4-tert-Butylbenzaldehyde

4-tert-Butylbenzaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.012.152 Edit this at Wikidata
EC Number
  • 213-367-9
UNII
  • InChI=1S/C11H14O/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-8H,1-3H3
    Key: OTXINXDGSUFPNU-UHFFFAOYSA-N
  • [H]C(=O)c1ccc(cc1)C(C)(C)C
Properties
C11H14O2
Molar mass 178.231 g·mol−1
Appearance colourless liquid
Density 0.97
Boiling point 248.7 °C (479.7 °F; 521.8 K)
120 mg/L
Hazards
GHS labelling:[1]
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H302, H317, H334, H361, H410
P203, P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P318, P321, P330, P333+P317, P342+P316, P362+P364, P391, P403, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-tert-Butylbenzaldehyde is an aromatic aldehyde and an important intermediate for the synthesis of synthetic aroma compounds.

Synthesis

4-tert-Butylbenzaldehyde is notable as a rare example of industrial-scale electrochemistry. It is produced by BASF and Givaudan (typically as its methanol acetal) through a double anodic oxidation of 4-tert-butyltoluene on greater than 10,000 ton per year scale.[2][3]

Applications

Aldol condensation with either propionaldehyde or acetaldehyde, followed by hydrogenation, gives the fragrance compounds lilial and bourgeonal, respectively.

References

  1. ^ "4-tert-Butylbenzaldehyde". pubchem.ncbi.nlm.nih.gov.
  2. ^ Möhle, Sabine; Zirbes, Michael; Rodrigo, Eduardo; Gieshoff, Tile; Wiebe, Anton; Waldvogel, Siegfried R. (22 May 2018). "Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products". Angewandte Chemie International Edition. 57 (21): 6018–6041. doi:10.1002/anie.201712732. PMC 6001547. PMID 29359378.
  3. ^ Botte, G. G. (1 January 2014). "Electrochemical Manufacturing in the Chemical Industry". Interface Magazine. 23 (3): 49–55. Bibcode:2014ECSIn..23c..49B. doi:10.1149/2.F04143if.