2,4-Dimethylimidazole Chemical Properties

Melting point:

85-87 °C

Boiling point:

266 °C (733 mmHg)

Density 

0.9678 (rough estimate)

refractive index 

1.5000 (estimate)

Flash point:

266°C/733mm

storage temp. 

Sealed in dry,Room Temperature

form 

Weak Mass or Viscous Liquid

pka

8.36(at 25℃)

color 

Yellow to orange

Water Solubility 

Soluble in water.

BRN 

1639

InChI

InChI=1S/C5H8N2/c1-4-3-6-5(2)7-4/h3H,1-2H3,(H,6,7)

InChIKey

LLPKQRMDOFYSGZ-UHFFFAOYSA-N

SMILES

C1(C)NC(C)=CN=1

CAS DataBase Reference

930-62-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-22

Safety Statements 

45-36/37/39-26

RIDADR 

3263

RTECS 

NI4839712

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29332990

MSDS

• Language:English Provider:2,4-Dimethylimidazole
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,4-Dimethylimidazole Usage And Synthesis

Chemical Properties

yellow to orange weak mass or viscous liquid

Uses

It is employed as a curing agent of epoxy resins. It is also widely used in the bonding, coating, capsulation of epoxy resins, or used for composite materials. It is also employed as medical raw material or used in organic synthesis.

Synthesis Reference(s)

Tetrahedron Letters, 12, p. 2205, 1971 DOI: 10.1016/S0040-4039(01)96820-0

Synthesis

The general procedure for the synthesis of 2,4-dimethylimidazole from the compound (CAS:52726-31-5) was as follows: in a 16 mL reaction flask equipped with a PTFE/silicone septum and a nitrogen bubbler device, N-benzylbenzimidazole (208.1 mg, 1.0 mmol), dry Pd/C catalyst (10 wt%, 20 mg), and THF ( 5 mL). Triethylsilane (320 μL, 2.0 mmol) was slowly added to the reaction mixture under nitrogen protection, followed by continuous stirring for 14 h at room temperature. Upon completion of the reaction, the reaction mixture was filtered using a 0.45 μm PTFE syringe filter and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting residue was purified by column chromatography (eluent: 0 to 10% methanol/dichloromethane gradient) to afford the target product benzimidazole as a colorless solid (117.6 mg, 0.996 mmol, 99% yield). It is worth noting that the reaction typically suffers from an induction period of 5 to 30 min, which can be observed as reaction initiation by the apparent release of gas from the reaction mixture (i.e., the bubbling phenomenon). In addition, the use of a dry Pd/C catalyst is essential for this reaction, with wet Pd/C leading to a significant reduction in the reaction yield or no reaction at all.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690

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