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Name	Florfenicol	EINECS	642-986-0
CAS No.	73231-34-2	Density	1.451 g/cm³
PSA	91.85000	LogP	2.70550
Solubility	N/A	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	N/A	Appearance	White crystalline powder
Safety	26-36	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
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;	Article Data	37

Florfenicol 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%

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: 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

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: 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

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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