Tetrahydrobenzaldehyde

1,2,3,6-Tetrahydrobenzaldehyde is an organic compound with the formula C6H9CHO. This colorless liquid is formally a partially hydrogenated derivative of benzaldehyde. It is produced by the Diels-Alder reaction of acrolein to butadiene. It is of interest as a precursor to 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexane carboxylate, a useful resin and precursor to industrial coatings. The conversion entails the Tishchenko reaction, i.e., base-catalyzed conversion to the ester followed by double epoxidation.[1]

Tishchenko reaction of tetrahydrobenzaldehyde
Tetrahydrobenzaldehyde
Names
Preferred IUPAC name
Cyclohex-3-ene-1-carbaldehyde
Other names
  • 3-Cyclohexene-1-carbaldehyde
  • 4-Formyl-1-cyclohexene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.599
EC Number
  • 202-858-3
UNII
UN number 2498
  • InChI=1S/C7H10O/c8-6-7-4-2-1-3-5-7/h1-2,6-7H,3-5H2
    Key: DCFDVJPDXYGCOK-UHFFFAOYSA-N
  • C1CC(CC=C1)C=O
Properties
C7H10O
Molar mass 110.156 g·mol−1
Appearance Colorless liquid
Density 0.94 g/mL
Melting point 2 °C (36 °F; 275 K)
Boiling point 163–164 °C (325–327 °F; 436–437 K)
Solubility Acetone
methanol
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Danger
H226, H312, H314, H315, H319, H335
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 57 °C (135 °F; 330 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Guenter Sienel; Robert Rieth; Kenneth T. Rowbottom. "Epoxides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_531.
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