1-Chloro-3,3,3-trifluoroacetone

• CAS: 431-37-8
• Catalog Number: ACM431378
• Category: Main Products
• Molecular Weight: 146.5
• Molecular Formula: C₃H₂ClF₃O
• Synonyms: 3-CHLORO-1,1,1-TRIFLUOROACETONE;1-CHLORO-3,3,3-TRIFLUOROACETONE;1-Chloro-3,3,3-trifluoroacetone,97%;1-Chloro-3,3,3-trifluoro-2-propanone;3-Chloro-1,1,1-trifluoropropan-2-one, 3-Chloro-2-oxo-1,1,1-trifluoropropane;3-Chloro-1,1,1-trifluoro-2-propanone
• IUPAC Name: 3-chloro-1,1,1-trifluoropropan-2-one
• SMILES: C(C(=O)C(F)(F)F)Cl
• InChI Key: OONJVQFMOZAXOI-UHFFFAOYSA-N
• Boiling Point: 71-72°C
• Density: 1,45 g/cm³
• Exact Mass: 145.97500
• Hazard Statements: F,T
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Safety Description: 16-23-26-36

Case Study

Application of 1-Chloro-3,3,3-trifluoroacetone in the Synthesis of Trifluoromethyl-Substituted PDE10A Inhibitors

Bartolomé-Nebreda, José Manuel, et al. Journal of Medicinal Chemistry 57.10 (2014): 4196-4212.

1-Chloro-3,3,3-trifluoroacetone (CF3-chloroacetone) was used as a building block to install a trifluoromethyl-substituted imidazo[1,2-a]pyrazine intermediate in the discovery route to selective phosphodiesterase 10A (PDE10A) inhibitors.
Approach & Role in Synthesis: In the reported medicinal-chemistry sequence, 1-chloro-3,3,3-trifluoroacetone was reacted with a pyrazine precursor at 100 °C for 16 h to produce 8-hydroxy-2-(trifluoromethyl)imidazo[1,2-a]pyrazine in 39% isolated yield. That intermediate was converted (POCl3/N,N-dimethylaniline) to the corresponding 8-chloro derivative (5e) in 99% yield and then carried forward through selective halogenation, cross-coupling and subsequent transformations to furnish the imidazo[1,2-a]pyrazine series. The CF3-bearing intermediate served as a key scaffold variation used in SAR studies that ultimately produced compound 11.
As a reagent, 1-chloro-3,3,3-trifluoroacetone offers a direct route to introduce a trifluoromethylated carbonyl fragment under straightforward conditions, enabling rapid access to CF3-substituted heterocycles useful in CNS drug discovery.

Custom Q&A

What is the molecular formula of 1-Chloro-3,3,3-trifluoroacetone?

The molecular formula is C3H2ClF3O.

What are the synonyms for 1-Chloro-3,3,3-trifluoroacetone?

The synonyms are 1-CHLORO-3,3,3-TRIFLUOROACETONE, 431-37-8, 3-chloro-1,1,1-trifluoropropan-2-one, and 3-chloro-1,1,1-trifluoroacetone.

What is the molecular weight of 1-Chloro-3,3,3-trifluoroacetone?

The molecular weight is 146.49 g/mol.

When was 1-Chloro-3,3,3-trifluoroacetone created?

It was created on July 19, 2005.

When was 1-Chloro-3,3,3-trifluoroacetone last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 1-Chloro-3,3,3-trifluoroacetone?

The IUPAC name is 3-chloro-1,1,1-trifluoropropan-2-one.

What is the InChI of 1-Chloro-3,3,3-trifluoroacetone?

The InChI is InChI=1S/C3H2ClF3O/c4-1-2(8)3(5,6)7/h1H2.

What is the InChIKey of 1-Chloro-3,3,3-trifluoroacetone?

The InChIKey is OONJVQFMOZAXOI-UHFFFAOYSA-N.

What is the Canonical SMILES of 1-Chloro-3,3,3-trifluoroacetone?

The Canonical SMILES is C(C(=O)C(F)(F)F)Cl.

What is the CAS number of 1-Chloro-3,3,3-trifluoroacetone?

The CAS number is 431-37-8.