(2-Bromophenylethynyl)Trimethylsilane

• CAS: 38274-16-7
• Catalog Number: ACM38274167
• Category: Main Products
• Molecular Weight: 253.21 g/mol
• Molecular Formula: C11H13BrSi
• Boiling Point: 91 °C(2 mmHg)
• Flash Point: >113 °C
• Density: 1.19 g/mL at 25 °C (lit.)
• Appearance: Light yellow to Brown clear liquid
• Storage: 0-10 °CStore under inert gas
• Hazard Statements: H315 : Causes skin irritation.; H319 : Causes serious eye irritation.
• MDL Number: MFCD01321391
• Precautionary Statements: P264 : Wash skin thoroughly after handling.; P280 : Wear protective gloves/ eye protection/ face protection.; P302 + P352 : IF ON SKIN: Wash with plenty of water.; P337 + P313 : If eye irritation persists: Get medical advice/ attention.; P362 + P364 : Take off contaminated clothing and wash it before reuse.; P332 + P313 : If skin irritation °Ccurs: Get medical advice/ attention.
• PubChem ID: 354333591
• Signal Word: Warning
• Specific Gravity: 1.2

Case Study

Application of [(2-Bromophenylethynyl)Trimethylsilane] in the Synthesis of Novel Acetylenic Cyclophanes with Helical Chirality

Collins SK, et al. Organic Letters, 2000, 2(20), 3189-3192.

(2-Bromophenylethynyl)Trimethylsilane can form robust carbon-carbon bonds making it an essential building block in the synthesis of acetylenic and benzenoid systems. This case study examines its application in the creation of novel acetylenic cyclophanes exhibiting helical chirality, a structural feature of particular interest for potential liquid crystalline materials.
Synthesis Strategy
In the context of this study, (2-Bromophenylethynyl)Trimethylsilane serves as a critical intermediate for the preparation of diacetylenic cyclophanes. The synthetic approach begins with lithium-halogen exchange, followed by transmetalation with ZnBr, yielding a zincate intermediate. This intermediate is coupled with 1,4-bis(bromoethynyl)benzene using Pd(PPh3)4 as a catalyst, providing a key cyclophane precursor. Deprotection of the trimethylsilyl groups in subsequent steps produces functional diacetylene structures.
Potential Applications in Liquid Crystals
One of the primary motivations behind this synthesis was the potential use of acetylenic cyclophanes as liquid crystal dopants. Their rigid, chirally twisted structures make them promising candidates for inducing polarization in smectic liquid crystals, which are highly desirable for ferroelectric applications. By modifying the alkyl chain length and acetylenic spacers, the cyclophanes can be tuned to achieve specific optical and liquid crystalline properties.

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August 05, 2023

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Custom Q&A

What is the molecular formula of (2-Bromophenylethynyl)trimethylsilane?

The molecular formula is C11H13BrSi.

What is the molecular weight of (2-Bromophenylethynyl)trimethylsilane?

The molecular weight is 253.21 g/mol.

What is the IUPAC name of (2-Bromophenylethynyl)trimethylsilane?

The IUPAC name is 2-(2-bromophenyl)ethynyl-trimethylsilane.

What is the InChI of (2-Bromophenylethynyl)trimethylsilane?

The InChI is InChI=1S/C11H13BrSi/c1-13(2,3)9-8-10-6-4-5-7-11(10)12/h4-7H,1-3H3.

What is the InChIKey of (2-Bromophenylethynyl)trimethylsilane?

The InChIKey is FABNGXSCLHXUOH-UHFFFAOYSA-N.

What is the canonical SMILES of (2-Bromophenylethynyl)trimethylsilane?

The canonical SMILES is C[Si](C)(C)C#CC1=CC=CC=C1Br.

What is the CAS number of (2-Bromophenylethynyl)trimethylsilane?

The CAS number is 38274-16-7.

What is the European Community (EC) number of (2-Bromophenylethynyl)trimethylsilane?

The European Community (EC) number is 689-923-3.

What is the DSSTox Substance ID of (2-Bromophenylethynyl)trimethylsilane?

The DSSTox Substance ID is DTXSID80404123.

Is (2-Bromophenylethynyl)trimethylsilane a covalently-bonded unit?

Yes, (2-Bromophenylethynyl)trimethylsilane is a covalently-bonded unit.

Synthetic Use

Downstream Synthesis Route 1

• 38274-16-7

• 766-46-1

Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 34, p. 11535 - 11545

Downstream Synthesis Route 2

• 38274-16-7

• 18238-34-1

Reference: [1]Schepper, Jonas D. W.; Orthaber, Andreas; Pammer, Frank
[Journal of Organic Chemistry, 2021, vol. 86, # 21, p. 14767 - 14776]

Downstream Synthesis Route 3

• 38274-16-7
• 139608-51-8

• 144192-98-3

Reference: [1]Schmidt-Radde, Rachel H.; Vollhardt, K. Peter C.
[Journal of the American Chemical Society, 1992, vol. 114, # 24, p. 9713 - 9715]
[2]Dosa, Peter I.; Whitener, Glenn D.; Vollhardt, K. Peter C.; Bond, Andrew D.; Teat, Simon J.
[Organic Letters, 2002, vol. 4, # 12, p. 2075 - 2078]

Downstream Synthesis Route 4

• 38274-16-7
• 536-74-3

• 143192-59-0

Reference: [1]Resa, Sandra; Reiné, Pablo; Álvarez De Cienfuegos, Luis; Guisán-Ceinos, Santiago; Ribagorda, Mariá; Longhi, Giovanna; Mazzeo, Giuseppe; Abbate, Sergio; Mota, Antonio J.; Miguel, Delia; Cuerva, Juan M.
[Organic and Biomolecular Chemistry, 2019, vol. 17, # 36, p. 8425 - 8434]
[2]Schmittel, Michael; Strittmatter, Marc
[Tetrahedron, 1998, vol. 54, # 45, p. 13751 - 13760]
[3]Grubbs, Robert H.; Kratz, Detlef
[Chemische Berichte, 1993, vol. 126, # 1, p. 149 - 158]
[4]Arndt, Sebastian; Borstelmann, Jan; Eshagh Saatlo, Rebeka; Antoni, Patrick W.; Rominger, Frank; Rudolph, Matthias; An, Qingzhi; Vaynzof, Yana; Hashmi, A. Stephen K.
[Chemistry - A European Journal, 2018, vol. 24, # 31, p. 7882 - 7889]

* For details of the synthesis route, please refer to the original source to ensure accuracy.