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Cas Database |
| Name |
Oxolinic acid |
EINECS | 238-750-8 |
| CAS No. | 14698-29-4 | Density | 1.483 g/cm3 |
| PSA | 77.76000 | LogP | 1.44830 |
| 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 | N/A | 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; |
Article Data | 22 |
Oxolinic acid 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 | 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 | 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 | 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 | 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
- 14698-29-4
oxolinic Acid
| 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 | 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 | 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 | 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 | 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 | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: (i) NaH, DMF, (ii) EtI, DMF 2: NaOCl, dioxane View Scheme |
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 NOx.
Hazard Codes: 
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.
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