Oxolinic acid supplier | CasNO.14698-29-4

Name
Oxolinic acid
EINECS 238-750-8
CAS No. 14698-29-4
Article Data22
CAS DataBase
Density 1.483 g/cm³
Solubility 3.214mg/L(temperature not stated)
Melting Point 314-316 °C (dec.)
Formula C₁₃H₁₁NO₅
Boiling Point 473.2 °C at 760 mmHg
Molecular Weight 261.234
Flash Point 240 °C
Transport Information
Appearance white crystalline powder
Safety 22-24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylicacid;5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid;Emyrenil;Inoxyl;Ossian;Oxoboi;Prodoxal;Starner;Starner 20WP;Urinox;Uritrate;Uroxol;W 4565;Galantamine Hydrobromide;
PSA 77.76000
LogP 1.44830

Synthetic route

: 16172-03-5
ethyl 5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo<4,5-g>quinoline-7-carboxylate

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
With water; sodium hydroxide for 0.05h; Microwave irradiation;	93%
Stage #1: ethyl 5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo<4,5-g>quinoline-7-carboxylate With sodium hydroxide In water for 0.0666667h; Microwave irradiation; Stage #2: With hydrogenchloride In water	93%
With hydrogenchloride for 1h; Heating;
With sodium hydroxide for 3h; Heating; Yield given;

: 32953-23-4
Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylate

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Stage #1: Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylate With sulfuric acid; acetic anhydride at 80 - 130℃; for 4h; Stage #2: In water at 90℃; for 3h;	92.4%
(i) polyphosphoric acid, (ii) aq. NaOH; Multistep reaction;
Multi-step reaction with 2 steps 1: POCl3 / 3 h / Heating 2: 10percent aq. NaOH / 3 h / Heating View Scheme

: 57147-33-8
nitrile of 1-ethyl-6,7-methylenedioxy-4-oxo-1,4-dihydroquinoline-3-carbonic acid

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 50℃; Reflux;	69%

: 425-75-2
trifluoromethanesulfonic acid ethyl ester

: 26893-30-1
ethyl [1,3]dioxolo[4,5-G]quinoline-7-carboxylate

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Stage #1: trifluoromethanesulfonic acid ethyl ester; ethyl [1,3]dioxolo[4,5-G]quinoline-7-carboxylate at 50℃; for 1h; Stage #2: With sodium hydroxide; potassium hexacyanoferrate(III) at 25℃; for 2h;	50%

: 425-75-2
trifluoromethanesulfonic acid ethyl ester

: methyl [1,3]dioxolo[4,5-g]quinoline-7-carboxylate

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Stage #1: trifluoromethanesulfonic acid ethyl ester; methyl [1,3]dioxolo[4,5-g]quinoline-7-carboxylate at 50℃; for 1h; Stage #2: With sodium hydroxide; potassium hexacyanoferrate(III) at 20℃; for 2h;	50%

: 34841-20-8
3-acetyl-1-ethyl-6,7-methylenedioxy-4-oxo-1,4-dihydroquinoline

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
With 1,4-dioxane; sodium hypochlorite

: 52546-94-8
8-amino-7-carboxy-5-ethyl-[1,3]dioxolo[4,5-g]quinolinium betaine

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
With sodium hydroxide

: 60792-24-7
8-amino-7-ethoxycarbonyl-5-ethyl-[1,3]dioxolo[4,5-g]quinolinium; iodide

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
With potassium hydroxide
With potassium hydroxide In methanol for 50h; Heating;
Multi-step reaction with 2 steps 1: aq. KOH 2: aq. NaOH View Scheme

: 32953-32-5
8-chloro-7-ethoxycarbonyl-5-ethyl-[1,3]dioxolo[4,5-g]quinolinium; iodide

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NH3 2: aq. NaOH View Scheme
Multi-step reaction with 3 steps 1: aq. NH3 / CHCl3 2: aq. KOH 3: aq. NaOH View Scheme
Multi-step reaction with 2 steps 1: aq. NH3 / CHCl3 2: aq. KOH View Scheme

: 34841-19-5
7-acetyl-5H-[1,3]dioxolo[4,5-g]quinolin-8-one

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaH, DMF, (ii) EtI, DMF 2: NaOCl, dioxane View Scheme

: 50332-64-4
2H-6,7-methylenedioxy-3,1-benzoxazine-2,4-(1-ethyl)-dione

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 2 h / 110 °C 2: aq. HCl / 1 h / Heating View Scheme

: 66176-21-4
4,5-methylenedioxyanthranilic acid hydrochloride

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: NaH / dimethylformamide 3: dimethylformamide / 2 h / 110 °C 4: aq. HCl / 1 h / Heating View Scheme

: 57385-14-5
1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH / dimethylformamide 2: dimethylformamide / 2 h / 110 °C 3: aq. HCl / 1 h / Heating View Scheme

: 32953-14-3
N-ethyl-3,4-(methylenedioxy)aniline

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diphenylether / 130 - 140 °C 2: diphenylether / 250 °C 3: sodium hydroxide / water / 0.07 h / Microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: 0.07 h / Microwave irradiation; Neat (no solvent) 2: sodium hydroxide / water / 0.07 h / Microwave irradiation View Scheme

: 8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / Reflux 2: acetic acid; sulfuric acid / 50 °C / Reflux View Scheme

: 15930-53-7
6-bromo-3,4-methylenedioxybenzaldehyde

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(l) chloride; oxygen; potassium hydroxide / N,N-dimethyl acetamide / 24 h / 20 °C 2: ammonium hydroxide; L-proline; potassium carbonate; copper dichloride / 20 h / Reflux 3: sodium hydride / tetrahydrofuran / Reflux 4: acetic acid; sulfuric acid / 50 °C / Reflux View Scheme

: 3-(6-bromobenzo[d][1,3]dioxol-5-yl)-3-oxopropanenitrile

: 14698-29-4
oxolinic Acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium hydroxide; L-proline; potassium carbonate; copper dichloride / 20 h / Reflux 2: sodium hydride / tetrahydrofuran / Reflux 3: acetic acid; sulfuric acid / 50 °C / Reflux View Scheme

: 14698-29-4
oxolinic Acid

: 51624-70-5
5-ethyl-9-nitro-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-a]quinolin-7-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid; potassium nitrate at 0 - 20℃; for 1h; Inert atmosphere;	98%

: 95-14-7
1,2,3-Benzotriazole

: 14698-29-4
oxolinic Acid

: 1131147-59-5
7-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-5-ethyl-[1,3]dioxolo[4,5-g]quinolin-8(5H)-one

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃;	96%
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 25℃; for 0.5h; Stage #2: oxolinic Acid In dichloromethane at 25℃; for 2h;	75%
With thionyl chloride In dichloromethane at 20℃;

: 14698-29-4
oxolinic Acid

: 19658-59-4
5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[4,5-g]quinoline-7-carbonyl chloride

Conditions

Conditions	Yield
With thionyl chloride for 12h;	86%
With thionyl chloride for 12h;	86%
With thionyl chloride In benzene for 12h; Heating;	24.3 g
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;

: Iron(III) nitrate nonahydrate

: 14698-29-4
oxolinic Acid

: [tris(oxalino)iron(III)]*1.5H2O

Conditions

Conditions	Yield
Stage #1: oxolinic Acid With sodium hydroxide In water Heating; Stage #2: Iron(III) nitrate nonahydrate In water pH=<=5 - 7; Reagent/catalyst;	84%

: sodium hexaflorophosphate

: [Ru([9]aneS3)(dmso)3](PF6)2

: 14698-29-4
oxolinic Acid

: [Ru([9]aneS3)(dmso-κS)(oxol-κ2O,O)](PF6)

Conditions

Conditions	Yield
With sodium methylate In methanol for 2h; Reflux;	82.8%

...Expand

: gallium(III) nitrate nonahydrate

: 14698-29-4
oxolinic Acid

: [tris(oxalino)gallium(III)]*3.5H2O

Conditions

Conditions	Yield
Stage #1: oxolinic Acid With sodium hydroxide In water Heating; Stage #2: gallium(III) nitrate nonahydrate In water for 0.5h; pH=<=5 - 7; Reagent/catalyst; Time;	82%

: nickel(II) chloride hexahydrate

: 7732-18-5
water

: 14698-29-4
oxolinic Acid

: 952485-93-7
Ni(5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid(-H))2(H2O)2

Conditions

Conditions	Yield
With potassium hydroxide In methanol 2 equiv. of oxolinic acid and KOH in CH3OH added to metal salt in CH3OH;refluxed for 2 h; filtered; left for slow evapn.; collected by filtration after a few days; washed with MeOH; dried; elem. anal.;	80%

...Expand

: vanadyl(IV) sulphate pentahydrate

: 7732-18-5
water

: 14698-29-4
oxolinic Acid

: VO(5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid(-H))2(H2O)

Conditions

Conditions	Yield
With potassium hydroxide In methanol 2 equiv. of oxolinic acid and KOH in CH3OH added to metal salt in CH3OH;refluxed for 2 h; filtered; left for slow evapn.; collected by filtration after a few days; washed with MeOH; dried; elem. anal.;	80%

...Expand

: FeCl3*3H2O

: 14698-29-4
oxolinic Acid

: 119088-56-1
Fe(5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid(-H))3

Conditions

Conditions	Yield
With potassium hydroxide In methanol 3 equiv. of oxolinic acid and KOH in CH3OH added to metal salt in CH3OH;refluxed for 2 h; filtered; left for slow evapn.; collected by filtration after a few days; washed with MeOH; dried; elem. anal.;	80%

: 7732-18-5
water

: 14698-29-4
oxolinic Acid

: 7646-85-7
zinc(II) chloride

: 952485-94-8
Zn(5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid(-H))2(H2O)2

Conditions

Conditions	Yield
With potassium hydroxide In methanol 2 equiv. of oxolinic acid and KOH in CH3OH added to metal salt in CH3OH;refluxed for 2 h; filtered; left for slow evapn.; collected by filtration after a few days; washed with MeOH; dried; elem. anal.;	75%

...Expand

: 67-56-1
methanol

: 66-71-7
1,10-Phenanthroline

: 14698-29-4
oxolinic Acid

: 7646-85-7
zinc(II) chloride

: 1426910-48-6
[Zn(oxo)(phen)Cl]*MeOH

Conditions

Conditions	Yield
Stage #1: oxolinic Acid With potassium hydroxide In methanol at 20℃; for 0.333333h; Stage #2: methanol; 1,10-Phenanthroline; zinc(II) chloride	75%

...Expand

: iron(III) chloride hexahydrate

: 14698-29-4
oxolinic Acid

: [Fe(oxolonic acid)3(Cl)3]

Conditions

Conditions	Yield
In methanol Reflux;	72%

: 14698-29-4
oxolinic Acid

: 18465-39-9
1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydroquinoline-3-carbonic acid

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -10℃; for 2h;	70%
With boron tribromide for 24h; Heating;
With boron tribromide In water

: aqueous cadmium chloride

: 7732-18-5
water

: 14698-29-4
oxolinic Acid

: 952485-95-9
Cd(5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid(-H))2(H2O)2

Conditions

Conditions	Yield
With potassium hydroxide In methanol 2 equiv. of oxolinic acid and KOH in CH3OH added to metal salt in CH3OH;refluxed for 2 h; filtered; left for slow evapn.; collected by filtration after a few days; washed with MeOH; dried; elem. anal.;	70%

...Expand

: cobalt(II) chloride hexahydrate

: 7732-18-5
water

: 14698-29-4
oxolinic Acid

: 952485-92-6
Co(5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid(-H))2(H2O)2

Conditions

Conditions	Yield
With potassium hydroxide In methanol 2 equiv. of oxolinic acid and KOH in CH3OH added to metal salt in CH3OH;refluxed for 2 h; filtered; left for slow evapn.; collected by filtration after a few days; washed with MeOH; dried; elem. anal.;	70%

...Expand

: bis(acetylacetonato)dioxomolybdenum(VI)

: 14698-29-4
oxolinic Acid

: bis(5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylato)dioxomolybdenum(VI)

Conditions

Conditions	Yield
With potassium hydroxide In methanol soln. of oxolinic acid (0.4 mmol) in MeOH treated with KOH (0.4 mmol); soln. added to soln. of MoO2(acac)2 (0.2 mmol) in MeOH; mixt. stirred for1 h; filtered; filtrate slowly evapd. for a few d; ppt. filtered off; washed with MeOH; dried; elem. anal.;	70%

: 366-18-7
[2,2]bipyridinyl

: 14698-29-4
oxolinic Acid

: 7646-85-7
zinc(II) chloride

: 1426910-60-2
[Zn(oxo)2(bipy)]

Conditions

Conditions	Yield
With potassium hydroxide In methanol	70%

...Expand

: 110-86-1
pyridine

: 7732-18-5
water

: 14698-29-4
oxolinic Acid

: 7646-85-7
zinc(II) chloride

: Zn(oxolinate)2(pyridine)2*6H2O

Conditions

Conditions	Yield
With KOH In methanol KOH added to MeOH soln. of oxolinic acid; added to MeOH soln. of ZnCl2; pyridine added; crystd. by slow evapn. after 10 d; elem. anal.;	65%

...Expand

: 67-56-1
methanol

: 366-18-7
[2,2]bipyridinyl

: cobalt(II) chloride hexahydrate

: 14698-29-4
oxolinic Acid

: C36H28CoN4O10*3CH4O

Conditions

Conditions	Yield
Stage #1: methanol; oxolinic Acid With potassium hydroxide for 0.5h; Stage #2: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate for 0.5h;	65%

...Expand

: 66-71-7
1,10-Phenanthroline

: cobalt(II) chloride hexahydrate

: 14698-29-4
oxolinic Acid

: C38H28CoN4O10

Conditions

Conditions	Yield
Stage #1: oxolinic Acid With potassium hydroxide In methanol for 0.5h; Stage #2: 1,10-Phenanthroline; cobalt(II) chloride hexahydrate In methanol for 0.5h;	65%

...Expand

: 110-86-1
pyridine

: cobalt(II) chloride hexahydrate

: 14698-29-4
oxolinic Acid

: C36H30CoN4O10

Conditions

Conditions	Yield
Stage #1: oxolinic Acid With potassium hydroxide In methanol for 0.5h; Stage #2: pyridine; cobalt(II) chloride hexahydrate In methanol for 0.5h;	65%

...Expand

: 67-56-1
methanol

: manganese(II) chloride tetrahydrate

: 14698-29-4
oxolinic Acid

: potassium hydroxide

: [KMn(oxolinato)3(MeOH)3]

Conditions

Conditions	Yield
Stage #1: methanol; oxolinic Acid; potassium hydroxide at 20℃; for 1h; Stage #2: methanol; manganese(II) chloride tetrahydrate at 20℃; for 0.5h;	60%

...Expand

: 66-71-7
1,10-Phenanthroline

: manganese(II) chloride tetrahydrate

: 14698-29-4
oxolinic Acid

: [Mn(oxolinato)2(1,10-phenanthroline)]

Conditions

Conditions	Yield
Stage #1: oxolinic Acid With potassium hydroxide In methanol Stage #2: 1,10-Phenanthroline; manganese(II) chloride tetrahydrate In methanol	60%

...Expand

Oxolinic acid Chemical Properties

Molecular Structure of Oxolinic acid (CAS NO.14698-29-4):

IUPAC Name: 5-Ethyl- 8-oxo- 5,8-dihydro [1,3] dioxolo [4,5-g] quinoline- 7-carboxylic acid
Molecular formula: C₁₃H₁₁NO₅
Molecular Weight: 261.23
Density: 1.483 g/cm³
Melting point: 314-316^°C (dec.)
Boiling point: 473.2 ^°C at 760 mmHg
Flash point: 240 ^°C
Merck: 13,7014
Stability: Stable. Combustible
Index of Refraction: 1.638
Molar Refractivity: 63.31 cm³
Molar Volume: 176.1 cm³
Polarizability: 25.1*10^-24cm³
Surface Tension: 63.9 dyne/cm
Enthalpy of Vaporization: 77.57 kJ/mol
Vapour Pressure: 9.24E-10 mmHg at 25^°C
Appearance: crystalline solid
EINECS: 238-750-8
Product Categories: Heterocyclic Compounds; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; veterinary medicine, APIs, pharmaceutical raw material
InChI
InChI=1/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
Smiles
c12c(cc3OCOc3c2)c(c(C(O)=O)cn1CC)=O

Oxolinic acid Toxicity Data With Reference

1.	mmo-esc 130 µg/L	AMACCQ Antimicrobial Agents and Chemotherapy. 17 (1980),763.
2.	oms-esc 50 mg/L	EJBCAI European Journal of Biochemistry. 62 (1976),491.
3.	orl-rat LD50:525 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 18 (1971),185.
4.	skn-rat LD50:>2 g/kg	JPIFAN Japan Pesticide Information.(55)(1989),21.
5.	orl-mus LD50:1890 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 18 (1971),185.

Oxolinic acid Safety Profile

Moderately toxic by ingestion. Low toxicity by skin contact. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes: Harmful Xn
Risk Statements:
R22:Harmful if swallowed.
Safety Statements:
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
WGK Germany: 3
RTECS: JI5075000
F: 10

Oxolinic acid Specification

Oxolinic acid , with CAS number of 14698-29-4, can be called 1-ethyl-6,7-methylenedioxo-4-quinoline-3-carboxlicacid ; 1-ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylicacid ; 5-g)quinoline-7-carboxylicacid,5-ethyl-5,8-dihydro-8-oxo-3-dioxolo(4;5-g]quinoline-7-carboxylicacid,5-ethyl-5,8-dihydro-8-oxo-3-dioxolo[4 ; dioxacin ; emyrenil ; gramurin ; 1-ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylicacid . It is a crystalline solid, used as quinolone antibacterial.

Product Name

Oxolinic acid

Synthetic route

Oxolinic acid Chemical Properties

Oxolinic acid Toxicity Data With Reference

Oxolinic acid Safety Profile

Oxolinic acid Specification

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