2,4-DIMETHYL-3-CYCLOHEXENECARBOXALDEHYDE
- CAS NO.:68039-49-6
- Empirical Formula: C9H14O
- Molecular Weight: 138.21
- MDL number: MFCD00221550
- EINECS: 268-264-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-21 22:41:43
What is 2,4-DIMETHYL-3-CYCLOHEXENECARBOXALDEHYDE?
Description
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.
Chemical properties
2,4-DIMETHYL-3-CYCLOHEXENECARBOXALDEHYDE is prepared as a mixture of its cis- and trans-isomers by a Diels–Alder reaction of 2-methyl-1,3-pentadiene and acrolein. It is a liquid with a strongly green, slightly herbaceous, citrus note. It is used for perfuming cosmetic preparations as well as household products.
The Uses of 2,4-DIMETHYL-3-CYCLOHEXENECARBOXALDEHYDE
2,4-Dimethyl-3-cyclohexenecarboxaldehyde is used in method for improving performance of fragrance or its mixture.
Trade name
Cyclal C (Givaudan), Lantral (Hangzhou), Triplal® (IFF), Vertocitral (Symrise).
Properties of 2,4-DIMETHYL-3-CYCLOHEXENECARBOXALDEHYDE
Melting point: | 85-90 °C |
Boiling point: | 196 °C(lit.) |
Density | 0.933 g/mL at 25 °C(lit.) |
refractive index | n |
Flash point: | 151 °F |
solubility | ≈300 mg/l |
appearance | colorless liquid |
form | clear liquid |
color | Colorless to Almost colorless |
Odor | at 10.00 % in dipropylene glycol. green aldehydic leafy cortex tart floral peely |
EPA Substance Registry System | 3-Cyclohexene-1-carboxaldehyde, 2,4-dimethyl- (68039-49-6) |
Safety information for 2,4-DIMETHYL-3-CYCLOHEXENECARBOXALDEHYDE
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H227:Flammable liquids H302:Acute toxicity,oral |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P330:Rinse mouth. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P370+P378:In case of fire: Use … for extinction. P403+P235:Store in a well-ventilated place. Keep cool. P501:Dispose of contents/container to..… |
Computed Descriptors for 2,4-DIMETHYL-3-CYCLOHEXENECARBOXALDEHYDE
New Products
6-Bromo 2-Iodo Indole Pyridine 2,4,6-Tricarboxaldehyde Fosfomycin EP impurity D Ivermectin EP Impurity B Rimegepant Impurity 3 Tubulysin F 2,2-diethoxyethanethioamide Tubulysin M Tubulysin H Potassium HMDS (1.0 M in THF) Diethyl Aluminium Cyanide (1.0 M in Toluene) (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine 2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol ethanedioate Calcium Sodium Phosphosilicate IH 2-(1-(Mercaptomethyl) cyclopropyl) acetonitrile Fuel shell 1-(4-Aminophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one 4,7-Dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine 2-Chloro-3-(chloromethyl)pyridine Methyl 4-amino-3-(piperidin-1-yl)benzoate 3,6-Bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 3,6-Bis(4-iodophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 3-bromo-5-fluorobenzaldehydeRelated products of tetrahydrofuran
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