Ciprofloxacin supplier | CasNO.85721-33-1

Name
Ciprofloxacin
EINECS 617-751-0
CAS No. 85721-33-1
Article Data62
CAS DataBase
Density 1.461 g/cm³
Solubility 86mg/L(25 oC)
Melting Point 255-257 °C
Formula C₁₇H₁₈F N₃ O₃
Boiling Point 581.774 °C at 760 mmHg
Molecular Weight 331.347
Flash Point 305.646 °C
Transport Information
Appearance White powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;1-Cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylicacid;BAY-q 3939;Catex;Ciflafin;Ciprine;Cipro IV;Ciprobay 100;Ciprofloxacillin;Ciprofloxacin;Ciprofloxacine;Ciprolet;Ciprolet DS;Cipromed;Cipropol;Ciprovet;Ciproxim;Ciproxina;Cunesin;Cyclofloxacin;Euciprin;Oftacifox;Procip;Quinox XR;
PSA 74.57000
LogP 1.97710

Synthetic route

: 93594-48-0
7-[4-tert-butoxycarbonyl-piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h;	98.7%

: 110-85-0
piperazine

: C15H16Cl2FNO3

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With 1-butyl-3-methylimidazolium hydroxide at 70℃; for 5h; Reagent/catalyst; Temperature;	96.2%

: 93107-08-5
ciprofloxacin hydrochloride

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water	96%
With sodium hydrogencarbonate In water	95%
With ammonium hydroxide In water at 30 - 55℃; for 4.41667h; pH=6.8; Temperature; Reagent/catalyst; pH-value;	82.52%

: 110-85-0
piperazine

: 86393-33-1
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.366667h; Reflux;	94%
at 150℃; Microwave irradiation;	90%
With aluminum tri-bromide In ethanol at 75℃; for 4h; Reagent/catalyst; Solvent; Temperature;	89.7%

: 1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid sodium salt

: 110-85-0
piperazine

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With aluminum (III) chloride In i-Amyl alcohol at 140℃; for 8h; Reagent/catalyst; Temperature;	91.2%

: 110-85-0
piperazine

: 93107-30-3
1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
In pyridine for 18h; Heating;	89%
In water
In dimethyl sulfoxide Heating;	960 mg

: 1-(t-butylmethylsilyl)piperazine

: 86393-33-1
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
	88%

: 110-85-0
piperazine

: 86393-33-1
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

A: 85721-33-1
ciprofloxacin

B: 1-cyclopropyl-7-chloro-6-piperazinyl-4-oxo-1,2-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
In water for 15h; Heating;	A 86% B n/a
In water at 150℃; for 5h;	A 65% B 10%
In dimethylsulfoxide-d6 at 120 - 130℃;	A 87 % Spectr. B 13 % Spectr.

...Expand

: 4-[10-(17'-Tetrabenzo[acgi]fluorenyl)decyloxy]benzyl 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With adsorption onto charcoal; trifluoroacetic acid 2.) dichloromethane;	57%
With adsorption onto charcoal; trifluoroacetic acid In dichloromethane Product distribution; solid/solution phase synthesis to eliminate impurities;
With water; pyrographite; trifluoroacetic acid In dichloromethane at 20℃; for 0.25h; Hydrolysis;

: 110-85-0
piperazine

: 98349-24-7
ethyl 2,4,5-trifluorobenzoylacetate

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 765-30-0
Cyclopropylamine

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 110-85-0
piperazine

: 119489-54-2
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid boron diacetate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With sodium hydroxide 1.) DMSO, 110 deg C, 2 h; 2.) reflux, 1 h; Yield given;

: C17H17BF3N3O3

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With sodium hydroxide for 1h; Heating;

: 86393-33-1
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / BF3*Et2O / diethyl ether; CH2Cl2 / 5 h / Heating 2: 96 percent / triethylamine / dimethylsulfoxide / 3 h / 60 °C 3: aq. NaOH / 1 h / Heating View Scheme

: 121322-20-1
C13H8BClF3NO3

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / triethylamine / dimethylsulfoxide / 3 h / 60 °C 2: aq. NaOH / 1 h / Heating View Scheme

: 104599-90-8
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Alkaline hydrolysis 2: butan-1-ol / 5 h / 135 °C View Scheme
Multi-step reaction with 2 steps 1: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 2: 79 percent / pyridine / 8 h / Heating View Scheme

: 104600-21-7
methyl 3-cyclopropylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / dimethylformamide / 5 h / 130 °C 2: Alkaline hydrolysis 3: butan-1-ol / 5 h / 135 °C View Scheme

: 98349-25-8
ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / Heating 2: 89 percent / pyridine / 18 h / Heating View Scheme
Multi-step reaction with 2 steps 1: dimethyl sulfoxide / Heating 2: sodium hydroxide / dimethyl sulfoxide / 90 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; water; acetic acid / 2.5 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 15 h / 140 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C View Scheme

: 101799-76-2
3-Cyclopropylamino-2-(2,4,5-trifluorbenzoyl)acrylsaeure-ethylester

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: t-BuOK / 2-methyl-propan-2-ol 2: aq. HCl / Heating 3: 89 percent / pyridine / 18 h / Heating View Scheme

: 86483-51-4
ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic anhydride / 2 h / Heating 2: 92 percent / ethanol / 1 h / Ambient temperature 3: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 4: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 5: 79 percent / pyridine / 8 h / Heating View Scheme

: 86483-53-6
3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-ethylester

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 2: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 3: 79 percent / pyridine / 8 h / Heating View Scheme

: 86483-54-7
ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 2: 79 percent / pyridine / 8 h / Heating View Scheme

: 86393-34-2
2,4-dichloro-5-fluorobenzoyl chloride

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / pyridine / dioxane / 1.) 2 h, room temperature, 2.) 1 h, 70 - 80 deg C. 2: 85 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 3: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 4: 79 percent / pyridine / 8 h / Heating View Scheme
Multi-step reaction with 7 steps 1: Mg/ethanol, CCl4 / ethanol; toluene / 1.) 0 to -5 deg C, 2.) 12 h, room temperature 2: p-toluenesulfonic acid / H2O / 5 h / Heating 3: acetic anhydride / 2 h / Heating 4: 92 percent / ethanol / 1 h / Ambient temperature 5: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 6: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 7: 79 percent / pyridine / 8 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: tributyl-amine / 1 h / 70 °C 1.2: 15 °C / 1520.1 Torr 2.1: sodium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene / 125 - 130 °C 2.2: 8 h / 85 °C View Scheme

: 105392-26-5
3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-methylester

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 2: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 3: 79 percent / pyridine / 8 h / Heating View Scheme

: 86483-50-3
diethyl 2,4-dichloro-5-fluoro-benzoyl-malonate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: p-toluenesulfonic acid / H2O / 5 h / Heating 2: acetic anhydride / 2 h / Heating 3: 92 percent / ethanol / 1 h / Ambient temperature 4: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 5: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 6: 79 percent / pyridine / 8 h / Heating View Scheme

: 72396-25-9
3-(Cyclopropylamino)acrylsaeure-methylester

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / pyridine / dioxane / 1.) 2 h, room temperature, 2.) 1 h, 70 - 80 deg C. 2: 85 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 3: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 4: 79 percent / pyridine / 8 h / Heating View Scheme

: 86483-52-5
2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / ethanol / 1 h / Ambient temperature 2: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 3: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 4: 79 percent / pyridine / 8 h / Heating View Scheme

: 346586-91-2
C17H18FN3O3*H3N

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Purification / work up; HPLC column;

: 93594-29-7
7-[4-(ethoxycarbonyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Stage #1: 7-[4-(ethoxycarbonyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid With potassium hydroxide; water for 3 - 6h; Heating / reflux; Stage #2: With hydrogenchloride In water at 20℃; for 0.5h; pH=7.7 - 7.9; Product distribution / selectivity;

: sodium 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinolone-3-carboxylate

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
Purification / work up; HPLC column;

: 24424-99-5
di-tert-butyl dicarbonate

: 85721-33-1
ciprofloxacin

: 93594-48-0
7-[4-tert-butoxycarbonyl-piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	100%
Stage #1: ciprofloxacin With sodium hydroxide In 1,4-dioxane; water Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 20℃; for 48h;	99%
With trimethylamine In tetrahydrofuran at 0 - 20℃; for 8.16667h;	97.3%

: 85721-33-1
ciprofloxacin

: 79-03-8
propionyl chloride

: 1‐cyclopropyl‐6‐fluoro‐4‐oxo‐7‐(4‐propionylpiperazin‐1‐yl)‐1,4‐dihydroquinoline‐3‐carboxylic acid

Conditions

Conditions	Yield
With TEA In tetrahydrofuran at 20℃;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 1.5h;	75%
Stage #1: ciprofloxacin With triethylamine In dichloromethane at 0℃; for 0.25h; Stage #2: propionyl chloride In dichloromethane at 0 - 20℃;

: 50-00-0
formaldehyd

: 1456620-74-8
{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1,3,4-oxadiazole-2-thiol

: 85721-33-1
ciprofloxacin

: C32H36FN7O5S

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.0833333h; Temperature; Time; Mannich Aminomethylation; Microwave irradiation; Sealed tube;	100%

...Expand

: 85721-33-1
ciprofloxacin

: 80-70-6
N,N,N',N'-tetramethylguanidine

: C17H18FN3O3*C5H13N3

Conditions

Conditions	Yield
In methanol; water at 20℃; for 3h;	100%

: 85721-33-1
ciprofloxacin

: 6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

: C17H18FN3O3*C9H16N2

Conditions

Conditions	Yield
In methanol; water at 20℃; for 2h;	100%

: 85721-33-1
ciprofloxacin

: 153207-76-2
toluenesulfonic acid 3-azidopropyl ester

: 1144106-71-7
7-(4-(3-azidopropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In acetonitrile Inert atmosphere; Reflux;	100%

: 50-00-0
formaldehyd

: 4-benzyl-5-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-one

: 85721-33-1
ciprofloxacin

: C39H43FN8O5

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.0833333h; Temperature; Time; Mannich Aminomethylation; Microwave irradiation; Sealed tube;	99%

...Expand

: 3001-72-7
DBN

: 85721-33-1
ciprofloxacin

: C17H18FN3O3*C7H12N2

Conditions

Conditions	Yield
In methanol; water at 20℃; for 2h;	99%

: 85721-33-1
ciprofloxacin

: 93107-08-5
ciprofloxacin hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water Heating;	98%
With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 1h;	95%
With hydrogenchloride In methanol; water at 45 - 50℃; for 2h; Product distribution / selectivity;

: 85721-33-1
ciprofloxacin

: 105-36-2
ethyl bromoacetate

: 1-cyclopropyl-7-(4-(2-ethoxy-2-oxoethyl)piperazin-1-yl)-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: ciprofloxacin With sodium In ethanol for 0.0666667h; Sealed tube; Microwave irradiation; Stage #2: ethyl bromoacetate In ethanol for 0.166667h; Microwave irradiation;	98%
With potassium iodide; triethylamine In N-methyl-acetamide; water

: 39716-58-0
pent-4-enoyl chloride

: 85721-33-1
ciprofloxacin

: 1-cyclopropyl-6-fluoro-4-oxo-7-(4-(pent-4-enoyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sodium acetate In dichloromethane at 20℃; for 0.166667h;	98%

: 50-00-0
formaldehyd

: 5-(thiomorpholinomethyl)-1,3,4-oxadiazole-2-thiol

: 85721-33-1
ciprofloxacin

: C25H29FN6O4S2

Conditions

Conditions	Yield
With indium(III) chloride In water; N,N-dimethyl-formamide at 20℃; for 4.5h; Reagent/catalyst; Mannich Aminomethylation;	98%

...Expand

: 2136-79-0
Dactal

: 85721-33-1
ciprofloxacin

: [ciprofloxacin] [tetrachloroterephthalic acid]*1.5

Conditions

Conditions	Yield
In methanol; water at 140℃; Concentration; Temperature;	98%

: 34619-03-9
tert-butyldicarbonate

: 85721-33-1
ciprofloxacin

: 93594-48-0
7-[4-tert-butoxycarbonyl-piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In methanol; chloroform	97%
In methanol; chloroform	97%

: 108-30-5
succinic acid anhydride

: 85721-33-1
ciprofloxacin

: 7-[4-(3-carboxypropionyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 95℃; for 12h; Inert atmosphere;	97%
In dimethyl sulfoxide at 95℃; for 24h;	59%
With sodium hydroxide In 1,4-dioxane; water

: 5,7-dichloro-4,6-dinitrobenzofuroxan 1-oxide

: 85721-33-1
ciprofloxacin

: 4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 5-chloro-4,6-dinitro-7-oxidobenzofuroxan

Conditions

Conditions	Yield
With water In dimethyl sulfoxide for 24h;	97%

: 50-00-0
formaldehyd

: 3-(4-benzyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-1-ethyl-7-methyl-1,8-naphthyridin-4(1H)-one

: 85721-33-1
ciprofloxacin

: 6-(4-{[4-benzyl-3-(1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridin-3-yl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl)-1-cyclopropyl-5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 50℃; for 0.0833333h; Temperature; Microwave irradiation;	97%

...Expand

: 50-00-0
formaldehyd

: 5-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-4-benzyl-4H-1,2,4-triazole-3-thiol

: 85721-33-1
ciprofloxacin

: C39H43FN8O4S

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.0833333h; Temperature; Time; Mannich Aminomethylation; Microwave irradiation; Sealed tube;	97%

...Expand

: 50-00-0
formaldehyd

: 4-phenyl-5-(thiomorpholinomethyl)-4H-1,2,4-triazol-3-ol

: 85721-33-1
ciprofloxacin

: C31H34FN7O4S

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In water; N,N-dimethyl-formamide at 20℃; for 4h; Reagent/catalyst; Mannich Aminomethylation;	97%

...Expand

: 50-00-0
formaldehyd

: benzyl-5-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}-4H-1,2,4-triazole-3-thiol

: 85721-33-1
ciprofloxacin

: 1-cyclopropyl-6-fluoro-7-{4-[(3-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}-4-benzyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-1-yl)methyl]piperazin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
In neat (no solvent) for 0.25h; Solvent; Mannich Aminomethylation; Microwave irradiation; Green chemistry;	97%

...Expand

: 50-00-0
formaldehyd

: 4-phenyl-5-(((6-(4-phenylpiperazin-1-yl)pyridin-3-yl)amino)methyl)-4H-1,2,4-triazole-3-thiol

: 85721-33-1
ciprofloxacin

: 1-cyclopropyl-6-fluoro-4-oxo-7-(4-((4-phenyl-3-(((6-(4-phenylpiperazin-1-yl)pyridin-3-yl)amino)methyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)methyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylicacid

Conditions

Conditions	Yield
With indium(III) chloride In N,N-dimethyl-formamide at 20℃; for 24h; Mannich Aminomethylation;	97%

...Expand

: 6404-29-1
6-(tert-butoxycarbonylamino)hexanoic acid

: 85721-33-1
ciprofloxacin

: 1407510-82-0
7-(4-(6-((tert-butoxycarbonyl)amino)hexanoyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 4h;	96%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 20℃;

: 39066-42-7
4-azido-2,3,5,6-tetrafluoropyridine

: 85721-33-1
ciprofloxacin

: 122-78-1
phenylacetaldehyde

: C30H24F5N5O3

Conditions

Conditions	Yield
In acetone at 20℃;	96%

...Expand

: 50-00-0
formaldehyd

: 5-[({3-fluoro-4-[4-(4-fluorophenyl)piperazin-1-yl]phenyl}amino)methyl]-1,3,4-oxadiazole-2(3H)-thione

: 85721-33-1
ciprofloxacin

: 1-cyclopropyl-6-fluoro-7-(4-{[5-[({3-fluoro-4-[4-(4-fluorophenyl)piperazin-1-yl]phenyl}amino)methyl]-2-thioxo-1,3,4-oxadiazol-3(2H)-yl]methyl}piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride at 50℃; for 0.333333h; Microwave irradiation; Sealed tube;	96%

...Expand

: 4-chloro-6-[1-(vinylsulfonyl)pyrrolidin-2-yl]benzene-1,3-diol

: 85721-33-1
ciprofloxacin

: 121-44-8
triethylamine

: C29H32ClFN4O7S*C6H15N

Conditions

Conditions	Yield
In ethanol; water Michael Addition; Reflux;	96%

...Expand

: 85721-33-1
ciprofloxacin

: 79-04-9
chloroacetyl chloride

: 7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 40℃; for 12h;	95%
Stage #1: ciprofloxacin With sodium hydrogencarbonate In dichloromethane for 0.333333h; Cooling with ice; Stage #2: chloroacetyl chloride In dichloromethane at -5℃;	85%
With triethylamine In dichloromethane at 0 - 20℃; for 1.4h;	73%

: 50-00-0
formaldehyd

: 5-{[(3-fluoro-4-thiomorpholin-4-ylphenyl)amino]methyl}-4-phenyl-4H-1,2,4-triazole-3-thiol

: 85721-33-1
ciprofloxacin

: 1-cyclopropyl-6-fluoro-7-{4-[(3-{[(3-fluoro-4-thiomorpholin-4-ylphenyl)amino]methyl}-4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)methyl]piperazin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylicacid

Conditions

Conditions	Yield
With hydrogenchloride In neat (no solvent) for 0.0833333h; Solvent; Mannich Aminomethylation; Microwave irradiation; Sealed tube; Green chemistry;	95%

...Expand

Ciprofloxacin Chemical Properties

IUPAC Name: 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate
Molecular Formula: C₁₇H₁₈FN₃O₃
Molecular Weight: 331.341523 g/mol
Appearance: White Powder
Melting Point: 255-257 °C
storage temp.: Store at 0-5 °C
Merck: 13,2337
Density: 1.461 g/cm³
Flash Point: 305.6 °C
Index of Refraction: 1.655
Surface Tension: 67.4 dyne/cm
Enthalpy of Vaporization: 91.5 kJ/mol
Boiling Point: 581.8 °C at 760 mmHg
Vapour Pressure: 2.24E-14 mmHg at 25 °C
Synonyms of Ciprofloxacin (CAS NO.85721-33-1): 1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarbox ; ciloxan; ciprobid ; ciproiv ; euciprin ; ciprobay ; ciprofloxacin ; 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
Categories: Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals

Ciprofloxacin History

Ciprofloxacin (CAS NO.85721-33-1) was first introduced as the broad-spectrum oral fluoroquinolone in 1987 by Bayer. In 1991 the intravenous formulation was introduced. Ciprofloxacin (85721-33-1) was first patented Jan 21, 1986, in Germany, and was later approved by the U.S. Food and Drug Administration on October 22, 1987.

Ciprofloxacin Uses

Ciprofloxacin (CAS NO.85721-33-1) is a third-generation quinolone antibiotics used for the treatment of respiratory tract infections, urinary tract, ENT, skin and soft tissue, gastrointestinal tract infections. It is also used as fluorinated quinolone antibacterial.

Ciprofloxacin Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	LDLo	oral	5714ug/kg/2D- (5.714mg/kg)	BEHAVIORAL: COMA LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: LIVER FUNCTION TESTS IMPAIRED	Lancet. Vol. 343, Pg. 738, 1994.
man	TDLo	oral	21mg/kg/3D-I (21mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED KIDNEY, URETER, AND BLADDER: PROTEINURIS KIDNEY, URETER, AND BLADDER: HEMATURIA	Annals of Pharmacotherpy. Vol. 29, Pg. 84, 1995.
man	TDLo	oral	21429ug/kg/3D (21.429mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS	Annals of Pharmacotherpy. Vol. 26, Pg. 930, 1992.
man	TDLo	oral	129mg/kg/6D-I (129mg/kg)	BEHAVIORAL: REGIDITY	Journal of Clinical Psychiatry. Vol. 54, Pg. 115, 1993.
man	TDLo	oral	200mg/kg (200mg/kg)	BEHAVIORAL: TREMOR GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: OTHER CHANGES	Annals of Pharmacotherpy. Vol. 28, Pg. 805, 1994.
mouse	LD50	intraperitoneal	1165mg/kg (1165mg/kg)		Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991.
mouse	LD50	intravenous	122mg/kg (122mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Korean Journal of Toxicology. Vol. 8, Pg. 161, 1993.
mouse	LD50	oral	5gm/kg (5000mg/kg)		Journal of Medicinal Chemistry. Vol. 33, Pg. 1344, 1990.
mouse	LD50	subcutaneous	> 1gm/kg (1000mg/kg)		Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.
rat	LD50	intravenous	207mg/kg (207mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Korean Journal of Toxicology. Vol. 8, Pg. 161, 1993.
rat	LD50	oral	> 2gm/kg (2000mg/kg)		Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.
rat	LD50	subcutaneous	> 1gm/kg (1000mg/kg)		Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.
women	TDLo	multiple routes	40mg/kg/6D-I (40mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Acta Clinica Belgica. Vol. 49, Pg. 173, 1994.
women	TDLo	oral	10mg/kg (10mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" GASTROINTESTINAL: NAUSEA OR VOMITING	Allergy. Vol. 50(Suppl,
women	TDLo	oral	40mg/kg/2D-I (40mg/kg)	BEHAVIORAL: HEADACHE BLOOD: EOSINOPHILIA	American Journal of Medicine. Vol. 87, Pg. 589, 1989.
women	TDLo	oral	135mg/kg/3D-I (135mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Archives of Internal Medicine. Vol. 153, Pg. 1258, 1993.
women	TDLo	oral	280mg/kg/2W-I (280mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"	American Journal of Kidney Diseases. Vol. 22, Pg. 598, 1993.

Ciprofloxacin Safety Profile

Safety Information of Ciprofloxacin (CAS NO.85721-33-1):
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
WGK Germany: 2
RTECS: VB1993800

Product Name

Ciprofloxacin

Synthetic route

Ciprofloxacin Chemical Properties

Ciprofloxacin History

Ciprofloxacin Uses

Ciprofloxacin Toxicity Data With Reference

Ciprofloxacin Safety Profile

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