5-叔丁基-2-甲氧基苯硼酸 | 128733-85-7

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-叔丁基-2-甲氧基苯硼酸
• 中文别名: 5-叔-丁基-2-甲氧基苯硼酸
• 英文名称: (5-(tert-butyl)-2-methoxyphenyl)boronic acid
• 英文别名: (5-tert-butyl-2-methoxyphenyl)boronic acid
• CAS: 128733-85-7
• 化学式: C₁₁H₁₇BO₃
• mdl: MFCD06201034
• 分子量: 208.065
• InChiKey: LXFOJKCQSAYVMF-UHFFFAOYSA-N

物化性质

• 熔点：
  103-106°C
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥处。确保工作环境具有良好的通风或排气设施。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-t-Butyl-2-methoxyphenylboronic 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.
5-t-Butyl-2-methoxyphenylboronic acid
Ingredient name:
CAS number: 128733-85-7

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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: C11H17BO3
Molecular weight: 208.1

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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.

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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：

  5-叔丁基-2-甲氧基苯硼酸 在 三溴化硼 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 27.33h， 生成 4-(tert-butyl)-2-(5-methylpyridin-2-yl)phenol
  参考文献：
  名称：

  HETEROARYL DERIVATIVES AND USES THEREOF

  摘要：

  本发明涉及抗疟疾化合物及其用于对抗疟原虫属Plasmodium的使用，包括对抗药物耐药Plasmodia菌株的使用。本发明还涉及含有这种化合物的组合物以及制备这些化合物的方法。

  公开号：

  US20140135320A1
• 作为产物：
  描述：

  4-叔丁基茴香醚 在 正丁基锂 、 碘 、 Selectfluor 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 4.58h， 生成 5-叔丁基-2-甲氧基苯硼酸
  参考文献：
  名称：

  Stable Axial Chirality in Metal Complexes Bearing 4,4′-Substituted BIPHEPs: Application to Catalytic Asymmetric Carbon–Carbon Bond-Forming Reactions

  摘要：

  不仅是电子效应，4,4′-取代基在BIPHEP衍生物及金属（Pd、Pt和Au）配合物中的空间效应也被证明会影响联苯单键旋转的稳定性。在4,4′-位置的电子供体或空间占位需求较大的取代基会使BIPHEP衍生物的轴向手性不稳定，而电子吸引或空间占位需求较小的取代基则会稳定轴向手性。特别是，带有t-Bu和CF3取代基的钯二氯化物配合物的轴向手性表现出最大的易变性和稳定性（在300 K时，ΔG≠ = 29.22和30.49 kcal mol−1；t1/2 = 7年和56年）。这些对映体纯的二阳离子BIPHEP–Pd配合物可用于催化对映选择性的芳烃化、烯烃化和烯反应，以良好至优异的产率和对映选择性生成相应的产品。重要的是，在三氟丙酮酸与异丁烯的羰基-烯反应中，周转频率（TOF）达到了58200 h−1。4,4′-取代基在BIPHEP衍生物中的显著影响可作为设计多用途高效配体的指导原则。

  DOI：

  10.1246/bcsj.20110309

文献信息

• Aryl Derivatives And Uses Thereof
  申请人：Jacobus Pharmaceutical Company, Inc

  公开号：US20140135360A1

  公开（公告）日：2014-05-15

  The present invention relates to antimalarial compounds and their use against protozoa of the genus Plasmodium , including drug-resistant Plasmodia strains. This invention further relates to compositions containing such compounds and a process for making the compounds.

  本发明涉及抗疟疾化合物及其用于对抗疟原虫属Plasmodium，包括耐药性Plasmodia菌株的用途。本发明还涉及含有这种化合物的组合物以及制备这些化合物的方法。
• Synthesis of Functionalized Cinnamaldehyde Derivatives by an Oxidative Heck Reaction and Their Use as Starting Materials for Preparation of <i>Mycobacterium tuberculosis</i> 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate Reductoisomerase Inhibitors
  作者：Anneli Nordqvist、Christofer Björkelid、Mounir Andaloussi、Anna M. Jansson、Sherry L. Mowbray、Anders Karlén、Mats Larhed

  DOI：10.1021/jo201715x

  日期：2011.11.4

  Cinnamaldehyde derivatives were synthesized in good to excellent yields in one step by a mild and selective, base-free palladium(II)-catalyzed oxidative Heck reaction starting from acrolein and various arylboronic acids. Prepared α,β-unsaturated aldehydes were used for synthesis of novel α-aryl substituted fosmidomycin analogues, which were evaluated for their inhibition of Mycobacterium tuberculosis

  从丙烯醛和各种芳基硼酸开始，通过温和且选择性的、无碱钯 (II) 催化的氧化 Heck 反应，一步合成肉桂醛衍生物，收率良好至极好。制备α，β不饱和醛被用于新的α -芳基膦胺霉素的类似物取代，将其评价它们的抑制的合成结核分枝杆菌1脱氧d -xylulose -5-磷酸还原。测量了介于 0.8 和 27.3 μM 之间的IC 50值。最好的化合物显示出与先前报道的最有效的 α-芳基取代的磷米霉素类抑制剂相当的活性。
• 1,2,4-Triazines in the Synthesis of Bipyridine Bisphenolate ONNO Ligands and Their Highly Luminescent Tetradentate Pt(II) Complexes for Solution-Processable OLEDs
  作者：Piotr Pander、Rachel Bulmer、Ross Martinscroft、Stuart Thompson、Frank W. Lewis、Thomas J. Penfold、Fernando B. Dias、Valery N. Kozhevnikov

  DOI：10.1021/acs.inorgchem.7b03175

  日期：2018.4.2

  rings. The new ligands were used to prepare highly luminescent ONNO-type Pt(II) complexes. The position of the cyclopentene rings significantly influences the solubility and photophysical properties of these complexes. Derivatives with closely positioned cyclopentene rings are soluble in organic solvents and proved to be the best candidate for solution-processable organic light-emitting devices (OLEDs)

  本文介绍了一种方便的合成ONNO型四齿6,6'-双（2-苯氧基）-2,2'-联吡啶（联吡啶双酚盐，BpyBph）配体及其铂（II）配合物的方法。该方法包括合成1,2,4-三嗪前体，然后通过Boger反应将其转化为官能化的吡啶。使用3，3′-和5，5′-双三嗪的两个互补途径允许中心吡啶环在不同位置上的修饰，这通过引入环戊烯环来举例说明。新的配体用于制备高发光度的ONNO型Pt（II）配合物。环戊烯环的位置显着影响这些配合物的溶解度和光物理性质。
• Programmed multiple complexation for the creation of helical structures from acyclic phenol–bipyridine oligomer ligands
  作者：Shigehisa Akine、Hiroki Nagumo、Tatsuya Nabeshima

  DOI：10.1039/c3dt51240a

  日期：——

  respectively. Each of the ligand moieties in these complexes formed a one-turn single helix. The zinc(II) complex [L1Zn2(OAc)] underwent a helix compression–extension motion in solution. The complexation of the H3L1 ligand with iron(III) chloride gave a dinuclear complex [(HL1)2Fe2Cl2] with a non-helical dimeric structure. The longer ligand H4L2 afforded a trinuclear complex [L2Zn3(OAc)2] with a 1.5-turn

  两个新的多齿配体H 3 L 1和H 4 L 2，具有联吡啶–苯酚设计了重复单元，以使多金属络合物能够以预编程的方式产生单螺旋结构。通过连续的钯催化的偶联反应合成了配体。H 3 L 1与锌（II）的络合镍（II）乙酸盐分别得到[L 1 Zn 2（OAc）]和[（L 1）2 Ni 4 ]（OAc）2。这些复合物中的每个配体部分形成一个单匝单螺旋。锌（II）配合物[L 1 Zn 2（OAc）]在溶液中经历了螺旋压缩-延伸运动。H 3 L 1配体与氯化铁（III）得到具有非螺旋二聚结构的双核络合物[（HL 1）2 Fe 2 Cl 2 ]。较长的配体H 4 L 2与三价配合物形成三环配合物[L 2 Zn 3（OAc）2 ]，具有1.5圈单螺旋结构。锌（II）乙酸盐。H 4 L 2配体与钴（II）乙酸盐在有氧条件下，得到具有两个三价和一个二价钴离子的混合价复合物[L 2 Co 3（OAc）3（OMe）
• Phenolate Substituent Effects on Ring-Opening Polymerization of ε-Caprolactone by Aluminum Complexes Bearing 2-(Phenyl-2-olate)-6-(1-amidoalkyl)pyridine Pincers
  作者：Wafaa Alkarekshi、Andrew P. Armitage、Olivier Boyron、Christopher J. Davies、Matifadza Govere、Andrew Gregory、Kuldip Singh、Gregory A. Solan

  DOI：10.1021/om301057d

  日期：2013.1.14

  = H (1a), But (1b), Cl (1c), F (1d)), as their acetonitrile adducts, in good yield. In each case, complexation results in concomitant C–C bond formation via methyl migration from aluminum to the corresponding imino unit in L1-H. On the other hand, reactions of the aldimine-containing compounds 2-(4′-R1-C6H3-2′–OH)-6-CH═N(2″,6″-i-Pr2C6H3)}C5H3N (R1 = H (L1e-H), But (L1f-H), Cl (L1g-H)) afford as the

  2-（苯基-2-醇）-6-酮亚氨基吡啶2-（4'-R 1 -C 6 H 3 -2'-OH）-6- CMe═N（2″，6″ -i）的相互作用-Pr 2 C 6 H 3）} C 5 H 3 N（R 1 = H（L1 a -H），Bu t（L1 b -H），Cl（L1 c -H），F（L1 d -H） ），然后在高温下用AlMe 3结晶，然后从乙腈中结晶，得到五配位的2-（苯基-2-油酸酯）-6-（2-酰胺基丙-2-基）吡啶铝-甲基络合物[2-（4'- [R 1C 6 H 3 -2′-O）-6- CMe 2 N（2″，6″ -i -Pr 2 C 6 H 3）} C 5 H 3 N] AlMe（NCMe）（R 1 = H（图1A），卜吨（1B），CL（1C），F（1D）），因为它们的乙腈的加合物，以良好的收率。在每种情况下，络合都会通过甲基从铝迁移到L1- H中相应的亚氨基单元而导致伴随的C-