Cas no 86521-05-3 (trimethyl-[2-(2-pyridyl)ethynyl]silane)

Trimethyl-[2-(2-pyridyl)ethynyl]silane is a specialized organosilicon compound featuring a pyridyl-ethynyl functional group. Its key advantages include its role as a versatile building block in organic synthesis, particularly in cross-coupling reactions and the preparation of heterocyclic frameworks. The trimethylsilyl (TMS) group enhances stability and facilitates further functionalization, while the ethynyl linkage enables efficient conjugation with aromatic systems. The pyridyl moiety introduces nitrogen-based coordination sites, making it useful in ligand design for catalysis or material science applications. This compound is valued for its synthetic flexibility and compatibility with a range of reaction conditions, including Sonogashira and Heck couplings. Proper handling under inert conditions is recommended due to its sensitivity to moisture and air.
trimethyl-[2-(2-pyridyl)ethynyl]silane structure
86521-05-3 structure
Product Name:trimethyl-[2-(2-pyridyl)ethynyl]silane
CAS No:86521-05-3
MF:C10H13NSi
MW:175.302423238754
MDL:MFCD00066349
CID:60995
PubChem ID:522859
Update Time:2025-05-21

trimethyl-[2-(2-pyridyl)ethynyl]silane Chemical and Physical Properties

Names and Identifiers

    • 2-((Trimethylsilyl)ethynyl)pyridine
    • 2-(Trimethylsilylethynyl)pyridine
    • C10H13NSi
    • trimethyl(2-pyridin-2-ylethynyl)silane
    • (2-Pyridylethynyl)trimethylsilane
    • 2-[(TRIMETHYLSILYL)ETHYNYL]PYRIDINE
    • WOFPTESETJKCBH-UHFFFAOYSA-N
    • trimethylsilylethynylpyridine
    • 2-Trimethylsilylethynylpyridine
    • 2-trimethylsilanylethynyl-pyridine
    • RW1995
    • VP15009
    • FCH1118061
    • TRA0004744
    • SY027118
    • AK101982
    • trime
    • trimethyl-[2-(2-pyridyl)ethynyl]silane
    • 2-[2-(Trimethylsilyl)ethynyl]pyridine (ACI)
    • Pyridine, 2-[(trimethylsilyl)ethynyl]- (9CI)
    • 2-Trimethylsilanylethynylpyridine
    • Trimethyl[(pyridin-2-yl)ethynyl]silane
    • DTXSID00335086
    • SB75047
    • SCHEMBL2160771
    • trimethyl-[2-(2-pyridinyl)ethynyl]silane
    • T3879
    • A841699
    • MFCD00066349
    • 2-[2-(TRIMETHYLSILYL)ETHYNYL]PYRIDINE
    • s19425
    • AKOS015839988
    • 86521-05-3
    • DTXCID50286175
    • CS-W017437
    • DS-3765
    • AC1357
    • MDL： MFCD00066349
    • Inchi： 1S/C10H13NSi/c1-12(2,3)9-7-10-6-4-5-8-11-10/h4-6,8H,1-3H3
    • InChI Key： WOFPTESETJKCBH-UHFFFAOYSA-N
    • SMILES： C(C1C=CC=CN=1)#C[Si](C)(C)C
    • BRN： 4176916

Computed Properties

  • Exact Mass: 175.08200
  • Monoisotopic Mass: 175.082
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 203
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 12.9

Experimental Properties

  • Color/Form: Colorless to yellow liquid
  • Density: 0.95
  • Melting Point: 42 °C
  • Boiling Point: 90°C/18mmHg(lit.)
  • Flash Point: 85-86°C/1mm
  • Refractive Index: 1.5330
  • Water Partition Coefficient: Insoluble in water.
  • PSA: 12.89000
  • LogP: 2.31050
  • λmax: 285(CH3CN)(lit.)
  • Solubility: Insoluble in water

trimethyl-[2-(2-pyridyl)ethynyl]silane Security Information

trimethyl-[2-(2-pyridyl)ethynyl]silane Customs Data

  • HS CODE：2933399090
  • Customs Data：

    China Customs Code:

    2933399090

    Overview:

    2933399090. Other compounds with non fused pyridine rings in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

trimethyl-[2-(2-pyridyl)ethynyl]silane Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI XIAN DING Biotechnology Co., Ltd.
T3879-1G
trimethyl-[2-(2-pyridyl)ethynyl]silane
 86521-05-3 98.0%(GC)
1G
 290.0CNY 2021-07-02
SHANG HAI XIAN DING Biotechnology Co., Ltd.
T3879-5G
trimethyl-[2-(2-pyridyl)ethynyl]silane
 86521-05-3 98.0%(GC)
5G
 990.0CNY 2021-07-02
Fluorochem
S19425-1g
2-(Trimethylsilylethynyl)pyridine
 86521-05-3 95%
1g
 ￡24.00 2022-02-28
Fluorochem
S19425-5g
2-(Trimethylsilylethynyl)pyridine
 86521-05-3 95%
5g
 ￡68.00 2022-02-28
Fluorochem
S19425-25g
2-(Trimethylsilylethynyl)pyridine
 86521-05-3 95%
25g
 ￡220.00 2022-02-28
Alichem
A029181391-25g
2-((Trimethylsilyl)ethynyl)pyridine
 86521-05-3 95%
25g
 $206.91 2023-08-31
TRC
T896585-50mg
2-(Trimethylsilylethynyl)pyridine
 86521-05-3
50mg
 $ 50.00 2022-06-02
TRC
T896585-100mg
2-(Trimethylsilylethynyl)pyridine
 86521-05-3
100mg
 $ 65.00 2022-06-02
TRC
T896585-500mg
2-(Trimethylsilylethynyl)pyridine
 86521-05-3
500mg
 $ 80.00 2022-06-02
SHANG HAI XIAN DING Biotechnology Co., Ltd.
B-JC294-200mg
trimethyl-[2-(2-pyridyl)ethynyl]silane
 86521-05-3 95+%
200mg
 52.0CNY 2021-07-15

trimethyl-[2-(2-pyridyl)ethynyl]silane Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: Copper bromide (CuBr) ,  (SP-4-3)-Chloro[2-(diphenylphosphino-κP)-N-[2-(diphenylphosphino-κP)phenyl]benze… Solvents: 1,4-Dioxane ;  74 h, 50 °C
Reference
Catalytic Sonogashira couplings mediated by an amido pincer complex of palladium
Hung, Yu-Ting; et al, Inorganic Chemistry Frontiers, 2014, 1(5), 405-413

Production Method 2

Reaction Conditions
1.1 Reagents: Diethylamine Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide
Reference
Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating
Erdelyi, Mate; et al, Journal of Organic Chemistry, 2001, 66(12), 4165-4169

Production Method 3

Reaction Conditions
1.1 Reagents: Diisopropylamine Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium ;  3 h, rt
Reference
Synthesis of 1,2-Dihydropyridines Catalyzed by Well-Defined Low-Valent Cobalt Complexes: C-H Activation Made Simple
Fallon, Brendan J.; et al, ACS Catalysis, 2015, 5(12), 7493-7497

Production Method 4

Reaction Conditions
Reference
Product class 1: pyridines
Spitzner, D., Science of Synthesis, 2005, 15, 11-284

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Toluene ;  30 min, -85 °C; 5 h, -85 °C; -85 °C → 33 °C; 3 h, 31 - 33 °C
2.1 Reagents: Sodium hydride Catalysts: 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, chloride (1:1) ;  25 min, 31 - 33 °C
Reference
NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions
Arde, Panjab; et al, RSC Advances, 2014, 4(91), 49775-49779

Production Method 6

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: Cuprous iodide ,  Tetrakis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  rt
Reference
Ru(II) coordination compounds of N-N bidentate chelators with 1,2,3 triazole and isoquinoline subunits: Synthesis, spectroscopy and antimicrobial properties
Kreofsky, Nicholas W.; et al, Polyhedron, 2020, 177,

Production Method 7

Reaction Conditions
1.1 Reagents: Diethylamine Catalysts: Triphenylphosphine ,  Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ;  25 min, 120 °C
Reference
Large accelerations from small thermal differences: case studies and conventional reproduction of microwave effects on palladium couplings
Yeboah, Kwadwo A.; et al, Reaction Kinetics, 2014, 112(2), 295-304

Production Method 8

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: Cuprous iodide ,  Tetrakis(triphenylphosphine)palladium ;  46 h, reflux
Reference
Palladium-catalyzed oxidative homocoupling reaction of terminal acetylenes using trans-bidentatable 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene
Atobe, Shingo; et al, Research on Chemical Intermediates, 2013, 39(1), 359-370

Production Method 9

Reaction Conditions
1.1 Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium Solvents: Diisopropylamine ;  overnight, rt
Reference
High-efficiency solution processable electrophosphorescent iridium complexes bearing polyphenylphenyl dendron ligands
Huang, Chun; et al, Journal of Organometallic Chemistry, 2009, 694(9-10), 1317-1324

Production Method 10

Reaction Conditions
1.1 Reagents: Sodium hydride Catalysts: 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, chloride (1:1) ;  25 min, 31 - 33 °C
Reference
NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions
Arde, Panjab; et al, RSC Advances, 2014, 4(91), 49775-49779

Production Method 11

Reaction Conditions
1.1 Solvents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone ;  24 h, 40 °C
1.2 Reagents: Ammonium chloride Solvents: Water
Reference
Highly Chemoselective DMPU-Mediated Trialkylsilylation of Terminal Alkynes Using Trifluoromethyltrialkylsilane
Nozawa-Kumada, Kanako; et al, Asian Journal of Organic Chemistry, 2017, 6(1), 63-66

Production Method 12

Reaction Conditions
1.1 Catalysts: Potassium bis(trimethylsilyl)amide Solvents: Acetonitrile ;  2 h, rt
Reference
Transition Metal-Free Catalytic C-H Silylation of Terminal Alkynes with bis(Trimethylsilyl)acetylene Initiated by KHMDS
Kucinski, Krzysztof; et al, ChemCatChem, 2022, 14(18),

Production Method 13

Reaction Conditions
1.1 Reagents: Diisopropylamine Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium ;  overnight, rt
Reference
Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis
Chiu, Hsin-Chun ; et al, Angewandte Chemie, 2018, 57(21), 6090-6094

Production Method 14

Reaction Conditions
1.1 Reagents: Diisopropylethylamine Catalysts: Tri-o-tolylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: Tetrahydrofuran
Reference
Palladium-catalyzed coupling of heteroaromatic triflates with acetylene and its application for a dynemicin A intermediate
Okita, Takaaki; et al, Tetrahedron, 1995, 51(13), 3737-44

Production Method 15

Reaction Conditions
1.1 Reagents: Diisopropylethylamine Catalysts: Tri-o-tolylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: Dimethylformamide
Reference
Introduction of acetylene moiety into amide-carbons via Pd-coupling and its application for a model of dynemicin A
Okita, Takaaki; et al, Synlett, 1994, (8), 589-90

Production Method 16

Reaction Conditions
Reference
Inhibitors to Overcome Secondary Mutations in the Stem Cell Factor Receptor KIT
Kaitsiotou, Helena; et al, Journal of Medicinal Chemistry, 2017, 60(21), 8801-8815

trimethyl-[2-(2-pyridyl)ethynyl]silane Raw materials

trimethyl-[2-(2-pyridyl)ethynyl]silane Preparation Products

trimethyl-[2-(2-pyridyl)ethynyl]silane Related Literature

Related Categories

86521-05-3 (trimethyl-[2-(2-pyridyl)ethynyl]silane) Related Products

Recommended suppliers
Essenoi Fine Chemical Co., Limited
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
Changzhou Guanjia Chemical Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Changzhou Guanjia Chemical Co., Ltd
Tiancheng Chemical (Jiangsu) Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Hangzhou Cedareal Technology Co., Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Hangzhou Cedareal Technology Co., Ltd.
上海帛亦醫(yī)藥科技有限公司
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent