2-甲基苯基硼酸, 丙二醇环酯 | 163517-56-4

• 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-甲基苯基硼酸, 丙二醇环酯
• 中文别名: 2-甲基苯硼酸1,3-丙二醇酯；2-甲基苯基硼酸,丙二醇环酯
• 英文名称: 2-(o-tolyl)-1,3,2-dioxaborinane
• 英文别名: 2-o-tolyl[1,3,2]dioxaborinane；2-(2-methylphenyl) 1,3,2-dioxaborinane；2-(2-Methylphenyl)-1,3,2-dioxaborinane
• CAS: 163517-56-4
• 化学式: C₁₀H₁₃BO₂
• mdl: MFCD06659935
• 分子量: 176.023
• InChiKey: UIDYFYHQHHMEKA-UHFFFAOYSA-N

物化性质

• 沸点：
  300.2±21.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在室温、干燥且密封的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Methylphenylboronic acid, propanediol cyclic ester
Product Name:
Synonyms: 2-Tolylboronic acid, propanediol cyclic ester

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Methylphenylboronic acid, propanediol cyclic ester
Ingredient name:
CAS number: 163517-56-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H13BO2
Molecular weight: 176.0

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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

反应信息

• 作为反应物：
  描述：

  2-甲基苯基硼酸, 丙二醇环酯 在 palladium diacetate 1,3-双(二苯基膦)丙烷 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以56%的产率得到2,2'-二甲基联苯
  参考文献：
  名称：

  Base-free oxidative homocoupling of arylboronic esters

  摘要：

  Base-free oxidative homocoupling reaction of arylboronic esters has been found to proceed using a catalytic amount of a palladium-1,3-bis(diphenylphosphino)propane (DPPP) complex under an oxygen atmosphere, affording a variety of biaryls in modest to excellent yields. Even arylboronic esters bearing a base-sensitive functional group are applicable to the reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00023-6
• 作为产物：
  描述：

  2-甲基苯硼酸 、 1,3-丙二醇 以 甲苯 为溶剂， 反应 1.0h， 以91.7%的产率得到2-甲基苯基硼酸, 丙二醇环酯
  参考文献：
  名称：

  基于硼酸的糖类光致电子转移（PET）荧光传感器†

  摘要：

  开发了一个简单的三步综合程序，以提供六个新颖的模块化传感器，其中包括三个对位传感器和三个元传感器，分别具有萘， 蒽 和 芘荧光团。六个传感器与糖类的相互作用：d葡萄糖， D-果糖， D-半乳糖， 和 D-甘露糖，进行了评估。当添加这些糖时，所有传感器均显示出增加的荧光强度，并且所有传感器均显示出相对于D-半乳糖，D-果糖和D-甘露糖增强的D-葡萄糖选择性。还观察到元传感器相对于对位传感器具有高亲和力（K obs）。萘和蒽元传感器对D的亲和力（K obs）特别高。-半乳糖。圆二色光谱用于探测形成的配合物的结构。在所有六个传感器和D-葡萄糖之间形成环状复合物。对D-半乳糖显示出高亲和力的萘和蒽元传感器也与该糖形成了环状复合物。

  DOI：

  10.1039/c0nj00578a

文献信息

• Generation of Organolithium Compounds bearing Super Silyl Ester and their Application to Matteson Rearrangement
  作者：Susumu Oda、Hisashi Yamamoto

  DOI：10.1002/anie.201304225

  日期：2013.7.29

  It's super‐silyl‐fragilithyl‐ester‐aryl‐docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives

  它是超级甲硅烷基-脆弱基-酯-芳基-docious：超级甲硅烷基是羧酸的强保护基团，提供了一种与酯部分相容的直接锂化方法。带有超级甲硅烷基酯的有机锂化合物可以与多种亲电子试剂发生高产率反应（参见方案）。锂化超级氯乙酸硅酯与硼化合物的反应通过 Matteson 重排产生酯部分的 α-官能化。
• Copper(<scp>i</scp>)-catalyzed amidation reaction of organoboronic esters and isocyanates
  作者：Tedrick Thomas Salim Lew、Diane Shu Wen Lim、Yugen Zhang

  DOI：10.1039/c5gc01374g

  日期：——

  A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using ligand-free copper(I) catalyst. The reaction system demonstrated broad substrate...

  使用不含配体的铜（I）催化剂已经完成了一种简单有效的方法，由易于获得的有机硼酸酯和异氰酸酯制备酰胺。反应体系显示出广泛的底物...
• Preparation process for beta-alkoxy acrylic acid
  申请人：Uclaf; Roussel

  公开号：US05744635A1

  公开（公告）日：1998-04-28

  A method for prerparing compounds of formula (I), wherein R is an optionally substituted alkenyl or alkynyl radical having up to 8 carbon atoms, or an optionally substituted mono- or polycyclic aryl or heteroaryl radical, and R.sub.1 and R.sub.2 are an alkyl radical having up to 4 carbon atoms. According to the method, a compound of the formula (II), wherein X is a halogen atom, is exposed to an organometallic compound of the formula (III): RZ, wherein R has the same meaning as before and Z is a metal or metal derivative. Alternatively, a compound of formula (II'), wherein Z' is a metal or metal derivative, is exposed to a compound of the formula (III'): RX', wherein X' is a nucleophilic reaction leaving group. ##STR1##

  一种制备式（I）化合物的方法，其中R为具有最多8个碳原子的可选取代烯烃或炔烃基团，或可选取代的单环或多环芳基或杂芳基，而R.sub.1和R.sub.2为最多具有4个碳原子的烷基基团。根据该方法，将式（II）化合物（其中X为卤素原子）暴露于式（III）的有机金属化合物中：RZ，其中R具有前述相同的含义，而Z为金属或金属衍生物。或者，将式（II'）化合物（其中Z'为金属或金属衍生物）暴露于式（III'）的化合物中：RX'，其中X'为亲核反应离去基团。
• Ruthenium(0)-Catalyzed sp³ C–H Bond Arylation of Benzylic Amines Using Arylboronates
  作者：Navid Dastbaravardeh、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/ol300627p

  日期：2012.4.6

  A Ru-catalyzed direct arylation of benzylic sp(3) carbons of acyclic amines with arylboronates is reported. This highly regioselective and efficient transformation can be performed with various combinations of N-(2-pyridyl) substituted benzylamines and arylboronates. Substitution of the pyridine directing group in the 3-position proved to be crucial in order to achieve high arylation yields. Furthermore, the pyridine directing group can be removed in high yields via a two-step protocol.
• Base-free oxidative homocoupling of arylboronic esters
  作者：Hiroto Yoshida、Yasuhito Yamaryo、Joji Ohshita、Atsutaka Kunai

  DOI：10.1016/s0040-4039(03)00023-6

  日期：2003.2

  Base-free oxidative homocoupling reaction of arylboronic esters has been found to proceed using a catalytic amount of a palladium-1,3-bis(diphenylphosphino)propane (DPPP) complex under an oxygen atmosphere, affording a variety of biaryls in modest to excellent yields. Even arylboronic esters bearing a base-sensitive functional group are applicable to the reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.