Chloramphenicol supplier

Name
Chloramphenicol
EINECS 200-287-4
CAS No. 56-75-7
Article Data73
CAS DataBase
Density 1.547 g/cm³
Solubility 2.5 g/L (25 °C) in water
Melting Point 148-150 °C(lit.)
Formula C₁₁H₁₂Cl₂N₂O₅
Boiling Point 644.913 °C at 760 mmHg
Molecular Weight 323.133
Flash Point 343.831 °C
Transport Information UN 2811
Appearance White to grey-white crystalline powder
Safety 53-45
Risk Codes 45
Molecular Structure
Hazard Symbols T
Synonyms Acetamide, 2, 2-dichloro-N-[2-hydroxy-1- (hydroxymethyl)-2-(4-nitrophenyl)ethyl]- , [R-(R*,R*)]-;Tega-Cetin;Tevcosin;D(-)-threo-2-Dichloroacetamido-1-p-nitrophenyl-1,3-propanediol;Chlorocaps;D-(-)-threo-1-p-Nitrophenyl-2-dichloracetamido-1,3-propanediol;Isophenicol;Comycetin;Acetamide, 2, 2-dichloro-N-[.beta.-hydroxy-.alpha.- (hydroxymethyl)-p-nitrophenet hyl]-, D-threo-(-)-;CPh;Synthomycine;Anacetin;Amphicol;Acetamide, 2, 2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenet hyl]-,D-(-)-threo-;Mycinol;Synthomycetin;D-threo-N-(1, 1-Dihydroxy-1-p-nitrophenylisopropyl)dichloroacetamide;Leukomyan;Medichol;Otophen;Ophtochlor;Biocetin;D-(-)-Chloramphenicol;Chlorocid;Chloro-25 vetag;D-(-)-threo-alpha, alpha-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide;Chlomin;2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide;Halomycetin;Enteromycetin;Ronphenil;Pantovernil;Myclocin;Cloramidina;Viceton;Levoplast;D-(-)-threo-2, 2-Dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)]-p-nitrophene thylacetamide;Cloramficin;Tifomycin;Austracol;Alficetyn;Chloricol;Paraxin;Dextromycetin;Chloramfilin;Soluthor;Cloromisan;Ismicetina;I 337A;Ciplamycetin;Chloroptic;Chloramphenicol Levo/palmitate/L-base;D-threo-Chloramphenicol;Chlorocol;Chlorocidin C;(-)-Chloramphenicol;Catilan;Chloramphenicol-levo;D-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol;Farmicetina;Biophenicol;Chloromycetin (TN);Chloroject L;Tiromycetin;Loromisin;Pentamycetin;Ambofen;Doctamicina;Cloramicol;2,2-Dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(hydroxy(oxido)amino)phenyl)ethyl)acetamide, (1R, 2R)-;;Chlomycol;Sintomicetina;GlovesGloveticol;Chlora-Tabs;Aquamycetin;2,2-dichloro-N-[(1S,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide;Chlorocide;Leukomycin;Acetamide,2,2-dichloro-N-[(1R,2R)-2- hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)- ethyl]-;Oleomycetin;Klorocid S;Loromisan;Detreomycine;Hortfenicol;Chloramsaar;Novomycetin;Micochlorine;Normimycin V;Isicetin;Chlorovules;Prestwick_51;Sno-Phenicol;D-threo-1-(p-Nitrophenyl)-2-(dichloroacetylamino)-1,3-propanediol;Chlornitromycin;Rivomycin;Chloramficin;Clorosintex;Acetamide, 2, 2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenet hyl];Isopto fenicol;Desphen;Intramycetin;Levomitsetin;Tifomycine;Unimycetin;Microcetina;Mychel;Glorous;Detreomycin;Chloromax;Leukamycin;D-(-)-2, 2-Dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenyl -ethyl)acetamide;Chemicetin;Chemicetina;Chloromycetin;Novophenicol;Levomycetin;
PSA 115.38000
LogP 1.82310

Synthetic route

: 116-54-1
dichloroacetic acid methyl ester

: 119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0
(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
In methanol at 23 - 40℃; for 9h; Inert atmosphere;	97%
at 90℃; for 1h;	80%
Amidation;	74%

: 912296-93-6
2,2-dichloro-N-[1-hydroxymethyl-2-methoxy-2-(4-nitrophenyl)-ethyl]-acetamide

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -20℃; for 12h;	80%

: diphenylmethyl (2S,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propanoate

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;	80%

: 116-54-1
dichloroacetic acid methyl ester

: 294637-52-8
(4R,5R)-5-(4-nitrophenyl)-4-hydroxymethyl-1,3-oxazolidin-2-one

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
Stage #1: (4R,5R)-5-(4-nitrophenyl)-4-hydroxymethyl-1,3-oxazolidin-2-one With sodium hydroxide In methanol; water at 25℃; Stage #2: dichloroacetic acid methyl ester at 90℃; for 3h;	78%
Stage #1: (4R,5R)-5-(4-nitrophenyl)-4-hydroxymethyl-1,3-oxazolidin-2-one With sodium hydroxide In water for 0.5h; Reflux; Stage #2: dichloroacetic acid methyl ester In water at 90℃; for 3h;	70%

: 382142-89-4
(2S)-(2,2-dichloroacetylamino)-(3R)-hydroxy-3-(4-nitrophenyl)-propionic acid ethyl ester

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;	74%

: 3018-12-0
dichloroacetonitrile

: (αR,2R)-α-(4-nitrophenyl)oxiranemethanol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
Stage #1: dichloroacetonitrile; (αR,2R)-α-(4-nitrophenyl)oxiranemethanol With sodium hydride In dichloromethane at 0 - 20℃; for 1h; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78 - 20℃; for 3h;	71%

: 123410-34-4
chloramphenicol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran for 16h; Ambient temperature;	70%

: 79-36-7
dichloroacethyl chloride

: 119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0
(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With dichloro-acetic acid und anschliessend mit wss.Aceton bei pH8-9;

: 302-17-0
chloral hydrate

: 119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0
(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

: 151-50-8
potassium cyanide

: 56-75-7
chloramphenicol

...Expand

: 1768-31-6
pentachloroacetone

: 119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0
(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With 1,4-dioxane

: 13916-40-0
bis-dichloroacetyl-amine

: 119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0
(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With ethanol

: 872302-03-9
dichloroacetyl-phosphorous acid diethyl ester

: 119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0
(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With methanol
With ethyl acetate

: 3144-16-9
(1S)-10-camphorsulfonic acid

: 56-75-7, 134-90-7, 579-51-1, 2787-09-9, 3419-87-2, 7384-89-6, 7387-98-6, 50762-99-7, 126787-77-7, 140694-65-1
chlorampenicol

A: 56-75-7
chloramphenicol

B: 134-90-7
L-threo-chloramphenicol

...Expand

: 119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0
(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

: ethyl dichloroacidimidate hydrochloride

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With ethanol

: 34718-53-1
(1R,2R)-3-dichloroacetoxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With acetone

: 56-75-7, 134-90-7, 579-51-1, 2787-09-9, 3419-87-2, 7384-89-6, 7387-98-6, 50762-99-7, 126787-77-7, 140694-65-1
chlorampenicol

A: 56-75-7
chloramphenicol

B: 134-90-7
L-threo-chloramphenicol

Conditions

Conditions	Yield
durch Chromatographie an einer Lactose-Saeule;
With chiral stationary phase derived from aminated silica gel, L-2-(p-toluenesulfonamido)-3-phenylpropionyl chloride and dendrimer In methanol; water at 25℃; Resolution of racemate;

: 907579-60-6
dichloroacetic acid-[(5R)-4c-(4-nitro-phenyl)-2-oxo-[1,3]dioxan-5r-ylamide]

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With hydrogenchloride

: 115082-34-3
dichloroacetic acid-[(5R)-4c-(4-nitro-phenyl)-2ξ-oxo-2λ4-[1,3,2]dioxathian-5r-ylamide]

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With hydrogenchloride

: 116081-46-0
(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-3-nitryloxy-propan-1-ol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With methanol; iron(II) ammonium sulfate
With aminosulfonic acid; water; iron(II) sulfate

: 56-75-7, 134-90-7, 579-51-1, 2787-09-9, 3419-87-2, 7384-89-6, 7387-98-6, 50762-99-7, 126787-77-7, 140694-65-1
chlorampenicol

: 57-24-9
strychnidin-10-one

A: 56-75-7
chloramphenicol

B: 134-90-7
L-threo-chloramphenicol

Conditions

Conditions	Yield
ueber das O3-<3-Carboxy-propionyl>-Derivat;

...Expand

: 76738-28-8
(R)-((R)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With acid Hydrolysis;

: 126109-35-1
threo (1R)-acetoxymethoxy-(2R)-dichloroacetamido-3-acetoxy-1-p-nitrophenylpropane

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With ammonium hydroxide In methanol

: 530-43-8
chloramphenicol Palmitate

A: 56-75-7
chloramphenicol

B: 57-10-3
1-hexadecylcarboxylic acid

Conditions

Conditions	Yield
With borate buffer pH 7.5; lipase at 37℃; for 5h; Rate constant; also addition of β-cyclodextrin, chloramphenicol or palmitic acid, var. of polymorphic forms;

: chloramphenicol palmitate β-cyclodextrin complex

A: 56-75-7
chloramphenicol

B: 57-10-3
1-hexadecylcarboxylic acid

Conditions

Conditions	Yield
With borate buffer pH 7.5; lipase at 37℃; for 5h; Rate constant; also addition of chloramphenicol or palmitic acid, var. of polymorphic forms;

: N-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-2,2-dichloro-acetamide

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran desilylation;

(1R,2R)-2-<2,2-dichloro-acetylamino>-1-<4-nitro-phenyl>-1,3-bis-nitryloxy-propane: (1R,2R)-2-<2,2-dichloro-acetylamino>-1-<4-nitro-phenyl>-1,3-bis-nitryloxy-propane

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With methanol; iron(II) ammonium sulfate
With aminosulfonic acid; water; iron(II) sulfate
With methanol; iron(II) chloride

(1R,2R)-2-<2,2-dichloro-acetylamino>-1-<4-nitro-phenyl>-3-nitryloxy-propane-1,3-diol: (1R,2R)-2-<2,2-dichloro-acetylamino>-1-<4-nitro-phenyl>-3-nitryloxy-propane-1,3-diol

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With methanol; iron(II) chloride

(2S,3R)-2-<2,2-dichloro-acetylamino>-3-hydroxy-3-<4-nitro-phenyl>-propionic acid-azide: (2S,3R)-2-<2,2-dichloro-acetylamino>-3-hydroxy-3-<4-nitro-phenyl>-propionic acid-azide

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With sodium tetrahydroborate; ethyl acetate

(2S,3R)-2-<2,2-dichloro-acetylamino>-3-hydroxy-3-<4-nitro-phenyl>-propionic acid ethyl ester: (2S,3R)-2-<2,2-dichloro-acetylamino>-3-hydroxy-3-<4-nitro-phenyl>-propionic acid ethyl ester

: 56-75-7
chloramphenicol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

3-nitro-1-palmitoyl-1H-1,2,4-triazole: 1104640-94-9
3-nitro-1-palmitoyl-1H-1,2,4-triazole

: 56-75-7
chloramphenicol

: 530-43-8
chloramphenicol Palmitate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h; regioselective reaction;	100%

: 56-75-7
chloramphenicol

tert-butyldimethylsilyl chloride: tert-butyldimethylsilyl chloride

: 864529-25-9
chloramphenicol

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane for 2h;	99%
With 1H-imidazole In N,N-dimethyl-formamide for 19h; Ambient temperature;	95%
With dmap; triethylamine In dichloromethane

: 693-38-9
vinyl palmitate

: 56-75-7
chloramphenicol

: 530-43-8
chloramphenicol Palmitate

Conditions

Conditions	Yield
With palmitic acid imprinted Thermomyces lanuginosus Lypozyme TL 100L lipase nanogel In acetonitrile at 20℃; for 48h; Temperature; Concentration; Reagent/catalyst; Green chemistry; Enzymatic reaction; regioselective reaction;	99%
With lipase encapsulated polyacrylamide nanogel In water; acetonitrile at 20℃; for 6h; Reagent/catalyst; Enzymatic reaction;	99%
With Novozym 435 In acetonitrile at 20℃; for 3h; Inert atmosphere; Enzymatic reaction; regioselective reaction;	91%

: 56-75-7
chloramphenicol

: 79-03-8
propionyl chloride

: 1304534-01-7
(1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(propanoyloxy)propyl propanoate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	99%

: 56-75-7
chloramphenicol

: 75-36-5
acetyl chloride

: 10318-17-9
(1R,2R)-3-(acetyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl acetate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	99%

: 56-75-7
chloramphenicol

: 98-59-9
p-toluenesulfonyl chloride

: 133227-81-3
Toluene-4-sulfonic acid (2R,3R)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propyl ester

Conditions

Conditions	Yield
With pyridine for 2h; Ambient temperature;	97%

: 56-75-7
chloramphenicol

: 644-97-3
Dichlorophenylphosphine

: 554-68-7
triethylamine hydrochloride

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran	96%

: 56-75-7
chloramphenicol

: 49785-01-5
ortho-xylenyl phosphoryl chloride

: Chloramphenicol ortho-xylenyl phosphate

Conditions

Conditions	Yield
With 1,2,2,6,6-pentamethylpiperidine; C15H12F6N2O In dichloromethane at 20℃; for 4h; Inert atmosphere;	96%

: 56-75-7
chloramphenicol

1,3-bis(2-hydroxy-3-chloropropyl)-6-methyluracil: 195963-39-4
1,3-bis(2-hydroxy-3-chloropropyl)-6-methyluracil

: C33H38Cl4N6O14

Conditions

Conditions	Yield
With potassium carbonate In methanol at 60℃; for 8h;	95%

: 56-75-7
chloramphenicol

: 35530-10-0
[(1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol] hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water for 2h; Heating;	93%
Multi-step reaction with 2 steps 1: pyridine; dioxane 2: HCl; diethyl ether; dioxane View Scheme
With hydrogenchloride Heating;

: 112-16-3
n-dodecanoyl chloride

: 56-75-7
chloramphenicol

: 41658-74-6
(1R,2R)-2-[(dichloroacetyl)amino]-3-(lauroyloxy)-1-(4-nitrophenyl)propyl laurate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	93%

: 4704-31-8
vinyl caprate

: 56-75-7
chloramphenicol

: 1303598-13-1
(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl decanoate

Conditions

Conditions	Yield
With Novozym 435 In acetonitrile at 20℃; for 3h; Inert atmosphere; Enzymatic reaction; regioselective reaction;	92%
With lipase cloned from Bacillus amyloliquefaciens In ethanol at 50℃; for 4h; Inert atmosphere; Enzymatic reaction; regioselective reaction;

: 56-75-7
chloramphenicol

: 2524-64-3
chlorophosphoric acid diphenyl ester

: Chloramphenicol diphenyl phosphate

Conditions

Conditions	Yield
With 1,2,2,6,6-pentamethylpiperidine; C15H12F6N2O In dichloromethane at 20℃; for 4h; Inert atmosphere;	92%

: 56-75-7
chloramphenicol

: 98-80-6
phenylboronic acid

: C17H15BCl2N2O5

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 18h; Inert atmosphere;	92%

: 56-75-7
chloramphenicol

: 112-67-4
n-hexadecanoyl chloride

: 530-43-8
chloramphenicol Palmitate

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide; toluene at -4 - 5℃; for 4.83333h; Solvent;	91.9%
With pyridine
With benzene
With benzene unter Zusatzt von Pyridin;

: 56-75-7
chloramphenicol

: 108-24-7
acetic anhydride

: 10318-17-9
(1R,2R)-3-(acetyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl acetate

Conditions

Conditions	Yield
With pyridine at 0 - 20℃;	91%
With pyridine

: 2146-71-6
vinyl laurate

: 56-75-7
chloramphenicol

: 16255-46-2
(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl laurate

Conditions

Conditions	Yield
With Novozym 435 In acetonitrile at 20℃; for 4h; Inert atmosphere; Enzymatic reaction; regioselective reaction;	91%
With lipase cloned from Bacillus amyloliquefaciens In ethanol at 50℃; for 4h; Inert atmosphere; Enzymatic reaction; regioselective reaction;

: 56-75-7
chloramphenicol

: 11113-50-1
boric acid

: C22H20BCl4N4O10(1-)*H(1+)

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 18h; Inert atmosphere;	91%

: 108-05-4
vinyl acetate

: 56-75-7
chloramphenicol

: 10318-16-8
(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl acetate

Conditions

Conditions	Yield
With Novozym 435 In acetonitrile at 20℃; for 3h; Inert atmosphere; Enzymatic reaction; regioselective reaction;	90%
With lipase cloned from Bacillus amyloliquefaciens In ethanol at 50℃; for 4h; Inert atmosphere; Enzymatic reaction; regioselective reaction;

: 105-38-4
vinyl propionate

: 56-75-7
chloramphenicol

: 33987-21-2
(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl propionate

Conditions

Conditions	Yield
With immobilised Pseudomonas cepacia lipase PSL-C I In 1,4-dioxane at 30℃; for 6h; Inert atmosphere; Enzymatic reaction; regioselective reaction;	90%
With lipase cloned from Bacillus amyloliquefaciens In 1,4-dioxane; ethanol at 50℃; for 8h; Catalytic behavior; Solvent; Temperature; Time; Inert atmosphere; Enzymatic reaction; regioselective reaction;

: 56-75-7
chloramphenicol

: 108-24-7
acetic anhydride

: 18162-48-6
tert-butyldimethylsilyl chloride

: 864529-27-1
(1R,2R)-3-((tert-butyldimethylsilyl)oxy)-2-(2,2-dichloroacetamido)-1-(4-nitrophenyl)propyl acetate

Conditions

Conditions	Yield
Stage #1: chloramphenicol; tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane at 25℃; for 0.5h; Stage #2: acetic anhydride With triethylamine In dichloromethane at 25℃; for 12h;	90%

...Expand

: 56-75-7
chloramphenicol

: 67-64-1
acetone

: 57345-88-7
dichloroacetic acid-[(5R)-2,2-dimethyl-4c-(4-nitro-phenyl)-[1,3]dioxan-5r-ylamide]

Conditions

Conditions	Yield
With 4 A molecular sieve; Amberlyst A 15 In tetrahydrofuran for 24h; Ambient temperature;	89.3%

: 56-75-7
chloramphenicol

: 450347-70-3
1,3-bis(2-hydroxy-3-chloropropyl)uracil

: 2,2-dichloro-N-{3-[3-(3-{dichloroacetyl-[2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-amino}-2-hydroxy-propyl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-2-hydroxy-propyl}-N-[2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-acetamide

Conditions

Conditions	Yield
With potassium carbonate In methanol at 60℃; for 8h;	87%

: 56-75-7
chloramphenicol

: 123-62-6
propionic acid anhydride

A: 1304534-01-7
(1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(propanoyloxy)propyl propanoate

B: 33987-21-2
(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl propionate

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane for 0.0833333h;	A 15% B 85%

...Expand

: 56-75-7
chloramphenicol

: 141-75-3
butyryl chloride

A: 1,3-dibutanoylchloramphenicol

B: 59005-99-1
threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-butanoate

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane for 0.0833333h;	A 15% B 85%

...Expand

: 56-75-7
chloramphenicol

: 100-83-4
meta-hydroxybenzaldehyde

: 97889-44-6
2,2-Dichloro-N-[(4R,5R)-2-(3-hydroxy-phenyl)-4-(4-nitro-phenyl)-[1,3]dioxan-5-yl]-acetamide

Conditions

Conditions	Yield
With 4 A molecular sieve; Amberlyst A 15 In tetrahydrofuran for 24h; Ambient temperature;	82%

: 108-30-5
succinic acid anhydride

: 56-75-7
chloramphenicol

: 3544-94-3
threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-succinate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; Reagent/catalyst;	81%
In 1,4-dioxane at 20℃; for 24h; lipase;	64%
With 1,4-dioxane; pyridine

: 56-75-7
chloramphenicol

: 112-13-0
n-decanoyl chloride

: 1303598-17-5
(1R,2R)-3-(decanoyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl decanoate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	80%

Chloramphenicol Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Chloramphenicol Specification

The Chloramphenicol, with the CAS registry number 56-75-7,is also known as 2,2-Dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide. It belongs to the product categories of Pharmaceuticals;API;Chiral Reagents;Pharmaceutical intermediate. Its EINECS number is 200-287-4. This chemical's molecular formula is C₁₁H₁₂Cl₂N₂O₅ and molecular weight is 323.13. What's more,Its systematic name is Chloramphenicol.It is a White to grey-white crystalline powder which is an antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic.This chemical may cause cancer. when you use it ,you should avoid exposure - obtain special instructions before use. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Physical properties about Chloramphenicol are:
(1)ACD/LogP: 1.103; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.10; (4)ACD/LogD (pH 7.4): 1.10; (5)ACD/BCF (pH 5.5): 4.06; (6)ACD/BCF (pH 7.4): 4.05; (7)ACD/KOC (pH 5.5): 94.80; (8)ACD/KOC (pH 7.4): 94.75; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.612; (13)Molar Refractivity: 72.559 cm3; (14)Molar Volume: 208.831 cm3; (15)Polarizability: 28.765 10-24cm3 ; (16)Surface Tension: 66.1240005493164 dyne/cm; (17)Density: 1.547 g/cm3; (18)Flash Point: 343.831 °C; (19)Enthalpy of Vaporization: 99.983 kJ/mol; (20)Boiling Point: 644.913 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:c1cc(ccc1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-];
(2)Std. InChI:InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1;
(3)Std. InChIKey:WIIZWVCIJKGZOK-RKDXNWHRSA-N.

Uses of Chloramphenicol:
Chloramphenicol may be used as a second-line agent in the treatment of tetracycline-resistant cholera. Because of its excellent CSF penetration (far superior to any of the cephalosporins), chloramphenicol remains the first choice treatment for staphylococcal brain abscesses. It is also useful in the treatment of brain abscesses due to mixed organisms or when the causative organism is not known. Chloramphenicol has been used in the U.S. in the initial empirical treatment of children with fever and a petechial rash. It has recently been discovered to be a life saving cure for chytridiomycosis in amphibians.

The toxicity data of Chloramphenicol are as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	unreported	250mg/kg/10D (250mg/kg)	BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE BLOOD: HEMORRHAGE LIVER: OTHER CHANGES	Clinical Pediatrics Vol. 14, Pg. 499, 1975.
dog	LD	intramuscular	> 101mg/kg (101mg/kg)		Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
dog	LD	oral	> 300mg/kg (300mg/kg)		Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
dog	LDLo	intravenous	150mg/kg (150mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Journal of Bacteriology. Vol. 55, Pg. 425, 1948.
guinea pig	LD50	intravenous	560mg/kg (560mg/kg)		Farmaco, Edizione Scientifica. Vol. 9, Pg. 21, 1954.
guinea pig	LD50	oral	500mg/kg (500mg/kg)		Farmaco, Edizione Scientifica. Vol. 10, Pg. 3, 1955.
infant	LDLo	intravenous	30mg/kg/3D-I (30mg/kg)	CARDIAC: CARDIAC OUTPUT VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Journal of Pediatrics. Vol. 103, Pg. 487, 1983.
infant	LDLo	unreported	200mg/kg/4D-I (200mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BLOOD: EOSINOPHILIA	Lancet. Vol. 1, Pg. 555, 1986.
infant	TDLo	intramuscular	250mg/kg/2D (250mg/kg)	VASCULAR: CHANGE IN PLASMA OR BLOOD VALUME	New England Journal of Medicine. Vol. 262, Pg. 787, 1960.
infant	TDLo	oral	440mg/kg (440mg/kg)		JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975.
infant	TDLo	oral	440mg/kg (440mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES	JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975.
mouse	LD50	intraperitoneal	1100mg/kg (1100mg/kg)		Dissertationes Pharmaceuticae. Vol. 14, Pg. 21, 1962.
mouse	LD50	intravenous	110mg/kg (110mg/kg)	BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
mouse	LD50	oral	1500mg/kg (1500mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 1, 1955.
mouse	LD50	subcutaneous	400mg/kg (400mg/kg)		"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 493, 1978.
rabbit	LD50	intravenous	117mg/kg (117mg/kg)		Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
rat	LD50	intraperitoneal	1811mg/kg (1811mg/kg)		Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat	LD50	intravenous	171mg/kg (171mg/kg)		Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
rat	LD50	oral	2500mg/kg (2500mg/kg)		Farmaco, Edizione Scientifica. Vol. 10, Pg. 3, 1955.
rat	LD50	subcutaneous	5gm/kg (5000mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Toxicology and Applied Pharmacology. Vol. 9, Pg. 445, 1966.
women	LDLo	oral	400mg/kg (400mg/kg)	BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: CYANOSIS VASCULAR: SHOCK	JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975

Product Name

Chloramphenicol

Synthetic route

Chloramphenicol Consensus Reports

Chloramphenicol Specification

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