2-(叔丁基二甲基甲硅烷基)-1-甲基-1H-咪唑 | 160425-48-9

• 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: 2-(叔丁基二甲基甲硅烷基)-1-甲基-1H-咪唑
• 中文别名: 2-(叔丁基二甲基硅基)-1-甲基-1H-咪唑；2-(叔丁基二甲基甲硅烷基)-1-甲基咪唑
• 英文名称: 2-(tert-Butyl-dimethyl-silanyl)-1-methyl-1H-imidazole
• 英文别名: 2-(tert-butyldimethylsilyl)-1-methyl-1H-imidazole；2-tert-butyl-dimethylsilyl-N-methylimidazole；2-(t-butyldimethylsilyl)-1-methylimidazole；tert-butyl-dimethyl-(1-methylimidazol-2-yl)silane
• CAS: 160425-48-9
• 化学式: C₁₀H₂₀N₂Si
• mdl: MFCD01863660
• 分子量: 196.368
• InChiKey: QXALJDVEKIUPAE-UHFFFAOYSA-N

物化性质

• 熔点：
  31-35 °C(lit.)
• 沸点：
  250-260 °C(lit.)
• 密度：
  0.89±0.1 g/cm3(Predicted)
• 闪点：
  219 °F
• 稳定性/保质期：

  在常温常压下稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933290090
• 安全说明：
  S26

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 2-(tert-Butyldimethylsilyl)-1-methyl-1H-imidazole

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
According to European Directive 67/548/EEC as amended.
Irritating to eyes, respiratory system and skin.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Hazard symbol(s)
Xi Irritant
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C10H20N2Si
Molecular Weight : 196,36 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
2-(tert-Butyldimethylsilyl)-1-methyl-1H-imidazole
160425-48-9 - - Skin Irrit. 2; Eye Irrit. 2; STOT -
SE 3; H315, H319, H335
Xi, R36/37/38
For the full text of the H-Statements mentioned in this Section, see Section 16.

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Section 4. FIRST AID MEASURES
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed
containers for disposal.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Normal measures for preventive fire protection.
Conditions for safe storage
Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully
resealed and kept upright to prevent leakage. Store in cool place.

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with
multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to
engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Hand protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without
touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves
after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Eye protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and
approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin and body protection
impervious clothing, The type of protective equipment must be selected according to the concentration
and amount of the dangerous substance at the specific workplace.
Hygiene measures
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form liquid
Safety data
pH no data available
Melting point 31 - 35 °C - lit.
Boiling point 250 - 260 °C - lit.
Flash point 104 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Water solubility no data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx),
Sulphur oxides, Hydrogen iodide

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Section 11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional
waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
Not dangerous goods

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.

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Section 16. OTHER INFORMATION
Text of H-code(s) and R-phrase(s) mentioned in Section 3
Eye Irrit. Eye irritation
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Xi Irritant
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2010 Co. License granted to make unlimited paper copies for internal use only.
The above information is believed to be correct but does not purport to be all inclusive and shall be used
only as a guide. The information in this document is based on the present state of our knowledge and is
applicable to the product with regard to appropriate safety precautions. It does not represent any guarantee
of the properties of the product. Co., shall not be held liable for any damage resulting from
handling or from contact with the above product. See reverse side of invoice or packing slip for additional
terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2-(叔丁基二甲基甲硅烷基)-1-甲基-1H-咪唑 在 四(三苯基膦)钯 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 4.25h， 生成 2-[2-(tert-butyl-dimethylsilyl)-3-methyl-3H-imidazol-4-yl]-7-chloro-thieno[3,2-b]pyridine
  参考文献：
  名称：

  大规模制备咪唑-噻吩并吡啶的交叉偶联方法：[2-(3-Methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl]-的合成(2-甲基-1H-吲哚-5-基)-胺

  摘要：

  [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl]-(2-methyl-1H-indol-5-yl)的数百克合成)-胺 (1) 描述了利用碘噻吩并吡啶 (3) 与 5-(三丁基甲锡烷基)-1-甲基咪唑 (11) 的 Stille 交叉偶联。评估了几种交叉偶联方法将噻吩并吡啶 3 转化为咪唑-噻吩并吡啶 2，但只有两种方法有效：Stille 偶联和源自 2-(叔丁基二甲基甲硅烷基)-1- 的有机锌试剂的 Negishi 交叉偶联甲基咪唑和碘噻吩并吡啶 (3)。后一种方法在实验室规模 (<50 g) 上运行良好，但在放大时反复无常。讨论了有机锡烷试剂放大的问题，包括有机锡水平的控制和分析。

  DOI：

  10.1021/op0340457
• 作为产物：
  描述：

  N-甲基咪唑 、 叔丁基二甲基氯硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2-(叔丁基二甲基甲硅烷基)-1-甲基-1H-咪唑
  参考文献：
  名称：

  自组装的环状三聚体和1-甲基-5-咪唑基钴（III）卟啉四聚体的动态平衡

  摘要：

  自组装的多卟啉系统的动态平衡是获得可转换的光响应材料的关注点，但鲜有报道。在此合成的1-甲基-5-咪唑基钴（III）卟啉（1Co）通过分子间咪唑-钴（III）的配位自动组装成环状三聚体和四聚体。三聚体-四聚体平衡取决于浓度和溶剂，如通过NMR光谱法所检查的。在CDCl 3中，由于三聚体与四聚体的比例在14.8 mM 1Co下为1：2 ，而在74 mM下变为1：8，因此在高浓度时四聚体的形成是有利的。此外，当将样品从CHCl 3溶液浓缩至干时，溶解时该比例增加至1:24。在CD 3中另一方面，OD在宽浓度范围内仅观察到三聚体。因此，可以通过选择浓度和溶剂选择性地制备三聚体和四聚体结构。

  DOI：

  10.1560/c64h-mnq6-58ma-ffq2

文献信息

• Highly regioselective C-5 alkynylation of imidazoles by one-pot sequential bromination and Sonogashira cross coupling
  作者：Fabio Bellina、Marco Lessi、Giulia Marianetti、Alessandro Panattoni

  DOI：10.1016/j.tetlet.2015.04.094

  日期：2015.6

  A variety of 2-substituted 5-alkynyl-1H-imidazoles were easily prepared by a one-pot sequential procedure involving a highly regioselective electrophilic C-5 bromination of 1,2-dimethyl-1H-imidazole, 2-chloro-1-methyl-1H-imidazole, and 2-aryl-1-methyl-1H-imidazoles, followed by an efficient palladium/copper co-catalyzed Sonogashira-type alkynylation.

  可通过一锅顺序程序轻松制备各种2取代的5-炔基-1 H-咪唑，该程序涉及1，2-二甲基-1 H-咪唑，2-氯-1的高度区域选择性亲电C-5溴化反应-甲基-1 H-咪唑和2-芳基-1-甲基-1 H-咪唑，然后进行有效的钯/铜共催化的Sonogashira型炔基化反应。
• Thienopyrimidine and thienopyridine derivatives useful as anticancer agents
  申请人：Pfizer Inc.

  公开号：US06492383B1

  公开（公告）日：2002-12-10

  The invention relates to compounds of the formulas 1 and 2 and to pharmaceutically acceptable salts and hydrates thereof, wherein X1, R1, R2 and R11 are as defined herein. The invention also relates to pharmaceutical compositions containing the compounds of formulas 1 and 2 and to methods of treating hyperproliferative disorders in a mammal by administering the compounds of formulas 1 and 2.

  本发明涉及式1和式2的化合物以及其药学上可接受的盐和溶剂合物，其中X1、R1、R2和R11如本文所定义。本发明还涉及包含式1和式2化合物的药物组合物，以及通过施用式1和式2的化合物治疗哺乳动物的过度增殖性疾病的方法。
• Quinolin-2-one derivatives useful as anticancer agents
  申请人：Pfizer Inc.

  公开号：US06495564B1

  公开（公告）日：2002-12-17

  The present invention relates to compounds of formula 1 and to pharmaceutically acceptable salts, prodrugs and solvates thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, and R11 are as defined herein. The above compounds of formula 1 are useful in the treatment of hyperproliferative disorders, such as cancer, in mammals. The invention also relates to pharmaceutical compositions containing the compounds of formula 1 and to methods of inhibiting abnormal cell growth, including cancer, in a mammal by administering the compounds of formula 1 to a mammal requiring such treatment.

  本发明涉及式1的化合物以及其药学上可接受的盐、前药和溶剂化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11如本文所定义。式1的上述化合物在哺乳动物中用于治疗高增殖性疾病，如癌症。本发明还涉及含有式1的化合物的药物组合物，以及通过向需要此类治疗的哺乳动物给予式1的化合物来抑制异常细胞生长，包括癌症的方法。
• Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis
  作者：Kyalo Stephen Kanyiva、Florian Löbermann、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1016/j.tetlet.2009.02.195

  日期：2009.7

  Nickel/Lewis acid binary catalysis is found effective to direct regioselective alkenylation of imidazoles through C–H bond activation and stereoselective insertion of alkynes. Use of P(t-Bu)3 as a ligand allows exclusive regioselective C(2)-alkenylation, while PCyp3 is found effective for C(5)-alkenylation of C(2)-substituted imidazoles. The reaction demonstrates a broad scope of imidazoles and internal

  发现镍/路易斯酸二元催化可通过C–H键活化和炔烃的立体选择性插入，有效地指导咪唑的区域选择性烯基化。P（t- Bu）3作为配体的使用允许排他性区域选择性C（2）-烯基化，而PCyp 3被发现对C（2）-取代的咪唑的C（5）-烯基化有效。该反应表明，咪唑和内部炔烃的范围很广，可以适度地以良好的收率高区域和立体选择性地产生三取代的乙烯。
• Alkynyl-substituted quinolin-2-one derivatives useful as anticancer agents
  申请人：Pfizer Inc

  公开号：US06579887B2

  公开（公告）日：2003-06-17

  The present invention relates to compounds of formula 1 and to pharmaceutically acceptable salts, prodrugs and solvates thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, and R11 are as defined herein. The above compounds of formula 1 are useful in the treatment of hyperproliferative disorders, such as cancer, in mammals. The invention also relates to pharmaceutical compositions containing the compounds of formula 1 and to methods of inhibiting abnormal cell growth, including cancer, in a mammal by administering the compounds of formula 1 to a mammal requiring such treatment

  本发明涉及公式1化合物及其药学上可接受的盐、前药和溶剂化物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11如本文所定义。公式1化合物可用于哺乳动物的高增殖性疾病治疗，例如癌症。本发明还涉及含有公式1化合物的制药组合物，以及通过向需要此类治疗的哺乳动物施用公式1化合物来抑制异常细胞生长，包括癌症的方法。

表征谱图