Citrazinic acid Chemical Properties

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

pka

2.54±0.20(Predicted)

form 

Powder

color 

Yellow

PH

3.1-3.5 (100g/l, H2O)(slurry)

Water Solubility 

practically insoluble

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

Citrazinic acid (99-11-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39-22

WGK Germany 

1

RTECS 

NS1400000

TSCA 

Yes

HS Code 

29333999

MSDS

• Language:English Provider:2,6-Dihydroxyisonicotinic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Citrazinic acid Usage And Synthesis

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.

Uses

2,6-Dihydroxypyridine-4-carboxylic acid (citrazinic 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

Citrazinic acid(99-11-6)Related Product Information

• Triclosan
• 2-Hydroxyisonicotinic acid
• 2,5-PYRIDINEDICARBOXYLIC ACID
• Glycine
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• 2-Hydroxy-5-pyridinecarboxylic acid
• 2,6-Lutidine
• 2-Hydroxypyridine
• Citraconic acid
• Chromium picolinate
• Isonicotinic acid
• Quinolinic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Butylated Hydroxytoluene
• 1,3-Dihydroxyacetone
• Methyl isonicotinate
• 2,6-Dichloroisonicotinic acid
• Citric acid