CAS No.73231-34-2,Florfenicol Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	73231-34-2
Name:	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:	Xi
Risk Codes:	36/37/38
Safety:	26-36
Transport Information:
PSA:	91.85000
LogP:	2.70550

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Synthetic route

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

: 73231-34-2
Florfenicol

Conditions

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

: 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

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;

: 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

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%

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

: 116-54-1
dichloroacetic acid methyl ester

: 73231-34-2
Florfenicol

Conditions

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

: C12H12Cl2FNO3S

: 73231-34-2
Florfenicol

Conditions

Conditions	Yield
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

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

: 116-54-1
dichloroacetic acid methyl ester

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

: 73231-34-2
Florfenicol

Conditions

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%

: 96795-01-6
C13H15Cl2NO6S2

: 73231-34-2
Florfenicol

Conditions

Conditions	Yield
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

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%

: 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

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%

: 857859-74-6
florfenicol phosphate

A: C12H14Cl2NO7PS

B: 73231-34-2
Florfenicol

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; triethylamine 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 4302-89-0
(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

: 73231-34-2
Florfenicol

Conditions

Conditions	Yield
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

Conditions	Yield
In methanol; water; toluene

...Expand

: 5398-77-6
para-methanesulfonylbenzaldehyde

: 73231-34-2
Florfenicol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

Raw Materials

76639-93-5

126428-97-5

79-36-7

5345-30-2

116-54-1

535-15-9

5398-77-6

3446-89-7

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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: C₁₂H₁₄C_l2FNO₄S
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: Irritant 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

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.