3,5-Bis(tert-butyl)benzaldehyde Chemical Properties

Melting point:

85-89 °C(lit.)

Boiling point:

132°C/5mmHg(lit.)

Density 

0.9445 (rough estimate)

refractive index 

1.5410 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

λmax

296nm(CHCl3)(lit.)

InChI

InChI=1S/C15H22O/c1-14(2,3)12-7-11(10-16)8-13(9-12)15(4,5)6/h7-10H,1-6H3

InChIKey

BRUITYMDHWNCIG-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1

CAS DataBase Reference

17610-00-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29122990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3,5-Bis(tert-butyl)benzaldehyde Usage And Synthesis

Chemical Properties

off-white powder

Uses

3,5-Di-tert-butylbenzaldehyde may be used in the synthesis of the following:

• 5-p-pyridyl-15-(3,5-di-tert-butylphenyl)porphyrin via condensation reaction with 4-pyridinecarboxaldehyde and 2,2′-dipyrrylmethane
• 3,5-di-tert-butylphenyl-dipyrromethane via reaction with pyrrole in the presence of trifluoroacetic acid
• 3,5-di-tert-butyl-2-nitrobenzaldehyde via nitration reaction

Synthesis

1-Bromo-3,5-di-tert-butylbenzene (5.00 g, 18.57 mmol) was dissolved in tetrahydrofuran (THF, 50 mL) under nitrogen protection. The reaction mixture was cooled to -78°C. n-Butyllithium (2.5 M hexane solution, 22.29 mL, 55.72 mmol) was slowly added, keeping the temperature at -78°C. The reaction mixture was stirred for 30 min at -78°C. The reaction mixture was then stirred for 30 min at -78°C. Subsequently, N,N-dimethylformamide (DMF, 4.31 mL, 55.72 mmol) was added dropwise. The reaction mixture was slowly warmed to 0°C and stirred at this temperature for 2.5 hours. Upon completion of the reaction, the reaction was quenched by the addition of aqueous ammonium chloride solution (30 mL). The reaction mixture was extracted with ethyl acetate (EtOAc, 3 x 20 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered, the filtrate collected and concentrated under reduced pressure. The residue was purified by fast column chromatography using a 0-10% ethyl acetate/petroleum ether gradient elution to afford 3,5-bis(tert-butyl)benzaldehyde (2.96 g, 73% yield) as a white solid.LC-ES/MS m/z 219 [M + H]+.

References

[1] Journal of the American Chemical Society, 2011, vol. 133, # 13, p. 4710 - 4713
[2] Patent: WO2013/66640, 2013, A1. Location in patent: Page/Page column 15

3,5-Bis(tert-butyl)benzaldehyde(17610-00-3)Related Product Information

• tert-Butyldimethylsilyl chloride
• tert-Butyl peroxyacetate
• 4-tert-Butylcatechol
• Diethylene glycol monobutyl ether
• Butyl acetate
• Cyhalofop-butyl
• 2-Butoxyethanol
• tert-Butyl hydroperoxide
• tert-Butanol
• 4-tert-Butylphenol
• Benzaldehyde
• tert-Butyl methyl ether
• tert-Butyllithium
• BUTYL OLEATE
• Buprofezin
• tert-Butyl ethyl ether
• Butyl acrylate
• 3,5-DI-TERT-BUTYLBENZOIC ACID