(tert-Butyldimethylsilyloxy)acetaldehyde

Base Information

• Chemical Name: (tert-Butyldimethylsilyloxy)acetaldehyde
• CAS No.: 102191-92-4
• Molecular Formula: C8H18O2Si
• Molecular Weight: 174.315
• Hs Code.: 29319090
• European Community (EC) Number: 629-471-6
• DSSTox Substance ID: DTXSID40400520
• Nikkaji Number: J703.743K
• Wikidata: Q72503001
• Mol file: 102191-92-4.mol

Synonyms:102191-92-4;(tert-Butyldimethylsilyloxy)acetaldehyde;(tert-butyldimethylsiloxy)acetaldehyde;2-(tert-butyldimethylsilyloxy)acetaldehyde;2-((tert-Butyldimethylsilyl)oxy)acetaldehyde;2-[tert-butyl(dimethyl)silyl]oxyacetaldehyde;t-butyldimethylsiloxyacetaldehyde;2-[(tert-butyldimethylsilyl)oxy]acetaldehyde;t-butyldimethylsilyloxyacetaldehyde;Acetaldehyde, [[(1,1-dimethylethyl)dimethylsilyl]oxy]-;{[tert-butyl(dimethyl)silyl]oxy}acetaldehyde;tert-Butyldimethylsilyloxy)acetaldehyde;SCHEMBL64584;DTXSID40400520;MEBFFOKESLAUSJ-UHFFFAOYSA-N;(tert-Butyldimethylsilyloxy)ethanal;t-butyldimethylsilyloxylacetaldehyde;tert-butyldimethylsiloxyacetaldehyde;t-butyldimethylsilyloxy acetaldehyde;(t-butyldimethylsilyloxy)acetaldehyde;tert-butyldimethylsilyloxyacetaldehyde;BBL103211;MFCD01321229;STL557021;t-butyldimethylsilanyloxy acetaldehyde;(t-butyldimethylsilyloxy) acetaldehyde;tert-butyldimethylsilyloxy acetaldehyde;tert-butyldimethylsilyloxy-acetaldehyde;2-(tert-butyldimethylsilyloxy)-ethanal;AKOS016003622;(tertbutyldimethylsilanyloxy)acetaldehyde;(tert-butyldimethylsilyl-oxy)acetaldehyde;(tert-butyldimethylsilyloxy) acetaldehyde;(tert-butyldimethylsilyloxy)-acetaldehyde;(tert-Butyldimethylsilanyloxy)acetaldehyde;2-tert-butyl-dimethylsilyloxy-acetaldehyde;BP-31208;BS-19212;(tert-butyl-dimethylsilanyloxy)acetaldehyde;(tert-butyl-dimethylsilanyloxy)-acetaldehyde;2-(tert-butyldimethylsilyloxy) acetaldehyde;2-(tert-butyldimethylsilyloxy)-acetaldehyde;(tert-butyl-dimethyl-silanyloxy)-acetaldehyde;2-(tert-butyl-dimethylsilanyloxy)acetaldehyd;2-(tert-butyl-dimethylsilanyloxy)acetaldehyde;B6269;FT-0694254;(tert-Butyldimethylsilyloxy)acetaldehyde, 90%;2-[tert-butyl (dimethyl)silyl]oxyacetaldehyde;DIMETHYL-TERT-BUTYLSILYLOXYACETALDEHYDE;{[(tert-butyl)(dimethyl)silyl]oxy}acetaldehyde;EN300-225896;[[(1,1-dimethylethyl)dimethylsilyl]oxy]acetaldehyde;J-506623;J-640403;J-800376;[[(1,1-dimethylethyl)-dimethylsilyl]-oxy]acetaldehyde;[[(1,1-dimethylethyl)dimethylsilyl]oxy]-acetaldehyde;{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}acetaldehyde;2-[(1,1-dimethylethyl)dimethylsilyloxy]-acetaldehyde;Acetaldehyde, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

Chemical Property of (tert-Butyldimethylsilyloxy)acetaldehyde

Chemical Property:

• Appearance/Colour: Clear colorless to straw colored liquid
• Vapor Pressure: 2.32mmHg at 25°C
• Melting Point: 165-167 oC
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 161 °C at 760 mmHg
• Flash Point: 42.7 °C
• PSA: 26.30000
• Density: 0.871 g/cm³
• LogP: 2.20710
• Storage Temp.: below 5° C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 174.107606347
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

95.0% ^*data from raw suppliers

(tert-?Butyldimethylsilylox?y)?acetaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC=O
• Uses: Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide.

Technology Process of (tert-Butyldimethylsilyloxy)acetaldehyde

There total 26 articles about (tert-Butyldimethylsilyloxy)acetaldehyde 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%

2-(tert-butyldimethylsilyloxy)ethanol (102229-10-7) → tert-butyldimethylsiloxyacetaldehyde (102191-92-4)

Guidance literature:

2-(tert-butyldimethylsilyloxy)ethanol; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 0.833333h; Inert atmosphere;

With triethylamine; In dichloromethane; dimethyl sulfoxide; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02162

Reference yield: 100.0%

(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene (132835-15-5) → tert-butyldimethylsiloxyacetaldehyde (102191-92-4)

Guidance literature:

(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo034011x

Reference yield: 98.0%

2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodec-6-ene (129377-90-8) → tert-butyldimethylsiloxyacetaldehyde (102191-92-4)

Guidance literature:

With ozone; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/acs.orglett.0c02182

upstream raw materials:

1-(tert-butyl-dimethyl-silanyloxy)propane-1,2-diol

2-(tert-butyldimethylsilyloxy)ethanol

Allyloxy-tert-butyl-dimethyl-silane

(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene

Downstream raw materials:

1-(5-Benzyloxymethyl-furan-2-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethanol

(Z)-N-(2-dimethyl-t-butylsilyloxyethylidene)benzylamine N-oxide

4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3-<(Z)-3-tert-butyldimethylsilyloxy-1-propenyl>-3-cephem-4-carboxylate

4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-tert-butyldimethylsilyloxy-1-propenyl>-3-cephem-4-carboxylate

Refernces

• 1、 Tanaka,Katsumura. "Novel synthesis of the ocular age pigment A2-E: new method for substituted pyridine synthesis via azaelectrocyclization.". . p. 373 - 375. Retrieved 2000.
• 2、 Ko, Ok Hyun,Hong, Joon Hee. "Synthesis and in vitro activity evaluation of 2',3'-c-dimethyl carbocyclic nucleoside analogues as potential anti-HCV agents". . p. 761 - 771. Retrieved 2009.
• 3、 Stork, Gilbert,Yamashita, Ayako,Hanson, Robert M.,Phan, Ly,Phillips, Eifion,Dubé, Daniel,Bos, Pieter H.,Clark, Andrew J.,Gough, Maxwell,Greenlee, Mark L.,Jiang, Yimin,Jones, Keith,Kitamura, Masato,Leonard, John,Liu, Tongzhu,Parsons, Philip J.,Venkatesan, Aranapakam M.. "Synthetic study toward total synthesis of (±)-germine: Synthesis of (±)-4-methylenegermine". . p. 5150 - 5153. Retrieved 2017.
• 4、 Song, Fengbin,Fidanze, Steve,Benowitz, Andrew B,Kishi, Yoshito. "Total synthesis of the mycolactones.". . p. 647 - 650. Retrieved 2002.
• 5、 Han, Seo-Jung,Stoltz, Brian M.. "A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams". . p. 2233 - 2235. Retrieved 2016.
• 6、 Craig, Donald,Ford, Mark J.,Stones, James A.. "Formation of medium-ring diolides via intramolecular Diels-Alder reactions of dicarboxylic ester-tethered trienes". . p. 535 - 538. Retrieved 1996.
• 7、 Alterman, Joshua L.,Halverson, Larry J.,Kraus, George A.,Stroud, Marissa Roghair,Vang, Dua X.. "Ozonolysis of Alkynes - A Flexible Route to Alpha-Diketones: Synthesis of AI-2". . p. 7424 - 7426. Retrieved 2020.
• 8、 Roos, Juergen,Effenberger, Franz. "Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes". . p. 2817 - 2828. Retrieved 1999.
• 9、 -. "Pyrimidine-4 (3H)-ketone heterocyclic compound, preparation method thereof and application of pyrimidine-4 (3H)-ketone heterocyclic compound in medicine". Paragraph 0349-0351; 0356-0359. . Retrieved 2021/07/21.
• 10、 -. "COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES". Paragraph 0382; 0385. . Retrieved 2021/04/23.