Trifluoroacetaldehyde

• CAT Number: M002928
• CAS Number: 75-90-1
• Molecular Formula: C2HF3O
• Molecular Weight: 98.024
• Purity: ≥95%
• Storage: Store at -20°C
• IUPAC Name: 2,2,2-trifluoroacetaldehyde
• InChI: InChI=1S/C2HF3O/c3-2(4,5)1-6/h1H
• InChIKey: JVTSHOJDBRTPHD-UHFFFAOYSA-N
• SMILES: C(=O)C(F)(F)F

Trifluoroacetaldehyde (CAS 75-90-1) is a useful industrial material for the synthesis of trifluoromethylated amino compounds. 

Reference

1: Borkin DA, Landge SM, Török B. Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids. Chirality. 2011 Sep;23(8):612-6. doi: 10.1002/chir.20982. Epub 2011 Jul 11. PubMed PMID: 21748810.
2: Prakash GK, Zhang Z, Wang F, Munoz S, Olah GA. Nucleophilic trifluoromethylation of carbonyl compounds: trifluoroacetaldehyde hydrate as a trifluoromethyl source. J Org Chem. 2013 Apr 5;78(7):3300-5. doi: 10.1021/jo400202w. Epub 2013 Feb 28. PubMed PMID: 23425346; PubMed Central PMCID: PMC3675896.
3: Funabiki K, Furuno Y, Yano Y, Sakaida Y, Kubota Y, Matsui M. A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde. Chem Asian J. 2015 Dec;10(12):2701-7. doi: 10.1002/asia.201500607. Epub 2015 Aug 17. PubMed PMID: 26206587.
4: Dowty ME, Hu G, Hua F, Shilliday FB, Dowty HV. Drug design structural alert: formation of trifluoroacetaldehyde through N-dealkylation is linked to testicular lesions in rat. Int J Toxicol. 2011 Oct;30(5):546-50. doi: 10.1177/1091581811413833. Epub 2011 Aug 25. PubMed PMID: 21868768.
5: Ramanjaneyulu BT, Mahesh S, Vijaya Anand R. N-heterocyclic carbene catalyzed highly chemoselective intermolecular crossed acyloin condensation of aromatic aldehydes with trifluoroacetaldehyde ethyl hemiacetal. Org Lett. 2015 Jan 2;17(1):6-9. doi: 10.1021/ol502581b. Epub 2014 Dec 16. PubMed PMID: 25512089.
6: Funabiki K, Matsunaga K, Gonda H, Yamamoto H, Arima T, Kubota Y, Matsui M. Reversal of diastereoselectivity in reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines: metal-free, complementary anti- and syn-selective synthesis of 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones. J Org Chem. 2011 Jan 7;76(1):285-8. doi: 10.1021/jo101733j. Epub 2010 Dec 3. PubMed PMID: 21126099.
7: Yang ZY, Zeng JL, Ren N, Meng W, Nie J, Ma JA. C(2)-Symmetric Chiral Bisoxazolines as Hydrogen-Bond-Acceptor Catalysts in Enantioselective Aldol Reaction of β-Carbonyl Acids with Trifluoroacetaldehyde Hemiacetals. Org Lett. 2016 Dec 16;18(24):6364-6367. Epub 2016 Nov 22. PubMed PMID: 27978693.