所有图片(2)
别名:
BTMSA
线性分子式:
(CH3)3SiC≡CSi(CH3)3
CAS号:
分子量:
170.40
Beilstein:
906870
EC 号:
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22
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质量水平
检测方案
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.)
储存温度
2-8°C
SMILES字符串
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 key
ZDWYFWIBTZJGOR-UHFFFAOYSA-N
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一般描述
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。
应用
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)。
警示用语：
Danger
危险分类
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
靶器官
Respiratory system
WGK
WGK 3
闪点(°F)
35.6 °F
闪点(°C)
2 °C
个人防护装备
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
法规信息
新产品
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)
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
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
Tetrahedron Letters, 35, 417-417 (1994)
商品
The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.
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