13361-64-3

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 NO: 13361-64-3
• Molecular Formula: C₆H₁₂Si
• Molecular Weight: 112.24
• EINECS: 236-427-6
• Mol File: 13361-64-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 148-151 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 91-93 °C(lit.)
• Flash Point: 13 °F
• Appearance: Clear yellow/Liquid
• Density: 0.753 g/mL at 25 °C(lit.)
• Vapor Pressure: 67.2mmHg at 25°C
• Refractive Index: n20/D 1.413(lit.)
• Storage Temp.: −20°C
• Solubility: sol ether, THF, CH2Cl2.
• BRN: 2036316
• CAS DataBase Reference: PROPARGYLTRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPARGYLTRIMETHYLSILANE(13361-64-3)
• EPA Substance Registry System: PROPARGYLTRIMETHYLSILANE(13361-64-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 13361-64-3(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

Physical properties

bp 91–93 °C/760 mmHg; 40 °C/140 mmHg; d 0.753 g mL?1; nD 20 1.4140.

Uses

Different sources of media describe the Uses of 13361-64-3 differently. You can refer to the following data:
1. 3-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.
2. Trimethyl(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.

Preparation

The main method of preparation is shown in eq 1. The title reagent can be obtained by other methods, but in poor yields.

General Description

Trimethyl(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 Methods

Fractionally 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.]

InChI:InChI=1/C6H12Si/c1-5-6-7(2,3)4/h1H,6H2,2-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 18295-60-8 propargyl magnesium bromide 
• 2857-97-8 trimethylsilyl bromide 
• 106-96-7 propargyl bromide 
• 14657-22-8 allenyltrimethylsilane 
• 2295-12-7 1,1-dimethylsilacyclobutane 
• 463-49-0 1,2-propanediene 

Downstream Products

• 131251-55-3 2-iodo-3-(2-propynyl)benzoic acid 
• 131467-47-5 N-(buta-2,3-dienyl)-N-methylaniline 
• 25203-83-2 (E)-1-cyclohexyl-1,3-butadiene 
• 143741-76-8 (E)-1-Cyclohexyl-4-trimethylsilanyl-but-2-en-1-ol 
• 162191-95-9 2-Methyl-6-phenyl-pyridine-3-carbaldehyde 
• 168132-21-6 [6-(2-Iodo-5-methoxy-4-methyl-phenyl)-hex-2-ynyl]-trimethyl-silane 
• 13362-80-6 4,8-dimethylquinoline 
• 31598-65-9 6-fluoro-4-methylquinoline 
• 41037-30-3 4-methyl-6-nitro-quinoline 
• 204582-41-2 1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-(3-trimethylsilanyl-prop-1-ynyl)-1H-pyrimidine-2,4-dione 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 90921-20-3 allenylmethylaniline 
• 205676-18-2 4-methylene-1,2,3,4-tetrahydroquinoline 

Related news

Action du PROPARGYLTRIMETHYLSILANE (cas 13361-64-3) sur les derives carbonyles en presence de fluorure de tetra-n-butylammonium: nouvelle voie d'acces aux alcools α-alleniques.07/30/2019

RésuméPropargyltrimethylsilane reacts with carbonyl compounds to produce α-allenic alcohols in the presence of tetra-n-butylammonium fluoride.detailed

Action du PROPARGYLTRIMETHYLSILANE (cas 13361-64-3) sur les derives carbonyles en presence de tetrachlorure de titane: nouvelle voie d'acces aux derives chloropreniques.07/29/2019

RésuméPropargyltrimethylsilane reacts with carbonyi compounds to produce chloroprenic derivatives in the presence of titanium tetrachloride.detailed

Relevant articles and documents

ACTION DE SILANES PROPARGYLIQUES SUR DES DERIVES CARBONYLES α-ETHYLENIQUES

Propargylsilanes RCCCH2Si(CH3)3 easily react with dialkyl alkylidenemalonates, in the presence of TiCl4, to lead to the only product corresponding to an 1,4-addition; the reaction takes place with propargylic rearrangement.

Temporary silicon connection strategies in intramolecular allylation of aldehydes with allylsilanes

(Chemical Equation Presented) Three γ-(amino)silyl-substituted allylsilanes 14a-c have been prepared in three steps from the corresponding dialkyldichlorosilane. The aminosilyl group has been used to link this allylsilane nucleophile to a series of β-hydroxy aldehydes through a silyl ether temporary connection. The size of the alkyl substituents at the silyl ether tether governs the outcome of the reaction on exposure to acid. Thus, treatment of aldehyde (E)-9aa, which contains a dimethylsilyl ether connection between the aldehyde and allylsilane, with a range of Lewis and Bronsted acid activators provides an (E)-diene product. The mechanism of formation of this undesired product is discussed. Systems containing a sterically more bulky diethylsilyl ether connection react differently: thus in the presence of TMSOTf and a Bronsted acid scavenger, intramolecular allylation proceeds smoothly to provide two out of the possible four diastereoisomeric oxasilacycles, 23 (major) and 21 (minor). A diene product again accounts for the remaining mass balance in the reaction. This side product can be completely suppressed by using a sterically even more bulky diisopropylsilyl ether connection in the cyclization precursor, although this is now at the expense of a slight erosion in the 1,3-stereoinduction in the allylation products. The sense of 1,3-stereoinduction observed in these intramolecular allylations has been rationalized by using an electrostatic argument, which can also explain the stereochemical outcome of a number of related reactions. Levels of 1,4-stereoinduction in the intramolecular allylation are more modest but can be significantly improved in some cases by using a tethered (Z)-allylsilane in place of its (E)-stereoisomer. Oxidation of the major diastereoisomeric allylation product 23 under Tamao-Kumada conditions provides an entry into stereodefined 1,2-anti-2,4-syn triols 28.