2-((Trimethylsilyl)ethynyl)aniline

Base Information

• Chemical Name: 2-((Trimethylsilyl)ethynyl)aniline
• CAS No.: 103529-16-4
• Molecular Formula: C11H15 N Si
• Molecular Weight: 189.332
• European Community (EC) Number: 626-608-1
• DSSTox Substance ID: DTXSID00402601
• Nikkaji Number: J966.621D
• Mol file: 103529-16-4.mol

Synonyms:103529-16-4;2-((Trimethylsilyl)ethynyl)aniline;2-[(Trimethylsilyl)ethynyl]aniline;2-(2-trimethylsilylethynyl)aniline;2-((TRIMETHYLSILYL)ETHYNYL)ANILINE 97;2-(trimethylsilylethynyl)aniline;2-[2-(TRIMETHYLSILYL)ETHYNYL]ANILINE;2-[2-(Trimethylsilyl)ethynyl]benzenamine;Benzenamine, 2-[(trimethylsilyl)ethynyl]-;SCHEMBL3150946;DTXSID00402601;ISXSBRZDPKQYSC-UHFFFAOYSA-N;MFCD02093646;AKOS015912997;AS-77198;2-[(Trimethylsilyl)ethynyl]aniline, 97%;CS-0217662;F79740;EN300-8118807;J-000995;InChI=1/C11H15NSi/c1-13(2,3)9-8-10-6-4-5-7-11(10)12/h4-7H,12H2,1-3H

Chemical Property of 2-((Trimethylsilyl)ethynyl)aniline

Chemical Property:

• Vapor Pressure: 0.0168mmHg at 25°C
• Refractive Index: n20/D 1.564(lit.)
• Boiling Point: 120 °C0.1 mm Hg(lit.)
• PKA: 4.17±0.10(Predicted)
• Flash Point: 110 °C
• PSA: 26.02000
• Density: 0.94 g/mL at 25 °C(lit.)
• LogP: 3.07890
• Storage Temp.: 2-8°C(protect from light)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 189.097376017
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

99.90% ^*data from raw suppliers

2-[(Trimethylsilyl)ethynyl]aniline 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CC=CC=C1N
• Uses: 2-[(Trimethylsilyl)ethynyl]aniline (2-(2-Trimethylsilylethynyl)aniline) may be used in the synthesis of:N-(2-trimethylsilylethynylphenyl)methanesulfonamide8-(2-((trimethylsilyl)ethynyl)phenylamino)-7H-naphtho[1,8-bc]acridin-7-one2-phenyl-4-alkoxy quinolines

Technology Process of 2-((Trimethylsilyl)ethynyl)aniline

There total 11 articles about 2-((Trimethylsilyl)ethynyl)aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-iodophenylamine (615-43-0) + trimethylsilylacetylene (1066-54-2) → 2-[(trimethylsilyl)ethynyl]aniline (103529-16-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/1521-3773(20020902)41:17<3281::AID-ANIE3281>3.0.CO;2-G

Reference yield: 93.0%

bis-trimethylsilyl acetylene + 2-iodophenylamine (615-43-0) → 2-[(trimethylsilyl)ethynyl]aniline (103529-16-4)

Guidance literature:

bis-trimethylsilyl acetylene; 2-iodophenylamine; With copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 5h;

With water; In tetrahydrofuran;

Reference yield: 84.0%

trimethyl((2-nitrophenyl)ethynyl)silane (75867-47-9) → 2-[(trimethylsilyl)ethynyl]aniline (103529-16-4)

Guidance literature:

With 5% Au/Fe2O3; hydrogen; In toluene; at 60 - 120 ℃; for 2h; under 750.075 - 15001.5 Torr; chemoselective reaction; Autoclave;

DOI:10.1021/ol902061j

upstream raw materials:

trimethyl((2-nitrophenyl)ethynyl)silane

2-iodophenylamine

trimethylsilylacetylene

2,2,2-trifluoro-N-(2-iodophenyl)acetamide

Downstream raw materials:

2-(4-chlorophenylethynyl)phenylamine

3-(2-aminophenyl)-1-(4-chlorophenyl)prop-2-yn-1-one

1-(4-((2-aminophenyl)ethynyl)phenyl)ethan-1-one

1-(4-acetylphenyl)-3-(2-aminophenyl)prop-2-yn-1-one

Refernces

• 1、 Carvajal-Miranda, Yendry,Prez-Salazar, Roy,Varela, Jess A.. "Synthesis of Dihydroindolo[2,3-c]carbazole as Potential Telomerase Inhibitor". . p. 762 - 766. Retrieved 2016.
• 2、 Lv, Jiahang,Zhao, Binlin,Han, Ying,Yuan, Yu,Shi, Zhuangzhi. "Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds". . p. 691 - 694. Retrieved 2021.
• 3、 Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay. "One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations". . p. 10987 - 10999. Retrieved 2016.
• 4、 Sakai, Norio,Annaka, Kimiyoshi,Konakahara, Takeo. "Palladium-catalyzed coupling reaction of terminal alkynes with aryl iodides in the presence of indium tribromide and its application to a one-pot synthesis of 2-phenylindole". . p. 1527 - 1530. Retrieved 2004.
• 5、 Erdelyi,Gogoll. "Rapid homogeneous-phase sonogashira coupling reactions using controlled microwave heating". . p. 4165 - 4169. Retrieved 2001.
• 6、 Yoshioka, Shohei,Fujii, Yuki,Tsujino, Hirofumi,Uno, Tadayuki,Fujioka, Hiromichi,Arisawa, Mitsuhiro. "One-pot enyne metathesis/Diels-Alder/oxidation to six-membered silacycles with a multi-ring core: Discovery of novel fluorophores". . p. 5970 - 5973. Retrieved 2017.
• 7、 Gottardo, Christine,Aguirre, Andrea. "Palladium-catalyzed carbon-carbon coupling reactions using aryl Grignards". . p. 7091 - 7094. Retrieved 2002.
• 8、 Points, Gary L.,Beaudry, Christopher M.. "Regioselective Synthesis of Substituted Carbazoles, Bicarbazoles, and Clausine C". supporting information. p. 6882 - 6885. Retrieved 2021/09/11.