Ethynyltrimethylsilane 三甲基乙炔基硅

CAS 1066-54-2 MFCD00008569

化学结构图

1066-54-2
SMILES: C#C[Si](C)(C)C

化学属性

Mol. FormulaC5H10Si
Mol. Weight98.22
Boiling Point52-53°C at 760 mmHg
TSCAT
Refractive index1.3890 to 1.3910
Density0.695
Flash Point-34°C
Vapor Pressure4.18 psi ( 20 °C)
Solubility起反应
Stability对空气和湿度敏感
Melting Point>0 °C
pH:A

别名和识别编码

Chemical NameEthynyltrimethylsilane
CAS Number1066-54-2
Alfabeta NameTRIMETHYLSILYLACETYLENE ()
MDL NumberMFCD00008569
Synonym (Trimethylsilanyl)acetylene {LY} (Trimethylsilanyl)acetylene {} {LY} (Trimethylsilanyl)acetylene {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Trimethylsilanyl)acetylene {} {} {} {} {} {} {} {} {} {} {} {
PubChem Substance ID87577015
Beilstein Registry Number906752
EC Number213-919-9
Reaxys-RN906752
Chemical Name Translation三甲基乙炔基硅
InChIKeyCWMFRHBXRUITQE-UHFFFAOYSA-N
LabNetwork Molecule IDLN00117256
InChIInChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3
Canonical SMILESC[Si](C)(C#C)C
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分类

  • Alkynes, Building Blocks, Chemical Synthesis, Organic Building Blocks, Terminal
  • {uni_hamburg} no charge; 1fragment
  • {SNA} Alkynes, Building Blocks, Chemical Synthesis, Organic Building Blocks, Terminal

产品应用

  • Ethynyltrimethylsilane was used in:
  • ? microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles
  • synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites
  • pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes

相关文献及参考

  • Beilstein: 4,IV,3937
  • For the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides, see: J. Org. Chem., 47, 2251 (1982).
  • Short: II/24A
  • Pd catalyzed coupling with aryl bromides or iodides gives aryl TMS alkynes, from which the TMS group is readily cleaved by K2CO3 in MeOH: Synthesis, 627 (1980); J. Org. Chem., 46, 2280 (1981). Coupling with 1-bromo-2-nitrobenzene or ethyl 2-bromocarbanilate gives indole precursors. Other terminal alkynes lead to 2-substituted indoles: Heterocycles, 24, 31 (1986):
  • Cross-coupling with aryl halides can also be catalyzed by Pd-C in the presence of Ph3P, CuI and Et3N: Synth. Commun., 20, 2059 (1990); for an example, see 2-Bromonaphthalene, A15300. Pd catalyzed coupling with quinolinol and isoquinolinol triflates has also been reported: Tetrahedron, 51, 3737 (1995). For coupling with vinyl halides catalyzed by Tetrakis(triphenyl­phosphine)­palladium(0)­, 10548 in the presence of CuI as an example of a route to enynes, see: Tetrahedron Lett., 30, 6997 (1989); Org. Synth. Coll., 9, 117 (1998). CuCl-TMEDA catalyzed oxidative (Hay) coupling gives bis(TMS)-1,3-butadiyne: Org. Synth. Coll., 8, 63 (1993).

安全信息

Warnings IRRITANT, KEEP COLD, FLAMMABLE
GHS Symbol
WGK Germany3
Hazard statements
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
Hazard Codes 3 F;Xi
Precautionary statements
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P233 Keep container tightly closed. ?保持容器密闭。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241+P242+P243
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P352+P332+P313+P362+P364
  • P303+P361+P353
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P370+P378
  • P403+P235
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S29 Do not empty into drains 不要排入下水道；
  • S33 Take precautionary measures against static discharges 对静电采取预防措施；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
Risk Statements
  • R11 Highly flammable 非常易燃
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
UN Number 1993 UN 1993 3/PG 2
Packing GroupII
Storage condition 2-8°C, protect from light, stored under nitrogen {LY} 2-8°C, protect from light, stored under nitrogen {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen
Hazard Class3

其他信息

  • 海关编码:29310095
  • 用途二:硅基保护基，用于通过对乙炔二氮化合物的1，3-两极环加成合成吡唑，镍催化的和苄腈偶联反应的底物。
  • MOL 文件:1066-54-2.mol
  • 三甲基乙炔基硅价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 xw010149 (三甲基硅烷基)乙炔 5ml 150元 2011/04/16 T1239 三甲基乙炔基硅 Trimethylsilylacetylene 250ML 8280元 2011/04/16 T1239 三甲基乙炔基硅 Trimethylsilylacetylene 25ML 1480元
  • 检测方法:GC,NMR
  • 用途一:1066-54-2（三甲基硅乙炔）是一种重要的香料、医药中间体，是重要的具硅基础化工原料之一，也是重要的炔基化试剂，在各种单炔，多炔烃的制备中是必不可少的合成基元。另外，在杂环化学，碳-碳偶联，药物合成，催化化学和材料工业中有很多应用。
  • 硅基保护基:三甲基硅基乙炔是一种硅基保护基，又称为三甲基乙炔基硅烷、三甲基硅乙炔、三甲基乙炔基硅、乙炔基三甲基硅烷， 室温下为无色透明液体，通过对乙炔二氮化合物的1，3-两极环加成合成吡唑，也是镍催化和苄腈偶联反应的底物。
  • Hazard Note:Flammable/Irritant
  • A substrate for nickel-catalyzed cross-coupling with benzonitriles. Pyrazole syntheses by 1,3-Dipolar cycloaddition of diazo compounds to acetylenes.
  • 蒸气压:4.18 psi ( 20 °C)
  • Sigma Aldrich:1066-54-2(sigmaaldrich)
  • MSDS 信息:Trimethylsilylacetylene(1066-54-2).msds
  • Alfa Aesar:(三甲基甲硅烷基）乙炔,98% (Trimethylsilyl)acetylene, 98%(1066-54-2)
  • Acros Organics:三甲基硅烷基乙炔/乙炔基三甲基硅烷 Trimethylsilylacetylene, 98%(1066-54-2)
  • 外观:无色至浅黄色透明液体，产品易燃，在空气中容易被氧化而颜色加深。
  • 包装:棕色玻璃瓶（避光）, 或50公斤内衬环氧树脂铁桶
  • TSCA:T
  • 上游原料:四氢呋喃 --> 钠 --> 甲苯 --> 溴乙烷 --> 三甲基氯硅烷 --> 硫酸镁 --> 乙炔
  • 和水反应，溶于大多数有机溶剂。
  • TCI Shanghai:三甲基乙炔基硅 Trimethylsilylacetylene,>;98.0%(GC)(1066-54-2)
  • 下游产品:4-氮杂吲哚 --> 1,3-二硫酸-2-硫因 --> 4-乙炔基苯胺
  • 生产厂家:南京纽安洁化工科技有限公司

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Alkynes 炔
  1. Chemical Synthesis 化学合成
  2. Chemical Biology 生物化学
  3. Conjugation Chemistry: Azides, Alkynes 共轭化学 (叠氮化物，炔烃等)
  4. Functionalized Alkynes 功能性炔烃
  1. Chemical Synthesis 化学合成
  2. Chemical Biology 生物化学
  3. Conjugation Chemistry: Azides, Alkynes 共轭化学 (叠氮化物，炔烃等)
  4. Functionalized Alkynes 功能性炔烃
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Alkynes 炔
  5. Terminal - Alkynes
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Alkynes 炔
  5. Internal
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Organosilicon 有机硅
  4. Silanes 硅烷
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Silicon Compounds for Organic Synthesis 硅化合物
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Acetylenes 炔烃
  1. Materials Science 材料科学
  2. Diacetylene Monocarboxylic Acids for LB Films