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187437

Sigma-Aldrich

双(三甲基甲硅烷基)乙炔

99%

同義詞:

BTMSA

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About This Item

線性公式:
(CH3)3SiC≡CSi(CH3)3
CAS號碼:
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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相關類別

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

從最近期的版本中選擇一個：

分析證明 (COA)

Lot/Batch Number
MKCQ8929
MKCN1903
MKCL0605
MKCK0428
MKCG7825

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Bis (trimethylsilyl) acetylene.
Bruckmann J and Kruger C.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 53(12), 1845-1846 (1997)
Titanium-catalyzed cycloaddition-cycloreversion cascade in the reaction of norbornadiene with bis (trimethylsilyl) acetylene.
Mach K, et al.
Organometallics, 5(6), 1215-1219 (1986)
MOCVD of Silver Thin Films from the (1, 1, 1, 5, 5, 5-Hexafluoro-2, 4-pentanedionato)-silver [bis (trimethylsilyl) acetylene] Complex.
Chi KM and Lu YH.
Chem. Vap. Deposition, 7(3), 117-120 (2001)
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
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文章

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

Diels–Alder Reaction

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.

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

Reagents for C–C Bond Formation

Reagents for C–C Bond Formation

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