(Trimethylsilyl)acetylene - ≥98% , CAS No.1066-54-2

CAS: 1066-54-2 Cat. No.: E106615 Molecular Weight: 98.22 Beilstein Registry Number: 906752 EC Number: 213-919-9

GRADE & PURITY ≥98%

Synonyms

(Trimethylsilyl)acetylene | (trimethyl-silyl)acetylene | (trimethylsilyl)-acetylene | 1-(Trimethylsilyl)acetylene | 1-Trimethylsilylethyne | 1-trimethylsilyl-ethyne | Trimethylsilylacetylene | trimethylsilyl-acetylene | trimetylsilyl acetylene | Acetylene

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

A substrate for nickel-catalyzed cross-coupling with benzonitriles. Pyrazole syntheses by 1,3-Dipolar cycloaddition of diazo compounds to acetylenes.

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

Specifications

Synonyms

(Trimethylsilyl)acetylene | (trimethyl-silyl)acetylene | (trimethylsilyl)-acetylene | 1-(Trimethylsilyl)acetylene | 1-Trimethylsilylethyne | 1-trimethylsilyl-ethyne | Trimethylsilylacetylene | trimethylsilyl-acetylene | trimetylsilyl acetylene | Acetylene

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C[Si](C)(C)C#C
• IUPAC Name: ethynyl(trimethyl)silane
• InChIKey: CWMFRHBXRUITQE-UHFFFAOYSA-N
• INCHI: 1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3
• Isomeric SMILES: C[Si](C)(C)C#C
• UN Number: 1993
• Molecular Weight: 98.22
• Beilstein: 906752
• Reaxy-Rn: 906752
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=906752&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organometallic compounds
    • Class Organometalloid compounds
      • Subclass Organosilicon compounds
        • Level5 Alkylsilanes
          • Level6 Trialkylsilanes

• Kingdom: Organic compounds
• Superclass: Organometallic compounds
• Class: Organometalloid compounds
• Subclass: Organosilicon compounds
• Intermediate Tree Nodes: Alkylsilanes
• Direct Parent: Trialkylsilanes
• Alternative Parents: Acetylides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trialkylsilane - Acetylide - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as trialkylsilanes. These are organosilicon compounds containing exactly one alkyl chain attached to the silicon atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Miscible with organic solvents.
• Sensitivity: Air and Moisture Sensitive
• Refractive Index: 1.3873-1.3903
• Flash Point(°F): -29.2 °F
• Flash Point(°C): -34℃
• Boil Point(°C): 53°C
• Molecular Weight: 98.220 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 98.0552 Da
• Monoisotopic Mass: 98.0552 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 77.800
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

1. Guiquan Liu, Guorong Wang, Zhiliang Jin.  (2023)  Subtly synthesized graphdiyne nano-lamellas as stable electrode material for supercapacitors.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2023.142866]

2. Song Wang, Xiewen Wu, Jing Fang, Feng Zhang, Yanli Liu, Hongbo Liu, Yu He, Min Luo, Run Li.  (2023)  Direct Z-Scheme Polymer/Polymer Double-Shell Hollow Nanostructures for Efficient NADH Regeneration and Biocatalytic Artificial Photosynthesis under Visible Light.  ACS Catalysis,      [PMID:] [10.1021/acscatal.2c05722]

3. Li Chen, Xiang Li, Mengmeng Xiong, Yimei Zhao, Suyi Liu, Cao Li, Kai Wang.  (2022)  Development of novel nanoporphyrin biomaterials for NIR-II activated photothermal therapy against tumor in vivo.  MATERIALS & DESIGN,      [PMID:] [10.1016/j.matdes.2022.111532]

4. Shuang Liu, Jing Yan, Junqin Shi, Xuezhuang Li, Junping Zhang, Xuanyi Wang, Ningjing Cai, Quanhai Fang, Qiuyu Zhang, Yi Yan.  (2022)  Rational design of cobaltocenium-containing polythioether type metallo-polyelectrolytes as HCl corrosion inhibitors for mild steel.  Polymer Chemistry,  14  (3): (330-342).  [PMID:] [10.1039/D2PY01263D]

5. Zhao Yuxiang, Yan Yaqian, Wu Zhuangzhuang, Li Chaokun, Fan Ruimei, Feng Lijuan, Wang Wenxin, Chen Qi.  (2022)  A novel fluorescent covalent organic framework for the selective detection of fluoride ion.  JOURNAL OF MATERIALS SCIENCE,  57  (28): (13425-13432).  [PMID:] [10.1007/s10853-022-07485-1]

6. Yana Zhang, Jiaoyang Chen, Guangpu Zhang, Jianqiang Xv, Jianhua Xv, Yubing Hu, Hu Guo, Fan guo, JiaJun Fu, Wei Jiang.  (2021)  Mechanically robust, highly adhesive and autonomously low-temperature self-healing elastomer fabricated based on dynamic metal − ligand interactions tailored for functional energetic composites.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2021.130665]

7. Sheng-Song Li, Yong-Chao Zheng, Xiao-Ming Zhu, Hong-Bo Wang, Long-Hui Liang, Xu-Zhe Wang, Ling Yuan, Fa-Heng Zhang, He Zheng, Chong-Lin Zhao.  (2021)  A novel BODIPY-based fluorescent probe for sensitive and selective detection of nerve agent simulants through base-assisted photo-induced electron transfer process.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2021.129804]

8. Xiaomei Zhang, Zhiming Gou, Yujing Zuo, Weiying Lin.  (2019)  A novel polythioether-based rhodamine B fluorescent probe via successive click reaction and its application in iron ion detection and cell imaging.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:31718966] [10.1016/j.saa.2019.117679]

9. Chao Xu, Ying Qian, Zheng-qing Qi, Chang-gui Lu, Yi-ping Cui.  (2018)  A conjugated BODIPY–triphenylamine multi-aldoxime: Sonogashira coupling, ratiometric chemodosimeter and rapid detection of hypochlorite with two-photon excited fluorescence.  NEW JOURNAL OF CHEMISTRY,  42  (9): (6910-6917).  [PMID:] [10.1039/C8NJ00368H]

10. Jiatao Wu, Chunyan Tan, Xinwen Zhou, Ying Tan, Pengyuan Yang, Yuyang Jiang.  (2017)  Molecular weight analysis of water-soluble poly(phenylene ethynylene)s using MALDI-TOF MS.  JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY,  55  (15): (2537-2543).  [PMID:] [10.1002/pola.28650]

11. Xuefeng Wang, Hua Wang, Shengyu Feng.  (2016)  A novel thiophene functionalized silicon-cored compounds: Aggregation-induced emission enhancement and aqueous fluorogenic Fe3+ probes in bovine serum albumin.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2016.09.168]

12. Yu-Mo Zhang, Fuli Xie, Wen Li, Yuyang Wang, Weiran Zhang, Xiaojun Wang, Minjie Li, Sean Xiao-An Zhang.  (2016)  A methyl ketone bridged molecule as a multi-stimuli-responsive color switch for electrochromic devices.  Journal of Materials Chemistry C,  4  (21): (4662-4667).  [PMID:] [10.1039/C5TC04236D]

13. Chunlei Yang, Xiu Wang, Lei Shen, Wenping Deng, Haiyun Liu, Shenguang Ge, Mei Yan, Xianrang Song.  (2016)  An aldehyde group-based P-acid probe for selective fluorescence turn-on sensing of cysteine and homocysteine.  BIOSENSORS & BIOELECTRONICS,      [PMID:26802748] [10.1016/j.bios.2016.01.044]

14. Xiang Han, Lei Zhao, Dong-En Wang, Juan Xu, Longlong Zhang, Mao-Sen Yuan, Qin Tu, Jinyi Wang.  (2015)  A TBET-based ratiometric probe for Au3+ and its application in living cells.  ANALYST,  141  (3): (1098-1104).  [PMID:26662283] [10.1039/C5AN01932J]

15. Kaiyuan You, Hongyan Yao, Yunhe Zhang, Yu Liu, Shanyou Liu, Ying Song, Shaowei Guan.  (2015)  Phenylethynyl- and naphthylethynyl-terminated hyperbranched polyimides with low melt viscosity.  HIGH PERFORMANCE POLYMERS,      [PMID:] [10.1177/0954008315570398]

16. Meiling Liu, Jianhui Deng, Cailang Lai, Qiong Chen, Qiangqing Zhao, Youyu Zhang, Haitao Li, Shouzhuo Yao.  (2012)  Synthesis, characterization of conjugated oligo-phenylene-ethynylenes and their supramolecular interaction with β-cyclodextrin for salicylaldehyde detection.  TALANTA,      [PMID:23141331] [10.1016/j.talanta.2012.08.008]

17. Xuefeng Wang, Hua Wang, Qin Jiang, Yong-Ill Lee, Shengyu Feng, Hong-Guo Liu.  (2017)  Highly selective and sensitive fluorogenic ferric probes based on aggregation-enhanced emission with − SiMe3 substituted polybenzene.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:28715687] [10.1016/j.saa.2017.07.016]

18. Dingming Xue, Xiaofei Yan, Fei Liu, Mengqi Liu, Houhu Zhang.  (2025)  Anthrathiophene-Based Covalent Organic Frameworks with Powerful π-Conjugation toward High-Efficiency CO2 Photoconversion.  ACS Applied Materials & Interfaces,      [PMID:41186443] [10.1021/acsami.5c17594]