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Merck
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文件

187437

Sigma-Aldrich

双(三甲基甲硅烷基)乙炔

99%

别名:

BTMSA

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About This Item

线性分子式:
(CH3)3SiC≡CSi(CH3)3
CAS号:
14630-40-1
分子量:
170.40
Beilstein:
906870
EC號碼:
238-671-9
MDL號碼:
MFCD00008276
分類程式碼代碼:
12352100
PubChem物質ID:
24851275
NACRES:
NA.22

化驗

99%

折射率

n20/D 1.427 (lit.)

bp

136-137 °C (lit.)

mp

21-24 °C (lit.)

密度

0.752 g/mL at 25 °C (lit.)

儲存溫度

2-8°C

SMILES 字串

C[Si](C)(C)C#C[Si](C)(C)C

InChI

1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3

InChI 密鑰

ZDWYFWIBTZJGOR-UHFFFAOYSA-N

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一般說明

双(三甲基硅基)乙炔(BTMSA)以亲核试剂的形式参与Friedel-Crafts酰化和烷基化反应。在铑催化条件下，BTMSA与二芳基乙炔进行加成反应。在存在CpCo(CO)2（Cp =环戊二烯基）的条件下，其与1,5-己二炔进行环加成反应，形成苯并环丁烯。 BTMSA的结构特征是三键（长度= 1.208(3)Å）存在对称中心。 据报道称，TiCl4-Et2AlCl可催化BTMSA与降冰片二烯的Diels-Alder反应。

應用

双(三甲基硅基)乙炔(BTMSA)被用作合成官能团化的4-R-1,2-双(三甲基硅基)苯的起始试剂。它还用于合成 (+)-巴西炔和(β-diketanato)Ag(BTMSA)。

象形圖

FlameExclamation mark
GHS02,GHS07

訊號詞

Danger

危險分類

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

標靶器官

Respiratory system

儲存類別代碼

3 - Flammable liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

35.6 °F - closed cup

閃點（°C）

2 °C - closed cup

個人防護裝備

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Titanium-catalyzed cycloaddition-cycloreversion cascade in the reaction of norbornadiene with bis (trimethylsilyl) acetylene.
Mach K, et al.
Organometallics, 5(6), 1215-1219 (1986)
Bis (trimethylsilyl) acetylene.
Bruckmann J and Kruger C.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 53(12), 1845-1846 (1997)
Scott E Denmark et al.
Journal of the American Chemical Society, 124(51), 15196-15197 (2002-12-19)
The first, total synthesis of (+)-brasilenyne (1) has been achieved in 19 steps from l-(S)-malic acid. The key elements of this approach are a highly diastereoselective ring-opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene) promoted by TiCl4 to set a propargylic stereocenter
Akinobu Horita et al.
Organic letters, 10(9), 1751-1754 (2008-04-10)
The addition of bis(trimethylsilyl)acetylene to diarylacetylenes proceeds efficiently and selectively in a formal anti fashion in the presence of [Rh(OH)(cod)]2/bisphosphine and phenol as catalyst and activator, respectively, accompanied by cleavage of one of the C-Si bonds to produce the corresponding
Tetrahedron Letters, 35, 417-417 (1994)
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Diels–Alder Reaction

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