| Bis(trimethylsilyl)acetylene Basic information |
| Product Name: | Bis(trimethylsilyl)acetylene |
| Synonyms: | BIS(TRIMETHYLSILYL)ACETYLENE;BSTMA;BTMSA;Bis(trimethylsilyl)acetylene 99%;1,2-BIS-TRIMETHYLSILANYL-ETHYNE;TIMTEC-BB SBB008997;ICLA-002;1,2-Bis(trimethylsilyl)acetylene |
| CAS: | 14630-40-1 |
| MF: | C8H18Si2 |
| MW: | 170.4 |
| EINECS: | 238-671-9 |
| Product Categories: | Alkynes;Building Blocks;organosilicon compounds;Chemical Synthesis;Internal;Organic Building Blocks;Industrial/Fine Chemicals;Acetylenes;Ethynylsilanes;Functionalized Acetylenes;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry |
| Mol File: | 14630-40-1.mol |
| Bis(trimethylsilyl)acetylene Chemical Properties |
| Melting point | 21-24 °C(lit.) |
| Boiling point | 136-137 °C(lit.) |
| density | 0.752 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 29 °C |
| storage temp. | 2-8°C |
| form | liquid |
| Specific Gravity | 0.770 |
| color | colorless |
| Water Solubility | MAY DECOMPOSE |
| Hydrolytic Sensitivity | 2: reacts with aqueous acid |
| BRN | 906870 |
| InChIKey | ZDWYFWIBTZJGOR-UHFFFAOYSA-N |
| CAS DataBase Reference | 14630-40-1(CAS DataBase Reference) |
| NIST Chemistry Reference | Silane, 1,2-ethynediylbis[trimethyl-(14630-40-1) |
| EPA Substance Registry System | Silane, 1,2-ethynediylbis[trimethyl- (14630-40-1) |
| Safety Information |
| Hazard Codes | F,Xi |
| Risk Statements | 11-36/37/38-10 |
| Safety Statements | 16-26-36 |
| RIDADR | UN 1993 3/PG 2 |
| WGK Germany | 3 |
| F | 10 |
| TSCA | Yes |
| HazardClass | 3 |
| PackingGroup | III |
| HS Code | 29310095 |
| MSDS Information |
| Provider | Language |
|---|---|
| Bis(trimethylsilyl)acetylene | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| Bis(trimethylsilyl)acetylene Usage And Synthesis |
| Chemical Properties | clear colorless liquid after melting |
| Uses | In the presence of CpCo(CO)2 (cat. no. 245259), undergoes cycloaddition with 1,5-hexadiynes to form benzocyclobutenes.1 |
| Uses | BTMSA is used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It is also used in the synthesis of (+)-brasilenyne2 and (β-diketanato)Ag(BTMSA). Bis(trimethylsilyl)acetylene is a ligand that binds to a central metal ion (e.g. Titanium) to create a coordination complex. One of its complexes, Permethyltitanocene-bis(trimethylsilyl)acetylene, is a catalyst for the head-to-tail dimerization of 1-alkynes (e.g. 3-Penten-1-yne [P227430]). |
| General Description | Bis(trimethylsilyl)acetylene (BTMSA) participates as nucleophile in Friedel-Crafts type acylations and alkylations. BTMSA undergoes rhodium catalyzed addition reaction with diarylacetylenes. It undergoes cycloaddition with 1,5-hexadiynes in the presence of CpCo(CO)2 (Cp=cyclopentadienyl) to form benzocyclobutenes. Structure of BTMSA was characterized by a centre of inversion present on triple bond (length=1.208(3)?). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported. |
| Purification Methods | Dissolve it in pet ether and wash it with ice-cold dilute HCl. The pet ether extract is dried (MgSO4), evaporated and fractionated at 760mm. [Walton & Waugh J Organomet Chem 37 45 1972, Beilstein 4 IV 3950.] |
| Bis(trimethylsilyl)acetylene Preparation Products And Raw materials |
| Raw materials | Tetrahydrofuran-->Magnesium-->Copper(I) chloride-->Bromoethane-->Chlorotrimethylsilane-->Acetylene |
| Preparation Products | 4,4'-DIFLUORODIPHENYLACETYLENE-->TRANS,TRANS,CIS-1,5,9-CYCLODODECATRIENE-->Lincomycin 2,7-diacetate-->Trimethyl(phenoxy)silane |
Please leave a message for us or use the following ways to contact us, we will reply to you as soon as possible, and provide you with the most sincere service, thank you.
日本语
한국어
Français
Deutsch
España
Türkiye