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73231-34-2

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Basic Information
CAS No.: 73231-34-2
Name: Florfenicol
Molecular Structure:
Molecular Structure of 73231-34-2 (Florfenicol)
Formula: C12H14Cl2FNO4S
Molecular Weight: 358.21
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
Solubility:
Appearance: White crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
PSA: 91.85000
LogP: 2.70550
Synthetic route
143026-79-3

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

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
116-54-1

dichloroacetic acid methyl ester

76639-93-5, 105182-37-4, 118015-48-8

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

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;
895571-10-5

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

535-15-9

ethyl 1,1-dichloroacetate

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

116-54-1

dichloroacetic acid methyl ester

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

73231-34-2

Florfenicol

Conditions
ConditionsYield
With methanol; sodium acetate at 60℃; for 1h; Reagent/catalyst;95%
126813-11-4

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

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
116-54-1

dichloroacetic acid methyl ester

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

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%
96795-01-6

C13H15Cl2NO6S2

73231-34-2

Florfenicol

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

dichloroacetic acid methyl ester

108656-28-6

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

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

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%
857859-74-6

florfenicol phosphate

A

C12H14Cl2NO7PS

B

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%
116-54-1

dichloroacetic acid methyl ester

108656-27-5

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

A

15318-45-3

thiamphenicol

B

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;
4302-89-0

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

73231-34-2

Florfenicol

Conditions
ConditionsYield
Multistep reaction;
116-54-1

dichloroacetic acid methyl ester

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

73231-34-2

Florfenicol

Conditions
ConditionsYield
In methanol; water; toluene
5398-77-6

para-methanesulfonylbenzaldehyde

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
5345-30-2, 88899-85-8

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

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
51458-28-7

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

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
125872-64-2

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

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

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
157142-64-8

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

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

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

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

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
23150-35-8

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

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
96795-21-0

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

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
96795-20-9

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

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
96795-22-1

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

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
108656-28-6

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

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
108656-26-4

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

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
108656-29-7

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

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
110-15-6

succinic acid

73231-34-2

Florfenicol

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%
49760-60-3

N-benzyloxycarbonyl-L-alanyl chloride

73231-34-2

Florfenicol

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%
73231-34-2

Florfenicol

79-22-1

methyl chloroformate

(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%
87052-59-3

N-Z-Leucine chloride

73231-34-2

Florfenicol

florfenicol-N-Cbz-L-leucine ester

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

succinic acid anhydride

73231-34-2

Florfenicol

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℃;
87052-60-6

Z-(L)-Val-Cl

73231-34-2

Florfenicol

florfenicol-N-Cbz-L-valine ester

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

Florfenicol

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%
61350-60-5, 61350-62-7, 89705-40-8, 106709-50-6

(S)-benzyloxycarbonyl-proline acid chloride

73231-34-2

Florfenicol

florfenicol-N-Cbz-L-proline ester

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

ethylenebis(chloroformate)

73231-34-2

Florfenicol

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%
73231-34-2

Florfenicol

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

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%
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

73231-34-2

Florfenicol

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;
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Chemistry

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

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.

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

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.