2-Methyl-1-(trimethylsilyloxy)-1-propene

Base Information

• Chemical Name: 2-Methyl-1-(trimethylsilyloxy)-1-propene
• CAS No.: 6651-34-9
• Molecular Formula: C7H16OSi
• Molecular Weight: 144.289
• Hs Code.: 2931900090
• European Community (EC) Number: 627-551-5
• NSC Number: 266194
• DSSTox Substance ID: DTXSID30216713
• Nikkaji Number: J258.812I
• ChEMBL ID: CHEMBL142371
• Mol file: 6651-34-9.mol

Synonyms:isobutyraldehyde trimethylsilyl enol ether;ITSE

Chemical Property of 2-Methyl-1-(trimethylsilyloxy)-1-propene

Chemical Property:

• Vapor Pressure: 19.2mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• Boiling Point: 119.3 °C at 760 mmHg
• Flash Point: 15.6 °C
• PSA: 9.23000
• Density: 0.803 g/cm³
• LogP: 2.76160
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 144.097041664
• Heavy Atom Count: 9
• Complexity: 107

Purity/Quality:

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

2-Methyl-1-(trimethylsilyloxy)-1-propene 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CO[Si](C)(C)C)C
• Uses: 1-(Trimethylsilyloxy)-2-methylpropene is used as a nucleophiles in Lewis Acid-Catalyzed reactions. 2-Methyl-1-(trimethylsilyloxy)-1-propene may be used as reagent in the direct conversion of α-amino acids into β-amino aldehydes.

Technology Process of 2-Methyl-1-(trimethylsilyloxy)-1-propene

There total 7 articles about 2-Methyl-1-(trimethylsilyloxy)-1-propene 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: 93.0%

chloro-trimethyl-silane (75-77-4) + isobutyraldehyde (78-84-2) → 2-methyl-1-(trimethylsilyloxy)-1-propene (6651-34-9)

Guidance literature:

With triethylamine; potassium iodide; In N,N-dimethyl-formamide; Petroleum ether; Ambient temperature;

DOI:10.1080/00397919708004194

Reference yield: 64.0%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + isobutyraldehyde (78-84-2) → 2-methyl-1-(trimethylsilyloxy)-1-propene (6651-34-9) + N-Trimethylsilylacetamide (13435-12-6)

Guidance literature:

With sodium; In N,N,N,N,N,N-hexamethylphosphoric triamide; Ambient temperature;

DOI:10.1016/S0022-328X(00)85896-9

Reference yield: 51.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + isobutyraldehyde (78-84-2) → 2-methyl-1-(trimethylsilyloxy)-1-propene (6651-34-9)

Guidance literature:

With triethylamine; In diethyl ether; for 1h; Ambient temperature;

upstream raw materials:

chloro-trimethyl-silane

2-methylprop-1-en-1-ol

isobutyraldehyde

bis-trimethylsilanyl-acetonitrile

Downstream raw materials:

3-Chloro-benzoic acid 2-hydroxy-2-methyl-1-trimethylsilanyloxy-propyl ester

1-(2,2-dimethyl-3-oxopropyl)perhydro-2-azepinone

1-(furan-2-yl)-2,2-dimethylpropane-1,3-diol

(+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol

Refernces

• 1、 Downey, C. Wade,Dixon, Grant J.,Ingersoll, Jared A.,Fuller, Claire N.,MacCormac, Kenneth W.,Takashima, Anna,Sediqui, Rohina. "One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents". supporting information. . Retrieved 2019/10/14.
• 2、 Hsu,Fang. "Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan". . p. 8573 - 8584. Retrieved 2007/10/03.