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1066-54-2 Usage

Silican-protected group

Trimethylsilylacetylene is a silican-protected group, also known as trimethylethynylsilane, trimethylethynyl silicon and ethynyltrimethylsilane. It is a colorless transparent liquid at room temperature. It could be used to synthesize parazole by the addition of 1,3-bipolar ring of acetylene diazide. It is also the substrate of nickel catalyzed reaction and benzonitrile coupling reaction.

Application

Common intermediate for asymmetric synthesis Silica reagent

Chemical Properties

CLEAR COLORLESS LIQUID

Physical properties

bp 53 °C; d 0.695 g cm?3.

Uses

(Trimethylsilyl)acetylene is used in the preparation of trimethylsilanyl-propiolic acid ethyl ester by reacting with carbonochloridic acid ethyl ester as well as in the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides. It is used as a nucleophile in Friedel-Crafts type acylations and alkylations reactions, as a ligand in organometallic chemistry and an useful reagent in cycloaddition reactions. It acts as a precursor to lithium trimethylsilylacetylide It finds application in the synthesis of (±)-estrone.

Uses

Ethynyltrimethylsilane was used in: ? microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes

Uses

Trimethylsilylacetylene is a valuable reagent used in ethynylation by palladium(0)-catalyzed coupling/condensation with aryl and vinyl halides and triflates, or by nucleophilic attack of the corresponding acetylide on electrophilic centers; reacts with alkyl iodides, tin hydrides,6 and dichloroketene in a regioselective and stereoselective manner, participating in the following synthesis reactions: Ethynylations, Palladium(0)-Catalyzed Coupling Reactions,Reaction of Trimethylsilylacetylides with Electrophiles, Radical-Initiated and Transition Metal-Catalyzed Additions, Cycloaddition Reactions, Ethynylations, Cycloaddition Reactions, Further Transformations etc.

General Description

Laser-induced polymerization of gaseous ethynyltrimethylsilane was used for efficient chemical vapour deposition of polycarbosilane films. Ethynyltrimethylsilane acts as substrate for nickel-catalyzed cross-coupling with benzonitriles.

Purification Methods

Distil it through an efficient column. The IR has bands at max 2041 (CC) and 3289 (C-H) cm-1. [Kr.hnke & Goss Chem Ber 92 30 1959, Beilstein 4 IV 3937.]
InChI:InChI=1/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3

1066-54-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (T1239)  Trimethylsilylacetylene  >98.0%(GC) 1066-54-2 5mL 120.00CNY Detail
TCI America (T1239)  Trimethylsilylacetylene  >98.0%(GC) 1066-54-2 25mL 390.00CNY Detail
TCI America (T1239)  Trimethylsilylacetylene  >98.0%(GC) 1066-54-2 250mL 2,990.00CNY Detail
Alfa Aesar (A12856)  (Trimethylsilyl)acetylene, 98%    1066-54-2 5g 409.0CNY Detail
Alfa Aesar (A12856)  (Trimethylsilyl)acetylene, 98%    1066-54-2 25g 1820.0CNY Detail
Alfa Aesar (A12856)  (Trimethylsilyl)acetylene, 98%    1066-54-2 100g 6457.0CNY Detail
Aldrich (218170)  Ethynyltrimethylsilane  98% 1066-54-2 218170-1G 306.54CNY Detail
Aldrich (218170)  Ethynyltrimethylsilane  98% 1066-54-2 218170-5G 510.12CNY Detail
Aldrich (218170)  Ethynyltrimethylsilane  98% 1066-54-2 218170-25G 2,149.29CNY Detail
Aldrich (218170)  Ethynyltrimethylsilane  98% 1066-54-2 218170-100G 7,154.55CNY Detail

1066-54-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethynyltrimethylsilane

1.2 Other means of identification

Product number -
Other names TriMethylsilylacetylene

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:1066-54-2 SDS

1066-54-2Synthetic route

4-bromo-3,3-dimethyl-1-(trimethylsilyl)-1-butyne

4-bromo-3,3-dimethyl-1-(trimethylsilyl)-1-butyne

A

isobutene
115-11-7

isobutene

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With diisobutylaluminium hydride In pentane at 25℃; for 0.5h;A n/a
B 100%
1-bromo-1-(trimethylsilyl)ethene
13683-41-5

1-bromo-1-(trimethylsilyl)ethene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 40 - 110℃; for 2h; Solvent;94%
tetrakis(triphenylphosphine) palladium(0)
tetrakis(triphenylphosphine) palladium(0) Mechanism;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

lithium acetylide
70277-75-7

lithium acetylide

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; lithium acetylide; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 0℃; for 2h;
Stage #2: With water In tetrahydrofuran at 20℃;
91.4%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

sodium acetylide
1066-26-8

sodium acetylide

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With diethylene glycol diethyl ester at 50℃; for 2h;80%
In tetrahydrofuran; xylene for 24h;75%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

acetylene
74-86-2

acetylene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
Stage #1: acetylene With ethidium Bromide; magnesium; ethylene dibromide at 5 - 10℃; Grignard reaction;
Stage #2: chloro-trimethyl-silane at 15 - 35℃; for 1h; Substitution;
80%
Stage #1: acetylene With butyl magnesium bromide In tetrahydrofuran at -5 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 15 - 20℃; for 1h; Inert atmosphere; Reflux;
75%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 25℃; for 10h;
With n-butyllithium 1.) THF, hexane, -78 deg C, 10 min, 2.) -78 deg C, 2.5 h; room temp., 2 h; Multistep reaction;
With sodium 1.) anisole, 110 deg C, 2.) 24 h; Yield given. Multistep reaction;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

sodium acetylide
1066-26-8

sodium acetylide

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;77%
bis(trimethylsilyl)ketene
19061-00-8

bis(trimethylsilyl)ketene

A

Hexamethylcyclotrisiloxane
541-05-9

Hexamethylcyclotrisiloxane

B

octamethylcyclotetrasiloxane
556-67-2

octamethylcyclotetrasiloxane

C

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
at 700℃; flash vacuum pyrolysis;A 22%
B 16%
C 76%
(trimethylsilyl)(dimethylsilyl)ketene
98991-82-3

(trimethylsilyl)(dimethylsilyl)ketene

A

Hexamethylcyclotrisiloxane
541-05-9

Hexamethylcyclotrisiloxane

B

octamethylcyclotetrasiloxane
556-67-2

octamethylcyclotetrasiloxane

C

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
at 700℃;A 22%
B 16%
C 76%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

triethylethynylstannane
994-39-8

triethylethynylstannane

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
In acetonitrile at 100℃; for 1h;74%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

triethylethynylstannane
994-39-8

triethylethynylstannane

A

triethyltin iodide
2943-86-4

triethyltin iodide

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
In acetonitrile mixt. heating for 1 h at 100°C; solvent washing out (water), Si-compd. isolation (vac. distn.);A n/a
B 74%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

sodium acetylide
1066-26-8

sodium acetylide

A

acetylene
74-86-2

acetylene

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

C

Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

Conditions
ConditionsYield
In various solvent(s) at 100℃;A 0.232 mol
B 29%
C 50%
lithium trimethylsilylacetylenide
54655-07-1

lithium trimethylsilylacetylenide

A

1,4-bis(trimethylsilyl)-1,3-butadiyne
4526-07-2

1,4-bis(trimethylsilyl)-1,3-butadiyne

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With dinitrogen tetraoxide In diethyl ether at -78℃; for 1h; Product distribution;A 44%
B 25%
C34H42N2Si3

C34H42N2Si3

trifluoroacetic acid
76-05-1

trifluoroacetic acid

A

C28H24F6N2O4Si

C28H24F6N2O4Si

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
In chloroform for 4h; Heating; Yields of byproduct given;A 41%
B n/a
4-Phenyl-1-butyne
16520-62-0

4-Phenyl-1-butyne

(acetato-κ2O,O')(2,6-bis((3aS,8aR)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)-4-nitrophenyl-κ3N,C1,N’)(trimethylsilylethynyl)rhodium(III)

(acetato-κ2O,O')(2,6-bis((3aS,8aR)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)-4-nitrophenyl-κ3N,C1,N’)(trimethylsilylethynyl)rhodium(III)

A

C38H30N3O6Rh

C38H30N3O6Rh

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
In (2)H8-toluene at 20℃; for 1.25h; Equilibrium constant; Inert atmosphere;A 38%
B n/a
Dimethyl-oxypropyl-ethinyl-silan
52673-44-6

Dimethyl-oxypropyl-ethinyl-silan

A

1,3-diethynyltetramethyldisiloxane
4180-02-3

1,3-diethynyltetramethyldisiloxane

B

Methyl-di-oxypropyl-ethinyl-silan
57914-14-4

Methyl-di-oxypropyl-ethinyl-silan

C

Tri-oxypropyl-ethinyl-silan
57914-15-5

Tri-oxypropyl-ethinyl-silan

D

1-({(E)-2-[(E)-2-(Dimethyl-propoxy-silanyl)-vinylsulfanyl]-vinyl}-dimethyl-silanyloxy)-propane

1-({(E)-2-[(E)-2-(Dimethyl-propoxy-silanyl)-vinylsulfanyl]-vinyl}-dimethyl-silanyloxy)-propane

E

1-({2-{2-(Dimethyl-propoxy-silanyl)-2-[(E)-2-(dimethyl-propoxy-silanyl)-vinylsulfanyl]-ethylsulfanyl}-1-[(E)-2-(dimethyl-propoxy-silanyl)-vinylsulfanyl]-ethyl}-dimethyl-silanyloxy)-propane

1-({2-{2-(Dimethyl-propoxy-silanyl)-2-[(E)-2-(dimethyl-propoxy-silanyl)-vinylsulfanyl]-ethylsulfanyl}-1-[(E)-2-(dimethyl-propoxy-silanyl)-vinylsulfanyl]-ethyl}-dimethyl-silanyloxy)-propane

F

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With hydrogen sulfide for 8h; Product distribution; Irradiation; var. time, traces of HCl and H2O;A n/a
B n/a
C n/a
D 30.1%
E n/a
F n/a
dimethylethoxyethynylsilane
32957-37-2

dimethylethoxyethynylsilane

A

triethoxyethynylsilane
5700-28-7

triethoxyethynylsilane

B

1,3-diethynyltetramethyldisiloxane
4180-02-3

1,3-diethynyltetramethyldisiloxane

C

(E)-1-(Ethoxy-dimethyl-silanyl)-2-[(E)-2-(ethoxy-dimethyl-silanyl)-vinylsulfanyl]-ethene

(E)-1-(Ethoxy-dimethyl-silanyl)-2-[(E)-2-(ethoxy-dimethyl-silanyl)-vinylsulfanyl]-ethene

D

(E)-1-(Ethoxy-dimethyl-silanyl)-2-(1-(ethoxy-dimethyl-silanyl)-2-{2-(ethoxy-dimethyl-silanyl)-2-[(E)-2-(ethoxy-dimethyl-silanyl)-vinylsulfanyl]-ethylsulfanyl}-ethylsulfanyl)-ethene

(E)-1-(Ethoxy-dimethyl-silanyl)-2-(1-(ethoxy-dimethyl-silanyl)-2-{2-(ethoxy-dimethyl-silanyl)-2-[(E)-2-(ethoxy-dimethyl-silanyl)-vinylsulfanyl]-ethylsulfanyl}-ethylsulfanyl)-ethene

E

diethoxyethynylmethylsilane
103084-89-5

diethoxyethynylmethylsilane

F

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With hydrogen sulfide for 4h; Product distribution; Irradiation; var. time, traces of HCl and H2O;A n/a
B n/a
C 13.7%
D n/a
E n/a
F n/a
Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With iron(III) chloride In octane at 25℃; Product distribution;5.5%
chloroethynyl-trimethyl-silane
7652-06-4

chloroethynyl-trimethyl-silane

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With phenyllithium
Bis(trimethylsilyl)thioketene
62827-97-8

Bis(trimethylsilyl)thioketene

A

tetramethylcyclodisilthiane
7796-59-0

tetramethylcyclodisilthiane

B

Trimethylsilanyl-ethenethione

Trimethylsilanyl-ethenethione

C

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

D

Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

Conditions
ConditionsYield
at 768℃; flash vacuum pyrolysis;A 4 % Chromat.
B 17 % Chromat.
C 11 % Chromat.
D 17 % Chromat.
[3H]ethynyl-trimethyl-silane
13139-83-8

[3H]ethynyl-trimethyl-silane

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With morpholine buffer; water at 25℃; Rate constant;
N,N-dimethyl-3-(trimethylsilyl)propiolamide
93641-74-8

N,N-dimethyl-3-(trimethylsilyl)propiolamide

A

dimethyl amine
124-40-3

dimethyl amine

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With water; Triethylgermyllithium Product distribution; 1.) -78 deg C, 1.5 h;
(trimethylsilyl)(dimethylsilyl)ketene
98991-82-3

(trimethylsilyl)(dimethylsilyl)ketene

A

dimethylsilanone
47956-45-6

dimethylsilanone

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
at 700℃; Mechanism;
N,N-diethyl-3-trimethylsilyl-2-propiolamide
87514-35-0

N,N-diethyl-3-trimethylsilyl-2-propiolamide

A

diethylamine
109-89-7

diethylamine

B

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With water; Triethylgermyllithium Product distribution; 1.) -78 deg C, 1.5 h;
(dimethylsilyl)(trimethylsilyl)thioketene

(dimethylsilyl)(trimethylsilyl)thioketene

A

hexamethylcyclotrisilathiane
3574-04-7

hexamethylcyclotrisilathiane

B

2,2,4,4,5,5-Hexamethyl-1,3-dithia-2,4,5-trisilacyclopentan
70740-65-7

2,2,4,4,5,5-Hexamethyl-1,3-dithia-2,4,5-trisilacyclopentan

C

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
at 700℃; flash vacuum pyrolysis;A 7 % Chromat.
B n/a
C 92 % Chromat.
at 700℃; flash vacuum pyrolysis;
With flash vacuum pyrolysis at 700℃;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

acetylene
74-86-2

acetylene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
In tetrahydrofuran for 1h;
ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With water; lithium 1.) hexane, 0 deg C, 12 h;
2-bromo-1-(trimethylsilylethynyl)benzene
38274-16-7

2-bromo-1-(trimethylsilylethynyl)benzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
With potassium carbonate In methanol for 1h; Ambient temperature; Yield given;
1,1-diethynyl-2,2,2-trimethyldisilane
210471-93-5

1,1-diethynyl-2,2,2-trimethyldisilane

A

Butadiyne
460-12-8

Butadiyne

B

1-silacyclopropenylidene
100899-98-7

1-silacyclopropenylidene

C

Diethynyl-silane

Diethynyl-silane

D

2-Ethynyl-silirene

2-Ethynyl-silirene

E

acetylene
74-86-2

acetylene

F

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

G

(CH3)3SiH

(CH3)3SiH

Conditions
ConditionsYield
In gaseous matrix at 1200℃; Product distribution; pulsed flash pyrolysis study;
phenylacetylene
536-74-3

phenylacetylene

Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

A

1-Phenyl-2-(trimethylsilyl)acetylene
2170-06-1

1-Phenyl-2-(trimethylsilyl)acetylene

B

acetylene
74-86-2

acetylene

C

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

Conditions
ConditionsYield
(Me2SiCp''2UBu)2O*2THF In tetrahydrofuran at 66℃; for 4h; Product distribution; Further Variations:; reaction time;A 172 mg
B n/a
C 31 mg
2-Iodothiophene
3437-95-4

2-Iodothiophene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-(trimethylsilylethynyl)thiophene
40231-03-6

2-(trimethylsilylethynyl)thiophene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 2h;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; trimethylamine for 0.5h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; Reflux;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;99%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-(trimethylsilylethynyl)pyridine
86521-05-3

2-(trimethylsilylethynyl)pyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 3h;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 20℃;97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Sonogashira Cross-Coupling; Inert atmosphere;97%
2,6-Dibromopyridine
626-05-1

2,6-Dibromopyridine

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2,6-bis(2-(trimethylsilyl)ethynyl)pyridine
75867-44-6

2,6-bis(2-(trimethylsilyl)ethynyl)pyridine

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In toluene at 20℃; Sonogashira Cross-Coupling;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In tetrahydrofuran at 50℃; for 6h; Inert atmosphere;98%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In toluene for 90h; Sonogashira Cross-Coupling; Inert atmosphere; Darkness;98%
3-bromoquinoline
5332-24-1

3-bromoquinoline

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

3-((trimethylsilyl)ethynyl)-quinoline
86521-08-6

3-((trimethylsilyl)ethynyl)-quinoline

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 50℃; for 24h; Inert atmosphere;100%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; for 24h;96%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 20℃; for 18h; Sonogashira coupling; Inert atmosphere;87%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(1R*,2S*)-2-(trimethylsilanylethynyl)cyclohexanol
142636-23-5

(1R*,2S*)-2-(trimethylsilanylethynyl)cyclohexanol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere;
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere;
Stage #3: cyclohexane-1,2-epoxide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
100%
Stage #1: trimethylsilylacetylene With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: cyclohexane-1,2-epoxide In tetrahydrofuran at -78℃; for 4h;
95%
Stage #1: trimethylsilylacetylene With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at 0℃;
Stage #2: cyclohexane-1,2-epoxide In tetrahydrofuran; hexane at 0℃; for 12h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
77%
With boron trifluoride
Yield given. Multistep reaction;
cyclohexanone
108-94-1

cyclohexanone

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-((trimethylsilyl)ethynyl)cyclohexanol
17962-22-0

1-((trimethylsilyl)ethynyl)cyclohexanol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃;
Stage #2: cyclohexanone In tetrahydrofuran; hexane at -78℃; Further stages.;
100%
With n-butyllithium In diethyl ether; hexane 1.) -78 deg C, 1 h, 2.) -78 deg C, 1 h; 0 deg C, 1 h;99%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere;
Stage #2: cyclohexanone In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Inert atmosphere;
95%
para-bromoacetophenone
99-90-1

para-bromoacetophenone

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

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

4'-(2-trimethylsilylethynyl)acetophenone

Conditions
ConditionsYield
With copper diacetate; triethylamine; triphenylphosphine; palladium dichloride at 100℃; for 1.5h;100%
With copper diacetate; triethylamine; triphenylphosphine; palladium dichloride at 100℃; for 1.5h;100%
With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine at 60℃; for 12h;98%
ethyl 2-bromo-3-pyridinecarbamate
112671-55-3

ethyl 2-bromo-3-pyridinecarbamate

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester
112671-57-5

(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 100℃; for 4h; Sealed tube;100%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 100℃; for 4h;100%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 100 - 110℃;
benzaldehyde
100-52-7

benzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-phenyl-3-trimethylsilylprop-2-yn-1-ol
89530-34-7

1-phenyl-3-trimethylsilylprop-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: benzaldehyde In tetrahydrofuran at 0℃; for 1h;
100%
With n-butyllithium In tetrahydrofuran at -78℃;100%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
100%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-(4-methoxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-ol
159351-36-7

1-(4-methoxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-ol

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran; diethyl ether 1 h, RT; -30 deg C to RT;100%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 0℃; for 1h;
100%
Stage #1: trimethylsilylacetylene With n-butyllithium In diethyl ether at -78℃;
Stage #2: 4-methoxy-benzaldehyde In diethyl ether at -78 - -10℃;
97%
hexanal
66-25-1

hexanal

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-trimethylsilyloct-1-yn-3-ol
69498-66-4

1-trimethylsilyloct-1-yn-3-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: hexanal In tetrahydrofuran; hexane at -78 - 20℃; for 3h;
100%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: hexanal In tetrahydrofuran; hexane at 0℃; for 4h;
96%
With n-butyllithium In hexane at 25℃; for 1.5h;80%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

4-[(trimethylsilyl)ethynyl]bezaldehyde
77123-57-0

4-[(trimethylsilyl)ethynyl]bezaldehyde

Conditions
ConditionsYield
With copper(l) iodide; diisopropylamine; polymer-supp. 11-(2-[Pd(OAc)2]-1-Mes-3-imidazolyl)undecanol In tetrahydrofuran at 20℃; for 2h; Sonogashira coupling;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;100%
Stage #1: 4-bromo-benzaldehyde With 5% Pd/C; triethylamine; triphenylphosphine for 0.0833333h; Sonogashira Cross-Coupling; Sealed tube; Sonication;
Stage #2: trimethylsilylacetylene for 3h; Sealed tube;
100%
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-(2-methoxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-ol
153889-90-8, 153889-99-7

1-(2-methoxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere;
Stage #2: ortho-anisaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
100%
Stage #1: trimethylsilylacetylene With n-butyllithium In diethyl ether at -78℃;
Stage #2: ortho-anisaldehyde In diethyl ether at -78 - -10℃;
90%
Stage #1: trimethylsilylacetylene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: ortho-anisaldehyde In diethyl ether; hexane at -78 - 20℃; Further stages.;
90%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-[2-(trimethylsilyl)ethynyl]benzaldehyde
77123-58-1

2-[2-(trimethylsilyl)ethynyl]benzaldehyde

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;100%
Stage #1: ortho-bromobenzaldehyde; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.25h; Sonogashira coupling; Inert atmosphere;
Stage #2: With copper(l) iodide at 50℃; for 2.5h; Sonogashira coupling; Inert atmosphere;
99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere;99%
cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propynol
133216-88-3, 112497-25-3

(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propynol

Conditions
ConditionsYield
With n-butyllithium Inert atmosphere;100%
With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at -15 - 20℃; for 3h; Inert atmosphere;100%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #2: cyclohexanecarbaldehyde In tetrahydrofuran; hexane at -78 - 24℃;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
92%
bromobenzene
108-86-1

bromobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-Phenyl-2-(trimethylsilyl)acetylene
2170-06-1

1-Phenyl-2-(trimethylsilyl)acetylene

Conditions
ConditionsYield
With copper(l) iodide; diisopropylamine; polymer-supp. 11-(2-[Pd(OAc)2]-1-Mes-3-imidazolyl)undecanol In tetrahydrofuran at 20℃; for 2.5h; Sonogashira coupling;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine for 24h; Sonogashira coupling; Inert atmosphere; Reflux;99%
With potassium carbonate In water at 60℃; for 2h;95%
3-bromo-1-trifluoromethylbenzene
401-78-5

3-bromo-1-trifluoromethylbenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

3-<(trimethylsilyl)ethynyl>benzotrifluoride
40230-93-1

3-<(trimethylsilyl)ethynyl>benzotrifluoride

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In ethyl acetate at 50℃; for 18h; Sonogashira Coupling;100%
With copper(l) iodide; palladium diacetate; triethylamine; phenylphosphane at 80℃; for 16h;66.9%
heptanal
111-71-7

heptanal

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

rac-1-(trimethylsilyl)-1-nonyn-3-ol
135501-86-9

rac-1-(trimethylsilyl)-1-nonyn-3-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: heptanal In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
100%
With n-butyllithium 1.) THF, -78 deg C, 1 h, 2.) THF, room temp., 1 h; Multistep reaction;
With n-butyllithium 1) THF, -78 deg C, 1 h, 2) THF, r. t., 1 h; Yield given. Multistep reaction;
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-cyclopropyl-4-trimethylsilanyl-but-3-yn-2-ol

2-cyclopropyl-4-trimethylsilanyl-but-3-yn-2-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In hexanes; diethyl ether at -78℃; for 1.16667h;
Stage #2: Cyclopropyl methyl ketone In hexanes; diethyl ether at 20℃; for 48h;
100%
With methyllithium 1.) ether, room temperature, 2 h; Multistep reaction;
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-(4-chlorophenyl)-2-trimethylsilylacetylene
78704-49-1

1-(4-chlorophenyl)-2-trimethylsilylacetylene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Sonogashira Cross-Coupling; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine for 2h; Ambient temperature;98%
With piperidine; copper(l) iodide; MCM-41-supported bidentate phosphine palladium(0) at 20℃; for 1.5h; Sonogashira coupling reaction;97%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

3-((trimethylsilyl)ethynyl)benzaldehyde
77123-55-8

3-((trimethylsilyl)ethynyl)benzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; diisopropylamine In 1,4-dioxane Inert atmosphere;100%
With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; diisopropylamine In 1,4-dioxane for 7h; Inert atmosphere;100%
With palladium diacetate; triethylamine; triphenylphosphine at 100℃; for 6h; Inert atmosphere;95%
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-(4-fluorophenyl)-2-trimethylsilylacetylene
130995-12-9

1-(4-fluorophenyl)-2-trimethylsilylacetylene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 6h; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 5h; Sonogashira Cross-Coupling; Inert atmosphere;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 18h;95%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-bromo-1-(trimethylsilylethynyl)benzene
38274-16-7

2-bromo-1-(trimethylsilylethynyl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;100%
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; Inert atmosphere;100%
2-bromonaphthalene
580-13-2

2-bromonaphthalene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

trimethyl(2-(naphthalen-2-yl)ethynyl)silane
40231-00-3

trimethyl(2-(naphthalen-2-yl)ethynyl)silane

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 60℃; for 72h;100%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 20 - 40℃; Inert atmosphere;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 40℃; for 5h; Sonogashira coupling;99%
carbon dioxide
124-38-9

carbon dioxide

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

3-(trimethylsilyl)prop-2-ynoic acid
5683-31-8

3-(trimethylsilyl)prop-2-ynoic acid

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at 78℃; for 0.5h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at 20℃; for 1h;
100%
With hydrogenchloride; C54H44Cu2N2P4S2; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;93%
With [CuI(1,1′-bis(di-tert-butylphosphino)ferrocene)]; caesium carbonate In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 24h; Inert atmosphere;90%
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-chloro-3-[2-(trimethylsilyl)ethynyl]benzene
227936-62-1

1-chloro-3-[2-(trimethylsilyl)ethynyl]benzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine at 80℃; for 4h; Sonogashira coupling; Inert atmosphere;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In toluene at 20 - 60℃; for 19h; Inert atmosphere;92%
With copper(l) iodide; palladium on activated charcoal; choline chloride; triethylamine; glycerol at 60℃; for 3h; Sonogashira Cross-Coupling;63%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(4-bromophenyl)(trimethylsilyl)acetylene
16116-78-2

(4-bromophenyl)(trimethylsilyl)acetylene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 100℃; for 0.5h; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Sonogashira Cross-Coupling; Inert atmosphere;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 0℃; Schlenk technique; Inert atmosphere;99%
para-diiodobenzene
624-38-4

para-diiodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1,4-Bis(trimethylsilylethynyl)benzene
17938-13-5

1,4-Bis(trimethylsilylethynyl)benzene

Conditions
ConditionsYield
Sonogashira cross-coupling;100%
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride Castro-Stephens/Sonogashira coupling; Heating;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In tetrahydrofuran at 50℃; for 21h; Sonogashira Cross-Coupling; Inert atmosphere;98%
2-iodochlorobenzene
615-41-8

2-iodochlorobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

((2-chlorophenyl)-ethynyl)trimethylsilane
105273-33-4

((2-chlorophenyl)-ethynyl)trimethylsilane

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 80℃; for 4h; Sonogashira coupling; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; for 22h; Sonogashira Cross-Coupling; Inert atmosphere;64%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine Yield given;
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