Identification | More | [Name]
3,5-Bis(tert-butyl)benzaldehyde | [CAS]
17610-00-3 | [Synonyms]
3,5-BIS(TERT-BUTYL)BENZALDEHYDE 3,5-DI-TERT-BUTYL-BENZALDEHYDE RARECHEM AQ A2 0001 3,5-BIS(TERT-BUTYL)BENZALDEHYDE 97% 3,5-BIS(TERT-BUTYL)BENZLDEHYDE | [EINECS(EC#)]
639-397-6 | [Molecular Formula]
C15H22O | [MDL Number]
MFCD00026298 | [Molecular Weight]
218.33 | [MOL File]
17610-00-3.mol |
Chemical Properties | Back Directory | [Appearance]
off-white powder | [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 Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29122990 |
Hazard Information | Back Directory | [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 |
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