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
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 pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H312, H314, H315, H318, H319, H335
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P322, P332+313, P337+313, P362, P363, P370+378
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