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1-(Trimethylsilyl)-1-propyne, also known as 1-Trimethylsilyl-1-propyne, is an alkynyl silane derivative characterized by the presence of a trimethylsilyl group attached to a propyne backbone. 1-(Trimethylsilyl)-1-propyne exhibits unique chemical properties due to the combination of the alkyne and silane functionalities, making it a versatile building block in organic synthesis.

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  • 6224-91-5 Structure
  • Basic information

    1. Product Name: 1-(Trimethylsilyl)-1-propyne
    2. 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
    3. CAS NO:6224-91-5
    4. Molecular Formula: C6H12Si
    5. Molecular Weight: 112.24
    6. EINECS: 228-314-5
    7. 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)
    8. Mol File: 6224-91-5.mol
  • Chemical Properties

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

    1. Hazard Codes: F,Xi
    2. Statements: 11-36/37/38
    3. Safety Statements: 16-26-36-37/39
    4. RIDADR: UN 1993 3/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. TSCA: Yes
    8. HazardClass: 3
    9. PackingGroup: II
    10. Hazardous Substances Data: 6224-91-5(Hazardous Substances Data)

6224-91-5 Usage

Uses

Used in Organic Synthesis:
1-(Trimethylsilyl)-1-propyne is used as a synthetic intermediate for the preparation of various alkynyl silane derivatives. Its unique structure allows for a wide range of applications in organic chemistry, including the formation of new carbon-carbon and carbon-heteroatom bonds.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, 1-(Trimethylsilyl)-1-propyne is used as a key building block for the synthesis of complex organic molecules, including potential drug candidates. Its ability to participate in palladium-catalyzed and rhodium-catalyzed reactions enables the efficient construction of diverse molecular frameworks.
Used in the Preparation of Highly Substituted Indenes:
1-(Trimethylsilyl)-1-propyne is employed in the synthesis of highly substituted indenes through palladium-catalyzed carboannulation. This reaction provides a convenient method for the construction of indene cores, which are prevalent in various natural products and pharmaceutical agents.
Used in the Preparation of Indenones:
1-(Trimethylsilyl)-1-propyne also plays a crucial role in the preparation of indenones through a rhodium-catalyzed reaction with 2-bromophenylboronic acids. Indenones are valuable synthetic intermediates and have been used in the synthesis of a variety of biologically active compounds.
Overall, 1-(Trimethylsilyl)-1-propyne is a valuable and versatile compound in the field of organic synthesis, with applications spanning across various industries, including pharmaceuticals and materials science. Its unique reactivity and the ability to participate in various catalytic reactions make it an essential component in the development of new synthetic methodologies and the construction of complex molecular architectures.

Check Digit Verification of cas no

The CAS Registry Mumber 6224-91-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,2,2 and 4 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 6224-91:
(6*6)+(5*2)+(4*2)+(3*4)+(2*9)+(1*1)=85
85 % 10 = 5
So 6224-91-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H12Si/c1-5-6-7(2,3)4/h1-4H3

6224-91-5 Well-known Company Product Price

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  • TCI America

  • (T1123)  1-(Trimethylsilyl)-1-propyne  >98.0%(GC)

  • 6224-91-5

  • 5mL

  • 590.00CNY

  • Detail
  • TCI America

  • (T1123)  1-(Trimethylsilyl)-1-propyne  >98.0%(GC)

  • 6224-91-5

  • 25mL

  • 1,890.00CNY

  • Detail
  • TCI America

  • (T1123)  1-(Trimethylsilyl)-1-propyne  >98.0%(GC)

  • 6224-91-5

  • 100mL

  • 4,900.00CNY

  • Detail
  • Alfa Aesar

  • (B24875)  1-Trimethylsilyl-1-propyne, 98%   

  • 6224-91-5

  • 1g

  • 370.0CNY

  • Detail
  • Alfa Aesar

  • (B24875)  1-Trimethylsilyl-1-propyne, 98%   

  • 6224-91-5

  • 5g

  • 1044.0CNY

  • Detail
  • Alfa Aesar

  • (B24875)  1-Trimethylsilyl-1-propyne, 98%   

  • 6224-91-5

  • 25g

  • 3202.0CNY

  • Detail
  • Aldrich

  • (244481)  1-(Trimethylsilyl)propyne  99%

  • 6224-91-5

  • 244481-5G

  • 1,422.72CNY

  • Detail
  • Aldrich

  • (244481)  1-(Trimethylsilyl)propyne  99%

  • 6224-91-5

  • 244481-25G

  • 5,266.17CNY

  • Detail

6224-91-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(Trimethylsilyl)-1-propyne

1.2 Other means of identification

Product number -
Other names trimethyl(prop-1-ynyl)silane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6224-91-5 SDS

6224-91-5Synthetic route

prop-1-yne
74-99-7

prop-1-yne

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
(Me2SiCp''2UBu)2O*2THF In tetrahydrofuran at 66℃; for 44h;100%
C10H26OSi3
83268-94-4

C10H26OSi3

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

trimethylsilan
993-07-7

trimethylsilan

C

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

D

ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

Conditions
ConditionsYield
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

[3-(trimethylsilyl)prop-2-yn-1-yl]magnesium bromide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 0 - 5℃;86%
trimethyl(prop-1-ynyl)silane

trimethyl(prop-1-ynyl)silane

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

trimethylsilylacetylene

methyl iodide
74-88-4

methyl iodide

trimethyl(prop-1-ynyl)silane

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
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;

A

trimethyl(prop-1-ynyl)silane

trimethyl(prop-1-ynyl)silane

B

trimethylsilan

trimethylsilan

C

D

ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

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

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

trimethylsilan
993-07-7

trimethylsilan

C

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

D

ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

Conditions
ConditionsYield
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 (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;23%
trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

1-propynylmagnesium bromide
16466-97-0, 13254-27-8

1-propynylmagnesium bromide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1-propynyl lithium
4529-04-8

1-propynyl lithium

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
In diethyl ether
In diethylene glycol dimethyl ether
In diethyl ether for 30h; Heating; Yield given;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

propargyl bromide
106-96-7

propargyl bromide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
With magnesium In N,N,N,N,N,N-hexamethylphosphoric triamide at 100 - 110℃;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

prop-1-yne
74-99-7

prop-1-yne

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
(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

chloro-trimethyl-silane

2-bromoprop-1-ene
557-93-7

2-bromoprop-1-ene

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

2-(trimethylsilyl)propene
18163-07-0

2-(trimethylsilyl)propene

C

1,3-bis(trimethylsilyl)propyne
21752-80-7

1,3-bis(trimethylsilyl)propyne

D

1-propynyl lithium
4529-04-8

1-propynyl lithium

Conditions
ConditionsYield
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

chloro-trimethyl-silane

bromo-2 trimethylsilyloxy-1 propene-1
61668-36-8

bromo-2 trimethylsilyloxy-1 propene-1

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

(Z)-2-Trimethylsilanyl-1-trimethylsilanyloxy-propene
154581-92-7

(Z)-2-Trimethylsilanyl-1-trimethylsilanyloxy-propene

Conditions
ConditionsYield
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

prop-1-yne

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
(Me2SiCp''2UBu)2O*2THF In tetrahydrofuran at 66℃; for 44h;100%
C10H26OSi3
83268-94-4

C10H26OSi3

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

trimethylsilan
993-07-7

trimethylsilan

C

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

D

ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

Conditions
ConditionsYield
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

[3-(trimethylsilyl)prop-2-yn-1-yl]magnesium bromide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 0 - 5℃;86%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

sodium propynide
10486-71-2

sodium propynide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
In various solvent(s) at 100℃; for 3h;81.6%
trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

methyl iodide
74-88-4

methyl iodide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
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

2-cyclopropyl-2-methoxyhexamethyltrisilane

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

trimethylsilan
993-07-7

trimethylsilan

C

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

D

ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

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

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

trimethylsilan
993-07-7

trimethylsilan

C

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

D

ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

Conditions
ConditionsYield
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 (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;23%
trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

1-propynylmagnesium bromide
16466-97-0, 13254-27-8

1-propynylmagnesium bromide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1-propynyl lithium
4529-04-8

1-propynyl lithium

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
In diethyl ether
In diethylene glycol dimethyl ether
In diethyl ether for 30h; Heating; Yield given;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

propargyl bromide
106-96-7

propargyl bromide

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
With magnesium In N,N,N,N,N,N-hexamethylphosphoric triamide at 100 - 110℃;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

prop-1-yne
74-99-7

prop-1-yne

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
(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

chloro-trimethyl-silane

2-bromoprop-1-ene
557-93-7

2-bromoprop-1-ene

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

2-(trimethylsilyl)propene
18163-07-0

2-(trimethylsilyl)propene

C

1,3-bis(trimethylsilyl)propyne
21752-80-7

1,3-bis(trimethylsilyl)propyne

D

1-propynyl lithium
4529-04-8

1-propynyl lithium

Conditions
ConditionsYield
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

chloro-trimethyl-silane

bromo-2 trimethylsilyloxy-1 propene-1
61668-36-8

bromo-2 trimethylsilyloxy-1 propene-1

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

(Z)-2-Trimethylsilanyl-1-trimethylsilanyloxy-propene
154581-92-7

(Z)-2-Trimethylsilanyl-1-trimethylsilanyloxy-propene

Conditions
ConditionsYield
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

chloro-trimethyl-silane

((Z)-2-Bromo-1-methyl-vinyloxy)-trimethyl-silane

((Z)-2-Bromo-1-methyl-vinyloxy)-trimethyl-silane

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

(Z)-1-Trimethylsilanyl-2-trimethylsilanyloxy-propene

(Z)-1-Trimethylsilanyl-2-trimethylsilanyloxy-propene

Conditions
ConditionsYield
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

Bis(trimethylsilyl)thioketene

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

tetramethylcyclodisilthiane
7796-59-0

tetramethylcyclodisilthiane

C

Trimethylsilanyl-ethenethione

Trimethylsilanyl-ethenethione

D

Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

Conditions
ConditionsYield
at 768℃; flash vacuum pyrolysis;A 13 % Chromat.
B 4 % Chromat.
C 17 % Chromat.
D 17 % Chromat.
Bis(trimethylsilyl)thioketene
62827-97-8

Bis(trimethylsilyl)thioketene

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

tetramethylcyclodisilthiane
7796-59-0

tetramethylcyclodisilthiane

C

2,2,4,4-tetramethyl-2,4-disilathiethane

2,2,4,4-tetramethyl-2,4-disilathiethane

D

Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

Conditions
ConditionsYield
at 768℃; flash vacuum pyrolysis;A 13 % Chromat.
B 4 % Chromat.
C 8 % Chromat.
D 17 % Chromat.
Bis(trimethylsilyl)thioketene
62827-97-8

Bis(trimethylsilyl)thioketene

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

Trimethylsilanyl-ethenethione

Trimethylsilanyl-ethenethione

C

2,2,4,4-tetramethyl-2,4-disilathiethane

2,2,4,4-tetramethyl-2,4-disilathiethane

D

Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

Conditions
ConditionsYield
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

1-(Phenylsulfonyl)-2-(trimethylsilyl)acetylene

methyllithium
917-54-4

methyllithium

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

benzenesulfonic acid
98-11-3

benzenesulfonic acid

Conditions
ConditionsYield
In tetrahydrofuran 1.) -78 deg C; 2.) up to RT; Yields of byproduct given;
methyl 3-(trimethylsilyl)prop-2-ynyl carbonate
141862-01-3

methyl 3-(trimethylsilyl)prop-2-ynyl carbonate

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

1,6--1,5-hexadiyne
1578-53-6

1,6--1,5-hexadiyne

C

3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

Conditions
ConditionsYield
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

ethyl 3-(trimethylsilyl)prop-2-ynyl carbonate

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

1,6--1,5-hexadiyne
1578-53-6

1,6--1,5-hexadiyne

C

3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

Conditions
ConditionsYield
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

3-(Trimethylsilyl)propargyl isopropyl carbonate

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

1,6--1,5-hexadiyne
1578-53-6

1,6--1,5-hexadiyne

C

3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

3,6-Bis(trimethylsilyl)-1,2-hexadien-5-yne

Conditions
ConditionsYield
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

prop-1-yne

Me3SiHal

Me3SiHal

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
(i) EtMgBr, ether, (ii) Me3SiHal; Multistep reaction;
3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne
36551-06-1

3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
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

3-trimethylsilyl-2-propyn-1-ol

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
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

Bis(trimethylsilyl)ethyne

pentacarbonyl<(cyclopropyl)methoxymethylene>chromium

pentacarbonyl<(cyclopropyl)methoxymethylene>chromium

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
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

RuCo2(CO)9(μ3-C(Me)SiMe3)

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
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 (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

allenyltrimethylsilane
14657-22-8

allenyltrimethylsilane

Conditions
ConditionsYield
With ethanol In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;
C10H19BNO2Si(1-)*H(1+)

C10H19BNO2Si(1-)*H(1+)

A

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

B

allenyltrimethylsilane
14657-22-8

allenyltrimethylsilane

Conditions
ConditionsYield
With water In chloroform-d1 at 20℃; for 18h; Inert atmosphere; regioselective reaction;
trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

3,4-di-O-acetyl-D-xylal
3152-43-0

3,4-di-O-acetyl-D-xylal

Acetic acid (3S,6R)-6-prop-1-ynyl-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (3S,6R)-6-prop-1-ynyl-3,6-dihydro-2H-pyran-3-yl ester

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -40 - -15℃; for 2h;99%
trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

2-morpholin-4-yl-benzo[d][1,3]oxazin-4-one
23494-28-2

2-morpholin-4-yl-benzo[d][1,3]oxazin-4-one

2-methyl-1-(morpholine-4-carbonyl)-3-(trimethylsilyl)quinolin-4(1H)-one
1333318-67-4

2-methyl-1-(morpholine-4-carbonyl)-3-(trimethylsilyl)quinolin-4(1H)-one

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

(R,E)-8-bromo-3,7-dimethyloct-6-en-1-yl benzoate

(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

(R,E)-3,7-dimethyl-11-(trimethylsilyl)undec-6-en-10-yn-1-ol

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

2-iodophenylamine
615-43-0

2-iodophenylamine

2-trimethylsilyl-3-methyl-1H-indole
135189-98-9

2-trimethylsilyl-3-methyl-1H-indole

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

A

trimethylpropylsilane
3510-70-1

trimethylpropylsilane

B

1-(trimethylsilyl)-1-propene
17680-01-2

1-(trimethylsilyl)-1-propene

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

1-(trimethylsilyl)-1-propene
17680-01-2

1-(trimethylsilyl)-1-propene

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

1-Oxo-1-(trimethylsilyl)-2-propanone
80594-34-9

1-Oxo-1-(trimethylsilyl)-2-propanone

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

isoprene
78-79-5

isoprene

(2,4-dimethylcyclohexa-1,4-dienyl)trimethylsilane
1309761-62-3

(2,4-dimethylcyclohexa-1,4-dienyl)trimethylsilane

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

1-bromo-3-(prop-1-yn-1-yl)benzene
66952-36-1

1-bromo-3-(prop-1-yn-1-yl)benzene

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

3--2-methylprop-1-ene
91230-06-7

3--2-methylprop-1-ene

tert-butyl ((1E,4E)-2,4-dimethyl-5-(trimethylsilyl)penta-1,4-dien-1-yl)carbamate

tert-butyl ((1E,4E)-2,4-dimethyl-5-(trimethylsilyl)penta-1,4-dien-1-yl)carbamate

Conditions
ConditionsYield
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In acetone at 20 - 80℃; Inert atmosphere; stereoselective reaction;98%
trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

1,1'-[ethyne-1,2-diylbis(4,1-phenylene)]diethanone
29619-42-9

1,1'-[ethyne-1,2-diylbis(4,1-phenylene)]diethanone

4'-(2-trimethylsilylethynyl)acetophenone
75883-03-3

4'-(2-trimethylsilylethynyl)acetophenone

Conditions
ConditionsYield
With [(Ph3SiO)3Mo≡CC6H4OMe] In toluene at 20℃; for 2h; Inert atmosphere; Molecular sieve;98%
trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

N-(quinolin-8-yl)-2-methylacrylamide
1616877-82-7

N-(quinolin-8-yl)-2-methylacrylamide

3,6-dimethyl-5-trimethylsilyl-1-(quinolin-8-yl)pyridin-2(1H)-one

3,6-dimethyl-5-trimethylsilyl-1-(quinolin-8-yl)pyridin-2(1H)-one

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester
232276-45-8

N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester

C20H17Cl2NO3

C20H17Cl2NO3

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

dimethyl(ethoxy)silane
14857-34-2

dimethyl(ethoxy)silane

C10H24OSi2

C10H24OSi2

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

C8H19ClSi2

C8H19ClSi2

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

ethyldichlorosilane
1789-58-8

ethyldichlorosilane

C8H18Cl2Si2

C8H18Cl2Si2

Conditions
ConditionsYield
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

trimethyl(prop-1-ynyl)silane

Triethoxysilane
998-30-1

Triethoxysilane

(E)-triethoxy(1-(trimethylsilyl)prop-1-en-2-yl)silane

(E)-triethoxy(1-(trimethylsilyl)prop-1-en-2-yl)silane

Conditions
ConditionsYield
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%

6224-91-5Relevant articles and documents

γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation

Jiang, Bo,Jia, Jingwen,Sun, Yufei,Wang, Yichun,Zeng, Jing,Bu, Xiubin,Shi, Liangliang,Sun, Xiaoying,Yang, Xiaobo

supporting information, p. 13389 - 13392 (2020/11/10)

A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is

Propargylic C(sp3)-H Bond Activation for Preparing η3-Propargyl/Allenyl Complexes of Yttrium

Nagae, Haruki,Kundu, Abhinanda,Tsurugi, Hayato,Mashima, Kazushi

, p. 3061 - 3067 (2017/09/05)

Propargylic C(sp3) - H bond activation of 1-substituted-1-propynes, such as 1-trimethylsilyl-1-propyne, 2-hexyne, and 1-phenyl-1-propyne, was achieved by treatment with an alkylyttrium complex 8 bearing an ene-diamido ligand to give the corresponding (η3-propargyl/allenyl)yttrium complexes 7a-c. A unique delocalized η3-propargyl/allenyl structure of these three complexes was revealed by NMR spectroscopy and X-ray single crystal analyses. To elucidate the reactivity of the η3-propargyl/allenyl unit of complexes 7a-c, we conducted two reactions with N-methylaniline and N,N′-dicyclohexylcarbodiimine. For protonation by N-methylaniline, we found that the product distribution of monosubstituted internal alkynes and allenes depended on the substituent on the η3-propargyl/allenyl moiety: 7a and 7b afforded the corresponding internal alkynes as the major products, whereas the major protonation product of 7c was phenylallene. For the insertion of N,N′-dicyclohexylcarbodiimine, complex 7a selectively yielded η3-{N,N′-dicyclohexyl-2-(3-trimethylsilylpropargyl)amidinate}yttrium 12a, while complex 7c produced η3-{N,N′-dicyclohexyl-2-(1-phenylallenyl)amidinate}yttrium complex 13c, though complex 7b gave a mixture of η3-{N,N′-dicyclohexyl-2-(3-normalpropylpropargyl)amidinate}yttrium complex 12b and η3-{N,N′-dicyclohexyl-2-(1-normalpropylallenyl)amidinate}yttrium 13b in an 83:17 ratio. On the basis of the product distributions in these two-types of reactions, (η3-propargyl/allenyl)yttrium complexes were shifted into preferentially favorable η1-allenyl species or η1-propargyl species depending on the substituents prior to the reaction with electrophiles via a four-membered cyclic mechanism.

Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of: O -methoxycarbonylphenylboronic acid with alkynes

Ueda, Mitsuhiro,Ueno, Tamami,Suyama, Yuki,Ryu, Ilhyong

supporting information, p. 13237 - 13240 (2016/11/17)

Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones in good yields. Excellent regioselectivities were observed, when silyl aryl alkynes were used. The intermediate 3-silyl-2-aryl-substituted indenones were converted to 2,3-diaryl indenones by a three-step protocol involving C-Si bromination and Suzuki-Miyaura coupling reaction.

Preparative synthesis via continuous flow of 4,4,5,5-tetramethyl-2-(3- trimethylsilyl-2-propynyl)-1,3,2-dioxaborolane: A general propargylation reagent

Fandrick, Daniel R.,Roschangar, Frank,Kim, Chunyoung,Hahm, Byoung J.,Cha, Myoung H.,Kim, Hyoun Y.,Yoo, Gyesang,Kim, Taeyun,Reeves, Jonathan T.,Song, Jinhua J.,Tan, Zhulin,Qu, Bo,Haddad, Nizar,Shen, Sherry,Grinberg, Nelu,Lee, Heewon,Yee, Nathan,Senanayake, Chris H.

supporting information; scheme or table, p. 1131 - 1140 (2012/08/13)

A scalable process for the preparation of 4,4,5,5-tetramethyl-2-(3- trimethylsilyl-2-propynyl)-1,3,2-dioxaborolane from trimethylsilylpropyne, isopropyl pinacol borate, and n-butyllithium is described. Problems associated with implementing a typical aqueous workup and batch process into production due to borolane ate equilibration and protonolysis are presented. To address these issues, a continuous-flow and distillation process was developed which efficiently produced 297 kg of the key propargylation reagent.

Regioselective allene synthesis and propargylations with propargyl diethanolamine boronates

Fandrick, Daniel R.,Reeves, Jonathan T.,Tan, Zhulin,Lee, Heewon,Song, Jinhua J.,Yee, Nathan K.,Senanayake, Chris H.

scheme or table, p. 5458 - 5461 (2010/03/01)

"Chemical Equation Presented" The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded wi

Unique σ-bond metathesis of silylalkynes promoted by an ansa-dimethylsilyl and oxo-bridged uranium metallocene

Wang, Jiaxi,Gurevich, Ylia,Botoshansky, Mark,Eisen, Moris S.

, p. 9350 - 9351 (2007/10/03)

The tetrachloride salt of uranium reacts with 1 equiv of the lithium ligand Li2[(C5Me4)2SiMe2] in DME to form the complex [η5-(C5Me4)2SiMe2]UCl2·2LiCl·2DME (1), which undergoes a rapid hydrolysis in toluene to yield the dimeric bridged monochloride, monooxide complex [{[η5-(C5Me4)2SiMe2]UCl}2(μ-O)(μ-Cl)?Li?1/2DME]2 (2). Metathesis of 2 with BuLi in DME gives the mono-bridged dibutyl complex {[η5-(C5Me4)2SiMe2]UBu}2(μ-O) (3). Complex 2 was characterized by solid-state X-ray analysis. Complex 3 was found to be an active catalyst for the disproportionation metathesis of TMSC≡CH (TMS = SiMe3) and the cross-metathesis of TMSC≡CH or TMSC≡CTMS with various terminal alkynes. The metathesis of TMSC≡CH gives TMSC≡CTMS and HC≡CH, whereas the cross-metathesis of TMSC≡CH or TMSC≡CTMS with terminal alkynes (RC≡CH) yields TMSC≡CTMS, TMSC≡CR, and HC≡CH. In addition, TMSC≡CCH3 also was found to react with tBuC≡CH, yielding TMSC≡CBut and CH3C≡CH. A plausible mechanism for the catalytic process is presented. Copyright

Trimethylsilylated 1,4-Diborinanes and 1,3-Diborolanes - Formation, Isomer Separation, and Characterisation

Koester, Roland,Seidel, Guenter,Lutz, Frank,Krueger, Carl,Kehr, Gerald,Wrackmeyer, Bernd

, p. 813 - 820 (2007/10/02)

Me3SiCCH (A) reacts with excess (Et2BH)2 via the compounds 1, 1' and 2, 2' to yield a mixture of four regio- and stereoisomeric 1,4-diethyl-2,5(6)-bis(trimethylsilyl)-1,4-diborinanes (3a-d) and minor amounts of 1,3-diethyl-2-methyl-trans-2,5-bis(trimethylsilyl)-1,3-diborolane(4a).The 2,5-ee-(Me3Si)2 compound 3d is isolated as the adduct 3d(Pic)2 (X-ray structure analysis), from which pure 3d is obtained with Et2O-BF3. 3d and Me3P form equilibria of the 1:1 and 1:2 addition compounds 3d(Me3P)n (n = 1,2) at room temperature.Me3SiCCMe (B) reacts with (Et2BH)2 via 5 to give 6 - 10, and Me3SiCCSiMe3 (C) reacts with (Et2BH)2 to form the ring compounds 12 and 13 via the presumably threo/erythro mixture of 11a and b. - Key Words: Hydroboration of 1-alkinylsilanes / Ethyldiboranes(6) / Alkyl substituent exchanges, >BH-borane-catalysed / 1,4-Diborinanes, trimethylsilyl-substituted, isomers of / Lewisbase - 1,4-Diborinanes

A new route to α,β-unsaturated aldehydes using the condensation of trimethylsilyl β-trimethylsilyl enol ethers with aldehydes

Duhamel, Lucette

, p. 7745 - 7748 (2007/10/02)

β-Trimethylsilyl enol ethers 1 (Z) obtained from β-bromoenolethers 2 were condensed with aliphatic and aromatic aldehydes in the presence of a catalytic quantity of trimethylsilyl triflate leading to ethylenic aldehydes 3 (E) with good yields (79-90%).

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