6224-91-5

Basic information

• Product Name: 1-(Trimethylsilyl)-1-propyne
• Synonyms: (1-Propynyl)trimethylsilane;1-Propynyltrimethylsilane;1-(Trimethylsilyl)-1-propyne,98%;1-(Trimethylsilyl)propyne,Trimethyl-1-propynylsilane;triMethyl(prop-1-yn-1-yl)silane;1-Methyl-2- triMethylsilylacetylene;Methyl(triMethylsilyl)ethyne;T 3728
• CAS NO: 6224-91-5
• Molecular Formula: C₆H₁₂Si
• Molecular Weight: 112.24
• EINECS: 228-314-5
• Product Categories: Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Acetylenes;Diyne Compounds (LB Films);Ethynylsilanes;Functional Materials;Functionalized Acetylenes;LB Films;Si (Classes of Silicon Compounds)
• Mol File: 6224-91-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: -69°C
• Boiling Point: 99-100 °C(lit.)
• Flash Point: 25 °F
• Appearance: Clear colorless/Liquid
• Density: 0.758 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 43.9mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: 0-6°C
• Solubility: Miscible with toluene.
• BRN: 1071311
• CAS DataBase Reference: 1-(Trimethylsilyl)-1-propyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Trimethylsilyl)-1-propyne(6224-91-5)
• EPA Substance Registry System: 1-(Trimethylsilyl)-1-propyne(6224-91-5)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 6224-91-5(Hazardous Substances Data)

Usage

Chemical Properties

1-(Trimethylsilyl)-1-propyne is CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 6224-91-5 differently. You can refer to the following data:
1. 1-(Trimethylsilyl)propyne is used in the synthesis of alkynyl silane derivative.
2. 1-Trimethylsilyl-1-propyne is employed in the preparation of alkynyl silane derivatives. It is also used to prepare highly substituted indenes using palladium-catalyzed carboannulation. Further, it plays an important role in the preparation of indenones through a rhodium-catalyzed reaction with 2-bromophenylboronic acids.

InChI:InChI=1/C6H12Si/c1-5-6-7(2,3)4/h1-4H3

Synthetic route

prop-1-yne (74-99-7) + trimethylsilylacetylene (1066-54-2) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
(Me2SiCp''2UBu)2O*2THF In tetrahydrofuran at 66℃; for 44h;	100%

C10H26OSi3 (83268-94-4) → trimethyl(prop-1-ynyl)silane (6224-91-5) + trimethylsilan (993-07-7) + Methoxytrimethylsilane (1825-61-2) + ethenyltrimethylsilane (754-05-2)

Conditions	Yield
at 650℃; under 0.0001 Torr;	A 18% B n/a C 87% D 28%

[3-(trimethylsilyl)prop-2-yn-1-yl]magnesium bromide (78012-45-0) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With hydrogenchloride In diethyl ether at 0 - 5℃;	86%

→ trimethyl(prop-1-ynyl)silane

Conditions	Yield
In various solvent(s) at 100℃; for 3h;	81.6%

trimethylsilylacetylene + methyl iodide (74-88-4) → trimethyl(prop-1-ynyl)silane

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 3h; Inert atmosphere;	76%
Stage #1: methyl iodide With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: trimethylsilylacetylene at 20℃; for 4h; Schlenk technique; Inert atmosphere;

→ trimethyl(prop-1-ynyl)silane + trimethylsilan + ethenyltrimethylsilane (754-05-2)

Conditions	Yield
at 590℃; under 0.0001 Torr;	A 18% B n/a C 72% D 27%

C10H26OSi3 (83268-92-2, 83268-93-3) → trimethyl(prop-1-ynyl)silane (6224-91-5) + trimethylsilan (993-07-7) + Methoxytrimethylsilane (1825-61-2) + ethenyltrimethylsilane (754-05-2)

Conditions	Yield
at 650℃; under 0.0001 Torr;	A 17% B n/a C 55% D 16%

trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane (129217-85-2) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With trifluoroacetic acid In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;	23%

trimethylsilyl bromide (2857-97-8) + 1-propynylmagnesium bromide (16466-97-0, 13254-27-8) → trimethyl(prop-1-ynyl)silane (6224-91-5)

chloro-trimethyl-silane (75-77-4) + 1-propynyl lithium (4529-04-8) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
In diethyl ether
In diethylene glycol dimethyl ether
In diethyl ether for 30h; Heating; Yield given;

chloro-trimethyl-silane (75-77-4) + propargyl bromide (106-96-7) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With magnesium In N,N,N,N,N,N-hexamethylphosphoric triamide at 100 - 110℃;

chloro-trimethyl-silane (75-77-4) + prop-1-yne (74-99-7) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
(i) nBuLi, THF, hexane, (ii) /BRN= 1209232/; Multistep reaction;
(i) nBuLi, hexane, (ii) /BRN= 1209232/; Multistep reaction;
(i) nBuLi, hexane, (ii) /BRN= 1209232/, pentane, THF; Multistep reaction;

chloro-trimethyl-silane (75-77-4) + 2-bromoprop-1-ene (557-93-7) → trimethyl(prop-1-ynyl)silane (6224-91-5) + 2-(trimethylsilyl)propene (18163-07-0) + 1,3-bis(trimethylsilyl)propyne (21752-80-7) + 1-propynyl lithium (4529-04-8)

Conditions	Yield
With lithium 1.) ether, 3 h, reflux, ultrasound; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

chloro-trimethyl-silane (75-77-4) + bromo-2 trimethylsilyloxy-1 propene-1 (61668-36-8) → trimethyl(prop-1-ynyl)silane (6224-91-5) + (Z)-2-Trimethylsilanyl-1-trimethylsilanyloxy-propene (154581-92-7)

Conditions	Yield
With tert.-butyl lithium; sodium carbonate 1.) pentane, THF, -70 deg C, 45 min; 2.) -70 deg C, 50 min; 3.) 0 deg C, 10 min; Multistep reaction;

prop-1-yne (74-99-7) + trimethylsilylacetylene (1066-54-2) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
(Me2SiCp''2UBu)2O*2THF In tetrahydrofuran at 66℃; for 44h;	100%

C10H26OSi3 (83268-94-4) → trimethyl(prop-1-ynyl)silane (6224-91-5) + trimethylsilan (993-07-7) + Methoxytrimethylsilane (1825-61-2) + ethenyltrimethylsilane (754-05-2)

Conditions	Yield
at 650℃; under 0.0001 Torr;	A 18% B n/a C 87% D 28%

[3-(trimethylsilyl)prop-2-yn-1-yl]magnesium bromide (78012-45-0) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With hydrogenchloride In diethyl ether at 0 - 5℃;	86%

chloro-trimethyl-silane (75-77-4) + sodium propynide (10486-71-2) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
In various solvent(s) at 100℃; for 3h;	81.6%

trimethylsilylacetylene (1066-54-2) + methyl iodide (74-88-4) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 3h; Inert atmosphere;	76%
Stage #1: methyl iodide With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: trimethylsilylacetylene at 20℃; for 4h; Schlenk technique; Inert atmosphere;

2-cyclopropyl-2-methoxyhexamethyltrisilane (83268-89-7) → trimethyl(prop-1-ynyl)silane (6224-91-5) + trimethylsilan (993-07-7) + Methoxytrimethylsilane (1825-61-2) + ethenyltrimethylsilane (754-05-2)

Conditions	Yield
at 590℃; under 0.0001 Torr;	A 18% B n/a C 72% D 27%

C10H26OSi3 (83268-92-2, 83268-93-3) → trimethyl(prop-1-ynyl)silane (6224-91-5) + trimethylsilan (993-07-7) + Methoxytrimethylsilane (1825-61-2) + ethenyltrimethylsilane (754-05-2)

Conditions	Yield
at 650℃; under 0.0001 Torr;	A 17% B n/a C 55% D 16%

trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane (129217-85-2) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With trifluoroacetic acid In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;	23%

trimethylsilyl bromide (2857-97-8) + 1-propynylmagnesium bromide (16466-97-0, 13254-27-8) → trimethyl(prop-1-ynyl)silane (6224-91-5)

chloro-trimethyl-silane (75-77-4) + 1-propynyl lithium (4529-04-8) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
In diethyl ether
In diethylene glycol dimethyl ether
In diethyl ether for 30h; Heating; Yield given;

chloro-trimethyl-silane (75-77-4) + propargyl bromide (106-96-7) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With magnesium In N,N,N,N,N,N-hexamethylphosphoric triamide at 100 - 110℃;

chloro-trimethyl-silane (75-77-4) + prop-1-yne (74-99-7) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
(i) nBuLi, THF, hexane, (ii) /BRN= 1209232/; Multistep reaction;
(i) nBuLi, hexane, (ii) /BRN= 1209232/; Multistep reaction;
(i) nBuLi, hexane, (ii) /BRN= 1209232/, pentane, THF; Multistep reaction;

chloro-trimethyl-silane (75-77-4) + 2-bromoprop-1-ene (557-93-7) → trimethyl(prop-1-ynyl)silane (6224-91-5) + 2-(trimethylsilyl)propene (18163-07-0) + 1,3-bis(trimethylsilyl)propyne (21752-80-7) + 1-propynyl lithium (4529-04-8)

Conditions	Yield
With lithium 1.) ether, 3 h, reflux, ultrasound; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

chloro-trimethyl-silane (75-77-4) + bromo-2 trimethylsilyloxy-1 propene-1 (61668-36-8) → trimethyl(prop-1-ynyl)silane (6224-91-5) + (Z)-2-Trimethylsilanyl-1-trimethylsilanyloxy-propene (154581-92-7)

Conditions	Yield
With tert.-butyl lithium; sodium carbonate 1.) pentane, THF, -70 deg C, 45 min; 2.) -70 deg C, 50 min; 3.) 0 deg C, 10 min; Multistep reaction;

chloro-trimethyl-silane (75-77-4) + ((Z)-2-Bromo-1-methyl-vinyloxy)-trimethyl-silane → trimethyl(prop-1-ynyl)silane (6224-91-5) + (Z)-1-Trimethylsilanyl-2-trimethylsilanyloxy-propene

Conditions	Yield
With tert.-butyl lithium; sodium carbonate 1.) pentane, THF, -70 deg C, 45 min; 2.) -70 deg C, 50 min; 3.) 0 deg C, 10 min; Yield given. Multistep reaction;

Bis(trimethylsilyl)thioketene (62827-97-8) → trimethyl(prop-1-ynyl)silane (6224-91-5) + tetramethylcyclodisilthiane (7796-59-0) + Trimethylsilanyl-ethenethione + Bis(trimethylsilyl)ethyne (14630-40-1)

Conditions	Yield
at 768℃; flash vacuum pyrolysis;	A 13 % Chromat. B 4 % Chromat. C 17 % Chromat. D 17 % Chromat.

Bis(trimethylsilyl)thioketene (62827-97-8) → trimethyl(prop-1-ynyl)silane (6224-91-5) + tetramethylcyclodisilthiane (7796-59-0) + 2,2,4,4-tetramethyl-2,4-disilathiethane + Bis(trimethylsilyl)ethyne (14630-40-1)

Conditions	Yield
at 768℃; flash vacuum pyrolysis;	A 13 % Chromat. B 4 % Chromat. C 8 % Chromat. D 17 % Chromat.

Bis(trimethylsilyl)thioketene (62827-97-8) → trimethyl(prop-1-ynyl)silane (6224-91-5) + Trimethylsilanyl-ethenethione + 2,2,4,4-tetramethyl-2,4-disilathiethane + Bis(trimethylsilyl)ethyne (14630-40-1)

Conditions	Yield
at 768℃; flash vacuum pyrolysis;	A 13 % Chromat. B 17 % Chromat. C 8 % Chromat. D 17 % Chromat.

1-(Phenylsulfonyl)-2-(trimethylsilyl)acetylene (32501-93-2) + methyllithium (917-54-4) → trimethyl(prop-1-ynyl)silane (6224-91-5) + benzenesulfonic acid (98-11-3)

Conditions	Yield
In tetrahydrofuran 1.) -78 deg C; 2.) up to RT; Yields of byproduct given;

methyl 3-(trimethylsilyl)prop-2-ynyl carbonate (141862-01-3) → trimethyl(prop-1-ynyl)silane (6224-91-5) + 1,6--1,5-hexadiyne (1578-53-6) + 3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In toluene for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

ethyl 3-(trimethylsilyl)prop-2-ynyl carbonate (167275-01-6) → trimethyl(prop-1-ynyl)silane (6224-91-5) + 1,6--1,5-hexadiyne (1578-53-6) + 3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In toluene for 1h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3-(Trimethylsilyl)propargyl isopropyl carbonate → trimethyl(prop-1-ynyl)silane (6224-91-5) + 1,6--1,5-hexadiyne (1578-53-6) + 3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In toluene for 1.5h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

prop-1-yne (74-99-7) + Me3SiHal → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
(i) EtMgBr, ether, (ii) Me3SiHal; Multistep reaction;

3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne (36551-06-1) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 9 h / 80 °C 2: pyridine / diethyl ether 3: Pd(PPh3)4 / toluene / 1 h / Heating View Scheme
Multi-step reaction with 3 steps 1: ethanol / 9 h / 80 °C 2: pyridine / diethyl ether 3: Pd(PPh3)4 / toluene / 1.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: ethanol / 9 h / 80 °C 2: pyridine / diethyl ether 3: Pd(PPh3)4 / toluene / 2 h / Heating View Scheme

3-trimethylsilyl-2-propyn-1-ol (5272-36-6) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / diethyl ether 2: Pd(PPh3)4 / toluene / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine / diethyl ether 2: Pd(PPh3)4 / toluene / 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine / diethyl ether 2: Pd(PPh3)4 / toluene / 2 h / Heating View Scheme

Bis(trimethylsilyl)ethyne (14630-40-1) + pentacarbonyl<(cyclopropyl)methoxymethylene>chromium → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / AlCl3 / CH2Cl2 / 12 h / Ambient temperature 2: tetrahydrofuran / 1.) -78 deg C; 2.) up to RT View Scheme

RuCo2(CO)9(μ3-C(Me)SiMe3) (124127-77-1) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
With I2 In tetrachloromethane to RuCo-compd. I2 added; (1)H-NMR;

trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane (129217-85-2) → trimethyl(prop-1-ynyl)silane (6224-91-5) + allenyltrimethylsilane (14657-22-8)

Conditions	Yield
With ethanol In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;

C10H19BNO2Si(1-)*H(1+) → trimethyl(prop-1-ynyl)silane (6224-91-5) + allenyltrimethylsilane (14657-22-8)

Conditions	Yield
With water In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;

trimethyl(prop-1-ynyl)silane (6224-91-5) + 3,4-di-O-acetyl-D-xylal (3152-43-0) → Acetic acid (3S,6R)-6-prop-1-ynyl-3,6-dihydro-2H-pyran-3-yl ester

Conditions	Yield
With titanium tetrachloride In dichloromethane at -40 - -15℃; for 2h;	99%

trimethyl(prop-1-ynyl)silane (6224-91-5) + 2-morpholin-4-yl-benzo[d][1,3]oxazin-4-one (23494-28-2) → 2-methyl-1-(morpholine-4-carbonyl)-3-(trimethylsilyl)quinolin-4(1H)-one (1333318-67-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); tributylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 24h; Inert atmosphere;	99%

trimethyl(prop-1-ynyl)silane (6224-91-5) + (R,E)-8-bromo-3,7-dimethyloct-6-en-1-yl benzoate → (R,E)-3,7-dimethyl-11-(trimethylsilyl)undec-6-en-10-yn-1-ol

Conditions	Yield
Stage #1: trimethyl(prop-1-ynyl)silane With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere; Stage #2: (R,E)-8-bromo-3,7-dimethyloct-6-en-1-yl benzoate In tetrahydrofuran; hexane at -20 - 0℃; for 12h; Inert atmosphere;	99%

trimethyl(prop-1-ynyl)silane (6224-91-5) + 2-iodophenylamine (615-43-0) → 2-trimethylsilyl-3-methyl-1H-indole (135189-98-9)

Conditions	Yield
With palladium diacetate; tetrabutyl-ammonium chloride; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 12h;	98%
With palladium diacetate; tetrabutyl-ammonium chloride; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 24h;	98%
Stage #1: 2-iodophenylamine With tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trimethyl(prop-1-ynyl)silane In N,N-dimethyl-formamide at 100℃; for 22h; Inert atmosphere; regioselective reaction;	91%

trimethyl(prop-1-ynyl)silane (6224-91-5) → trimethylpropylsilane (3510-70-1) + 1-(trimethylsilyl)-1-propene (17680-01-2)

Conditions	Yield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;	A n/a B 98%

trimethyl(prop-1-ynyl)silane (6224-91-5) → 1-(trimethylsilyl)-1-propene (17680-01-2)

Conditions	Yield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760.051 Torr;	98%
With diisobutylaluminium hydride In diethyl ether Inert atmosphere;
With tri-n-butyl-tin hydride In tetrahydrofuran Inert atmosphere;

trimethyl(prop-1-ynyl)silane (6224-91-5) → 1-Oxo-1-(trimethylsilyl)-2-propanone (80594-34-9)

Conditions	Yield
With [1,4,7-Me3-1,4,7-triazacyclononane(CF3CO2)RuIVO2]ClO4; trifluoroacetic acid In acetonitrile at 20℃; for 5h;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + isoprene (78-79-5) → (2,4-dimethylcyclohexa-1,4-dienyl)trimethylsilane (1309761-62-3)

Conditions	Yield
With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane at 20℃; Diels-Alder reaction; Inert atmosphere; regioselective reaction;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + 1-Bromo-3-iodobenzene (591-18-4) → 1-bromo-3-(prop-1-yn-1-yl)benzene (66952-36-1)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Schlenk technique; Inert atmosphere;	98%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrafluoroammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Inert atmosphere;	86%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrafluoroammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Inert atmosphere;	86%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrafluoroammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Inert atmosphere;	86%
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 20℃; Inert atmosphere;	80%

trimethyl(prop-1-ynyl)silane (6224-91-5) + 3--2-methylprop-1-ene (91230-06-7) → tert-butyl ((1E,4E)-2,4-dimethyl-5-(trimethylsilyl)penta-1,4-dien-1-yl)carbamate

Conditions	Yield
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In acetone at 20 - 80℃; Inert atmosphere; stereoselective reaction;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + 1,1'-[ethyne-1,2-diylbis(4,1-phenylene)]diethanone (29619-42-9) → 4'-(2-trimethylsilylethynyl)acetophenone (75883-03-3)

Conditions	Yield
With [(Ph3SiO)3Mo≡CC6H4OMe] In toluene at 20℃; for 2h; Inert atmosphere; Molecular sieve;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + N-(quinolin-8-yl)-2-methylacrylamide (1616877-82-7) → 3,6-dimethyl-5-trimethylsilyl-1-(quinolin-8-yl)pyridin-2(1H)-one

Conditions	Yield
Stage #1: trimethyl(prop-1-ynyl)silane; N-(quinolin-8-yl)-2-methylacrylamide With 1,2-Dichloropropane; ZnBr2*C6H16N2; (trimethylsilyl)methylmagnesium chloride; cis-1,2-bis-(diphenylphosphino)ethene In tetrahydrofuran at 20℃; Schlenk technique; Stage #2: With iron(III)-acetylacetonate In tetrahydrofuran at 40℃; for 20h; Reagent/catalyst; Schlenk technique;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester (232276-45-8) → C20H17Cl2NO3

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 24h;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + dimethyl(ethoxy)silane (14857-34-2) → C10H24OSi2

Conditions	Yield
With cross-linked polysiloxane stabilized platinum nanoparticles (Pt-Nano) In benzene at 20℃; for 10h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + dimethylmonochlorosilane (1066-35-9) → C8H19ClSi2

Conditions	Yield
With cross-linked polysiloxane stabilized platinum nanoparticles (Pt-Nano) In benzene at 20℃; for 10h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + ethyldichlorosilane (1789-58-8) → C8H18Cl2Si2

Conditions	Yield
With cross-linked polysiloxane stabilized platinum nanoparticles (Pt-Nano) In benzene at 20℃; for 10h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

trimethyl(prop-1-ynyl)silane (6224-91-5) + Triethoxysilane (998-30-1) → (E)-triethoxy(1-(trimethylsilyl)prop-1-en-2-yl)silane

Conditions	Yield
With cross-linked polysiloxane stabilized platinum nanoparticles (Pt-Nano) In benzene at 20℃; for 10h; Inert atmosphere; Schlenk technique; regioselective reaction;	97%
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In dichloromethane at 20℃; for 24h; Inert atmosphere; stereoselective reaction;	88%

Upstream product

• 2857-97-8 trimethylsilyl bromide 
• 16466-97-0 1-propynylmagnesium bromide 
• 75-77-4 chloro-trimethyl-silane 
• 557-93-7 2-bromoprop-1-ene 
• 61668-36-8 bromo-2 trimethylsilyloxy-1 propene-1 
• 78012-45-0 [3-(trimethylsilyl)prop-2-yn-1-yl]magnesium bromide 
• 83268-94-4 C₁₀H₂₆OSi₃ 
• 83268-92-2 C₁₀H₂₆OSi₃ 
• 141862-01-3 methyl 3-(trimethylsilyl)prop-2-ynyl carbonate 
• 5272-36-6 3-trimethylsilyl-2-propyn-1-ol 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 124127-77-1 RuCo2(CO)9(μ3-C(Me)SiMe3) 
• 100-61-8 N-methylaniline 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 21752-80-7 1,3-bis(trimethylsilyl)propyne 
• 109863-03-8 Dicyclohexyl-((E)-1-trimethylsilanyl-propenyl)-borane 
• 40277-01-8 1-(trimethylsilyl)-4-phenyl-1-butyne 
• 109-09-1 2-chloropyridine 
• 40925-52-8 2-(prop-1-yn-1-yl)pyridine 
• 372-48-5 2-fluoropyridine 
• 125358-15-8 bis(1-propynyl)cyclopropenone 
• 57266-90-7 (Z)-1-(trimethylsilyl)-1-phenyl-1-propene 
• 110598-48-6 [(Z)-1-(4-Methoxy-phenyl)-propenyl]-trimethyl-silane 
• 117924-34-2 1,4-bis(trimethylsilyl)-2,3-dimethyl-(1E,3E)-butadiene 
• 144675-71-8 C₁₉H₂₇NO₂ 
• 144675-67-2 C₂₅H₃₉NO₂Si 
• 142039-46-1 2-benzoyl-5-methyl-4-propyl-6-(trimethylsilyl)phenol 
• 110598-41-9 [(E)-2-(4-Methoxy-phenyl)-propenyl]-trimethyl-silane 

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