Methyl 4-imidazolecarboxylate Chemical Properties

Melting point:

154-156 °C (lit.)

Boiling point:

318.2±15.0 °C(Predicted)

Density 

1.46 g/cm3

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

10.89±0.10(Predicted)

form 

Crystalline Powder

color 

White

InChI

InChI=1S/C5H6N2O2/c1-9-5(8)4-2-6-3-7-4/h2-3H,1H3,(H,6,7)

InChIKey

DVLGIQNHKLWSRU-UHFFFAOYSA-N

SMILES

C1NC(C(OC)=O)=CN=1

CAS DataBase Reference

17325-26-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich

Methyl 4-imidazolecarboxylate Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

Methyl 4-imidazolecarboxylate was used as a starting material in the synthesis of 1-(3-prop-1-enyl)-imidazole-4-carboxyaldehyde and osmium(2,2′-bipyridyl)2(methyl 4-imidazolcarboxylate)dichloride.

General Description

Methyl 4-imidazolecarboxylate is an alkyl ester of imidazole carboxylic acid.

Synthesis

Step 1 Synthesis of methyl 1H-imidazole-4-carboxylate: 1H-imidazole-4-carboxylic acid (1.0 g, 8.9 mmol) was mixed with concentrated sulfuric acid (1 mL) in methanol (30 mL), stirred and heated to 0 °C. The reaction mixture was reacted under reflux conditions overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure and subsequently partitioned between cold water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure to afford methyl 1H-imidazole-4-carboxylate (1 g, 89% yield).

References

[1] Patent: US2010/160323, 2010, A1. Location in patent: Page/Page column 23-24
[2] Patent: CN108314654, 2018, A. Location in patent: Paragraph 0086-0088
[3] Inorganic Chemistry Communications, 2017, vol. 78, p. 32 - 36
[4] Patent: WO2012/143599, 2012, A1. Location in patent: Page/Page column 79

Methyl 4-imidazolecarboxylate(17325-26-7)Related Product Information

• Methyl salicylate
• Dimethyl 4,5-imidazoledicarboxylate
• Methyl formate
• Methyl acetate
• Methyl benzoate
• Methyl 4-cyanobenzoate
• 1H-Imidazole-4-carboxylic acid
• Methylparaben
• Kresoxim-methyl
• Methyl anthranilate
• Methyl carbamate
• Bensulfuron methyl
• METSULFURON METHYL
• Ethyl imidazole-4-carboxylate
• ETHYL IMIDAZOLE-2-CARBOXYLATE
• 4,5-Imidazoledicarboxylic acid
• Thiophanate-methyl
• 1H-IMIDAZOLE-2-CARBOXYLIC ACID METHYL ESTER