Methyl 4,6-dihydroxypyridazine-3-carboxylate

Methyl 4,6-dihydroxypyridazine-3-carboxylate Property

Density 

1.58±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.50±1.00(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C6H6N2O4/c1-12-6(11)5-3(9)2-4(10)7-8-5/h2H,1H3,(H2,7,9,10)

InChIKey

SHJHUIKJFYHTDY-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NNC(=O)C=C1O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

Methyl 4,6-dihydroxypyridazine-3-carboxylate Chemical Properties,Usage,Production

Synthesis

Step 2 Synthesis of methyl 4,6-dihydroxypyridazine-3-carboxylate: dimethyl 2-diazo-3-oxoglutarate (50.0 g, 249.8 mmol) and triphenylphosphine (65.5 g, 249.8 mmol) were dissolved in ethyl ether (500 mL) and stirred at room temperature for 24 hours. After the reaction was completed, the organic solvent was removed under vacuum. Acetic acid (500 mL) and water (50 mL) were added to the residue and the reaction was refluxed for 10 hours. The reaction mixture was concentrated under reduced pressure to give a viscous residue. The residue was ground with ethyl acetate to give a yellow solid. The solid was purified by silica gel column chromatography (100-200 mesh, eluent: dichloromethane solution of 1-5% methanol) to give methyl 4,6-dihydroxypyridazine-3-carboxylate (12.8 g, 30% yield) as a yellow solid.LC-MS: m/z 169.2 [M + H]+.

References

[1] Patent: US2013/178478, 2013, A1. Location in patent: Paragraph 0299;0300
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2683 - 2691
[3] Patent: US2004/77653, 2004, A1. Location in patent: Page 18