4-tert-Butylbenzaldehyde

4-*tert*-Butylbenzaldehyde
Identifiers
CAS Number	939-97-9;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL242962;
ChemSpider	63507;
ECHA InfoCard	100.012.152
EC Number	213-367-9;
PubChem CID	70324;
UNII	QXF0QY8503;
CompTox Dashboard (EPA)	DTXSID6027343 ;
	InChI InChI=1S/C11H14O/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-8H,1-3H3 Key: OTXINXDGSUFPNU-UHFFFAOYSA-N;
	SMILES [H]C(=O)c1ccc(cc1)C(C)(C)C;
Properties
Chemical formula	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)
Solubility in water	120 mg/L
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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

^ "4-tert-Butylbenzaldehyde". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ 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.

[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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[2]

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Identifiers

CAS Number	939-97-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL242962
ChemSpider	63507
ECHA InfoCard	100.012.152
EC Number	213-367-9
PubChem CID	70324
UNII	QXF0QY8503
CompTox Dashboard (EPA)	DTXSID6027343
InChI InChI=1S/C11H14O/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-8H,1-3H3 Key: OTXINXDGSUFPNU-UHFFFAOYSA-N
SMILES [H]C(=O)c1ccc(cc1)C(C)(C)C
Properties
Chemical formula	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)
Solubility in water	120 mg/L
Hazards
GHS labelling:^[1]
Pictograms
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 [77 °F], 100 kPa). Infobox references