Wikipedia

trans-2-Methyl-2-butenal

trans-2-Methyl-2-butenal is an organic compound with the formula CH3CH=C(CH3)CHO. This colorless liquid is a building block in organic synthesis. It is an α,β-unsaturated aldehyde related to the better-known crotonaldehyde. The European rabbit, Oryctolagus cuniculus, uses 2-methyl-2-butenal as a pheromone.[1] The rabbit pheromone, trans-2-methyl-2-butenal, was reported to be involved in the communication between species, defined under the class of "interomone."[2]

trans-2-Methyl-2-butenal
Names
Preferred IUPAC name
(2E)-2-Methylbut-2-enal
Other names
(E)-2-Methylbut-2-enal
trans-2-Methyl-2-butenal
trans-2,3-Dimethylacrolein
Tiglic aldehyde
Tiglinaldehyde
Tiglaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.122 Edit this at Wikidata
UNII
  • InChI=1S/C5H8O/c1-3-5(2)4-6/h3-4H,1-2H3/b5-3+ checkY
    Key: ACWQBUSCFPJUPN-HWKANZROSA-N checkY
  • InChI=1/C5H8O/c1-3-5(2)4-6/h3-4H,1-2H3/b5-3+
    Key: ACWQBUSCFPJUPN-HWKANZROBA
  • O=C/C(=C/C)C
Properties
C5H8O
Molar mass 84.12
Appearance colorless liquid
Density 0.871
Melting point −78 °C (−108 °F; 195 K)
Boiling point 116 to 119 °C (241 to 246 °F; 389 to 392 K) (752 mm Hg)
Hazards
Flash point 65 °C (149 °F; 338 K)
Related compounds
Related alkenals
 Citral

Citronellal
Methacrolein

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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References

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  1. ^ Schaal, B.; Coureaud, G.; Langlois, D.; Ginles, C.; Semon, E.; Perrier, G. (2003). "Chemical and behavioural characterization of the rabbit mammary pheromone". Nature. 424 (6944): 68–72. Bibcode:2003Natur.424...68S. doi:10.1038/nature01739. PMID 12840760. S2CID 4428155.
  2. ^ "The Pheromone Site | Research | Animal Welfare | TTU". www.depts.ttu.edu. Retrieved 2016-05-09.
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