2,3,6-三甲氧基苯硼酸 | 380430-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,3,6-三甲氧基苯硼酸
• 中文别名: 2,3,6-三甲氧基苯基硼酸
• 英文名称: 2,3,6-trimethoxyphenylboronic acid
• 英文别名: (2,3,6-trimethoxyphenyl)boronic acid
• CAS: 380430-67-1
• 化学式: C₉H₁₃BO₅
• mdl: MFCD03411944
• 分子量: 212.01
• InChiKey: PBJYOPCURLYSAG-UHFFFAOYSA-N

物化性质

• 熔点：
  34-40℃
• 沸点：
  405.7±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  储存温度为2-8°C，并需保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2,3,6-Trimethoxyphenylboronic acid
Product Name:
Synonyms:

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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.
2,3,6-Trimethoxyphenylboronic acid
Ingredient name:
CAS number: 380430-67-1

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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, 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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H13BO5
Molecular weight: 212.0

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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：

  2,3,6-三甲氧基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 咪唑 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 碘 、 三溴化硼 、 二异丁基氢化铝 、 caesium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~105.0 ℃ 、413.7 kPa 条件下， 反应 108.5h， 生成 10-methoxy-9-trifluoromethanesulfonyloxy-5-(2-propenyl)-2,5-dihydro-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline
  参考文献：
  名称：

  非甾体选择性糖皮质激素调节剂：C-10取代对5-烯丙基-2,5-二氢-2,2,4-三甲基-1H- [1]苯并吡喃[3,4-f]的受体选择性和功能效能的影响喹啉。

  摘要：

  一系列C-10取代的5-烯丙基-2,5-二氢-2,2,4-三甲基-1H- [1]苯并吡喃并[3,4-f]喹啉的制备和表征描述了糖皮质激素受体的配体。用线性，两个原子的附件（OCH（3），OCF（2）H，NHMe，SMe，CH = CH（2），Ctbd1; CH，CH（2）OH ）提供了对人糖皮质激素受体（hGR）的高亲和力（K（i）= 2-8 nM）分子，与其他类固醇受体（PR，MR，AR，ER）的交叉反应性有限。相对于泼尼松龙，最佳的类似物在报告基因试验中显示出稍弱但有效的E-选择素抑制作用，并且GRE激活功效水平降低。在C-9和C-10位置含有取代基的类似物的初步SAR鉴定为9-OH，10-OMe类似物50和9-OH，10-Cl类似物58为化合物，它们在伴刀豆球蛋白A刺激的啮齿动物和人全血单核细胞中均表现出有效的，GR介导的抑制作用。当评估它们在大鼠角叉菜胶诱发的爪水肿中的体内作用时，

  DOI：

  10.1021/jm020335m
• 作为产物：
  描述：

  1,2,4-三甲氧基苯 在 正丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 乙醚 、 水 、 乙酸乙酯 为溶剂， 生成 2,3,6-三甲氧基苯硼酸
  参考文献：
  名称：

  [EN] ENHANCING AUTOPHAGY OR INCREASING LONGEVITY BY ADMINISTRATION OF UROLITHINS OR PRECURSORS THEREOF
  [FR] AMÉLIORATION DE L'AUTOPHAGIE OU AUGMENTATION DE LA LONGÉVITÉ PAR L'ADMINISTRATION D'UROLITHINES OU DE PRÉCURSEURS DE CELLES-CI

  摘要：

  公开号：

  WO2014004902A3

文献信息

• Enantioselective construction of sterically hindered tertiary α-aryl ketones: a catalytic asymmetric synthesis of isoflavanones
  作者：Michael P. Carroll、Helge Müller-Bunz、Patrick J. Guiry

  DOI：10.1039/c2cc36452b

  日期：——

  A method for the catalytic asymmetric alpha-arylation of ketones bearing very sterically hindered aryl rings has been developed. This reaction occurs under mild conditions, in short reaction times and has been applied to the first catalytic asymmetric synthesis of isoflavanones.

  已经开发出一种用于催化具有非常空间受阻的芳基环的酮的催化不对称α-芳基化的方法。该反应在温和的条件下在短的反应时间内发生，并已被用于异黄酮的第一催化不对称合成。
• Synthesis of 1,2,4-Trimethoxybenzene and Its Selective Functionalization at C-3 by Directed Metalation
  作者：Ana P. L. Alves、Jose Augusto B. C. Júnior、Glaucia B. A. Slana、Jari N. Cardoso、Qiang Wang、Rosangela S. C. Lopes、Claudio C. Lopes

  DOI：10.1080/00397910902805598

  日期：2009.9.18

  A new and efficient strategy was developed for the preparation of 1,2,4-trimethoxybenzene (3, a powerful attractant of Euglossini bees) and its C-3 derivatives (7a-j), from vanillin (2) in 56% overall yield.
• Synthesis of axially chiral 1,8-diarylnaphthalene ligands and application in asymmetric catalysis: an intriguing fluorine effect
  作者：Harisadhan Ghosh、Ravishashidhar Vavilala、Alex M. Szpilman

  DOI：10.1016/j.tetasy.2014.12.008

  日期：2015.2

  A fluorinated and a non-fluorinated axially chiral 1,8-diarylnaphthalene ligand have been synthesized through an Ullmann and Suzuki coupling reaction based strategy. A practical methodology for the successful chiral resolution of the newly synthesized catechol based moiety is presented. We also disclose the preliminary application of these axially chiral molecules as ligands in asymmetric transformation reactions. (C) 2014 Elsevier Ltd. All rights reserved.
• [EN] ENHANCING AUTOPHAGY OR INCREASING LONGEVITY BY ADMINISTRATION OF UROLITHINS OR PRECURSORS THEREOF<br/>[FR] AMÉLIORATION DE L'AUTOPHAGIE OU AUGMENTATION DE LA LONGÉVITÉ PAR L'ADMINISTRATION D'UROLITHINES OU DE PRÉCURSEURS DE CELLES-CI
  申请人：AMAZENTIS SA

  公开号：WO2014004902A3

  公开（公告）日：2014-03-06
• Nonsteroidal Selective Glucocorticoid Modulators:  The Effect of C-10 Substitution on Receptor Selectivity and Functional Potency of 5-Allyl-2,5-dihydro-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolines
  作者：Philip R. Kym、Michael E. Kort、Michael J. Coghlan、Jimmie L. Moore、Rui Tang、James D. Ratajczyk、Daniel P. Larson、Steven W. Elmore、John K. Pratt、Michael A. Stashko、H. Douglass Falls、Chun W. Lin、Masake Nakane、Loan Miller、Curtis M. Tyree、Jeffery N. Miner、Peer B. Jacobson、Denise M. Wilcox、Phong Nguyen、Benjamin C. Lane

  DOI：10.1021/jm020335m

  日期：2003.3.1

  receptors (PR, MR, AR, ER). Optimal analogues showed slightly less potent but highly efficacious E-selectin repression with reduced levels of GRE activation efficacy in reporter gene assays relative to prednisolone. Preliminary SAR of analogues containing substitution at the C-9 and C-10 positions identified the 9-OH, 10-OMe analogue 50 and the 9-OH, 10-Cl analogue 58 as compounds that demonstrated potent

  一系列C-10取代的5-烯丙基-2,5-二氢-2,2,4-三甲基-1H- [1]苯并吡喃并[3,4-f]喹啉的制备和表征描述了糖皮质激素受体的配体。用线性，两个原子的附件（OCH（3），OCF（2）H，NHMe，SMe，CH = CH（2），Ctbd1; CH，CH（2）OH ）提供了对人糖皮质激素受体（hGR）的高亲和力（K（i）= 2-8 nM）分子，与其他类固醇受体（PR，MR，AR，ER）的交叉反应性有限。相对于泼尼松龙，最佳的类似物在报告基因试验中显示出稍弱但有效的E-选择素抑制作用，并且GRE激活功效水平降低。在C-9和C-10位置含有取代基的类似物的初步SAR鉴定为9-OH，10-OMe类似物50和9-OH，10-Cl类似物58为化合物，它们在伴刀豆球蛋白A刺激的啮齿动物和人全血单核细胞中均表现出有效的，GR介导的抑制作用。当评估它们在大鼠角叉菜胶诱发的爪水肿中的体内作用时，