20154-03-4 | 3-Trifluoromethyl-1H-pyrazole

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$5.00	$4.00
5g	95%	in stock	$10.00	$7.00
10g	95%	in stock	$13.00	$10.00
25g	98%	in stock	$30.00	$21.00

Description

• Catalog Number: AB10588
• Chemical Name: 3-Trifluoromethyl-1H-pyrazole
• CAS Number: 20154-03-4
• Molecular Formula: C4H3F3N2
• Molecular Weight: 136.0752
• MDL Number: MFCD00115018
• SMILES: FC(c1cc[nH]n1)(F)F

Computed Properties

• Complexity: 101
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 1
• XLogP3: 1.1

Upstream Synthesis Route

The synthesis of 3-trifluoromethyl-1H-pyrazole typically involves the construction of the pyrazole ring followed by the introduction of the trifluoromethyl group at the 3-position. Here's a general upstream synthesis route:

1. **Synthesis of Hydrazine Derivative**: Start with an appropriate aliphatic or aromatic hydrazine derivative that will form the pyrazole ring. Acetone hydrazone could be a starting point, derived from hydrazine and acetone.

2. **Formation of Pyrazole Ring**: Subject the hydrazine derivative to cyclization conditions to form the unsubstituted pyrazole ring. This can be achieved by dehydrating agents or by reaction with α-haloketones under basic conditions.

3. **Introduction of Trifluoromethyl Group**: The trifluoromethyl group can be introduced either before the formation of the pyrazole ring or, more typically, after its formation. One approach is the direct introduction using trifluoromethylating agents such as Togni's reagent or Umemoto's reagent.

For introducing the trifluoromethyl group at the 3-position of the pyrazole ring, various reagents can be used. For example, a nucleophilic addition with sodium trifluoroacetate under acidic conditions followed by decarboxylation can introduce the CF3 group.

Alternatively, if the starting hydrazine has an alkyl or aryl group bearing the CF3 group in the correct position, no further transformation would be needed after the formation of the pyrazole.

4. **Purification**: Purify the final pyrazole compound by crystallization, chromatography, or other suitable purification methods to obtain 3-trifluoromethyl-1H-pyrazole with the desired purity.

Each step should be optimized for yield, purity, and scale suitable for the intended application. The intermediate and final compounds should be characterized by standard analytical techniques such as NMR, IR, MS, and possibly X-ray crystallography.

Literature

• Estradiol meets notch signaling in developing neurons.

  Frontiers in endocrinology 20110101

• Structure-activity relationship and pharmacokinetic profile of 5-ketopyrazole factor Xa inhibitors.

  Bioorganic & medicinal chemistry letters 20080115

• Unambiguous assignment of trifluoromethylpyrazole regioisomers by 19F-15N correlation spectroscopy.

  Magnetic resonance in chemistry : MRC 20070101

• Fluorous synthesis of disubstituted pyrimidines.

  Organic letters 20030403