简介
有机硅烷类化合物主要应用在有机合成及有机硅材料领域。在有机合成中,硅烷作为羟基 保护基大量存在,如三甲基氯硅烷,TBSCI,有时作为一个合成子载体存在,如乙烯基三甲基 硅烷,烯丙基三甲基硅烷,六甲基二硅硫烷等,从而实现相应的官能团化反应。有机硅材料领域有硅烷偶联剂、硅油(硅脂、硅乳液、硅表面活性剂)、高温硫化硅橡胶、液体硅橡胶、硅 树脂、封端剂,含硅复合共聚物等。
应用介绍及参考文献
1.如乙烯基三甲基硅烷作为一个“乙烯”合成子,用于3+2环加成反应,应用于有机合成过程中。

图片来源于期刊:Vinyltrimethylsilane, Glenn J. Fegley Gerald L. Larson, Encyclopedia of Reagents for Organic Synthesis, 2008.
2.如烯丙基三甲基硅烷,作为一个烯丙基化试剂,应用于艾日布林或者前列素类似物的合成中。

图片来源于期刊:W020050118565, WO2019102490

图片来源于期刊:Gary A. Sulikowski et al Org. Lett. 2019, 21, 10048-10051
3.作为聚合引发剂,或者烯姪共聚物,参与烯姪聚合,形成功能性有机硅材料,如耐水性硅胶 粘合剂,修饰聚氟乙烯等
技术优势
产品纯度高,具有百公斤生产能力
Chemical Name | Allyltrimethylsilane |
Synonym |
Allyltrimethylsilane
{LY} Allyltrimethylsilane
allyltrimethylsilane
{} {LY} Allyltrimethylsilane
{} {} {LY} Allyltrimethylsilane
{} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {} {
{} {} {} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allyltrimethylsilane
{} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} |
MDL Number | MFCD00008635 |
CAS Number | 762-72-1 |
EC Number | 212-104-5 |
Beilstein Registry Number | 906755 |
PubChem Substance ID | 69808 |
Reaxys-RN | 906755 |
Chemical Name Translation | 烯丙基三甲基硅烷 |
LabNetwork Molecule ID | LN00008514 |
InChI | InChI=1S/C6H14Si/c1-5-6-7(2,3)4/h5H,1,6H2,2-4H3 |
Canonical SMILES | C[Si](C)(C)CC=C |
Signal word |
Danger |
GHS Symbol
WGK Germany | 3 |
Safety Statements | |
- S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
- S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾;
- 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;
- 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;
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
- S37 Wear suitable gloves 戴适当手套;
- 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
|
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 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
- P242 Use only non-sparking tools. 只能使用无火花工具。
- P243 Take precautionary measures against static discharge. 采取预防措施,防止静电放电。
- 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。
- P264+P265
- P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
- 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
- P302+P352+P312+P362+P364
- P303+P361+P353
- P304+P340
- P305+P351+P338
- P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
- P319
- P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
- P332+P313
- P332+P317
- P337+P313
- P337+P317
- 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
- P362+P364
- P370+P378
- P403+P233
- P403+P235
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
|
Packing Group | II |
UN Number |
1993
UN 1993 3/PG 2 |
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 |
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
Hazard Codes |
3
F;Xi |
Hazard Class | 3 |
Storage condition |
2-8°C, stored under nitrogen
{LY} 2-8°C, stored under nitrogen
{} {LY} 2-8°C, stored under nitrogen
{} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen
{} {} {} {} {} {} {} {} {} {} {} {} {} {} { |
用于高分子有机硅化合物的合成
{ALF} Has also been used, in the presence of a catalyst such as p-TsOH, I2, Br2 or TfOH, as a silylating agent for alcohols, phenols and carboxylic acids: Tetrahedron Lett., 21, 835 (1980); J. Org. Chem., 46, 5212 (1981). The advantage over more conventional silylation methods is that the only by-product is the neutral gas propene.
{ALF} Reactions with electrophiles illustrate the ß-effect (see Appendix 4); e.g. acid chlorides with a Lewis acid give allyl ketones: J. Organomet. Chem., 85, 149 (1975):
{uni_hamburg} Short: III/35C4
{ALF} More recent studies have shown that TMS cyclopentanes are also formed in these reactions via a competing [3+2] cycloaddition mechanism: Tetrahedron, 49, 9955 (1993). Chemoselective addition to aldehydes can be accomplished in the presence of a ketone, using Scandium(III)­ trifluoromethanesulfonate hydrate, 40566 as catalyst: Synthesis, 1822 (1998).
{ALF} In the presence of F-, functions as an allyl anion equivalent, affording homoallylic alcohols from carbonyl compounds: Tetrahedron Lett., 3043 (1978), and adding to a variety of Michael acceptors: Tetrahedron Lett., 25, 3213 (1984); J. Org. Chem., 51, 1745 (1986). For a review of reactivity in the presence of Lewis acids and F-, see: J. Prakt. Chem./ Chem. Ztg., 336, 375 (1994).
{ALF} Similarly, carbonyl compounds are converted to homoallylic alcohols: J. Organomet. Chem., 69, C15 (1974). In the TiCl4 promoted reaction with enones, behaves as an allyl anion equivalent, giving the product of conjugate addition (Hosomi-Sakurai reaction): J. Am. Chem. Soc., 99, 1673 (1977); 105, 2354 (1983); Org. Synth. Coll., 7, 443 (1990):
{ALD} Merck: 14,10335
{uni_hamburg} Short: III/35F
{ALD} Merck: 14,10335
Beilstein:4(3)1854