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

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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

References

^ Guenter Sienel; Robert Rieth; Kenneth T. Rowbottom. "Epoxides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_531. ISBN 978-3527306732.

[UllmannEpoxides-1] Guenter Sienel; Robert Rieth; Kenneth T. Rowbottom. "Epoxides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_531. ISBN 978-3527306732.

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