Imidazol-1-yl-acetic acid Chemical Properties

Melting point:

258 °C

Boiling point:

392.1±25.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Water (Slightly)

pka

3.37±0.10(Predicted)

form 

Solid

color 

White to Pale Beige

InChI

InChI=1S/C5H6N2O2/c8-5(9)3-7-2-1-6-4-7/h1-2,4H,3H2,(H,8,9)

InChIKey

QAFBDRSXXHEXGB-UHFFFAOYSA-N

SMILES

C1N(CC(O)=O)C=CN=1

CAS DataBase Reference

22884-10-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-39

HazardClass 

IRRITANT

HS Code 

2933399090

Imidazol-1-yl-acetic acid Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

An impurity arising in the synthesis of zoledronic acid (Z623500).

Definition

ChEBI: Imidazol-1-ylacetic acid is an imidazolyl carboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by an imidazol-1-yl group. It has a role as a metabolite. It is functionally related to an acetic acid.

Synthesis

The general procedure for the synthesis of (1-imidazolyl)acetic acid from the compound (CAS: 83468-75-1) was as follows: first, water (15.1 kg) was added to the reactor, followed by removal of chloroform by distillation, controlling the jacket temperature at 60-65 °C (boiling point of the azeotrope is 53 °C) and returning the aqueous phase back to the reactor by using a Dean-Stark water separator. After the chloroform is completely removed, the reactor jacket temperature is slowly raised to 115°C, at which point the tert-butanol and water form an azeotrope (boiling point of 80°C) that is distilled out. After the alcohol was completely removed, the remaining aqueous solution was cooled to room temperature and then drained from the reactor, resulting in 17.54 kg of solution containing (1-imidazolyl)acetic acid. The actual amount of (1-imidazolyl)acetic acid in the solution was determined by NMR to be 3.77 kg (29.9 mol) in 82.2% yield.

References

[1] Patent: WO2007/109542, 2007, A2. Location in patent: Page/Page column 4; 6

Imidazol-1-yl-acetic acid(22884-10-2)Related Product Information

• Trifluoroacetic acid
• Levamisole
• Imidazole
• Acetylferrocene
• THIODIGLYCOLIC ACID
• Trichloroacetic acid
• N-ACETYL-L-TYROSINE ETHYL ESTER
• 1-Methylimidazole
• Acetic acid
• Ethyl acetate
• Ethyl 2-(Chlorosulfonyl)acetate
• Acetylacetone
• Ethyl 1H-imidazole-1-acetate
• Zoledronic acid hydrate
• Zoledronic Acid Trihydrate
• 1H-Imidazole-2-carboxylic acid
• Ethyl imidazole-4-carboxylate
• ETHYL IMIDAZOLE-2-CARBOXYLATE