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4-tert-Butylbenzaldehyde

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4-tert-Butylbenzaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.012.152 Edit this at Wikidata
EC Number
  • 213-367-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H14O/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-8H,1-3H3Key: OTXINXDGSUFPNU-UHFFFAOYSA-N
SMILES
  • C(=O)c1ccc(cc1)C(C)(C)C
Properties
Chemical formula C11H14O2
Molar mass 178.231 g·mol
Appearance colourless liquid
Density 0.97
Boiling point 248.7 °C (479.7 °F; 521.8 K)
Solubility in water 120 mg/L
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H302, H317, H334, H361, H410
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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.

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.
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