烯丙基二氯甲基硅烷 | 1873-92-3

• 物质功能分类: 化学试剂 - 有机试剂 - 硅烷
• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 烯丙基二氯甲基硅烷
• 中文别名: 烯丙基甲基二氯硅烷；丙烯基甲基二氯硅烷；烯丙基二氯甲基硅；烯丙基甲基二氯硅烷,95％；烯
• 英文名称: allyldichloromethylsilane
• 英文别名: allyl (methyl)-dichlorosilane；dichloro-methyl-prop-2-enylsilane
• CAS: 1873-92-3
• 化学式: C₄H₈Cl₂Si
• mdl: MFCD00045141
• 分子量: 155.099
• InChiKey: YCEQUKAYVABWTE-UHFFFAOYSA-N

物化性质

• 沸点：
  119.5 °C (lit.)
• 密度：
  1.067 g/mL at 25 °C (lit.)
• 闪点：
  57 °F
• 稳定性/保质期：
  在常温常压下稳定，但应避免与不相容材料、火源、湿空气和水接触。它会与潮湿的空气、水、酸、碱、醇、胺、氨、过氧化物以及醛类（如乙醛、丙烯醛、三氯乙醛、甲醛）、酮类（如丙酮、苯乙酮、丁酮、甲基异丁基酮）发生反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  F,C
• 安全说明：
  S16,S26,S36/37/39,S45
• 危险类别码：
  R11
• WGK Germany：
  1
• 海关编码：
  2931900090
• 危险品运输编号：
  UN 2985 3/PG 2
• 包装等级：
  II
• 危险类别：
  3
• 储存条件：
  密封存储于阴凉、干燥的库房中，避免与潮湿和水源接触，并用干燥的惰性气体进行保护。

SDS

Name:	Allyldichloromethylsilane 97% Material Safety Data Sheet
Synonym:
CAS:	1873-92-3

Section 1 - Chemical Product MSDS Name:Allyldichloromethylsilane 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1873-92-3	Allyldichloromethylsilane	97	217-498-2

Hazard Symbols: F C
Risk Phrases: 11 14 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Reacts violently with water. Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes chemical burns to the respiratory tract. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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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. Vapors can travel to a source of ignition and flash back. Water Reactive. Material will react with water and may release a flammable and/or toxic gas. Containers may explode in the heat of a fire. Flammable liquid and vapor.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide. DO NOT USE WATER!

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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. Provide ventilation. Do not expose spill to water.

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Section 7 - HANDLING and STORAGE
Handling:
Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Keep away from sources of ignition. Store in a cool, dry place.
Store in a tightly closed container. Keep away from water.
Flammables-area. Store under an inert atmosphere.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1873-92-3: Personal Protective Equipment Eyes: Wear chemical splash goggles.
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 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Clear
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 119-120 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 20 deg C ( 68.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: reacts with water
Specific Gravity/Density: 1.0670g/cm3
Molecular Formula: CH2CHCH2Si(CH3)Cl2
Molecular Weight: 155.10

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, exposure to moist air or water.
Incompatibilities with Other Materials:
Oxidizing agents, acids, bases, alcohols, amines, ammonia, peroxides, aldehydes (e.g. acetaldehyde, acrolein, chloral hydrate, formaldehyde), ketones (e.g. acetone, acetophenone, MEK, MIBK).
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, carbon dioxide, silicon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1873-92-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Allyldichloromethylsilane - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Chlorosilanes, Flammable, Corrosive, N.O.S.
Hazard Class: 3
UN Number: 2985
Packing Group: II
IMO
Shipping Name: Chlorosilanes, Flammable, Corrosive, N.O.S.
Hazard Class: 3
UN Number: 2985
Packing Group: II
RID/ADR
Shipping Name: Chlorosilanes, Flammable, Corrosive, N.O.S.
Hazard Class: 3
UN Number: 2985
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F C
Risk Phrases:
R 11 Highly flammable.
R 14 Reacts violently with water.
R 34 Causes burns.
Safety Phrases:
S 8 Keep container dry.
S 16 Keep away from sources of ignition - No
smoking.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1873-92-3: No information available.
Canada
CAS# 1873-92-3 is listed on Canada's NDSL List.
CAS# 1873-92-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1873-92-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

可由甲基三氯硅烷与烯丙基溴化镁反应来制取。

合成制备方法

同样可以采用甲基三氯硅烷与烯丙基溴化镁的反应来进行制备。

用途简介

该物质主要用于合成有机硅中间体及高分子聚合物。

用途

它也被广泛用于合成有机硅中间体及高分子聚合物。

反应信息

• 作为反应物：
  描述：

  烯丙基二氯甲基硅烷 在 氢溴酸 、 过氧化苯甲酰 作用下， 生成 (3-bromopropyl)dichloromethylsilane
  参考文献：
  名称：

  Mironow, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1959, p. 1862;engl.Ausg.S.1781

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯丙基甲基二氯硅烷 生成 烯丙基二氯甲基硅烷
  参考文献：
  名称：

  Dehydrohalogenation of some organosilicon compounds and the rearrangement of trichloro(1,2-dichloroalkyl)silanes in their dehydrochlorination with aluminum chloride

  摘要：

  DOI：

  10.1007/bf00912262

文献信息

• Synthesis and conversion reactions of alkenyl- and hydride siloxanes
  作者：K.A. Andrianov、V.I. Sidorov、L.M. Khananashvili

  DOI：10.1016/s0022-328x(00)80325-3

  日期：1965.11

  organosiloxanes containing the vinyl group in the α- and β-positions, with diazomethane and phenyl azide have been studied. It is concluded that siloxanes containing the vinyl group in the α-position react with diazomethane and phenyl azide but not siloxanes with the vinyl group in the β-position. The 1-pyrazolin-3-yl derivatives of organosiloxanes formed decompose when heated yielding the corresponding

  已经研究了在α-和β-位含有乙烯基的有机硅氧烷与重氮甲烷和叠氮化苯的反应。结论是，在α位上具有乙烯基的硅氧烷与重氮甲烷和叠氮化物反应，但在β位上具有乙烯基的硅氧烷不与之反应。加热时形成的有机硅氧烷的1-吡唑啉-3-基衍生物分解，得到相应的烯丙基衍生物。
• Catalytic Synthesis of Functional Silicon-Stereogenic Silanes through<i>Candida antarctica</i>Lipase B Catalyzed Remote Desymmetrization of Silicon-Centered Diols
  作者：Xing Lu、Li Li、Wei Yang、Kezhi Jiang、Ke-Fang Yang、Zhan-Jiang Zheng、Li-Wen Xu

  DOI：10.1002/ejoc.201300932

  日期：2013.9

  A series of silicon-containing diols are synthesized and used in lipase-catalyzed remote desymmetrization. This synthetic method is valuable in the construction of optically active silicon-stereogenic organosilicon compounds. Good enantioselectivities of the remote desymmetrization was achieved with Candida antarctica lipase B (CAL-B) (up to 90:10er).

  一系列含硅二醇被合成并用于脂肪酶催化的远程去对称化。这种合成方法在构建光学活性硅-立体有机硅化合物方面很有价值。使用南极念珠菌脂肪酶 B (CAL-B)（高达 90:10er）实现了远程去对称化的良好对映选择性。
• PROCESS FOR PREPARING ORGANOCHLOROSILANES BY DEHYDROHALOGENATIVE COUPLING REACTION OF ALKYL HALIDES WITH CHLOROSILANES
  申请人：——

  公开号：US20020082438A1

  公开（公告）日：2002-06-27

  The present invention relates to a process for preparing organochlorosilanes and more particularly, to the process for preparing organochlorosilanes of formula I by a dehydrohalogenative coupling of hydrochlorosilanes of formula II with organic halides of formula III in the presence of quaternary phosphonium salt as a catalyst to provide better economical matter and yield compared with conventional methods, because only catalytic amount of phosphonium chloride is required and the catalyst can be separated from the reaction mixture and recycled easily, 1 wherein R 1 represents hydrogen, chloro, or methyl; X represents chloro or bromo; R 2 is selected from the group consisting of C 1-17 alkyl, C 1-10 fluorinated alkyl with partial or full fluorination, C 2-5 alkenyl, silyl containing alkyl group represented by (CH 2 ) n SiMe 3-m Cl m wherein n is an integer of 0 to 2 and m is an integer of 0 to 3, aromatic group represented by Ar(R′) q wherein Ar is C 6-14 aromatic hydrocarbon, R′ is C 1-4 alkyl, halogen, alkoxy, or vinyl, and q is an integer of 0 to 5, haloalkyl group represented by (CH 2 ) p X wherein p is an integer of 1 to 9 and X is chloro or bromo, and aromatic hydrocarbon represented by ArCH 2 X wherein Ar is C 6-14 aromatic hydrocarbons and X is a chloro or bromo; R 3 is hydrogen, C 1-6 alkyl, aromatic group represented by Ar(R′) q wherein Ar is C 6-14 aromatic hydrocarbon, R′ is C 1-4 alkyl, halogen, alkoxy, or vinyl, and q is an integer of 0 to 5; and R 4 in formula I is the same as R 2 in formula III and further, R 4 can also be (CH 2 ) p SiR 1 Cl 2 or ArCH 2 SiR 1 Cl 2 , when R 2 in formula III is (CH 2 ) p X or ArCH 2 X, which is formed from the coupling reaction of X—(CH 2 ) p+1 —X or XCH 2 ArCH 2 X with the compounds of formula II; or when R 2 and R 3 are covalently bonded to each other to form a cyclic compounds of cyclopentyl or cyclohexyl group, R 3 and R 4 are also covalently bonded to each other in the same fashion.

  本发明涉及一种制备有机氯硅烷的方法，更具体地说，涉及一种通过在四元磷盐存在下，将式II的氯硅烷与式III的有机卤化物脱卤偶联以制备式I的有机氯硅烷的方法，与传统方法相比，该方法提供了更好的经济性和产量，因为只需要催化量的磷盐氯化物，并且催化剂可以从反应混合物中分离并轻松回收， 其中 R 1 代表氢、氯或甲基； X代表氯或溴； R 2 选自由C 1-17 烷基、C 1-10 部分或全氟化的氟烷基、C 2-5 烯基、含有(CH 2 ) n SiMe 3-m Cl m 的硅基烷基，其中n为0至2的整数，m为0至3的整数，由Ar(R′) q 表示的芳香族，其中Ar为C 6-14 芳香烃，R′为C 1-4 烷基、卤素、烷氧基或乙烯基，q为0至5的整数，由(CH 2 ) p X表示的卤代烷基，其中p为1至9的整数，X为氯或溴，以及由ArCH 2 X表示的芳香烃，其中Ar为C 6-14 芳香烃，X为氯或溴； R 3 为氢、C 1-6 烷基、由Ar(R′) q 表示的芳香族，其中Ar为C 6-14 芳香烃，R′为C 1-4 烷基、卤素、烷氧基或乙烯基，q为0至5的整数；以及 式I中的R 4 与式III中的R 2 相同，此外，当式III中的R 2 为(CH 2 ) p X或ArCH 2 X时，R 4 还可以是(CH 2 ) p SiR 1 Cl 2 或ArCH 2 SiR 1 Cl 2 ，其中R 2 在式III中为(CH 2 ) p X或ArCH 2 X，它由X—(CH 2 ) p+1 —X或XCH 2 ArCH 2 X与式II的化合物的偶联反应形成；或 当R 2 和R 3 以共价键结合形成环戊基或环己基化合物时，R 3 和R 4 也以相同方式共价键结合。
• Process for preparing organochlorosilanes by dehydrohalogenative coupling reaction of alkyl halides with chlorosilanes
  申请人：Korea Institute of Science and Technology

  公开号：US06392077B1

  公开（公告）日：2002-05-21

  The present invention relates to a process for preparing organochlorosilanes and more particularly, to the process for preparing organochlorosilanes of R4R3CHSiR1Cl2 (I) by a dehydrohalogenative coupling of hydrochlorosilanes of HSiR1Cl2 (II) with organic halides of R2R3 CHX (III) in the presence of quaternary phosphonium salt as a catalyst to provide better economical matter and yield compared with conventional methods, because only a catalytic amount of phosphonium chloride is required and the catalyst can be separated from the reaction mixture and recycled easily.

  本发明涉及一种制备有机氯硅烷的方法，更具体地说，涉及一种通过在四元磷盐存在下，将氯硅烷HSiR1Cl2（II）与有机卤化物R2R3CHX（III）进行脱氢卤代偶联，从而制备R4R3CHSiR1Cl2（I）的方法。与传统方法相比，本方法提供更好的经济效益和产量，因为只需要少量的磷盐氯化物作为催化剂，并且催化剂可以从反应混合物中分离并轻松回收。
• Dehydrohalogenative coupling reaction of organic halides with silanes
  申请人：Korea Institute of Science and Technology

  公开号：US06251057B1

  公开（公告）日：2001-06-26

  The present invention relates to methods for making the compounds of formula I which is a dehydrohalogenative coupling of hydrochlorosilanes of formula II with organic halides of formula III in the presence of a Lewis base catalyst. R3CH2SiR1Cl2  (I) HSiR1Cl2  (II) R2CH2X  (III) In formulas I and II, R1 represents a hydrogen, chloro, or methyl; in formula III, X represents a chloro or bromo; in formula III, R2 can be selected from the group consisting of a C1-17 alkyl, a C1-10 fluorinated alkyl with partial or full fluorination, a C1-5 alkenyl groups, a silyl group containing alkyls, (CH2)nSiMe3-mClm wherein n is 0 to 2 and m is 0 to 3, aromatic groups, Ar(R′)1 wherein Ar is C6-14 aromatic hydrocarbon, R′ is a C1-4 alkyl, halogen, alkoxy, or vinyl, and q is 0 to 5, a haloalkyl group, (CH2)pX wherein p is 1 to 9 and X is a chloro or bromo; or an aromatic hydrocarbon, Ar CH2X wherein Ar is C6-14 aromatic hydrocarbon and X is a chloro or bromo. in formula I, R3 is the same as R2 in formula III and further, R3 can also be (CH2)pSiR1Cl2 or ArCH2SiR1Cl2 when R2 in formula III is (CH2)pX or ArCH2X, because of the coupling reaction of X with the compound of formula II.

  本发明涉及一种制备式I化合物的方法，该方法是在Lewis碱催化剂存在下，通过式II的氢氯硅烷与式III的有机卤化物的脱氢卤代偶联而得到的。 R3CH2SiR1Cl2  (I) HSiR1Cl2  (II) R2CH2X  (III) 在式I和II中，R1代表氢、氯或甲基；在式III中，X代表氯或溴；在式III中，R2可以选择自C1-17烷基、C1-10氟化烷基（部分或完全氟化）、C1-5烯基、含有矽烷基的矽基团（CH2)nSiMe3-mClm，其中n为0至2，m为0至3，芳香族基团、Ar(R′)1，其中Ar为C6-14芳香烃烃基，R′为C1-4烷基、卤素、烷氧基或乙烯基，q为0至5，卤代烷基、(CH2)pX，其中p为1至9，X为氯或溴；或芳香烃基、Ar CH2X，其中Ar为C6-14芳香烃烃基，X为氯或溴。在式I中，R3与式III中的R2相同，此外，R3也可以是(CH2)pSiR1Cl2或ArCH2SiR1Cl2，当式III中的R2为(CH2)pX或ArCH2X时，因为X与式II化合物的偶联反应。

表征谱图