CAS No.153-61-7,(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	153-61-7
Name:	(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Article Data:	33

Formula:	C₁₆H₁₆N₂O₆S₂
Molecular Weight:	396.445
Synonyms:	5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7R)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R-trans)-;3-(Acetoxymethyl)-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid;7-(2-Thienylacetamido)cephalosporanic acid;7-(Thiophene-2-acetamido)cephalosporin;7-[2-(2-Thienyl)acetylamido]cephalosporanic acid;
EINECS:	205-815-7
Density:	1.569 g/cm³
Melting Point:	160-161 °C
Boiling Point:	757.222 °C at 760 mmHg
Flash Point:	411.753 °C
Solubility:	158 mg/L in water
Appearance:	white crystal powder
PSA:	166.55000
LogP:	0.92110

Synthetic route

: 39098-97-0
2-thienylacetic acid chloride

: 957-68-6
7-Aminocephalosporanic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Stage #1: 7-Aminocephalosporanic acid With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 25 - 30℃; Inert atmosphere; Stage #2: 2-thienylacetic acid chloride In dichloromethane at 10℃; for 1h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;	92%
With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile Inert atmosphere;	85%
With tetrabutylammomium bromide; sodium hydrogencarbonate In dichloromethane; water at -5 - 0℃; Temperature;

: 1918-77-0
Thiophene-2-acetic acid

: 957-68-6
7-Aminocephalosporanic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 30℃; for 2h; Time; Reagent/catalyst; Green chemistry;	85%

: 1918-77-0
Thiophene-2-acetic acid

: 54769-22-1
1-methanesulfonyloxy-1,2,3-benzotriazole

: 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
With sodium acetate; acetic acid; triethylamine In dichloromethane	70%

...Expand

: 80927-95-3
3-(trimethylsiloxy)-8-oxo-7-(2-(2-thienyl) acetamido)-5-thiazabicyclo [4.2.0]Carboxylic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
With water; hydrogen cation Yield given;

: 5317-29-3
2,2,2-trichloroethyl (6R,7R)-3-acetoxymethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate

: 153-61-7
cephalothin

Conditions

Conditions	Yield
With Deacidite FF ion-exchange resin; zinc(II) chloride; zinc 1.) formic acid, RT, 5 h; Multistep reaction;

: 64-19-7
acetic acid

: 5-Methylene-2-[propylcarbamoyl-(2-thiophen-2-yl-acetylamino)-methyl]-5,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid

A: 107-10-8
propylamine

B: 153-61-7
cephalothin

Conditions

Conditions	Yield
With potassium chloride In water at 30℃; Equilibrium constant;

...Expand

: 39098-97-0
2-thienylacetic acid chloride

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / ethylene oxide / CH2Cl2 / 0.07 h 2: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C 3: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme
Multi-step reaction with 5 steps 1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH2Cl2, 0-5 deg C, 45 min 2: 66 percent / sodium iodide / acetone / 1.5 h 3: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme

Yield

Multi-step reaction with 4 steps
1: 92 percent / ethylene oxide / CH2Cl2 / 0.07 h
2: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C
3: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C
4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h
View Scheme

Multi-step reaction with 5 steps
1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH2Cl2, 0-5 deg C, 45 min
2: 66 percent / sodium iodide / acetone / 1.5 h
3: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C
4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C
5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h
View Scheme

: 1918-77-0
Thiophene-2-acetic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C 2: 66 percent / sodium iodide / acetone / 1.5 h 3: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme

: 85904-87-6
2,2,2-trichloroethyl (1S,6R,7R)-3-chloromethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 66 percent / sodium iodide / acetone / 1.5 h 2: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 3: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme

: 33492-83-0
2,2,2-trichloroethyl (1S,6R,7R)-3-bromomethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C 2: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 3: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme

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Specification

The Cephalothin, with the CAS registry number 153-61-7, is also known as 7-(2-Thienylacetamido)cephalosporanic acid. Its EINECS number is 205-815-7. This chemical's molecular formula is C₁₆H₁₆N₂O₆S₂ and molecular weight is 396.44. What's more, its systematic name is (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Its classification codes are: (1)Anti-Bacterial Agents; (2)Anti-Infective Agents; (3)Antibiotics; (4)Drug / Therapeutic Agent; (5)Mutation data; (6)Reproductive Effect. This chemical is a cephalosporin antibiotic. It should be sealed and stored in a cool, ventilated and dry place.

Physical properties of Cephalothin are: (1)ACD/LogP: 0.089; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.69; (4)ACD/LogD (pH 7.4): -3.62; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 166.55 Å²; (13)Index of Refraction: 1.676; (14)Molar Refractivity: 95.075 cm³; (15)Molar Volume: 252.75 cm³; (16)Polarizability: 37.691×10^-24cm³; (17)Surface Tension: 78.1 dyne/cm; (18)Density: 1.569 g/cm³; (19)Flash Point: 411.753 °C; (20)Enthalpy of Vaporization: 115.752 kJ/mol; (21)Boiling Point: 757.222 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of Cephalothin: it can be used to produce (6R)-3-acetoxymethyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester at the ambient temperature. It will need reagent NaHCO₃ and solvents dimethylformamide, dioxane. The yield is about 74%.

Cephalothin can be used to produce (6R)-3-acetoxymethyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester at the ambient temperature.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O
(2)Std. InChI: InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
(3)Std. InChIKey: XIURVHNZVLADCM-IUODEOHRSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intracrebral	81mg/kg (81mg/kg)		Antimicrobial Agents and Chemotherapy Vol. -, Pg. 863, 1965.
mouse	LD50	intramuscular	7gm/kg (7000mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
mouse	LD50	intravenous	4990mg/kg (4990mg/kg)		Chemotherapy Vol. 26(Suppl,
mouse	LD50	subcutaneous	> 4gm/kg (4000mg/kg)		Antimicrobial Agents and Chemotherapy. Vol. 3, Pg. 40, 1973.
rat	LD50	intraperitoneal	4296mg/kg (4296mg/kg)		Antibiotiki. Vol. 26, Pg. 44, 1981.
rat	LD50	intravenous	> 5gm/kg (5000mg/kg)	LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Chemotherapy Vol. 31(Suppl,
rat	LD50	parenteral	23mg/kg (23mg/kg)		Antimicrobial Agents and Chemotherapy Vol. -, Pg. 863, 1965.
rat	LD50	subcutaneous	10gm/kg (10000mg/kg)	KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Chemotherapy Vol. 27