Production Method 1

2247388-96-9

89343-06-6

Reaction Conditions

1.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane ,  Water
1.2 Reagents: Potassium hydroxide ,  Manganese oxide (MnO2) Solvents: Diethyl ether

Reference

Organocatalytic Enantioselective 1,3-Difunctionalizations of Morita-Baylis-Hillman Carbonates

Chen, Zhi-Chao; Chen, Peng; Chen, Zhi; Ouyang, Qin ; Liang, Hua-Ping; et al, Organic Letters, 2018, 20(19), 6279-6283

Production Method 2

1174908-08-7

89343-06-6

125251-42-5

Reaction Conditions

1.1 Reagents: Sodium methoxide ,  Benzeneacetic acid, α-diazo-, methyl ester Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium ,  BINAP Solvents: Toluene ;  1 h, 90 °C; 90 °C → rt

Reference

Rhodium(I)-Catalyzed Sequential C(sp)-C(sp3) and C(sp3)-C(sp3) Bond Formation through Migratory Carbene Insertion

Xia, Ying; Feng, Sheng; Liu, Zhen; Zhang, Yan; Wang, Jianbo, Angewandte Chemie, 2015, 54(27), 7891-7894

Production Method 3

136449-68-8

89343-06-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol

Reference

Biphenyldialkylsilyl chlorides: reagents for the formation of crystalline derivatives of small terminal alkynes

Anthony, John; Diederich, Francois, Tetrahedron Letters, 1991, 32(31), 3787-90

Production Method 4

13154-24-0

4301-14-8

89343-06-6

Reaction Conditions

Reference

Silicon-directed Nazarov reactions. III. Stereochemical and mechanistic considerations

Jones, Todd K.; Denmark, Scott E., Helvetica Chimica Acta, 1983, 66(8), 2397-411

Production Method 5

925-90-6

13154-24-0

89343-06-6

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt; 4 h, rt; overnight, rt

Reference

Silylation of Alcohols, Phenols, and Silanols with Alkynylsilanes - an Efficient Route to Silyl Ethers and Unsymmetrical Siloxanes

Kucinski, Krzysztof; Stachowiak, Hanna ; Hreczycho, Grzegorz, European Journal of Organic Chemistry, 2020, 2020(26), 4042-4049

Production Method 6

111409-79-1

89343-06-6

Reaction Conditions

Reference

Selenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles

Liao, Lihao; Zhang, Hang; Zhao, Xiaodan, ACS Catalysis, 2018, 8(7), 6745-6750

Production Method 7

865605-32-9

89343-06-6

865605-35-2

67385-09-5

Reaction Conditions

1.1 Catalysts: 1,1-Bis(diphenylphosphino)ferrocene ,  Hydrotetrakis(triphenylphosphine)rhodium Solvents: Acetone ;  1 h, reflux

Reference

Equilibrating C-S Bond Formation by C-H and S-S Bond Metathesis. Rhodium-Catalyzed Alkylthiolation Reaction of 1-Alkynes with Disulfides

Arisawa, Mieko; Fujimoto, Kenji; Morinaka, Satoshi; Yamaguchi, Masahiko, Journal of the American Chemical Society, 2005, 127(35), 12226-12227

Triisopropylsilylacetylene Raw materials

• Ethylmagnesium Bromide (3M in Et2O)
• Benzene, 1-methoxy-4-[[[3-[tris(1-methylethyl)silyl]-2-propyn-1-yl]oxy]methyl]-
• 3-Butyn-2-ol, 2-methyl-4-[tris(1-methylethyl)silyl]-
• (2-Bromoethynyl)tris(propan-2-yl)silane
• chlorotris(propan-2-yl)silane
• ETHYNYLMAGNESIUM BROMIDE
• 1,1'-Biphenyl, 4-[dimethyl[2-[tris(1-methylethyl)silyl]ethynyl]silyl]-
• Carbamic acid, [2-[[[tris(1-methylethyl)silyl]ethynyl]thio]ethyl]-, 1,1-dimethylethyl ester

Triisopropylsilylacetylene Preparation Products

• Silane, 1,3-butadiyne-1,4-diylbis[tris(1-methylethyl)- (125251-42-5)
• Triisopropylsilylacetylene (89343-06-6)
• SILANE, TRIS(1-METHYLETHYL)[(OCTYLTHIO)ETHYNYL]- (865605-35-2)
• 2-(Boc-amino)ethanthiol (>90%) (67385-09-5)

• 1. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330
• 2. Emerging investigator series: heterogeneous reactions of sulfur dioxide on mineral dust nanoparticles: from single component to mixed components?
  Tao Wang,Yangyang Liu,Yue Deng,Hongbo Fu,Jianmin Chen Environ. Sci.: Nano, 2018,5, 1821-1833
• 3. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 4. Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)–
  Chem. Commun., 1998, 1501-1502
• 5. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130

• Solvents and Organic Chemicals Organic Compounds Organometallic compounds Organometalloid compounds Organosilicon compounds Alkylsilanes
• Other Chemical Reagents Organic Metal Reagents
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

Triisopropylsilylacetylene: A Comprehensive Overview

Triisopropylsilylacetylene, also known as TIPS acetylene or 1,1,1-triisopropylsilyl acetylene, is a versatile organosilicon compound with the CAS number 89343-06-6. This compound has garnered significant attention in the fields of organic synthesis, materials science, and catalysis due to its unique chemical properties and reactivity. The molecule consists of an acetylene group (-C≡CH) substituted with a triisopropylsilyl (TIPS) group, which imparts stability and facilitates various chemical transformations.

The TIPS group, which is a bulky silyl protecting group, plays a crucial role in stabilizing the acetylenic moiety. This stabilization allows Triisopropylsilylacetylene to undergo a wide range of reactions that would otherwise be challenging with unprotected acetylenes. Recent studies have highlighted its utility in cross-coupling reactions, such as the Sonogashira coupling, where it serves as an excellent substrate for forming carbon-heteroatom bonds. The use of Triisopropylsilylacetylene in these reactions has been shown to enhance selectivity and yield, making it a valuable tool in modern organic synthesis.

In addition to its role in traditional organic synthesis, Triisopropylsilylacetylene has found applications in the synthesis of complex natural products and bioactive molecules. For instance, researchers have employed this compound in the construction of polycyclic structures, where its reactivity and stability are particularly advantageous. The ability to perform multiple transformations on the same molecule without interfering with other functional groups has made it a preferred choice for synthesizing intricate architectures.

The development of new catalytic systems has further expanded the scope of Triisopropylsilylacetylene. Recent advancements in transition metal catalysis have enabled the use of this compound in enantioselective reactions, paving the way for the asymmetric synthesis of chiral acetylenic compounds. These developments are particularly relevant in drug discovery, where chirality plays a critical role in molecular activity and selectivity.

Beyond organic synthesis, Triisopropylsilylacetylene has also been explored for its potential in materials science. Its ability to undergo controlled polymerization under specific conditions has led to the development of novel siloxane-based polymers with unique mechanical and thermal properties. These materials hold promise for applications in high-performance coatings, adhesives, and electronic devices.

Recent research has also focused on the environmental compatibility and sustainability aspects of using Triisopropylsilylacetylene. Studies have demonstrated that certain reaction conditions can minimize waste generation and improve atom economy when employing this compound. Such findings align with the growing emphasis on green chemistry principles within the scientific community.

In conclusion, Triisopropylsilylacetylene is a multifaceted compound with a wide range of applications across various disciplines. Its unique combination of stability and reactivity makes it an invaluable tool for researchers seeking to tackle complex chemical challenges. As ongoing research continues to uncover new possibilities for this compound, its role in advancing science and technology is expected to grow significantly.

• 626231-15-0(SILANE, [[BIS(1-METHYLETHYL)SILYL]ETHYNYL]TRIMETHYL-)
• 82192-57-2(1-(Triisopropylsilyl)-1-propyne)
• 160481-43-6(Silane, (iodoethynyl)tris(1-methylethyl)-)
• 1777-03-3((Triethylsilyl)acetylene)
• 753504-85-7(Silane, (fluoroethynyl)tris(1-methylethyl)-)
• 82192-58-3(Lithium, [3-[tris(1-methylethyl)silyl]-2-propynyl]-)
• 478184-36-0(Chlorozinc(1+);ethynyl-tri(propan-2-yl)silane)
• 138714-25-7(Lithium, [[tris(1-methylethyl)silyl]ethynyl]-)
• 84397-70-6(SILANE, ETHYNYLDIMETHYL(1-METHYLETHYL)-)
• 86318-61-8(Tert-Butyldimethylsilylacetylene)