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N,O-双(三甲基硅烷基)三氟乙酰胺 | 25561-30-2

中文名称
N,O-双(三甲基硅烷基)三氟乙酰胺
中文别名
N,O-双(三甲基硅烷)三氟乙酰胺;双(三甲基硅基)三氟乙酰胺;N,O-双(三甲基硅)三氟乙酰胺;N,O-双(三甲基硅基)三氟乙酰胺BSTFA;N,O-双(三甲基硅基)三氟乙酰胺;BSTFA;N,O-双(三甲基硅烷基)三氟乙酰胺(BSTFA);N,O-双(三甲硅基)三氟乙酰胺;双(三甲基甲硅烷基)三氟乙酰胺;N,O-双三甲硅基三氟乙酰胺;二(三甲基硅基)三氟乙酰胺;双三甲基硅烷三氟乙酰
英文名称
N,O-Bis(trimethylsilyl)trifluoroacetamide
英文别名
BSTFA;trimethylsilyl 2,2,2-trifluoro-N-trimethylsilylethanimidate
N,O-双(三甲基硅烷基)三氟乙酰胺化学式
CAS
25561-30-2
化学式
C8H18F3NOSi2
mdl
——
分子量
257.403
InChiKey
XCOBLONWWXQEBS-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    -10°C
  • 沸点:
    45-50 °C14 mm Hg(lit.)
  • 密度:
    0.97 g/mL(lit.)
  • 闪点:
    75 °C
  • 溶解度:
    与氯仿混溶。
  • 保留指数:
    887
  • 稳定性/保质期:

    如果按照规定使用和储存,则不会分解。应避免接触氧化物和酸。

计算性质

  • 辛醇/水分配系数(LogP):
    3.63
  • 重原子数:
    15
  • 可旋转键数:
    3
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.88
  • 拓扑面积:
    21.6
  • 氢给体数:
    0
  • 氢受体数:
    5

ADMET

毒理性
  • 副作用
Dermatotoxin - 皮肤烧伤。
Dermatotoxin - Skin burns.
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

  • TSCA:
    Yes
  • 危险等级:
    3
  • 危险品标志:
    C
  • 安全说明:
    S16,S26,S36/37/39,S45
  • 危险类别码:
    R34,R10
  • WGK Germany:
    3
  • 海关编码:
    29310095
  • 危险品运输编号:
    UN 2924 3/PG 3
  • 危险类别:
    3
  • 包装等级:
    III
  • 危险标志:
    GHS02,GHS05,GHS07
  • 危险性描述:
    H225,H302,H314
  • 危险性防范说明:
    P210,P280,P305 + P351 + P338,P310
  • 储存条件:
    | 2-8℃ |

SDS

SDS:c05557794780f884302d94fbbf5967ff
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Name: Bis(trimethylsilyl)trifluoroacetamide packaged in 1 ml ampules Material Safety Data Sheet
Synonym: BSTF
CAS: 25561-30-2
Section 1 - Chemical Product MSDS Name:Bis(trimethylsilyl)trifluoroacetamide packaged in 1 ml ampules Material Safety Data Sheet
Synonym:BSTF

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
25561-30-2 Bis(trimethylsilyl)trifluoroacetamide, 99+% 247-103-9
Hazard Symbols: XI
Risk Phrases: 10 36/37/38

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable. Irritating to eyes, respiratory system and skin.Moisture sensitive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
No information regarding eye irritation and other potential effects was found.
Skin:
No information regarding skin irritation and other potential effects was found.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
The toxicological properties of this substance have not been fully investigated.
Chronic:
Not available.

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Flammable liquid and vapor.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Remove all sources of ignition.
Use a spark-proof tool.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use only in a well-ventilated area.
Ground and bond containers when transferring material. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29CFR 1910.134 or European Standard EN 149. Always use a NIOSH or European Standard EN 149 approved respirator when necessary.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Appearance: clear, colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 45.0 - 50.0 deg C @
Freezing/Melting Point: -10 deg C
Autoignition Temperature: > 300 deg C (> 572.00 deg F)
Flash Point: 43 deg C ( 109.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: hydrolysis
Specific Gravity/Density: .9690g/cm3
Molecular Formula: CF3C=NSi(CH3)3OSi(CH3)3
Molecular Weight: 257.39

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, electrical sparks.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride, nitrogen, silicon oxide.
Hazardous Polymerization: Has not been reported.

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 25561-30-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Bis(trimethylsilyl)trifluoroacetamide, packaged in 1 ml ampules - Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION


Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: FLAMMABLE LIQUID, N.O.S.*
Hazard Class: 3
UN Number: 1993
Packing Group: III
IMO
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3.3
UN Number: 1993
Packing Group: III
RID/ADR
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Dangerous Goods Code: 3(31C)
UN Number: 1993

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 10 Flammable.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 25561-30-2: No information available.
United Kingdom Occupational Exposure Limits
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 25561-30-2 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
US FEDERAL
TSCA
CAS# 25561-30-2 is not listed on the TSCA inventory.
It is for research and development use only.


SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

N,O-双三甲基三乙酰胺是一种重要的医药中间体,能够降低含羟基化合物的极性,增加其挥发性,使其更适合GC分析。它主要用作中性硅烷化试剂,在基、氨基酸羧酸及烯醇的硅烷化保护中发挥重要作用。作为一种温和的中性硅烷化试剂,该物质具有反应活性高、选择性好以及反应收率高和后处理简单的优点。

制备

N,O-双三甲基三乙酰胺(分子式为CF₃CON[(CH₃)₃Si]₂)是一种甲基化试剂,由原料三甲基氯硅烷三乙胺和三乙酰胺组成。其特征在于原料按摩尔比分别为1.2~4:2~4:1。

合成工艺如下:向反应釜中加入三乙胺和三乙酰胺并搅拌1小时后,在氮气保护下,逐滴加入三甲基氯硅烷,并控制温度在50℃以下。2-6小时内加完后,在40-65℃内保护反应8-16小时。反应结束后,降温至35℃以下出料。

将反应产物加入封闭离心机中进行固液分离,母液送入浓缩釜进行浓缩,控制温度在60-100℃之间,压力为-0.2至-0.8大气压。再将浓缩后的母液送入精馏釜进行精馏,精馏条件:温度控制在60-100℃之间,压力为-0.2至-0.998大气压,塔高6-15米。最终得到无色透明的液体,在氮气保护下包装得到成品。

此外,N,O-双三甲基三乙酰胺还可用作医药中间体。99%纯度级别可用于GC-MS系统分析食品中的糠醛含量。它也用作气相色谱的硅烷化试剂和衍生化试剂

反应信息

  • 作为反应物:
    参考文献:
    名称:
    von Halasz,S.P.; Glemser,O., Chemische Berichte, 1970, vol. 103, p. 553 - 560
    摘要:
    DOI:
  • 作为产物:
    参考文献:
    名称:
    Lidy,W.; Sundermeyer,W., Chemische Berichte, 1976, vol. 109, p. 2542 - 2546
    摘要:
    DOI:
  • 作为试剂:
    描述:
    T406石油添加剂2-氟苯甲醛乙二醇甲醚对甲苯磺酸N,O-双(三甲基硅烷基)三氟乙酰胺 作用下, 以 2-甲基四氢呋喃 为溶剂, 生成 O-(2-methoxyethyl) N1-benzotriazole hemiaminal 、 O-(2-methoxyethyl) N2-benzotriazole hemiaminal 、 2-fluorobenzaldehyde bis(2-methoxyethyl)acetal
    参考文献:
    名称:
    用于合成 3-Oxo-3H-spiro[苯并呋喃-2,4′-哌啶]结构单元的 Umpolung 流动化学
    摘要:
    一种高效且可扩展的路线,用于合成3-oxo-3 H-螺环[苯并呋喃-2,4'-哌啶]-1'-甲酸叔丁酯,这是合成 SHP2 抑制剂GDC-1971 ( migoprotafib ) 的中心前手性中间体,已实现。从容易获得的 2-氟苯甲醛制备标题化合物包括形成改性的 Katritzky 苯并三唑半缩醛,其在被正丁基锂去质子化后,通过 1,2-加成到 4-氧代哌啶-1-甲酸叔丁酯参与反极性反应。 ( N -Boc-4-哌啶酮)。最值得注意的是,该反应被开发为一种强大的活塞流工艺,可以在数公斤上执行,而不需要在低温下运行的中试规模反应容器。用草酸处理所得四面体中间体导致塌陷成相应的4-(2-氟苯甲酰基)-4-羟基哌啶,其通过结晶分离为固体。合成以优化的分子内 S N Ar 反应和最终结晶结束,生成稳定的高质量中间体3-oxo-3 H-螺环[苯并呋喃-2,4'-哌啶]-1'-甲酸叔丁酯适合针对GDC-1971进行进一步功能化。
    DOI:
    10.1021/acs.joc.4c00337
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文献信息

  • Total Synthesis of Nucleoside Antibiotics Plicacetin and Streptcytosine A
    作者:Jiqiang Fu、Stephane Laval、Biao Yu
    DOI:10.1021/acs.joc.8b00006
    日期:2018.7.6
    Disaccharide nucleoside antibiotics plicacetin and streptcytosine A (also named rocheicoside A) were effectively synthesized through the common precursor cytosamine. The amosamine and amicetose moieties were efficiently assembled through an α-selective O-glycosylation, and the cytosine nucleus was subsequently introduced through a β-selective gold(I)-catalyzed N-glycosylation. Further microwave-assisted
    通过普通的前体胞嘧啶有效地合成了二糖核苷抗生素plicacetin和链胞嘧啶A(也称为rocheicoside A)。通过α-选择性的O-糖基化有效地组装了阿莫胺和amic糖部分,随后通过β-选择性的(I)催化的N-糖基化引入了胞嘧啶核。进一步的微波辅助酰胺化反应完成了模块合成。
  • Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of <i>Camellia oleifera</i>—Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects—
    作者:Sachiko Sugimoto、Guihua Chi、Yasuyo Kato、Seikou Nakamura、Hisashi Matsuda、Masayuki Yoshikawa
    DOI:10.1248/cpb.57.269
    日期:——
    The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia oleifera ABEL were found to exhibit inhibitory effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. The ethyl acetate- and 1-butanol-soluble fractions also showed inhibitory effects on rat lens aldose reductase and scavenging effects on 1,1-diphenylpicryl-2-hydrazyl radical and superoxide. From the 1-butanol-soluble fraction, four new acylated oleanane-type triterpene oligoglycosides, yuchasaponins A, B, C, and D, were isolated and their structures were elucidated on the basis of chemical and physicochemical evidence. On the other hand, quercetin 3-O-α-L-rhamnopyranoside and kaempferol 3-O-α-L-rhamnopyranoside were isolated from the ethyl acetate- and 1-butanol-soluble fractions as the principal constituents, and their gastroprotective effects were examined.
    山茶花(Camellia oleifera ABEL)花蕾的甲醇提取物及其丁醇可溶部分对大鼠乙醇吲哚美辛诱导的胃黏膜损伤显示出抑制作用。乙酸乙酯丁醇可溶部分还表现出对大鼠晶状体醛糖还原酶的抑制作用以及对1,1-二苯基-2-苦基自由基和超氧自由基的清除效果。从丁醇可溶部分中分离出四种新的酰化齐墩果烷型三萜寡糖苷,命名为玉茶皂苷A、B、C和D,其结构根据化学和物理化学证据得以阐明。另一方面,从乙酸乙酯丁醇可溶部分中分离出槲皮素3-O-α-L-鼠李糖苷和山柰酚3-O-α-L-鼠李糖苷作为主要成分,并对其胃保护作用进行了研究。
  • Strong influence of intramolecular Si⋯O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N -trimethylsilyl carboxamide derivatives
    作者:Roland Szalay、Veronika Harmat、János Eőri、Gábor Pongor
    DOI:10.1016/j.tetlet.2017.04.057
    日期:2017.6
    basis of DFT calculations, a good correlation between reactivity and the Si⋯O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides
    提出了比较简单的杂环羧酰胺(内酰胺,酰亚胺)的N-甲硅烷基化衍生物的醇解研究。二阶速率常数值的范围高达三个数量级。根据DFT计算,在每个化合物族中都发现反应性与Si⋯O距离之间具有良好的相关性。使用循环尿素同系物的甲醇分解的详细计算机制研究,评估了两种不同反应途径的生存能力。还讨论了三甲基甲硅烷基和三甲基甲硅烷氧基邻苯二甲酰亚胺的单晶X射线衍射结构中的特殊性。
  • Stereo-Inversion in the (4R)-γ-Decanolactone Synthesis by Saccharomyces cerevisiae: (2E,4S)-4-Hydroxydec-2-enoic Acid Acts as a Key Intermediate
    作者:Gunnar Köhler、Paul Evans、Leif-Alexander Garbe
    DOI:10.1002/hlca.201100280
    日期:2011.12
    erythro‐3,4‐dihydroxydecanoic acid and erythro‐3‐hydroxy‐γ‐decanolactone from methyl (2E,4S)‐4‐hydroxydec‐2‐enoate supports a net inversion to (4R)‐γ‐decanolactone via 4‐oxodecanoic acid. As postulated in a previous work, (2E,4S)‐4‐hydroxydec‐2‐enoic acid was shown to be a key intermediate during (4R)‐γ‐decanolactone formation via degradation of (3S,4S)‐dihydroxy fatty acids and precursors by Saccharomyces
    (2 E,4 R)-4-羟基癸-2-烯酸甲酯,(2 E,4 S)-4-羟基癸-2-烯酸甲酯和(±)-(2 E)-4-羟基癸酸乙酯[4 ‐ 2 H] dec-2-烯酸酯是化学合成的,并在酿酒酵母中孵育。观察到这些底物的最初C链伸长至C 12,并在较小程度上观察到C 14脂肪酸,随后形成γ-癸内酯。(2 E,4 R)-4-羟基癸-2-烯酸甲酯和(2 E,4 S)-4-羟基癸-2-烯酸甲酯的代谢转化均导致(4 R)γ-癸醇内酯的ee分别> 99%和ee达到80%。乙基的生物转化(±) - (2 ë)-4-羟基(4- 2 2H)癸-2-烯酸甲酯,得到(4 - [R )- γ - [ 2 H]癸与61%2 ħ标签保持和90%ee表明存在立体倒置途径。4-羟基癸酸的电子冲击质谱分析(图4)显示出C(4)→C(2)2 H的部分位移。的形成赤-3,4- dihydroxydecanoic酸和赤-3-羟基γ
  • Synthesis of Theophylline and 6-Thiotheophylline 7-Ribosyl Nucleosides
    作者:Rodrigo Rico-Gómez、Angel Rodríguez-González、Josefa Ríos-Ruíz、Francisco Nájera、J. Manuel López-Romero
    DOI:10.1002/ejoc.200300377
    日期:2003.10
    The syntheses of theophylline and thiotheophylline 7-ribopyranose and 7-ribofuranose nucleosides, both by direct coupling of the base and the sugar and by construction of the imidazole ring, are reported. The conformational syn/anti equilibrium of the peracetyl derivatives was studied by molecular mechanics and by the low-temperature line-shape/1H NMR method. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451
    报告了茶碱和茶碱 7-核糖和 7-呋喃核糖核苷的合成,包括碱基和糖的直接偶联以及咪唑环的构建。通过分子力学和低温线形/1H NMR 方法研究了过乙酰基衍生物的构象同步/反平衡。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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同类化合物

(2-溴乙氧基)-特丁基二甲基硅烷 鲸蜡基聚二甲基硅氧烷 骨化醇杂质DCP 马沙骨化醇中间体 马来酸双(三甲硅烷)酯 顺式-二氯二(二甲基硒醚)铂(II) 顺-N-(1-(2-乙氧基乙基)-3-甲基-4-哌啶基)-N-苯基苯酰胺 降钙素杂质13 降冰片烯基乙基三甲氧基硅烷 降冰片烯基乙基-POSS 间-氨基苯基三甲氧基硅烷 镓,二(1,1-二甲基乙基)甲基- 镁,氯[[二甲基(1-甲基乙氧基)甲硅烷基]甲基]- 锑,二溴三丁基- 铷,[三(三甲基甲硅烷基)甲基]- 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 钾(4-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-1-丁炔-1-基)(三氟)硼酸酯(1-) 金刚烷基乙基三氯硅烷 酰氧基丙基双封头 达格列净杂质 辛醛,8-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]- 辛甲基-1,4-二氧杂-2,3,5,6-四硅杂环己烷 辛基铵甲烷砷酸盐 辛基衍生化硅胶(C8)ZORBAX?LP100/40C8 辛基硅三醇 辛基甲基二乙氧基硅烷 辛基三甲氧基硅烷 辛基三氯硅烷 辛基(三苯基)硅烷 辛乙基三硅氧烷 路易氏剂-3 路易氏剂-2 路易士剂 试剂Cyanomethyl[3-(trimethoxysilyl)propyl]trithiocarbonate 试剂3-[Tris(trimethylsiloxy)silyl]propylvinylcarbamate 试剂3-(Trimethoxysilyl)propylvinylcarbamate 试剂2-(Trimethylsilyl)cyclopent-2-en-1-one 试剂11-Azidoundecyltriethoxysilane 西甲硅油杂质14 衣康酸二(三甲基硅基)酯 苯胺,4-[2-(三乙氧基甲硅烷基)乙基]- 苯磺酸,羟基-,盐,单钠聚合甲醛,1,3,5-三嗪-2,4,6-三胺和脲 苯甲醇,a-[(三苯代甲硅烷基)甲基]- 苯并磷杂硅杂英,5,10-二氢-10,10-二甲基-5-苯基- 苯基二甲基氯硅烷 苯基二甲基乙氧基硅 苯基二甲基(2'-甲氧基乙氧基)硅烷 苯基乙酰氧基三甲基硅烷 苯基三辛基硅烷 苯基三甲氧基硅烷