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56-75-7

Basic Information
CAS No.: 56-75-7
Name: Chloramphenicol
Article Data: 73
Molecular Structure:
Molecular Structure of 56-75-7 (Chloramphenicol)
Formula: C11H12Cl2N2O5
Molecular Weight: 323.133
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;
EINECS: 200-287-4
Density: 1.547 g/cm3
Melting Point: 148-150 °C(lit.)
Boiling Point: 644.913 °C at 760 mmHg
Flash Point: 343.831 °C
Solubility: 2.5 g/L (25 °C) in water
Appearance: White to grey-white crystalline powder
Hazard Symbols: ToxicT
Risk Codes: 45
Safety: 53-45
Transport Information: UN 2811
PSA: 115.38000
LogP: 1.82310
Synthetic route
116-54-1

dichloroacetic acid methyl ester

56-75-7

chloramphenicol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 16h; Ambient temperature;70%
79-36-7

dichloroacethyl chloride

56-75-7

chloramphenicol

Conditions
ConditionsYield
With dichloro-acetic acid und anschliessend mit wss.Aceton bei pH8-9;
302-17-0

chloral hydrate

151-50-8

potassium cyanide

56-75-7

chloramphenicol

1768-31-6

pentachloroacetone

56-75-7

chloramphenicol

Conditions
ConditionsYield
With 1,4-dioxane
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Consensus Reports

 Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

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

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