2-[2-(溴甲基)苯基]-5,5-二甲基-1,3,2-二氧硼杂环己烷 | 166821-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[2-(溴甲基)苯基]-5,5-二甲基-1,3,2-二氧硼杂环己烷
• 中文别名: 2-溴甲基苯基硼酸,新戊二醇酯
• 英文名称: 5,5-dimethyl-2-(2-bromomethylphenyl)-1,3,2-dioxaborinane
• 英文别名: 2-(2-(bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane；2,2-dimethylpropane-1,3-diol [o-(bromomethyl)phenyl]boronate；2,2-dimethylpropane-1,3-diyl [o-(bromomethyl)phenyl]boronate；2-[2-(Bromomethyl)phenyl]-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 166821-88-1
• 化学式: C₁₂H₁₆BBrO₂
• 分子量: 282.973
• InChiKey: KPXRRKYYMYMEKC-UHFFFAOYSA-N

物化性质

• 沸点：
  368.6±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P260,P264,P270,P280,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P363,P405,P501
• 危险品运输编号：
  3265
• 危险性描述：
  H302,H314
• 储存条件：
  存储条件：2-8°C，干燥

SDS

Name:	2-[2-(Bromomethyl)phenyl]-5 5-dimethyl-1 3 2-dioxaborinane Material Safety Data Sheet
Synonym:	None Known
CAS:	166821-88-1

Section 1 - Chemical Product MSDS Name:2-[2-(Bromomethyl)phenyl]-5 5-dimethyl-1 3 2-dioxaborinane Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
166821-88-1	1,9-Diphenyl-1,3,6,8-nonatetraen-5-one	90+%	unlisted

Hazard Symbols: C
Risk Phrases: 22 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Harmful if swallowed. Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
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:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Use only in a chemical fume hood. Discard contaminated shoes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 166821-88-1: Personal Protective Equipment Eyes: Wear chemical splash goggles and face shield.
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: Colourless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H16BBrO2
Molecular Weight: 282.98

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen bromide, oxides of boron, borane.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 166821-88-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,9-Diphenyl-1,3,6,8-nonatetraen-5-one - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing Group: III
IMO
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 22 Harmful if swallowed.
R 34 Causes burns.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
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# 166821-88-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 166821-88-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 166821-88-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-[2-(溴甲基)苯基]-5,5-二甲基-1,3,2-二氧硼杂环己烷 在 1,8-双二甲氨基萘 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  一个用于摄取葡萄糖的两光子开启探针。

  摘要：

  我们报告了一个双光子开启探针（AS1），它可以被780 nm飞秒脉冲激发，并通过双光子显微镜观察葡萄糖的摄取以及活细胞和组织中细胞内葡萄糖浓度的变化。

  DOI：

  10.1039/c2cc16792a
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 36.0h， 生成 2-[2-(溴甲基)苯基]-5,5-二甲基-1,3,2-二氧硼杂环己烷
  参考文献：
  名称：

  模块化固相合成方法可优化寡硼酸受体和传感器的结构和电子性能，以进行寡糖的水相识别。

  摘要：

  本文介绍了第一种完全模块化，平行固相合成方法的设计和优化，该方法用于生成定义明确的多胺寡硼酸受体和复杂寡糖的荧光传感器。合成方法允许有效构建受体多胺主链，然后控制胺苄基侧链的多样化。这种方法能够以模块化的方式测试被无阻碍的对位吸电子基团或供电子基团取代的不同芳基硼酸单元的作用。还通过使用Irori MiniKan技术组装受体子库，研究了这种自动合成方法的可行性。合成了包含两个或三个芳基硼酸的蒽封端的传感器的几个子库，并在中性水性介质中检查了它们与一系列模型二糖的结合。通过荧光滴定法对缔合常数的计算证实，聚胺主链中胺间间隔基结构的细微变化可对所得配合物的稳定性产生重大影响。最重要的是，这项研究导致确定了芳基硼酸酯单元的首选电子特性，并暗示了新一代的含有非常贫电子的芳基硼酸的受体可能会导致结合亲和力的显着改善。通过荧光滴定法对缔合常数的计算证实，聚胺主链中胺间间隔基结构的细微变化可对所得配合物

  DOI：

  10.1002/chem.200305400

文献信息

• NEAR-IR GLUCOSE SENSORS
  申请人：Profusa, Inc.

  公开号：US20180179233A1

  公开（公告）日：2018-06-28

  Glucose-sensing luminescent dyes, polymers, and sensors are provided. Additionally, systems including the sensors and methods of using these sensors and systems are provided.

  提供了葡萄糖感应荧光染料、聚合物和传感器。此外，还提供了包括传感器的系统以及使用这些传感器和系统的方法。
• Coupling a Natural Receptor Protein with an Artificial Receptor to Afford a Semisynthetic Fluorescent Biosensor
  作者：Eiji Nakata、Tsuyoshi Nagase、Seiji Shinkai、Itaru Hamachi

  DOI：10.1021/ja035631i

  日期：2004.1.1

  An artificial receptor and a signal transducer have been engineered on a lectin (saccharide-binding protein) surface by a post-photoaffinity labeling modification method. Saccharide binding can be directly and selectively read out by the fluorescence changes of the fluorophore via photoinduced electron transfer (PET) mode. Fluorescence titration with various saccharides reveals that molecular recognition

  通过光亲和后标记修饰方法在凝集素（糖结合蛋白）表面设计了人工受体和信号转导器。通过光诱导电子转移 (PET) 模式，荧光团的荧光变化可以直接和选择性地读出糖的结合。用各种糖类进行荧光滴定表明，人工受体的分子识别成功地与凝集素的天然结合位点偶联，产生了一种新型荧光糖类生物传感器，显示出调节的特异性和增强的亲和力。通过结合亲和力的比较定量证明了人工和天然分子识别模块之间设计的协同性，它代表了一种新的分子识别策略。通过使用合适的人工受体和各种天然凝集素，这种方法可以为糖类衍生物如糖脂和糖肽/蛋白质提供许多新的半合成生物传感器。一个基于凝集素的生物传感器的扩展库被设想用于糖组研究，这是后基因组时代的一个新兴领域。
• p<i>K</i>_a Values and Geometries of Secondary and Tertiary Amines Complexed to Boronic AcidsImplications for Sensor Design
  作者：Sheryl L. Wiskur、John J. Lavigne、Hassan Ait-Haddou、Vincent Lynch、Yu Hung Chiu、James W. Canary、Eric V. Anslyn

  DOI：10.1021/ol0156805

  日期：2001.5.1

  [structure in text] The pK(a) values and the geometries of secondary and tertiary amines adjacent to boronic acids were determined using potentiometric and (11)B NMR titrations. The studies showed that the secondary ammonium ion has a pK(a) similar to that of the tertiary ammonium species, which leads to the formation of tetrahedral boron centers at pH values above approximately 5.5. Therefore, secondary

  [文字结构]使用电位滴定法和（11）B NMR滴定法测定硼酸附近的仲胺和叔胺的pK（a）值和几何形状。研究表明，仲铵离子的pK（a）与叔铵物种的pK（a）相似，这导致在pH值大于5.5时形成四面体硼中心。因此，当仲胺和叔胺放置在硼中心附近时，可用于在中性pH下生成四面体硼酸以进行二醇络合。
• Ni‐Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX₂**
  作者：Roshan K. Dhungana、Rishi R. Sapkota、Laura M. Wickham、Doleshwar Niroula、Bijay Shrestha、Ramesh Giri

  DOI：10.1002/anie.202110459

  日期：2021.10.11

  with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate-limiting

  我们报告了镍催化的烯基芳烃与苄基卤和芳基锌试剂的区域选择性芳基苯甲基化反应。该反应提供了不同取代的 1,1,3-三芳基丙基结构，让人想起低聚白藜芦醇天然产物的核心。该反应也适用于内烯烃、仲苄基卤和各种取代的芳基锌试剂的偶联。动力学研究表明，该反应以限速单电子转移过程进行，并由原位生成的 ZnX 2自催化。添加 ZnX 2后，通过自催化作用，反应速率提高了三倍。
• Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(sp³)–C(sp³) Bonds
  作者：Roshan K. Dhungana、Rishi R. Sapkota、Laura M. Wickham、Doleshwar Niroula、Ramesh Giri

  DOI：10.1021/jacs.0c09778

  日期：2020.12.16

  We disclose a Ni-catalyzed vicinal difunctionalization of alkenes with benzyl halides and alkylzinc reagents, which produces products with two new alkyl-alkyl bonds. This alkene dialkylation is effective in combining secondary benzyl halides and secondary alkylzinc reagents with internal alkenes, which furnishes products with three contiguous all-carbon secondary stereocenters. The products can be

  我们公开了用苄基卤化物和烷基锌试剂对烯烃进行 Ni 催化的邻位双官能化，其产生具有两个新的烷基-烷基键的产物。这种烯烃二烷基化可有效地将仲苄基卤化物和仲烷基锌试剂与内部烯烃结合，从而提供具有三个连续的全碳仲立构中心的产物。这些产品可以很容易地得到复杂的四烯、苯并丁二烯和双环癸烯核心。该反应也是迄今为止最有效的烯烃双官能化过程，催化剂负载量低至 500 ppm，催化转化数 (TON) 和转化频率 (TOF) 在室温下分别高达 2 × 103 和 165 h-1。