4-[(tert-Butyldimethylsilyl)oxy]benzaldehyde

Base Information

• Chemical Name: 4-[(tert-Butyldimethylsilyl)oxy]benzaldehyde
• CAS No.: 120743-99-9
• Molecular Formula: C13H20 O2 Si
• Molecular Weight: 236.386
• Hs Code.: 29310099
• European Community (EC) Number: 626-141-3
• DSSTox Substance ID: DTXSID90446892
• Nikkaji Number: J432.755A
• Wikidata: Q82265635
• Mol file: 120743-99-9.mol

Synonyms:120743-99-9;4-(t-Butyldimethylsilyloxy)benzaldehyde;4-[(tert-Butyldimethylsilyl)oxy]benzaldehyde;4-[tert-butyl(dimethyl)silyl]oxybenzaldehyde;4-(tert-butyldimethylsilyloxy)benzaldehyde;4-((tert-Butyldimethylsilyl)oxy)benzaldehyde;4-((t-butyldimethylsilyl)oxy)benzaldehyde;4-{(t-Butyldimethylsilyl)oxy}benzaldehyde;4-[[tert-butyl(dimethyl)silyl]oxy]benzaldehyde;4-{[tert-butyl(dimethyl)silyl]oxy}benzaldehyde;SCHEMBL896879;Benzaldehyde, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-;DTXSID90446892;XACWSBWCLJXKGI-UHFFFAOYSA-N;VEA74399;MFCD05865174;4-tert-butyldimethylsilyloxybenzaldehyde;4-((tert-Butyldimethylsilyl)oxy)benzald&;BS-23138;4(tert-butyldimethylsilanyloxy)benzaldehyde;4-(tert-butydimethylsilyloxy)-benzaldehyde;4-(tert-butyidimethylsilanyloxy)benzaldehyde;4-(tert-butyldimethylsilanyloxy)benzaldehyde;CS-0204863;FT-0721902;4-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde;F70001;EN300-1706062;4-[(1,1-dimethylethyl)dimethylsilyloxy]benzaldehyde;4-[(I,1-dimethylethyl)dimethylsilyloxy]benzaldehyde;4-[(tert-Butyldimethylsilyl)oxy]benzaldehyde, 97%;J-004392;Z2044777014

Chemical Property of 4-[(tert-Butyldimethylsilyl)oxy]benzaldehyde

Chemical Property:

• Vapor Pressure: 0.00467mmHg at 25°C
• Refractive Index: n20/D 1.5110(lit.)
• Boiling Point: 224-226 °C(lit.)
• Flash Point: >230 °F
• PSA: 26.30000
• Density: 0.957 g/mL at 25 °C(lit.)
• LogP: 3.88310
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 236.123256411
• Heavy Atom Count: 16
• Complexity: 235

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(tert-Butyldimethylsilyloxy)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1=CC=C(C=C1)C=O
• Uses: 4-(tert-Butyldimethylsilyloxy)benzaldehyde is used as a reagent in the synthesis of many organic compounds including that of benzimidazoles which are important structural motifs due to application of their various biological properties.

Technology Process of 4-[(tert-Butyldimethylsilyl)oxy]benzaldehyde

There total 27 articles about 4-[(tert-Butyldimethylsilyl)oxy]benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + tert-butyldimethylsilyl chloride (18162-48-6) → p-[(tert-butyldimethylsilyl)oxy]benzaldehyde (120743-99-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0960-894X(01)00230-X

Reference yield: 96.0%

1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene (117635-46-8) → p-[(tert-butyldimethylsilyl)oxy]benzaldehyde (120743-99-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1055/s-1998-1810

Reference yield: 96.0%

(4-((tert-butyldimethylsilyl)oxy)phenyl)methanol (138585-08-7) → p-[(tert-butyldimethylsilyl)oxy]benzaldehyde (120743-99-9)

Guidance literature:

With N-Bromosuccinimide; β‐cyclodextrin; In methanol; water; acetone; at 20 ℃; for 8h;

DOI:10.1002/adsc.200303164

upstream raw materials:

4-hydroxy-benzaldehyde

tert-butyldimethylsilyl chloride

1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene

4-bromo-benzaldehyde

Downstream raw materials:

1-[4-(tert-butyldimethylsilanyloxy)phenyl]-3-trimethylsilanylprop-2-yn-1-ol

4-(tert-butyldimethylsilyloxy)-α-(3'-methoxyphenyl)benzyl alcohol

(4-(1,3-dithian-2-yl)phenoxy)(tert-butyl)dimethylsilane

(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethene

Refernces

• 1、 Nishihara, Ryo,Suzuki, Hideyuki,Hoshino, Emi,Suganuma, Sakura,Sato, Moritoshi,Saitoh, Tsuyoshi,Nishiyama, Shigeru,Iwasawa, Naoko,Citterio, Daniel,Suzuki, Koji. "Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution". . p. 391 - 394. Retrieved 2015.
• 2、 Lu, Gonghao,Guo, Yuxin,Zhuo, Jiezhen,Li, Xue,Chi, Haijun,Zhang, Zhiqiang. "A General Strategy for Through-Bond Energy Transfer Fluorescence Probes Combining Intramolecular Charge Transfer: A Silyl Ether System for Endogenous Peroxynitrite Sensing". . p. 16350 - 16357. Retrieved 2019.
• 3、 Aggen, David H.,Arnold, Joshua N.,Hayes, Patrick D.,Smoter, Nathaniel J.,Mohan, Ram S.. "Bismuth compounds in organic synthesis. Bismuth nitrate catalyzed chemoselective synthesis of acylals from aromatic aldehydes". . p. 3675 - 3679. Retrieved 2004.
• 4、 Adamczyk, Maciej,Johnson, Donald D.,Mattingly, Phillip G.,Pan, You,Reddy, Rajarathnam E.. "Synthesis of coelenterazine". . p. 477 - 485. Retrieved 2001.
• 5、 Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna. "Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions". supporting information. p. 9047 - 9052. Retrieved 2021/12/06.
• 6、 Murugesan, Vetrivelan,Ganguly, Anirban,Karthika, Ardra,Rasappan, Ramesh. "C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis". supporting information. p. 5389 - 5393. Retrieved 2021/07/21.