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56750

Sigma-Aldrich

Imidazole

puriss. p.a., ≥99.5% (GC)

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Synonym(s):
1,3-Diaza-2,4-cyclopentadiene, Glyoxaline
Empirical Formula (Hill Notation):
C3H4N2
CAS Number:
Molecular Weight:
68.08
Beilstein:
103853
EC Number:
MDL number:
eCl@ss:
39161001
PubChem Substance ID:
NACRES:
NA.21

vapor pressure

<1 mmHg ( 20 °C)

Quality Level

grade

puriss. p.a.

Assay

≥99.5% (GC)

form

flakes
powder or crystals

ign. residue (900 °C)

≤0.1%

pH

9.5-11.0 (25 °C, 50 mg/mL in H2O)

pKa (25 °C)

6.95

bp

256 °C (lit.)

mp

88-91 °C (lit.)
88-91 °C

solubility

alcohol: soluble(lit.)
chloroform: soluble(lit.)
pyridine: soluble(lit.)
water: soluble(lit.)

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤50 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

SMILES string

c1c[nH]cn1

InChI

1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)

InChI key

RAXXELZNTBOGNW-UHFFFAOYSA-N

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1 of 4

This Item
56749I239956748
Imidazole puriss. p.a., &#8805;99.5% (GC)

Sigma-Aldrich

56750

Imidazole

-
Imidazole BioUltra, &#8805;99.5% (GC)

Sigma-Aldrich

56749

Imidazole

Premium Grade
Imidazole ACS reagent, &#8805;99% (titration)

Sigma-Aldrich

I2399

Imidazole

-
Imidazole BioUltra, for molecular biology, &#8805;99.5% (GC)

Sigma-Aldrich

56748

Imidazole

Premium Grade
form

flakes, powder or crystals

form

powder or crystals

form

-

form

flakes, powder or crystals

bp

256 °C (lit.)

bp

256 °C (lit.)

bp

256 °C (lit.)

bp

256 °C (lit.)

mp

88-91 °C (lit.)

mp

88-91 °C (lit.)

mp

88-91 °C (lit.)

mp

88-91 °C (lit.)

solubility

alcohol: soluble(lit.), chloroform: soluble(lit.), pyridine: soluble(lit.), water: soluble(lit.)

solubility

H2O: 0.1 M at 20 °C, clear, colorless

solubility

-

solubility

H2O: 0.1 M at 20 °C, clear, colorless

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

General description

Imidazole is an aromatic heterocyclic compound with a five-membered planar ring. It is an amphoteric compound because of the presence of both an acidic NH and a basic nitrogen atom. Imidazole is an essential component of many important molecules including natural products, bioactive molecules, ionic liquids, and imidazolium. It serves as a building block for the synthesis of various drug molecules.

Application

Imidazole can be used as a catalyst:      
  • For the silylation of alcohols, carboxylic acids, and amines in the presence of silyl chloride in DMF.     
  • In the peptide coupling using the triphenyl phosphite.
  • To prepare acid chlorides from the corresponding carboxylic acids and phosgene.

It can also be used in the following reactions:      
  • Imidazole-PPh3/I2 catalytic system used in the conversion of alcohols into iodides      
  • Imidazole-PPh3/I2 is used in the diol deoxygenation reaction.

Excellent for buffers in the range of pH 6.2-7.8

Other Notes

For titration of aspartic acid and glutamic acid

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1B - Skin Corr. 1C

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

293.0 °F - closed cup

Flash Point(C)

145 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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CJ Mathews, et al.
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Three 3D Coordination Polymers Constructed by Cd (II) and Zn (II) with Imidazole-4, 5-Dicarboxylate and 4, 4 `-Bipyridyl Building Blocks
WG Lu, et al.
Crystal Growth & Design, 6, 564-571 (2006)
Z. Anal. Chem., 261, 38-38 (1972)
Eagleson M.
Concise Encyclopedia Chemistry, 523-524 (1994)
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