Cephalothin supplier | CasNO.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
EINECS 205-815-7
CAS No. 153-61-7
Article Data33
CAS DataBase
Density 1.569 g/cm³
Solubility 158 mg/L in water
Melting Point 160-161 °C
Formula C₁₆H₁₆N₂O₆S₂
Boiling Point 757.222 °C at 760 mmHg
Molecular Weight 396.445
Flash Point 411.753 °C
Transport Information
Appearance white crystal powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
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

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

: 33465-64-4
2,2,2-trichloroethyl (1S,6R,7R)-3-iodomethyl-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: 50 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

: 33492-84-1
2,2,2-trichloroethyl (1S,6R,7R)-3-acetoxymethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide

: 153-61-7
cephalothin

Conditions

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

: 85904-86-5
2,2,2-trichloroethyl (1S,6R,7R)-7-amino-3-bromomethylceph-3-em-4-carboxylate 1-oxide hydrobromide

: 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

: 85904-84-3
2,2,2-trichloroethyl (1S,6R,7R)-7-amino-3-chloromethylceph-3-em-4-carboxylate 1-oxide

: 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

: 33465-56-4
2,2,2-trichloroethyl (1S,6R,7R)-3-bromomethyl-7-formamidoceph-3-em-4-carboxylate 1-oxide

: 153-61-7
cephalothin

Conditions

Conditions	Yield
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
Multi-step reaction with 4 steps 1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH2Cl2, 0-5 deg C, 45 min 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: 98 percent / phosphorus tribromide / methanol; diethyl ether / 1.17 h / 0 - 10 °C 2: 92 percent / ethylene oxide / CH2Cl2 / 0.07 h 3: 68 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
Multi-step reaction with 6 steps 1: 46.2 percent / conc. hydrochloric acid / tetrahydrofuran / 30 h / 6 °C 2: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C 3: 66 percent / sodium iodide / acetone / 1.5 h 4: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 5: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 6: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme

: 52646-45-4
p-methoxybenzyl 7β-(2-thienylacetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme

: 80927-93-1
(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methyl-benzyl ester

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CDCl3 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme

: 80927-92-0
(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2-methyl-benzyl ester

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CDCl3 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme

: 35607-83-1
(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 benzhydryl ester

: 153-61-7
cephalothin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme

: 39098-97-0
2-thienylacetic acid chloride

: 3741-34-2
2-diethylamino-1,3,2-dioxaphospholane

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

: 153-61-7
cephalothin

Conditions

Conditions	Yield
With sodium hydroxide; chloro-trimethyl-silane In water; ethyl acetate; acetonitrile

...Expand

: 39098-97-0
2-thienylacetic acid chloride

: 1192-03-6
2-chloro-[1,3,2]dioxaborolane

: 957-68-6
7-Aminocephalosporanic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
With sodium hydrogencarbonate; triethylamine In dichloromethane; water; acetone

...Expand

: 19432-68-9
methyl 2-thiopheneacetate

: 957-68-6
7-Aminocephalosporanic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
With ammonium hydroxide; penicillin G amidase In water at 20℃; pH=6.5 - 7; Enzymatic reaction;

: 93799-48-5
2-thiopheneacetyl N-hydroxysuccinimide ester

: 957-68-6
7-Aminocephalosporanic acid

: 153-61-7
cephalothin

Conditions

Conditions	Yield
In 1,2-dimethoxyethane at 15 - 25℃; for 1h; Solvent; Temperature; Concentration; Irradiation;	154 g

: 7440-44-0
pyrographite

: 108-98-5
thiophenol

: 107-06-2
1,2-dichloro-ethane

: 153-61-7
cephalothin

: 3-((PHENYLTHIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; ethanol; Isopropyl acetate; water; ethyl acetate	19.4%

...Expand

: 153-61-7
cephalothin

: 58-71-9
sodium cephalothin

Conditions

Conditions	Yield
With sodium 2-ethylhexanoic acid In acetone	26%

: 40126-72-5
2,2,2-trichloroethyl glycinate*HBr

: 153-61-7
cephalothin

: 113322-14-8
{[(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-amino}-acetic acid 2,2,2-trichloro-ethyl ester

Conditions

Conditions	Yield
With triethylamine; diisopropyl-carbodiimide In dichloromethane	28%

: 113322-02-4
H2N-TrpOTce

: 153-61-7
cephalothin

: 113322-16-0
(S)-2-{[(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionic acid 2,2,2-trichloro-ethyl ester

Conditions

Conditions	Yield
With methyl(diethylamino)acetylene In dichloromethane	31%

: 13183-79-4
1-methyl-5-mercaptotetrazole

: 153-61-7
cephalothin

: 3-(((1H-TETRAZOL-5-YL)THIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
In acetic acid	31%

: 29490-19-5
2-mercapto-5-methyl-1,3,4-thiadiazole

: 153-61-7
cephalothin

: 3-(((5-METHYL-1,3,4-THIADIAZOL-2-YL)THIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
In acetonitrile	33.9%

: 6265-73-2
N-(2-hydroxyethyl)nicotinamide

: 153-61-7
cephalothin

A: 2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ2

B: 154777-98-7
2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 20 - 25℃; for 20h;	A 17.9% B 35.9%

...Expand

1-(carboxymethyl)-1-H-tetrazole-5-thiol: 1-(carboxymethyl)-1-H-tetrazole-5-thiol

: 153-61-7
cephalothin

: 3-(((1-(CARBOXYMETHYL)-1H-TETRAZOL-5-YL)THIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
In hexane; ethyl acetate; acetonitrile	38%

: 111-88-6
Octanethiol

: 153-61-7
cephalothin

: N-((6R,7R)-3-((octylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl)-2-(thiophen-2-yl)acetamide

Conditions

Conditions	Yield
With 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 60℃; for 5h; Tsuji-Trost Allylation; Schlenk technique; regioselective reaction;	39%

: 2032-04-4
vinyldiazomethane

: 75-05-8
acetonitrile

: 153-61-7
cephalothin

A: 104949-45-3
allyl 7β-(2-(thien-2-yl)acetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate

B: C21H23N3O6S2

Conditions

Conditions	Yield
In diethyl ether	A 40% B 36%

...Expand

: 106-45-6
para-thiocresol

: 153-61-7
cephalothin

: (6R,7R)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-3-((p-tolylthio)methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 40℃; for 7h; Tsuji-Trost Allylation; Schlenk technique; regioselective reaction;	41%

: 7440-44-0
pyrographite

: 13183-79-4
1-methyl-5-mercaptotetrazole

: 153-61-7
cephalothin

: 3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-7-(2-(2-thienyl)acetamido)-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
With methanesulfonic acid; sodium hydrogencarbonate In water; ethyl acetate; butanone	41.6%

...Expand

: 5-mercapto-3-methyl-1,2,4-oxadiazole

: 153-61-7
cephalothin

: 3-(((3-METHYL-1,2,4-OXADIAZOL-5-YL)THIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
With sodium chloride; sodium hydrogencarbonate In 1,1,2-trichloroethane; ethyl acetate	48%

: 202116-96-9
5-[(tetrazol-1-yl)methyl]-1,3,4-thiadiazole-2-thiol

: 153-61-7
cephalothin

: 7-{[(thiophen-2-yl)acetyl]amino}-3-{[5-[(tetrazol-1-yl)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.025h; Condensation; microwave irradiation;	51%

: 239468-65-6
5-[(quinolin-8-yloxy)methyl]-1,3,4-thiadiazole-2-thiol

: 153-61-7
cephalothin

: 7-{[(thiophen-2-yl)acetyl]amino}-3-{[5-[(quinolin-8-yloxy)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.0166667h; Condensation; microwave irradiation;	53%

: 202116-95-8
5-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-1,3,4-thiadiazole-2-thiol

: 153-61-7
cephalothin

: 7-{[(thiophen-2-yl)acetyl]amino}-3-{[5-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.0166667h; Condensation; microwave irradiation;	54%

: 113351-77-2
H2N-OTroc-TyrOTce

: 153-61-7
cephalothin

: 113322-17-1
(S)-2-{[(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-amino}-3-[4-(2,2,2-trichloro-ethoxycarbonyloxy)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester

Conditions

Conditions	Yield
With methyl(diethylamino)acetylene In dichloromethane	55%

: 144-55-8
sodium hydrogencarbonate

: 13183-79-4
1-methyl-5-mercaptotetrazole

: 153-61-7
cephalothin

: 3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-7-(2-(2-thienyl)acetamido)-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
In diethyl ether; nitromethane; ethyl acetate	56.2%

...Expand

: 371-42-6
4-Fluorothiophenol

: 153-61-7
cephalothin

: (6R,7R)-3-(((4-fluorophenyl)thio)methyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 40℃; for 7h; Tsuji-Trost Allylation; Schlenk technique; regioselective reaction;	58%

: 239468-67-8
5-[(4-methylquinolin-2-yloxy)methyl]-1,3,4-thiadiazole-2-thiol

: 153-61-7
cephalothin

: 7-{[(thiophen-2-yl)acetyl]amino}-3-{[5-[(4-methylquinolin-2-yloxy)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.0333333h; Condensation; microwave irradiation;	59%

: 507-09-5
thioacetic acid

: 153-61-7
cephalothin

: 23958-17-0
(6R,7R)-3-(acetylthiomethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate	60%

: 29490-19-5
2-mercapto-5-methyl-1,3,4-thiadiazole

: 153-61-7
cephalothin

: 26970-95-6
7β-(thiophen-2-acetamido)-3-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-ceph-3-em-4-carboxylic acid

Conditions

Conditions	Yield
With phosphate buffer pH 6.4; sodium hydrogencarbonate at 60℃; for 5h;	62%
With phosphate buffer; sodium carbonate at 55 - 60℃; for 6h;

: 36988-21-3
3-methyl-5-mercapto-1,2,4-thiadiazole

: 153-61-7
cephalothin

: 3-(((3-METHYL-1,2,4-THIADIAZOL-5-YL)THIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
In ethyl acetate; 1,2-dichloro-ethane	65%

: 131242-36-9
2-sulfanylpyrimidine

: 153-61-7
cephalothin

: 3-(((2-PYRIMIDINYL)THIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
With sodium acetate In acetic acid	70.5%
In acetonitrile

: 101-83-7
N-cyclohexyl-cyclohexanamine

: 13183-79-4
1-methyl-5-mercaptotetrazole

: 153-61-7
cephalothin

: 3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-7-(2-(2-thienyl)acetamido)-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
In ethanol; acetonitrile	71%
In ethanol; propiononitrile	39%
In ethanol; acetonitrile
In ethanol; 1,2-dichloro-ethane

...Expand

: 21094-62-2
3-mercapto-4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazine

: 153-61-7
cephalothin

: 3-(((4,5-DIHYDRO-6-HYDROXY-4-METHYL-5-OXO-1,2,4-TRIAZIN-3-YL)THIO)METHYL)-7-(2-(2-THIENYL)ACETAMIDO)-3-CEPHEM-4-CARBOXYLIC ACID

Conditions

Conditions	Yield
In acetonitrile	72.6%

Cephalothin 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

Product 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

Synthetic route

Cephalothin Specification

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