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Trimethylsilylacetylene

CAS：1066-54-2
MW:98.22
MF：C5H10Si

Trimethylsilylacetylene, with the chemical formula C5H10Si and CAS registry number 1066-54-2, is a compound utilized extensively in organic synthesis as a protecting group for alkynes. This colorless liquid, also known as TMS acetylene, is notable for its ability to undergo various reactions while maintaining the integrity of the alkyne functionality. It finds widespread application in the preparation of numerous organic compounds, serving as a valuable tool in the field of synthetic chemistry. Trimethylsilylacetylene plays a crucial role in the development of pharmaceuticals, agrochemicals, and materials science, contributing to the advancement of diverse research areas. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Trimethylsilylacetylene

1.2 Synonyms: (Thrimethylsilyl)acetylene; (Trimethylsilanyl)acetylene; (Trimethylsilyl)acetylene; (Trimethylsilyl)ethyne; 1-(Trimethylsilyl)acetylene; 1-Trimethylsilylethyne; 2,2-Dimethyl-2-sila-3-butyne; Acetylenyltrimethylsilane; Ethynyltrimethylsilane; Ethynyltrimethylsilane~TMS acetylene; Silane, ethynyltrimethyl-; Thimethylsilylacetylene; TMS acetylene; TMS-Acetylene; Trimethylethynylsilane; Trimethylsil yace tylene; Trimethylsilanylethyne;

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1.3 CAS No.: 1066-54-2

1.4 CID: 66111

1.5 EINECS: 213-919-9

1.6 Molecular Formula: C5H10Si

1.7 Inchi: InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3

1.8 InChkey: CWMFRHBXRUITQE-UHFFFAOYSA-N

1.9 Canonical Smiles: C[Si](C)(C)C#C

1.10 Isomers Smiles: C[Si](C)(C)C#C

2. Properties

2.1 Solubility: Miscible with organic solvents.

2.2 Appearance: clear colorless liquid

2.3 Storage: Keep Cold.

2.4 Chemical Properties: CLEAR COLORLESS LIQUID

2.5 Color/Form: colorless

2.6 Water Solubility: reacts

2.7 Stability: Materials containing similar functional groups can decompose at elevated temperatures. Has not been fully evaluated.

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Description: CLEAR COLORLESS LIQUIDTrimethylsilylacetylene 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.

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3.2 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.] Trimethylsilylacetylene Preparation Products And Raw materials Raw materials

3.3 Usage: 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

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4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 2

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H225 Highly flammable liquid and vapour H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Mass spectrum (electron ionization)

6. Synthesis Route

1066-54-2Total: 25 Synthesis Route

754-05-2 74 Suppliers

1066-54-2 234 Suppliers

7652-06-4

1066-54-2 234 Suppliers

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7. Precursor and Product

precursor:

14630-40-1

13683-41-5

754-05-2

54655-07-1

38274-16-7

87514-35-0

93641-74-8

13139-83-8

7652-06-4

product:

622-76-4

935-14-8

4526-07-2

754-05-2

875-66-1

7299-46-9

5624-60-2

624-74-8

2975-46-4

536-74-3

8. Computed Properties

Molecular Weight：98.22g/mol
Molecular Formula：C₅H₁₀Si
Compound Is Canonicalized：True
XLogP3-AA：98.055176853
Monoisotopic Mass：98.055176853
Complexity：77.8
Rotatable Bond Count：1
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：0
Topological Polar Surface Area：0
Heavy Atom Count：：6
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBgAAgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGBAAAAAAAACAIABCAAAAAAFACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9.Other Information

Usage: (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.

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10. Toltal 223 Suppliers View more

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11. Related Questions

: What are the Advanced Applications and Potential Value of Ethynyltrimethylsilane in Chemical Synthesis and Materials Science?Abstract This paper explores the advanced applications and potential value of Ethynyltrimethylsilane in chemical synthesis and materials science. It introduces the basic physical and chemical properti..; What are the applications and synthesis routes of Trimethylsilylacetylene?Introduction Trimethylsilylacetylene is a colorless and transparent liquid with a boiling point of 53℃/760mmHg. It is flammable and easily oxidized in the air, resulting in a darker color. It has man..; What is Trimethylsilylacetylene and how is it used?Trimethylsilylacetylene can be used as a biochemical reagent or even as a raw material in the chemical industry. Its applications are quite diverse and it can even be used as an intermediate product i..; Can Trimethylsilylacetylene be used to prepare organic silicon materials?Trimethylsilylacetylene, as a silicon-containing organic compound, is becoming increasingly popular in the market. This is closely related to the high precision of organic silicon materials. When prep..

12. Realated Product Infomation