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
CAS Number	100-50-5
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3188123
ChemSpider	21106029
ECHA InfoCard	100.002.599
EC Number	202-858-3
PubChem CID	7508
UNII	GAK9539347
UN number	2498
CompTox Dashboard (EPA)	DTXSID1026661
InChI InChI=1S/C7H10O/c8-6-7-4-2-1-3-5-7/h1-2,6-7H,3-5H2 Key: DCFDVJPDXYGCOK-UHFFFAOYSA-N
SMILES C1CC(CC=C1)C=O
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H226, H312, H314, H315, H319, H335
Precautionary statements	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