2-((二异丙基氨基)甲基)苯硼酸 | 95753-26-7

• 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-((二异丙基氨基)甲基)苯硼酸
• 中文别名: 2-((二异丙基氨基)甲基)苯基硼酸
• 英文名称: N,N-diisopropylbenzylamine-2-boronic acid
• 英文别名: 2-[(N,N-diisopropylamino)methyl]phenylboronic acid；2-[(diisopropylamino)methyl]phenyl boronic acid；o-(diisopropylaminomethyl)phenylboronic acid；N,N-diisopropyl-2-(borono)phenylmethylamine；(2-((Diisopropylamino)methyl)phenyl)boronic acid；[2-[[di(propan-2-yl)amino]methyl]phenyl]boronic acid
• CAS: 95753-26-7
• 化学式: C₁₃H₂₂BNO₂
• 分子量: 235.134
• InChiKey: OZJANVKXMUYIQC-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  355.7±44.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 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-((Diisopropylamino)methyl)phenylboronic 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-((Diisopropylamino)methyl)phenylboronic acid
CAS number: 95753-26-7

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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.
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: C13H22BNO2
Molecular weight: 235.1

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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, nitrogen oxides.

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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

反应信息

• 作为反应物：
  描述：

  2-((二异丙基氨基)甲基)苯硼酸 在 potassium hydrogen difluoride 作用下， 以 甲醇 、 水 为溶剂， 反应 0.67h， 以82%的产率得到N,N-diisopropyl-2-(trifluoroboronyl)phenylmethylamine
  参考文献：
  名称：

  潜在的路易斯酸-路易斯碱双功能催化剂的合成和结构：2- N，N-二异丙基氨基苯基硼酸酯衍生物

  摘要：

  定向的邻金属化用于将硼官能团引入N，N-二异丙基苯甲酰胺中，从而导致硼酸酯和硼酸酯衍生物的形成。Ñ，Ñ -Diisopropylbenzamide邻-硼酸频哪醇酯可以与硼氢化钠-的TMSCl导致减小Ñ，Ñ -diisopropylbenzylamino邻-硼酸。该化合物的X射线晶体学分析和11 B NMR清楚地表明，受阻的异丙基氨基基团足以阻止B–N分子内配位，这与N，N-二甲基苄基氨基形成对比原硼酸。

  DOI：

  10.1016/j.jorganchem.2005.07.108
• 作为产物：
  描述：

  二异丙基(2-(二异丙基氨基甲酰基)苯基)硼酸酯 在 盐酸 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 136.0h， 生成 2-((二异丙基氨基)甲基)苯硼酸
  参考文献：
  名称：

  潜在的路易斯酸-路易斯碱双功能催化剂的合成和结构：2- N，N-二异丙基氨基苯基硼酸酯衍生物

  摘要：

  定向的邻金属化用于将硼官能团引入N，N-二异丙基苯甲酰胺中，从而导致硼酸酯和硼酸酯衍生物的形成。Ñ，Ñ -Diisopropylbenzamide邻-硼酸频哪醇酯可以与硼氢化钠-的TMSCl导致减小Ñ，Ñ -diisopropylbenzylamino邻-硼酸。该化合物的X射线晶体学分析和11 B NMR清楚地表明，受阻的异丙基氨基基团足以阻止B–N分子内配位，这与N，N-二甲基苄基氨基形成对比原硼酸。

  DOI：

  10.1016/j.jorganchem.2005.07.108
• 作为试剂：
  描述：

  6-methyl-2-chromanol 在 2-((二异丙基氨基)甲基)苯硼酸 、 1-[(1R,2R)-2-(dimethylamino)cyclohexyl]-3-(4-methoxy-2-methylphenyl)thiourea 、 三氟乙酸 作用下， 以 四氯化碳 、 二氯甲烷 、 甲基叔丁基醚 、 甲苯 为溶剂， 反应 26.5h， 生成 (S)-2-(6-methylchroman-2-yl)acetic acid
  参考文献：
  名称：

  α，β-不饱和羧酸的不对称分子内杂-迈克尔反应的双芳基硼酸-氨基硫脲催化体系

  摘要：

  双官能氨基硼酸已被首次用于促进α，β-不饱和羧酸的分子内氮杂和氧杂-迈克尔反应。芳基硼酸与手性氨基硫脲的结合使这些反应以对映选择性的方式成功进行，从而以高收率和ee（高达96％ee）提供所需的杂环。该双催化体系的整体效用通过（+）-赤藓糖酰胺B的一锅对映选择性合成得到证明，该合成通过顺序的迈克尔和酰胺化反应进行。

  DOI：

  10.1021/ol501954r

文献信息

• The <i>ortho</i>-substituent on 2,4-bis(trifluoromethyl)phenylboronic acid catalyzed dehydrative condensation between carboxylic acids and amines
  作者：Ke Wang、Yanhui Lu、Kazuaki Ishihara

  DOI：10.1039/c8cc02558d

  日期：——

  2,4-Bis(trifluoromethyl)phenylboronic acid is a highly effective catalyst for dehydrative amidation between carboxylic acids and amines. Mechanistic studies suggest that a 2 : 2 mixed anhydride is expected to be the only active species, and the ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom of the active species, thus accelerating the amidation

  2,4-双（三氟甲基）苯基硼酸是用于羧酸和胺之间的脱水酰胺化的高效催化剂。机理研究表明，预计2：2混合酸酐是唯一的活性物质，硼酸的原取代基在防止胺与活性物质的硼原子配位方面起关键作用，从而促进酰胺化。该催化剂可用于α-二肽合成。
• [EN] BIFUNCTIONAL AMINO-BORON LEWIS ACID - LEWIS BASE CATALYST<br/>[FR] CATALYSEURS BIFONCTIONNELS
  申请人：UNIV DURHAM

  公开号：WO2004113351A3

  公开（公告）日：2005-04-07
• Lauer, Manfred; Boehnke, Helmut; Grotstollen, Reiner, Chemische Berichte, 1985, vol. 118, # 1, p. 246 - 260
  作者：Lauer, Manfred、Boehnke, Helmut、Grotstollen, Reiner、Salehnia, Mohammad、Wulff, Guenter

  DOI：——

  日期：——
• Probing Intramolecular B−N Interactions in <i>Ortho</i>-Aminomethyl Arylboronic Acids
  作者：Byron E. Collins、Steven Sorey、Amanda E. Hargrove、Shagufta H. Shabbir、Vincent M. Lynch、Eric V. Anslyn

  DOI：10.1021/jo900187a

  日期：2009.6.5

  This work investigates the interplay between the intramolecular B-N dative bonding and solvent insertion in various ortho-methylamino arylboronic acids in protic media. B-11 NMR experiments were conducted to study the effect that the degree of substitution of the amine group has on B-N bonding versus solvent insertion. It was found that there is a slight increase in the amount of B-N dative bonding on going from a tertiary to a secondary to a primary amine group, but that solvent insertion dominates in all cases of the boronate esters. A X-ray crystal structure gives further insight into the structure of the solvent-inserted boronate esters, showing that the inserted solvent has its hydrogen primarily on the amine. Lastly, studies of the use of boronate esters as receptors for simple alcohols and carboxylic acids are described.
• LAUER, M.;BOEHNKE, H.;GROTSTOLLEN, R.;SALEHNIA, MOHAMMAD;WULFF, G., CHEM. BER., 1985, 118, N 1, 246-260
  作者：LAUER, M.、BOEHNKE, H.、GROTSTOLLEN, R.、SALEHNIA, MOHAMMAD、WULFF, G.

  DOI：——

  日期：——