ethanol / 3 h / Heating
3: 81 percent / H2O2 / H2O / 20 h / 45 °C
4: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
5: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
6: 70 percent / KOH / methanol / 7 h / -30 °C
7: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
Multi-step reaction with 7 steps
1: K2CO3 / H2O / 1 h / Ambient temperature
2: t-BuOK / toluene / 3 h / Heating
3: 81 percent / H2O2 / H2O / 20 h / 45 °C
4: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
5: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
6: 70 percent / KOH / methanol / 7 h / -30 °C
7: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
Multi-step reaction with 4 steps
1: 1.) K2CO3, 2.) CH3CO3H / 1.) ethylene glycol, glycerol, 105 deg C, 18 h, 2.) AcOH, 20-25 deg C , 1 h
2: 95 percent Chromat. / (1,1,2,3,3,3-hexafluoropropyl)diethylamine (FPA) / CH2Cl2 / 2 h / 100 °C / 5171.5 Torr
3: 95 percent / 6 N HCl / 12 h / 100 - 105 °C
4: 84 percent / Et3N / methanol / 18 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 1.) K2CO3, 2.) CH3CO3H / 1.) ethylene glycol, glycerol, 105 deg C, 18 h, 2.) AcOH, 20-25 deg C , 1 h
2: (2-chloro-1,1,2-trifluoroethyl)diethylamine (FAR) / CH2Cl2 / 5 h / 100 °C
3: 95 percent / 6 N HCl / 12 h / 100 - 105 °C
4: 84 percent / Et3N / methanol / 18 h / Ambient temperature
View Scheme
(4R,5R)-4-hydroxymethyl-5-<4-(methylthio)phenyl>-2-oxazolidinone
96795-21-0

(4R,5R)-4-hydroxymethyl-5-<4-(methylthio)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 81 percent / H2O2 / H2O / 20 h / 45 °C
2: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
3: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
4: 70 percent / KOH / methanol / 7 h / -30 °C
5: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylthio)phenyl>-1,3-propanediol
96795-20-9

(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylthio)phenyl>-1,3-propanediol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: t-BuOK / ethanol / 3 h / Heating
2: 81 percent / H2O2 / H2O / 20 h / 45 °C
3: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
4: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
5: 70 percent / KOH / methanol / 7 h / -30 °C
6: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
Multi-step reaction with 6 steps
1: t-BuOK / toluene / 3 h / Heating
2: 81 percent / H2O2 / H2O / 20 h / 45 °C
3: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
4: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
5: 70 percent / KOH / methanol / 7 h / -30 °C
6: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
(4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
96795-22-1

(4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
2: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
3: 70 percent / KOH / methanol / 7 h / -30 °C
4: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
Multi-step reaction with 3 steps
1: hexafluoropropene-diethylamine adduct / dichloromethane / 1 h / 105 - 110 °C / Autoclave
2: hydrogenchloride / 1 h / Reflux
3: triethylamine / methanol / 20 °C
View Scheme
(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
108656-28-6

(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
2: 70 percent / KOH / methanol / 7 h / -30 °C
3: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / 1 h / Reflux
2: triethylamine / methanol / 20 °C
View Scheme
(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol
108656-26-4

(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: EtONa / ethanol
2: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h
3: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h
4: 70 percent / KOH / methanol / 7 h / -30 °C
5: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
(4S,5R)-N-(2,3-dimethylbenzoyl)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
108656-29-7

(4S,5R)-N-(2,3-dimethylbenzoyl)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / KOH / methanol / 7 h / -30 °C
2: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h
View Scheme
succinic acid
110-15-6

succinic acid

Florfenicol
73231-34-2

Florfenicol

sodium 4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoate
1073342-32-1

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

Conditions
ConditionsYield
Stage #1: succinic acid; Florfenicol With triethylamine In ethyl acetate at 20℃; for 1h;
Stage #2: With sodium hydrogencarbonate In ethyl acetate at 0 - 5℃; for 2h; Solvent;		97.8%
N-benzyloxycarbonyl-L-alanyl chloride
49760-60-3

N-benzyloxycarbonyl-L-alanyl chloride

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-alanine ester

florfenicol-N-Cbz-L-alanine ester

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at 20 - 90℃; for 10h; Reagent/catalyst; Solvent; Temperature;94.3%
Florfenicol
73231-34-2

Florfenicol

methyl chloroformate
79-22-1

methyl chloroformate

(1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl methyl carbonate

(1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl methyl carbonate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 0℃;93%
N-Z-Leucine chloride
87052-59-3

N-Z-Leucine chloride

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-leucine ester

florfenicol-N-Cbz-L-leucine ester

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 8h; Reflux;89.64%
succinic acid anhydride
108-30-5

succinic acid anhydride

Florfenicol
73231-34-2

Florfenicol

4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoic acid
1073342-33-2

4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoic acid

Conditions
ConditionsYield
With dmap In acetone at 60℃; for 4h;88.1%
With dmap In acetone at 40 - 70℃;
Z-(L)-Val-Cl
87052-60-6

Z-(L)-Val-Cl

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-valine ester

florfenicol-N-Cbz-L-valine ester

Conditions
ConditionsYield
With pyridine; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 10h; Reflux;83.29%
Florfenicol
73231-34-2

Florfenicol

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl) hydrogen phosphate
1450713-53-7

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl) hydrogen phosphate

Conditions
ConditionsYield
Stage #1: Florfenicol With pyridine; trichlorophosphate In acetonitrile at 0 - 25℃; for 12.5h;
Stage #2: With water In acetonitrile at 0 - 25℃; for 8.16667h; Reagent/catalyst; Solvent;		80.72%
(S)-benzyloxycarbonyl-proline acid chloride
61350-60-5, 61350-62-7, 89705-40-8, 106709-50-6

(S)-benzyloxycarbonyl-proline acid chloride

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-proline ester

florfenicol-N-Cbz-L-proline ester

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 10h; Reflux;70.39%
ethylenebis(chloroformate)
124-05-0

ethylenebis(chloroformate)

Florfenicol
73231-34-2

Florfenicol

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl)ethane-1,2-diyl dicarbonate

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl)ethane-1,2-diyl dicarbonate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃;62%
Florfenicol
73231-34-2

Florfenicol

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
148926-02-7

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

2,2-dichloro-N-[(1R,2S)-3-fluoro-1-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

2,2-dichloro-N-[(1R,2S)-3-fluoro-1-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

Conditions
ConditionsYield
Stage #1: 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside With trifluoromethylsulfonic anhydride; beta-pinene In dichloromethane at -50℃; for 0.75h;
Stage #2: Florfenicol In dichloromethane at -50 - 20℃; for 18h; stereoselective reaction;		55%
N,O-bis-(trimethylsilyl)-acetamide
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

Florfenicol
73231-34-2

Florfenicol

2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-(4-methanesulfonyl-phenyl)-2-trimethylsilanyloxy-ethyl]-acetamide

2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-(4-methanesulfonyl-phenyl)-2-trimethylsilanyloxy-ethyl]-acetamide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 0.166667h;

Florfenicol Chemical Properties

Molecular Structure of Florfenicol (CAS NO.73231-34-2):

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

Florfenicol Toxicity Data With Reference

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.

Florfenicol Safety Profile

Hazard Codes: IrritantXi
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 Specification

 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.

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