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Sigma-Aldrich

Imidazole

Imidazole
1 of 1 reviewers received a sample product or took part in a promotion

puriss. p.a., ≥99.5% (GC)

Synonym(s):

1,3-Diaza-2,4-cyclopentadiene, Glyoxaline

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100 G
$81.40
500 G
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1 KG
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About This Item

Empirical Formula (Hill Notation):
C3H4N2
CAS Number:
288-32-4
Molecular Weight:
68.08
Beilstein/REAXYS Number:
103853
EC Number:
206-019-2
MDL number:
MFCD00005183
UNSPSC Code:
12352005
eCl@ss:
39161001
PubChem Substance ID:
57651598
NACRES:
NA.21

$81.40

Available to ship onApril 22, 2025Details

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vapor pressure

<1 mmHg ( 20 °C)

Quality Level

200

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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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.[1][2]

Application

Excellent for buffers in the range of pH 6.2-7.8
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.

Other Notes

For titration of aspartic acid and glutamic acid[3]

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Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 2

flash_point_f

293.0 °F - closed cup

flash_point_c

145 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9994
BCCM8163
STBL4159
STBL4116
WXBF4792V

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Novel palladium imidazole catalysts for Suzuki cross-coupling reactions
CJ Mathews, et al.
Journal of Molecular Catalysis. B, Enzymatic, 206, 77-82 (2003)
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)
Eagleson M.
Concise Encyclopedia Chemistry, 523-524 (1994)
Z. Anal. Chem., 261, 38-38 (1972)
Peter Canning et al.
Journal of molecular biology, 426(13), 2457-2470 (2014-04-29)
The discoidin domain receptors (DDRs), DDR1 and DDR2, form a unique subfamily of receptor tyrosine kinases that are activated by the binding of triple-helical collagen. Excessive signaling by DDR1 and DDR2 has been linked to the progression of various human
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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Reviews

1 of 1 reviewers received a sample product or took part in a promotion

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  1. Netherlands
    • Reviews 2
    • Votes 6
    4 out of 5 stars.

    Abs at 280, otherwise great

    Good imidazole. Does have absorbance at 280nm, am still looking for better quality in that area

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