• Name

  Cefoxitin

• EINECS 252-641-2
• CAS No. 35607-66-0
• Article Data12
• CAS DataBase
• Density 1.63 g/cm³
• Solubility Predicted solubility in water is less than 0.2mg/ml
• Melting Point 149 - 150oC
• Formula C₁₆H₁₇N₃O₇S₂
• Boiling Point 843.4 °C at 760 mmHg
• Molecular Weight 427.459
• Flash Point 463.9 °C
• Transport Information UN 3077
• Appearance White to off-white crystalline powder
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6R,7S)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6R-cis)-;Cephoxitin;
• PSA 201.80000
• LogP 1.12770

Synthetic route

1476-46-6

desacetyl cephalosporin C

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Stage #1: desacetyl cephalosporin C With N,N'-dibenzylethylenediamine diacetate In dichloromethane; water at 25℃; Stage #2: With isocyanate de chlorosulfonyle In dichloromethane at -40℃; Temperature; Further stages;	96%

1189-71-5

isocyanate de chlorosulfonyle

2C15H16N2O6S2*C16H20N2

35607-66-0

cefoxitin

Conditions

Conditions	Yield
In acetone at -35 - -30℃;	82.8%

1189-71-5

isocyanate de chlorosulfonyle

3-hydroxymethyl-7α-[(2-thienyl)acetamido]-4-cephalosporanic acid benzathine salt

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Stage #1: isocyanate de chlorosulfonyle; 3-hydroxymethyl-7α-[(2-thienyl)acetamido]-4-cephalosporanic acid benzathine salt In acetone at -50 - -45℃; for 2h; Stage #2: With water In acetone at 8 - 10℃;	65%
In tetrahydrofuran Cooling;
Stage #1: isocyanate de chlorosulfonyle; 3-hydroxymethyl-7α-[(2-thienyl)acetamido]-4-cephalosporanic acid benzathine salt In tetrahydrofuran at -50 - -45℃; for 1h; Stage #2: With water In tetrahydrofuran at 10 - 12℃; for 0.5h; Stage #3: With hydrogenchloride In water at 0 - 34℃; for 1.5h; pH=1.9 - 2.1; Solvent; Temperature;

35607-68-2

diphenylmethyl (6R, 7S)-7-(2'-thienyl)acetamido-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylate

35607-66-0

cefoxitin

Conditions

Conditions	Yield
With trifluoroacetic acid In various solvent(s) 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min;	56%

39098-97-0

2-thienylacetic acid chloride

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 2: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme

32178-84-0

cephamycin C

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 5 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 4: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 5: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 6 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 4: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 5: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 6: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 5 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 4: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 5: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme

35664-28-9

(6R)-7t-[(R)-5-benzhydryloxycarbonyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-pentanoylamino]-3-carbamoyloxymethyl-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 3: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 4 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 3: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 5 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 3: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 4: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 5: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 4 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 3: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme

52390-38-2

diphenylmethyl (6R, 7S)-7-amino-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylate

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 2: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme

66893-40-1

diphenylmethyl (6R,7S)-7-carboxycarbonylamino-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylate

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 2: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 3 steps 1: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 2: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 3: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme

68318-53-6

(6R)-7t-hydroxyoxalylamino-3-(hydroxyoxalylcarbamoyloxy-methyl)-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

35607-66-0

cefoxitin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 2: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 3: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme
Multi-step reaction with 4 steps 1: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 2: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 3: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme

Cefoxitin History

Cefoxitin Specification