| Identification | More | [Name]
Citrazinic acid | [CAS]
99-11-6 | [Synonyms]
2,6-DIHYDROXY-4-CARBOXYPYRIDINE
2,6-DIHYDROXYISONICOTINIC ACID
2,6-DIHYDROXYPYRIDINE-4-CARBOXYLIC ACID
2,6-DIOXYPYRIDINE-4-CARBOXYLIC ACID
4-PYRIDINECARBOXYLIC ACID, 2,6-DIHYDROXY-
AKOS BBS-00003808
AKOS NCG1-0104
CITRAZINIC ACID
LABOTEST-BB LT00071696
1,2-dihydro-6-hydroxy-2-oxo-4-pyridinecarboxylicaci
1,2-Dihydro-6-hydroxy-2-oxo-4-pyridinecarboxylicacid
1,2-dihydro-6-hydroxy-2-oxo-isonicotinicaci
2,6-Dihydroxy-4-pyridinecarboxylic acid
2,6-dihydroxy-4-Pyridinecarboxylicacid
2,6-dihydroxy-isonicotinicaci
4-Pyridinecarboxylic acid, 1,2-dihydro-6-hydroxy-2-oxo-
6-Hydroxy-2-oxo-1,2-dihydro-4-pyridinecarboxylic acid
citrazinicacfd
Kyselina citrazinova
kyselinacitrazinova | [EINECS(EC#)]
202-731-2 | [Molecular Formula]
C6H5NO4 | [MDL Number]
MFCD00006274 | [Molecular Weight]
155.11 | [MOL File]
99-11-6.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow powder | [Melting point ]
>300 °C(lit.)
| [Boiling point ]
278.88°C (rough estimate) | [density ]
0.65 g/cm3 | [refractive index ]
1.5423 (estimate) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
practically insoluble | [form ]
Powder | [pka]
2.54±0.20(Predicted) | [color ]
Yellow | [PH]
3.1-3.5 (100g/l, H2O)(slurry) | [Water Solubility ]
practically insoluble | [Detection Methods]
HPLC | [Merck ]
14,2325 | [BRN ]
383736 | [InChIKey]
CSGQJHQYWJLPKY-UHFFFAOYSA-N | [CAS DataBase Reference]
99-11-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Isonicotinic acid, 2,6-dihydroxy-,(99-11-6) | [EPA Substance Registry System]
99-11-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
1
| [RTECS ]
NS1400000
| [TSCA ]
Yes | [HS Code ]
29333999 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow powder | [Uses]
2,6-Dihydroxypyridine-4-carboxylic acid was used to prepare 2,6-dibromo-4-(hexoxymethyl)pyridine. It was also used to synthesize the derivatives of oxazinones and pyrimidinones. | [Definition]
ChEBI: CITRAZINIC ACID is an aromatic carboxylic acid and a member of pyridines. | [Synthesis]
(1) Weigh 1.2188 g (0.0058 mol) of citric acid and 1.3932 g (0.0231 mol) of urea, dissolve in 60 ml of deionized water, and ultrasonicate for 10 min to ensure adequate mixing; (2) Transfer the mixed solution to a reaction vessel and place it in an oven preheated to 185 ℃, and maintain the reaction in hydrothermal conditions for 2 h; after completion of the reaction, cool naturally to After the reaction was completed, it was cooled naturally to room temperature to obtain a dark green solution; (3) the above solution was placed in a constant temperature water bath at 60 ℃, and 98% sulfuric acid was added dropwise slowly under magnetic stirring to adjust the pH of the solution to 2-3; at this time, a large number of yellow solids were precipitated, and the solution was centrifuged at 12,000 rpm for 10 minutes, the supernatant was discarded, and the precipitate was washed with deionized water for several times and drained; finally, the yellow precipitate was dried in the oven at 60 ℃, and citrazinic acid was obtained, with a yield of 85.18%. The yield was 85.18%. | [Purification Methods]
The acid is normally a yellow powder with a greenish shade, but is white when ultra pure and turns blue on long standing. It is insoluble in H2O but slightly soluble in hot HCl and soluble in alkali or carbonate solutions. It is purified by precipitation from alkaline solutions with dilute HCl, and dried in a vacuum over P2O5. The ethyl ester has m 232o (evacuated tube) and a pKa of 4.81 in MeOCH2CH2OH [IR: Pitha Coll Czech Chem Comm 28 1408 1963]. [Beilstein 22/7 V 24.] | [References]
[1] Patent: CN108164458, 2018, A. Location in patent: Paragraph 0010; 0012; 0013
[2] Journal of the American Pharmaceutical Association (1912-1977), 1956, vol. 45, p. 478 |
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