1-Methyl-1H-imidazole-2-carboxylic acid

1-Methyl-1H-imidazole-2-carboxylic acid Property

Melting point:

104 °C (dec.)

Boiling point:

339.4±25.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Methanol (Slightly), Water (Slightly)

form 

Solid

pka

1.24±0.31(Predicted)

color 

White to Off-White

Sensitive 

Hygroscopic

Stability:

Temperature Sensitive

InChI

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

InChIKey

WLDPWZQYAVZTTP-UHFFFAOYSA-N

SMILES

C1(C(O)=O)N(C)C=CN=1

CAS DataBase Reference

20485-43-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29332900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

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.

1-Methyl-1H-imidazole-2-carboxylic acid Chemical Properties,Usage,Production

Chemical Properties

White Crystalline Solid

Uses

It is useful for solid phase synthesis of polyamides containing imidazole.

Uses

1-Methyl-1H-imidazole-2-carboxylic acid is a useful synthetic intermediate for solid phase synthesis of polyamides containing imidazole

Definition

ChEBI: 1-methyl-imidazole-2-carboxylic acid is an imidazolyl carboxylic acid that is 1H-imidazole with methyl and carboxylic acid group substituents at positions 1 and 2 respectively. It has a role as a metabolite.

Synthesis

The general procedure for the synthesis of 1-methyl-1H-imidazole-2-carboxylic acid from 1-methyl-1H-imidazole-2-carboxaldehyde is as follows: first, 1-methyl-1H-imidazole-2-carboxaldehyde was prepared by referring to the method described in literature [23]. Subsequently, the synthetic procedure for Im2COOH (1b) was followed, and the reaction yield was up to quantitative levels after removal of water under high vacuum (without diethyl ether/water washing). Note that heating may cause decarboxylation to occur. Product yield: 100%. Melting point range is 99-101 °C. NMR hydrogen spectrum (400MHz, D2O): δH 7.42, 7.39 (2H, single peak, imidazolium cyclic-H), 4.08 ppm (3H, single peak, N-CH3); NMR carbon spectrum (400MHz, D2O): δC 158.67, 139.68, 125.83, 118.46, 36.73 ppm. infrared spectrum ( KBr press method): ν 3347 (medium intensity), 3119 (medium intensity), 2663 (weak), 1641 (strong), 1683 (medium intensity), 1507 (strong), 1449 (medium intensity), 1388 (strong), 1338 (strong), 1285 (strong), 1173 (medium intensity), 1123 (strong), 961 (medium intensity), 910 (medium), 776 (strong), 685 (strong) cm-1. Calculated values from elemental analysis (C5H8N2O3, molecular weight 144.12): C, 41.67%; H, 5.59%; N, 19.44%. Measured values: C, 41.28%; H, 5.23%; N, 19.12%.

References

[1] South African Journal of Chemistry, 2010, vol. 63, p. 95 - 104
[2] Journal of Inorganic Biochemistry, 2015, vol. 145, p. 11 - 18
[3] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238