CAS No.56-75-7,Chloramphenicol Suppliers

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Basic Information

Molecular Structure:
CAS No.:	56-75-7
Name:	Chloramphenicol
Article Data:	73
Cas Database

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:	T
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

: 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

Raw Materials

56-75-7

530-43-8

57-24-9

302-17-0

Downstream Products

119-62-0

56-75-7

3544-94-3

554-68-7

16255-48-4

134-90-7

530-43-8

555-16-8

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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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