2,2-二甲基乙烯硼酸 | 14559-88-7

• 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: 2,2-二甲基乙烯硼酸
• 中文别名: 2,2-二甲基乙炔基硼酸
• 英文名称: 2,2-dimethylethenylboronic acid
• 英文别名: (2-methylprop-1-en-1-yl)boronic acid；2-methylprop-1-enylboronic acid；2,2-dimethylvinylboronic acid
• CAS: 14559-88-7
• 化学式: C₄H₉BO₂
• mdl: MFCD01074609
• 分子量: 99.9253
• InChiKey: FWJRSOGVYOIVOC-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  190.6±23.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,2-Dimethylethenylboronic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2,2-Dimethylethenylboronic acid
CAS number: 14559-88-7

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, under −20◦C.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C4H9BO2
Molecular weight: 99.9

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

2,2-二甲基乙炔基硼酸是一种羧酸类衍生物，用作有机中间体，广泛应用于有机合成及实验研究。

制备

1. 步骤一：在10~60℃条件下，使用二氯甲烷作为溶剂，与3,3-二甲基丙烯酸反应生成2,2-二甲基乙烯基溴。具体操作为：加入溴素，在10~60℃下反应3~4小时。随后，用碱性物质调节pH至9~10，并在30~60℃条件下继续反应2~3小时。完成后静置分层，蒸馏有机层以得到2,2-二甲基乙烯基溴。

2. 步骤二：在-76~-40℃低温条件下，使用四氢呋喃作为溶剂，在金属锂和硼化试剂的作用下与2,2-二甲基乙烯基溴反应。反应完成后，用盐酸调节pH至3~4，并通过乙酸乙酯进行萃取。浓缩有机层后，在非极性烃类溶剂中打浆过滤并干燥，最终得到2,2-二甲基乙烯基硼酸。

反应信息

• 作为反应物：
  描述：

  2,2-二甲基乙烯硼酸 在 potassium hydrogen difluoride 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 potassium 2,2-dimethylethenyltrifluoroborate
  参考文献：
  名称：

  Brak, Katrien; Ellman, Jonathan A., Journal of the American Chemical Society, 2009, vol. 131, p. 3850 - 3851

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Methyl-1-Propenylmagnesium Bromide 在 硼酸三甲酯 、 N-甲基亚氨二乙酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.83h， 生成 2,2-二甲基乙烯硼酸
  参考文献：
  名称：

  蒎烯衍生的亚氨基二乙酸 (PIDA)：一种强大的配体，用于 C(sp3) 硼酸酯结构单元的立体选择性合成和迭代交叉偶联

  摘要：

  有效获取立体化学纯形式的手性 C(sp3) 硼酸酯对于实现此类构建块在复杂分子合成中的巨大潜力至关重要。我们在此报告蒎烯衍生的亚氨基二乙酸 (PIDA) 配体能够从相应的烯烃中高度非对映选择性地合成各种环氧乙烷基 C(sp3) 硼酸酯。反过来，这些环氧乙烷基 PIDA 硼酸酯可以通过硼酸酯基团的新型 1,2-迁移很容易地转化为前所未有的稳定的 α-硼醛，该迁移可以完全保持立体化学纯度。含有双 sp3 杂化 C 中心的 B 保护卤硼酸可通过该平台轻松访问，

  DOI：

  10.1021/ja205912y
• 作为试剂：
  描述：

  5-(1-((2-bromoallyl)oxy)allyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole 在 2,2-二甲基乙烯硼酸 、 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以31%的产率得到5-(3,4-dimethylenetetrahydrofuran-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole
  参考文献：
  名称：

  Raputimonoindoles AC和同类物的合成

  摘要：

  Braun的多米诺骨牌Heck-Suzuki偶联是从秘鲁树Raputia simulans合成raputimonoindole A的关键步骤，从而可以确定绝对构型。哈特维格（Hartwig）的Ir催化呋喃3-羧酸甲酯的5硼酸酯化反应，然后原位与5-溴吲哚进行的Suzuki-Miyaura交叉偶联使得高效地获得了RaputimonoindoleB。

  DOI：

  10.1002/ejoc.201900583

文献信息

• Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones
  作者：Amy Boylan、Thien S. Nguyen、Brian J. Lundy、Jian-Yuan Li、Ravikrishna Vallakati、Sasha Sundstrom、Jeremy A. May

  DOI：10.3390/molecules26061615

  日期：——

  Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the

  影响烯基硼酸与杂芳基连接的烯酮共轭加成反应速率的两个关键因素：感应吸电子杂原子与成键位点的接近度以及可用杂原子孤对对稳定产生的正电荷的共振贡献在烯酮β-位。对于前者，杂原子距离烯酮β-碳越近，反应越快。对于后者，苄基阳离子电荷的共振稳定性更强，可加速反应。因此，反应速率通过感应吸电子元件的更接近而增加，但如果涉及共振效应，则观察到具有给电子能力的速率增加。提出了异构底物这些趋势的证据，并且这些见解的应用允许反应条件改善与以前有问题的底物的反应性。
• [EN] HETEROAROMATIC AND HETEROBICYCLIC AROMATIC DERIVATIVES FOR THE TREATMENT OF FERROPTOSIS-RELATED DISORDERS<br/>[FR] DÉRIVÉS AROMATIQUES HÉTÉROBICYCLIQUES ET HÉTÉROAROMATIQUES POUR LE TRAITEMENT DE TROUBLES LIÉS À LA FERROPTOSE
  申请人：COLLABORATIVE MEDICINAL DEV LLC

  公开号：WO2020185738A1

  公开（公告）日：2020-09-17

  The present application discloses heteroaromatic and heterobicyclic aromatic derivative compounds and compositions, and methods for treating ferroptosis-related disorders and diseases in patients using the compounds and compositions as disclosed herein.

  本申请公开了杂芳和杂双环芳香衍生物化合物和组合物，以及利用所公开的化合物和组合物治疗患者的铁死亡相关疾病和疾病的方法。
• Electrochemical Synthesis of (Aza)indolines<i>via</i>Dehydrogenative [3+2] Annulation: Application to Total Synthesis of (±)-Hinckdentine A
  作者：Zhong-Wei Hou、Hong Yan、Jin-Shuai Song、Hai-Chao Xu

  DOI：10.1002/cjoc.201800301

  日期：2018.10

  An electrochemical synthesis of functionalized (aza)indolines through dehydrogenative [3+2] annulation of arylamines with tethered alkenes has been developed. Previous reported syntheses through similar inter‐ and intramolecular annulation reactions required noble‐metal catalysts and are mostly limited to terminal alkenes or 1,3‐dienes. The electrosynthesis employs the easily available and inexpensive

  已经开发了通过芳胺与链状烯烃的脱氢[3 + 2]环合进行官能化（氮杂）二氢吲哚的电化学合成方法。先前报道的通过类似的分子间和分子内环化反应进行的合成需要贵金属催化剂，并且大多限于末端烯烃或1,3-二烯。电合成采用容易获得且便宜的二茂铁作为分子催化剂，并与二，三，甚至四取代的烯烃相容，以构建二氢吲哚以及更具挑战性的氮杂二氢吲哚。利用新开发的电合成作为关键步骤，已从市售材料中分12个步骤（最长的线性序列）完成了海洋生物碱（±）-扁桃碱A的全合成。
• [EN] SUBSTITUTED THIAZOLE COMPOUNDS<br/>[FR] COMPOSÉS THIAZOLES SUBSTITUÉS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014086697A1

  公开（公告）日：2014-06-12

  The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of manufacturing and using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds of formula (I) are LMP7 inhibitors and may be useful in treating associated inflammatory diseases and disorders such as, for example, rheumatoid arthritis, lupus and irritable bowel disease.

  这项发明涉及式(I)的化合物及其药学上可接受的盐。此外，本发明涉及制造和使用式(I)的化合物的方法，以及含有这种化合物的药物组合物。式(I)的化合物是LMP7抑制剂，可能在治疗相关的炎症性疾病和紊乱方面有用，例如类风湿性关节炎、红斑狼疮和肠易激综合征。
• Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines
  作者：Luuk Steemers、Linda Wijsman、Jan H. van Maarseveen

  DOI：10.1002/adsc.201800914

  日期：2018.11.5

  Efficient and scalable Cu(II)‐mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2‐substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N‐hydroxyimides

  提出了一种高效，可扩展的Cu（II）介导的烯基环硼氧烷和硼酸羧酸的烯醇酯化方法。该反应在脂肪族和芳香族羧酸与几种烯基环硼氧烷化合物的组合中显示出广泛的范围。对于2取代的烯基硼氧烷，双键构型完全保留在烯醇酯产品中。N-羟基酰亚胺和酰亚胺也可以在相应的酰氧基乙烯基烯醇醚和乙烯基酰胺中转化。最后，除甲硫氨酸外，所有其他19种规范氨基酸都显示出它们的相容性，从而以立体选择性方式生成烯醇酯。