PROPARGYLTRIMETHYLSILANE

PROPARGYLTRIMETHYLSILANE Basic information
Product Name:PROPARGYLTRIMETHYLSILANE
Synonyms:Propargyltrimethylsilane, stabilized, 80-90%;PropargyltriMethylsilane, stabilized, 8;triMethyl(prop-2-yn-1-yl)silane;TriMethyl(propargyl)silane contains 500 ppM BHT as stabilizer;Silane,trimethyl-2-propyn-1-yl-;3-TRIMETHYLSILYL-1-PROPYNE;3-(TRIMETHYLSILYL)PROPYNE;2-PROPYNYL-TRIMETHYLSILANE
CAS:13361-64-3
MF:C6H12Si
MW:112.25
EINECS:236-427-6
Product Categories:
Mol File:13361-64-3.mol
PROPARGYLTRIMETHYLSILANE Structure
PROPARGYLTRIMETHYLSILANE Chemical Properties
Melting point 148-151 °C(Solv: ethyl ether (60-29-7))
Boiling point 91-93 °C (lit.)
density 0.753 g/mL at 25 °C (lit.)
refractive index n20/D 1.413(lit.)
Fp 13 °F
storage temp. -20°C
solubility sol ether, THF, CH2Cl2.
form Liquid
color Clear yellow
BRN 2036316
CAS DataBase Reference13361-64-3
EPA Substance Registry SystemSilane, trimethyl-2-propynyl- (13361-64-3)
Safety Information
Hazard Codes F,Xi
Risk Statements 11-36/37/38
Safety Statements 16-26-36
RIDADR UN 1993 3/PG 2
WGK Germany 3
HazardClass 3.1
PackingGroup II
HS Code 29310099
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
PROPARGYLTRIMETHYLSILANE Usage And Synthesis
Chemical PropertiesClear yellow liquid
Physical propertiesbp 91–93 °C/760 mmHg; 40 °C/140 mmHg; d 0.753 g mL?1; nD 20 1.4140.
Uses3-Trimethylsilyl-1-propyne is used as propargylation agent; allenylation agent; can give addition reactions on the triple bond. It takes part in the following reactions: Propargylation Reactions, Alkylation Reactions, Reactions with Epoxides,Reactions with Aldehydes and Ketones, Reactions with Chloroformates, Reactions with Polyoxymethylene and Amines, Allenylation Reactions, Substitution Reactions, Reactions with Acetals and Hemiacetals, Reactions with Aldehydes and Ketones, Reactions with in situ Generated Iminium and α-Acyl Iminium Ions, Reactions with Acid Chlorides, Reactions with Conjugated Heteroatomic Systems, Reactions of the Triple Bond etc.
UsesTrimethyl(propargyl)silane is suitable for use in the synthesis of diverse end-functionalized (ω-carboxyl, ω-hydroxy, ω-methyl-vinyl, ω-trimethylsilane, and ω-glycidyl-ether) via ′′click′′ reaction. It may be used in the synthesis of γ-allenyl-GABA (γ-aminobutyric acid), via Lewis acid mediated reaction with ω-ethoxy lactams.
PreparationThe main method of preparation is shown in eq 1. The title reagent can be obtained by other methods, but in poor yields.

13361-64-3 synthesis

General DescriptionTrimethyl(propargyl)silane (2-Propynyl-trimethylsilane) is a clear colorless liquid and contains 500ppm of butylated hydroxytoluene (BHT) as stabilizer. It undergoes GaCl3-catalyzed dehydrogenation reaction with aldimines to afford 4-methylquinoline.
Purification MethodsFractionally distil it and add 2,6-di-tert-butyl-p-cresol (~0.5%) to stabilise it. [Petrov et al. Doklady Acad Nauk USSR 93 293 1953, cf Chem Abstr 48 13616 1954, Beilstein 4 IV 3938.]
PROPARGYLTRIMETHYLSILANE Preparation Products And Raw materials
Raw materialsSilane, trimethyl-1,2-propadien-1-yl--->bromo-2-propynyl-Magnesium-->3-Bromopropyne-->Bromotrimethylsilane-->Chlorotrimethylsilane
Preparation Products1,1-dimethyl-2,5-dihydrosilole
TRIMETHYLSILANE 1-TRIFLUOROMETHYL-4-(Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)BENZENE PROPARGYLTRIMETHYLSILANE 1-METHOXY-4-(Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)BENZENE Propyne 1-METHYL-4-(Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)BENZENE 1-NITRO-4-(Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)BENZENE (Z)-4-TRIMETHYLSILANYL-5-TRIMETHYLSILANYLETHYNYLOCTA-4,7-DIEN-2-YNOIC ACID ETHYL ESTER (Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)BENZENE (Z)-5-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLUNDECA-1,4-DIEN-6-YNE 1-CHLORO-4-(Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)BENZENE 1,3-DICHLORO-2-(Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)BENZENE 1-(Z-3-TRIMETHYLSILANYL-4-TRIMETHYLSILANYLETHYNYLHEPTA-3,6-DIEN-1-YNYL)CYCLOHEXENE

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