3,5-Dimethylpyrazole

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3,5-Dimethylpyrazole
File:3,5-Dimethylpyrazole v2.svg
File:3,5-Dimethylpyrazole.jpg
Names
Preferred IUPAC name
3,5-Dimethyl-1H-pyrazole
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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EC Number
  • 200-657-5
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UNII
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  • InChI=1S/C5H8N2/c1-4-3-5(2)7-6-4/h3H,1-2H3,(H,6,7)
    Key: SDXAWLJRERMRKF-UHFFFAOYSA-N
  • CC1=CC(=NN1)C
Properties
C5H8N2
Molar mass 96.133 g·mol−1
Appearance White solid
Density 1.027 g/cm3
Melting point 107.5 °C (225.5 °F; 380.6 K)
Boiling point 218 °C (424 °F; 491 K)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H302, H315, H319, H335, H361, H373
P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,5-Dimethylpyrazole is an organic compound with the formula (CH3C)2CHN2H. It is one of several isomeric derivatives of pyrazole that contain two methyl substituents. The compound is unsymmetrical but the corresponding conjugate acid (pyrazolium) and conjugate base (pyrazolide) have C2v symmetry. It is a white solid that dissolves well in polar organic solvents.

It is a precursor to a variety of ligands that are widely studied in coordination chemistry including trispyrazolylborate, a trispyrazolylmethane, and a pyrazolyldiphosphine.[1][2]

Condensation of acetylacetone and hydrazine gives 3,5-dimethylpyrazole:[3]

CH3C(O)CH2C(O)CH3   +   N2H4   →   (CH3C)2CHN2H   +   2 H2O

It has found use as a blocking agent for isocyanates.[4]

References

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