2-氰基甲基苯基硼酸频哪醇酯 | 325141-71-7

• 物质功能分类: 表面活性剂 - 非离子表面活性剂 - 多元醇酯型
• 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-氰基甲基苯基硼酸频哪醇酯
• 中文别名: 2-(3-甲氧基羰基苯基)异烟酸；(2-氰基甲基苯基)硼酸频那醇酯
• 英文名称: 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile
• 英文别名: [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetonitrile；2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile
• CAS: 325141-71-7
• 化学式: C₁₄H₁₈BNO₂
• mdl: MFCD02179457
• 分子量: 243.113
• InChiKey: FIARMBRSPSECPP-UHFFFAOYSA-N

物化性质

• 沸点：
  379.1±25.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  18
• 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：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  UN 3276
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P310,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H301,H315,H319,H335
• 储存条件：
  存放在2-8℃环境中，应保持干燥并密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Cyanomethylphenylboronic acid, pinacol ester
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Cyanomethylphenylboronic acid, pinacol ester
CAS number: 325141-71-7

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H18BNO2
Molecular weight: 243.1

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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-氰基甲基苯基硼酸频哪醇酯 在 sodium chlorite 作用下， 以 水 为溶剂， 反应 0.75h， 以91%的产率得到2-羟基苯乙腈
  参考文献：
  名称：

  以亚氯酸钠为氧化剂在水中对芳基硼酸和硼酸酯进行羟基化

  摘要：

  开发了一种简便有效的方法，用于芳基硼酸在水中通过羟基化生成苯酚。一系列富含电子和缺电子的芳基硼酸通过该方案顺利进行同位羟基化，从而以优异的产率提供产品。此外，该协议适用于硼酸酯。在大多数情况下，酚类产品以纯形式获得，无需任何色谱纯化。

  DOI：

  10.1002/ejoc.201301228
• 作为产物：
  描述：

  邻溴氰苄 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以75%的产率得到2-氰基甲基苯基硼酸频哪醇酯
  参考文献：
  名称：

  一锅合成新的氮杂和二氮杂氨基菲

  摘要：

  使用有效的一锅法已经完成了一系列苯并（异）喹啉和菲咯啉衍生物的合成。它先经过Suzuki-Miyaura交叉耦合，再经过微波辐射下的Dieckmann-Thorpe闭环，可以轻松访问其他方法不易获得的构件。

  DOI：

  10.1016/j.tet.2011.05.116

文献信息

• [EN] ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'ECTONUCLÉOTIDASES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CALITHERA BIOSCIENCES INC

  公开号：WO2020257429A1

  公开（公告）日：2020-12-24

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  这项发明涉及新颖的杂环化合物及其药物制剂。该发明还涉及使用该发明的新颖杂环化合物治疗或预防癌症的方法。
• Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines
  作者：Hirokazu Tsukamoto、Taishi Ikeda、Takayuki Doi

  DOI：10.1021/acs.joc.5b02378

  日期：2016.3.4

  palladium(II) complexes catalyze the annulation of internal alkynes with 2-(cyanomethyl)phenylboronates to provide 3,4-disubstituted-2-naphthalenamines in good yields. The annulation reaction proceeds under mild and neutral conditions and requires methanol as an essential solvent. In addition to symmetrical alkynes, unsymmetrical alkynes substituted by aryl, alkyl, and alkynyl groups participate in

  1,2-双（二苯基膦基）乙烷（dppe）连接的钯（II）配合物催化内部炔烃与2-（氰基甲基）苯基硼酸酯的环化反应，从而以良好的收率提供3,4-二取代的-2-萘胺。环化反应在温和和中性条件下进行，需要甲醇作为必要溶剂。除对称炔烃外，被芳基，烷基和炔基取代的不对称炔烃也参与环化反应，得到相应的带有吸电子sp 2的2-萘胺。-和sp-carbons优先位于C-3位置。在硼酸酯中包括在氰基甲基部分上的烷基或烷氧基和在苯环上的卤素原子的取代基与反应条件相容。通过用硼酸酯和炔烃插入钯（II）配合物进行金属转移，然后将生成的烯基钯（II）亲核加成到分子内氰基中来进行环化。化学计量反应表明，甲醇溶剂对于重金属化和催化剂再生均有效。
• ISOPROPYL TRIAZOLO PYRIDINE COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：US20160333005A1

  公开（公告）日：2016-11-17

  The present invention provides a compound of the Formula (I) below: Wherein R 1 is selected from the group consisting of H, CH 3 , CN, CH 2 CN, C(CH 3 ) 2 CN, and F; R 2 is selected from the group consisting of H, O(C 1 -C 3 alkyl)R 5 , CH 2 CN, and CN; R 3 is selected from the group consisting of H, OCH 3 , CN, C(CH 3 ) 2 CN, and CH2CN; R 4 is selected from the group consisting of H and CH 3 ; R 5 is selected from the group consisting of H, CN, C(CH 3 ) 2 CN, OCH 3 , S(O) 2 CH 3 , and C(CH 3 ) 2 OH; provided that at least one selected from the group consisting of R1, R2, R3 and R4 is H; or a pharmaceutically acceptable salt thereof, methods of treating diabetes using the compound and a process for preparing the compound.

  本发明提供了以下式（I）的化合物：其中R1选择自H、CH3、CN、CH2CN、C(CH3)2CN和F组成的群体中；R2选择自H、O(C1-C3烷基)R5、CH2CN和CN组成的群体中；R3选择自H、OCH3、CN、C(CH3)2CN和CH2CN组成的群体中；R4选择自H和CH3组成的群体中；R5选择自H、CN、C(CH3)2CN、OCH3、S(O)2CH3和C(CH3)2OH组成的群体中；至少选择自R1、R2、R3和R4中的一个为H；或其药学上可接受的盐，使用该化合物治疗糖尿病的方法以及制备该化合物的过程。
• Direct One-Pot Synthesis of Phenanthrenes via Suzuki−Miyaura Coupling/Aldol Condensation Cascade Reaction
  作者：Young Ha Kim、Hyuk Lee、Yeong Joon Kim、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1021/jo702001n

  日期：2008.1.1

  We have developed an efficient cascade reaction, a Suzuki−Miyaura coupling followed by an aldol condensation, for the construction of phenanthrene derivatives using microwave irradiation. For example, the reaction of methyl 2-bromophenylacetamide with 2-formylphenylboronic acid in the presence of a palladium catalyst and a base provided a biaryl intermediate, which underwent in situ cyclization to

  我们已经开发出了一种有效的级联反应，一种铃木-宫浦偶合，然后进行醛醇缩合，以利用微波辐射来构建菲衍生物。例如，在钯催化剂和碱的存在下，甲基2-溴苯基乙酰胺与2-甲酰基苯基硼酸的反应提供了联芳基中间体，其进行原位环化以高产率提供相应的菲。
• Asymmetric Synthesis of Axially Chiral 2-Aminobiaryls by Rhodium-Catalyzed Benzannulation of 1-Arylalkynes with 2-(Cyanomethyl)phenylboronates
  作者：Fei Xue、Tamio Hayashi

  DOI：10.1002/anie.201806324

  日期：2018.8.6

  Asymmetric benzannulation of 1‐arylalkynes, where the aryl group is an ortho‐substituted aromatic group, with 2‐(cyanomethyl)phenylboronate was catalyzed by a rhodium complex coordinated with a chiral diene ligand to give high yields of axially chiral 2‐aminobiaryls with greater than 90 % ee.

  铑配合物与手性二烯配体配合催化1-芳基炔的不对称苯环，其中芳基为邻位取代的芳基，与2-（氰基甲基）苯基硼酸酯催化，得到高收率的轴向手性2-氨基联芳基超过90％ee。