溴甲基苯甲酸频那酯 | 166330-03-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 溴甲基苯甲酸频那酯
• 中文别名: 2-(溴甲基)-4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷；溴甲基硼酸频哪醇酯；(溴甲基)硼酸频哪醇酯
• 英文名称: pinacol (bromomethyl)boronate
• 英文别名: 2-(bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；bromomethylboronic acid pinacol ester；(bromomethyl)pinacolborane
• CAS: 166330-03-6
• 化学式: C₇H₁₄BBrO₂
• 分子量: 220.902
• InChiKey: KBGMAXNDJAGTDD-UHFFFAOYSA-N

物化性质

• 沸点：
  68 °C / 6mmHg
• 密度：
  1.26
• 闪点：
  62.8±22.6℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P210,P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313,P403+P235,P501
• 危险性描述：
  H227,H315,H319,H335
• 储存条件：
  存储条件为：0-10°C，需置于惰性气体中，并远离潮湿环境以防分解和受热。

SDS

2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2- Revision number: 1
dioxaborolane
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: 2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS
Flammable liquids Category 4
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements
Pictograms or hazard symbols
Warning
Signal word
Hazard statement Combustible liquid
Causes skin irritation
Causes serious eye irritation
Precautionary statements
[Prevention] Keep away from flames and hot surfaces.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
[Response] IF IN EYES: 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.
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.
[Storage] Store in a well-ventilated place. Keep cool.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance
Substance/mixture:
Component(s): 2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
>90.0%(GC)(T)
Percent:
CAS Number: 166330-03-6
Synonyms: (Bromomethyl)boronic Acid Pinacol Ester
2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-
dioxaborolane

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Chemical Formula: C7H14BBrO2

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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.
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.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Extinguishing media not to Solid streams of water
be used:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: 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.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapor or mist. Keep away from flames and hot surfaces. Take
measures to prevent the build up of electrostatic charge. Use explosion-proof
equipment. Wash hands and face thoroughly after handling.
Use a closed system, ventilation.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Storage conditions: Keep container tightly closed. Store in a refrigerator.
Store under inert gas.
Protect from moisture.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.
2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-
dioxaborolane

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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.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
clear
Form:
Color: Colorless - Yellow
No data available
Odor:
pH: No data available
Melting point/freezing point:No data available
Boiling Point/Range: 68 °C/0.8kPa
Flash Point: No data available
Explosive limits
No data available
Lower:
Upper: No data available
1.26
Density:
Solubility: No data available

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Conditions to avoid: Heat-sensitive, Moisture-sensitive
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Boron oxides , Hydrogen bromide
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):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):
2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-
dioxaborolane

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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.

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

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): 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

制备方法与用途

用途

溴甲基苯甲酸频那酯是一种有机硼化合物，因其在有机合成和催化中的潜在应用而受到广泛研究。它是一种多功能试剂，具有广泛的反应性，适用于狄尔斯-阿尔德反应、迈克尔反应和维蒂希反应等多种反应。此外，BMTMD 还被证明可作为催化剂用于合成各种化合物，如杂环、胺、聚合物（包括聚酯和聚酰胺）以及有机金属化合物（包括硼酸盐、硼酸酯和硼酸）。

反应信息

• 作为反应物：
  描述：

  溴甲基苯甲酸频那酯 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以97%的产率得到碘甲基硼酸频哪醇酯
  参考文献：
  名称：

  直接光获取 α-硼基自由基：在烯丙基硼酯立体发散合成中的应用**

  摘要：

  α-硼基自由基作为多功能中间体重新出现，通过相邻的 C−C 键形成来获取有机硼。我们公开了使用光和路易斯碱轻松活化α-卤代硼酸酯以允许均裂。添加到苯乙烯中可以构建E-烯丙基硼酸酯。活化的简单性允许与能量转移催化的战略合并，从而实现Z异构体的立体发散合成。

  DOI：

  10.1002/anie.202307540
• 作为产物：
  描述：

  频哪醇 在 正丁基锂 、 硼酸三异丙酯 、 甲烷磺酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.0h， 以68%的产率得到溴甲基苯甲酸频那酯
  参考文献：
  名称：

  Fluoroboron compound, aminomethylating agent for aromatic ring made of the same, and production method of compound containing aminomethyl aromatic ring using aminomethylating agent

  摘要：

  本发明涉及一种含有一级、二级或三级氨甲基芳环的化合物的生产方法，包括以下步骤：使用由式（I）表示的氟硼化合物或其二聚体或溶剂化物作为芳环的氨甲基化试剂；在金属催化剂（如钯化合物）的存在下，将氨甲基化试剂与能够与其反应的含芳环化合物反应，从而进行芳环的直接氨甲基化。式（I）如下：Ra(Rb)N—CH2—BF3M   (I)

  公开号：

  US20080015351A1

文献信息

• Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (−)-Filiformin
  作者：Daniel J. Blair、Catherine J. Fletcher、Katherine M. P. Wheelhouse、Varinder K. Aggarwal

  DOI：10.1002/anie.201400944

  日期：2014.5.26

  developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps have been applied to the shortest enantioselective synthesis of (−)‐filiformin

  已经开发了锂化/硼氢化方法学，用于合成无环四级-三级基序，并且可以完全控制相对和绝对立体化学，因此可以生成立体二价体的所有四种可能的异构体。新型的分子内Zweifel型烯化反应使无环立体控制转变为环立体控制。迄今为止，这些关键步骤已应用于具有完全立体控制的最短对映选择性合成（-）-filiformin（9个步骤）。
• [EN] THERAPEUTIC METHODS<br/>[FR] PROCÉDÉS THÉRAPEUTIQUES
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2013025992A1

  公开（公告）日：2013-02-21

  The present invention features a method for the treatment of Hepatitis C in a human in need thereof comprising administering a compound of Formulas (II) or (IIB) described herein or a pharmaceutically acceptable salt thereof in combination with one or more alternative Hepatitis C therapeutic agents

  本发明涉及一种治疗丙型肝炎的方法，包括在需要的人体内给予本文描述的II式或IIB式化合物或其药用盐与一种或多种替代丙型肝炎治疗药物的组合治疗
• The total synthesis of (−)-aplysin via a lithiation–borylation–propenylation sequence
  作者：Catherine J. Fletcher、Daniel J. Blair、Katherine M.P. Wheelhouse、Varinder K. Aggarwal

  DOI：10.1016/j.tet.2012.05.095

  日期：2012.9

  A concise, highly enantioselective synthesis of sesquiterpene natural products (−)-debromoaplysin and (−)-aplysin has been completed. The key steps included lithiation–borylation of a secondary benzylic carbamate to give a tertiary boronic ester followed by propenylation which installed the quaternary stereocenter with complete enantioselectivity. Subsequent RCM followed by deprotection and in situ

  倍半萜烯天然产物（-）-溴代aplysinsin和（-）-aplysins的简洁，高对映选择性的合成已经完成。关键步骤包括锂化-仲氨基甲酸苄酯的硼化，生成叔硼酸酯，然后进行丙烯基化，从而完成对映体选择性的四级立体中心的安装。随后的RCM，然后进行脱保护和原位环化，产生具有良好非对映选择性的去溴粘蛋白，只需八步即可从中制备目标化合物。
• [EN] COMPOUNDS USEFUL AS KINASE INHIBITORS<br/>[FR] COMPOSÉS UTILISÉS COMME INHIBITEURS DE KINASE
  申请人：REDX PHARMA PLC

  公开号：WO2017103611A1

  公开（公告）日：2017-06-22

  This invention relates to novel compounds. The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK).The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia and immunological diseases.

  这项发明涉及新颖的化合物。该发明的化合物是酪氨酸激酶抑制剂。具体来说，该发明的化合物可用作布鲁顿氏酪氨酸激酶（BTK）的抑制剂。该发明还考虑了利用这些化合物治疗通过抑制布鲁顿氏酪氨酸激酶可治疗的疾病，例如癌症、淋巴瘤、白血病和免疫性疾病。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2012067663A1

  公开（公告）日：2012-05-24

  The present invention features compounds of formula (I): and salts thereof, pharmaceutical compositions comprising said compounds, and uses of such compounds in treating or preventing viral infections, such as HCV infections, and diseases associated with such infections.

  本发明涉及式(I)的化合物及其盐，包括所述化合物的药物组合物，以及利用这些化合物治疗或预防病毒感染，如HCV感染，以及与此类感染相关的疾病。