亚甲基双[二甲基(2-吡啶基)硅烷] | 243468-48-6

• 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: 亚甲基双[二甲基(2-吡啶基)硅烷]
• 中文别名: 2,2'-[亚甲基双(二甲基硅烯)]双吡啶
• 英文名称: bis(2-pyridyldimethylsilyl)methane
• 英文别名: Methylenebis[dimethyl(2-pyridyl)silane]；[dimethyl(pyridin-2-yl)silyl]methyl-dimethyl-pyridin-2-ylsilane
• CAS: 243468-48-6
• 化学式: C₁₅H₂₂N₂Si₂
• 分子量: 286.524
• InChiKey: WZXVWYFOAXHQGL-UHFFFAOYSA-N

物化性质

• 沸点：
  358.5±27.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 储存条件：
  存放于惰性气体中，并避免接触湿气（以免发生分解）。

SDS

Methylenebis[dimethyl(2-pyridyl)silane] Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Methylenebis[dimethyl(2-pyridyl)silane]

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Methylenebis[dimethyl(2-pyridyl)silane]
Percent: >95.0%(GC)
CAS Number: 243468-48-6
Synonyms: Bis[dimethyl(2-pyridyl)silyl]methane , 2,2'-[Methylenebis(dimethylsilylene)]bispyridine
C15H22N2Si2
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Methylenebis[dimethyl(2-pyridyl)silane]

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapour or mist. Wash hands and face thoroughly after
handling.
Use a ventilation, local exhaust if vapour or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Protect from moisture.
Store away from incompatible materials such as oxidizing agents.
Moisture-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.
Methylenebis[dimethyl(2-pyridyl)silane]

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Pale yellow - Yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Silicon oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.
Methylenebis[dimethyl(2-pyridyl)silane]

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  亚甲基双[二甲基(2-吡啶基)硅烷] 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.5h， 生成 [bis(2-pyridyldimethylsilyl)methyl]lithium
  参考文献：
  名称：

  [双（2-吡啶基二甲基甲硅烷基）甲基]锂的简便生成及其与羰基化合物的反应。立体选择性合成乙烯基硅烷的新方法

  摘要：

  的产生（2- PyMe 2 Si）的2 CHLi容易被（2- PyMe的去质子化来实现2 Si）的2 CH 2使用Ñ在Et正丁基锂2 O的1（2- PyMe的H NMR分析2的Si ）Et 2 O- d 10中的2 CHLi显示两个吡啶基均与锂配位。发现由此生成的（2-PyMe 2 Si）2 CHLi与多种醛和酮反应，以极高的收率和完全的立体选择性（> 99％E）得到相应的乙烯基硅烷。

  DOI：

  10.1016/s0040-4020(01)00348-9
• 作为产物：
  描述：

  2-三甲基硅基吡啶 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 1.5h， 以63%的产率得到亚甲基双[二甲基(2-吡啶基)硅烷]
  参考文献：
  名称：

  [Bis(2-pyridyldimethylsilyl)methyl]lithium. New Reagent for the Stereoselective Synthesis of Vinylsilanes

  摘要：

  The generation of (2-PyMe2Si)(2)CHLi was easily accomplished by the deprotonation of (2-PyMe2Si)(2)CH2 using n-BuLi in Et2O. Thus generated (2-PyMe2Si)(2)CHLi was found to react with a variety of aldehydes and ketones to give the corresponding vinylsilanes in extremely high yields with complete stereoselectivities.

  DOI：

  10.1021/ol005735n

文献信息

• (2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent
  作者：Kenichiro Itami、Koichi Mitsudo、Jun-ichi Yoshida

  DOI：10.1016/s0040-4039(99)01028-x

  日期：1999.7

  (2-Pyridyldimethylsilyl)methyl lithium was found to react with organic bromides, aldehydes, ketones, and hydrosilanes in good to excellent yields. The resultant adducts were further oxidized with H2O2/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for hydroxymethylation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (2-吡啶基二甲基硅基)甲基锂被发现能与有机溴化物、醛、酮和氢硅烷反应，产率良好至优异。所得的加成物进一步用H₂O₂/KF氧化，以优异的产率生成相应的醇。因此，这一两步转化提供了一种高效的羟甲基化方法。（C）1999 Elsevier Science Ltd. 保留所有权利。
• Pyridyl Group Assisted Deprotonation of a Methyl Group on Silicon:  Complex Induced Proximity Effect and Novel Hydroxymethylation
  作者：Kenichiro Itami、Toshiyuki Kamei、Koichi Mitsudo、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.1021/jo015528g

  日期：2001.6.1

  A novel methodology for the deprotonation of a methyl group on silicon has been developed. This newly developed cr-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the a-silyl carbanion together with the inherent silicon a effect. It was found that the deprotonation (t-BuLi/Et(2)O/-78 degreesC) occurs with 2-pyridyltrimethylsilane but not with other related silanes such as phenyltrimethylsilane, 3-pyridyltrimethylsilane, and 4-pyridyltrimethylsilane. It seems that this deprotonation proceeded through the agency of the complex-induced proximity effect (CIPE) of a 2-pyridyl group on silicon. (1)H NMR analysis of (2-pyridyldimethylsilyl)methyllithium revealed the intramolecular coordination of a pyridyl group to lithium. ( 2-Pyridyldimethylsilyl)-methyllithium was found to react with chlorosilanes, hydrosilanes, chlorostannanes, bromine, iodine, organic bromides, aldehydes, and ketones in good to excellent yields. The resultant adducts were further oxidized with H(2)O(2)/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for the nucleophilic hydroxymethylation.
• Facile generation of [bis(2-pyridyldimethylsilyl)methyl]lithium and its reaction with carbonyl compounds. New method for the stereoselective synthesis of vinylsilanes
  作者：Kenichiro Itami、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.1016/s0040-4020(01)00348-9

  日期：2001.6

  (2-PyMe2Si)2CHLi in Et2O-d10 revealed the coordination of both pyridyl groups to lithium. Thus generated (2-PyMe2Si)2CHLi was found to react with a variety of aldehydes and ketones to give the corresponding vinylsilanes in extremely high yields with complete stereoselectivities (>99% E).

  的产生（2- PyMe 2 Si）的2 CHLi容易被（2- PyMe的去质子化来实现2 Si）的2 CH 2使用Ñ在Et正丁基锂2 O的1（2- PyMe的H NMR分析2的Si ）Et 2 O- d 10中的2 CHLi显示两个吡啶基均与锂配位。发现由此生成的（2-PyMe 2 Si）2 CHLi与多种醛和酮反应，以极高的收率和完全的立体选择性（> 99％E）得到相应的乙烯基硅烷。
• [Bis(2-pyridyldimethylsilyl)methyl]lithium. New Reagent for the Stereoselective Synthesis of Vinylsilanes
  作者：Kenichiro Itami、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.1021/ol005735n

  日期：2000.5.1

  The generation of (2-PyMe2Si)(2)CHLi was easily accomplished by the deprotonation of (2-PyMe2Si)(2)CH2 using n-BuLi in Et2O. Thus generated (2-PyMe2Si)(2)CHLi was found to react with a variety of aldehydes and ketones to give the corresponding vinylsilanes in extremely high yields with complete stereoselectivities.