Trivertal

October 14, 2019
I’m a fragrance, but I found my way into catalytic chemistry.
What molecule am I?

Trivertal (2,4-dimethyl-3-cyclohexenecarboxaldehyde) is an organic molecule with two chiral centers, as shown in the 2-D image. The manufactured product, a common fragrance ingredient, contains 95% of the two cis enantiomers and 5% of the trans isomers. In the fragrance industry, trivertal is called “2,4-ivy carbaldehyde”.

Commercial trivertal is likely contaminated with isomers that have the methyl groups in different positions on the ring. Thus, the melting point is depressed, and the mixture is a liquid. Purer forms are solids with a melting range of 85 to 90 ºC.

At the recent ACS National Meeting in San Diego, Guy Bertrand of the University of California, Riverside, spoke about his research group’s studies of stable cyclic (alkyl)(amino)carbenes, one of which was prepared from trivertal. The dimethylcyclohexene structure of trivertal and related compounds stabilizes the carbene, which can be used as a ligand for transition-metal catalysts.

As a proof of concept, the authors used the carbenes in gold(I) catalysts for the hydroamination of internal alkynes with secondary dialkylamines to synthesize complex quinoline derivatives in high yields. In his presentation, Bertrand discussed the mechanisms of the reactions that he reported earlier in a journal article.

Trivertal hazard information

GHS classification*: flammable liquids, category 4
H227—Combustible liquid Chemical Safety Warning
GHS classification: skin corrosion/irritation, category 2
H315—Causes skin irritation** Chemical Safety Warning
GHS classification: skin sensitization, category 1
H317—May cause an allergic skin reaction** Chemical Safety Warning
GHS classification: serious eye damage/eye irritation, category 2A
H319—Causes serious eye irritation** Chemical Safety Warning

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

**Not all material safety data sheets contain these warnings.

Trivertal fast facts

CAS Reg. No. 68039-49-6
Empirical formula C9H14O
Molar mass 138.21 g/mol
Appearance Colorless liquid
Boiling point 196 ºC
Water solubility ≈300 mg/L
Chemical Abstract Service - a division of ACS

Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.

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