(5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基)硼酸 | 169126-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基)硼酸
• 中文别名: 硼酸,(5,6,7,8-四氢-5,5,8,8-四甲基-2-萘基)-
• 英文名称: (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid
• 英文别名: 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-boronic acid；5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthylboronic Acid；(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)boronic acid
• CAS: 169126-63-0
• 化学式: C₁₄H₂₁BO₂
• 分子量: 232.131
• InChiKey: NXBNRLONOXGRCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  195-197℃
• 沸点：
  362.0±52.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338,P304+P340,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-boronic acid
Product Name:
Synonyms: 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenylboronic acid

---

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.
5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-boronic acid
Ingredient name:
CAS number: 169126-63-0

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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: C14H21BO2
Molecular weight: 232.1

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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：

  (5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基)硼酸 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 potassium phosphate monohydrate 、 caesium carbonate 、 sodium iodide 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 乙二醇甲醚 为溶剂， 反应 49.0h， 生成 Ethyl 5-[4-[6-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)pyridin-2-yl]piperazin-1-yl]pentanoate
  参考文献：
  名称：

  INHIBITORS OF SPHINGOSINE KINASE

  摘要：

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、M1、M2、M3、M4、Y1、Y2、V、W、n、m和o具有权利要求1中给出的含义，以及其生理上可接受的盐、衍生物、前药、溶剂合物、互变异构体和立体异构体，包括所有比例的混合物，用于治疗受Sph激酶1抑制影响的疾病。

  公开号：

  US20120252789A1
• 作为产物：
  描述：

  6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘 在 magnesium 、 硼酸三甲酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基)硼酸
  参考文献：
  名称：

  官能团耐受的镍催化交叉偶联反应用于对映选择性构建叔甲基立构中心

  摘要：

  报道了第一个根岸镍催化仲苄酯的立体定向交叉偶联反应。评估了一系列无痕导向基团促进与二甲基锌交叉偶联的能力。由市售的 2-(甲硫基)乙酸衍生的具有螯合硫醚的酯是最有效的。形成的产品收率高，且具有优异的立体定向性。该反应可耐受多种官能团，包括烯烃、炔烃、酯、胺、酰亚胺以及 O-、S- 和 N- 杂环。这种转化的实用性在视黄酸受体激动剂和脂肪酸酰胺水解酶抑制剂的对映选择性合成中得到强调。

  DOI：

  10.1021/ja4034999

文献信息

• Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
  作者：Oriol Planas、Vytautas Peciukenas、Josep Cornella

  DOI：10.1021/jacs.0c05343

  日期：2020.7.1

  Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)–O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies

  在此，我们提出了基于 Bi(III)/Bi(V) 氧化还原循环的芳基硼酸与全氟烷基磺酸盐的 Bi 催化交叉偶联。缺电子的砜配体被证明是成功实施该协议的关键，它允许使用市售的 NaOTf 和 KONf 作为偶联伙伴构建 C(sp2)-O 键。初步的机理研究和理论研究揭示了高度亲电子的 Bi(V) 物种的中间体，它可以快速消除三氟甲磺酸苯酯。
• Efficient synthetic approach to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skeleton via diverse palladium-catalyzed tandem reactions
  作者：Magali Szlosek-Pinaud、Philippe Diaz、Jean Martinez、Frédéric Lamaty

  DOI：10.1016/j.tet.2007.02.035

  日期：2007.4

  Various palladium-catalyzed cascade reactions of O-alkylated 2-iodophenol were explored in order to synthesize novel dihydrobenzofurans. An efficient tandem cyclization/anion capture reaction was developed to yield 3,3-disubstituted-2,3-dihydrobenzofurans. A small library of these compounds was prepared with a parallel organic synthesizer. A multi-component version of this reaction involving 2-iodophenol

  为了合成新型的二氢苯并呋喃，探索了各种钯催化的O-烷基化的2-碘苯酚的级联反应。开发了有效的串联环化/阴离子捕获反应以产生3,3-二取代的2,3-二氢苯并呋喃。这些化合物的小型文库是用平行有机合成仪制备的。该反应的多组分形式涉及2-碘苯酚，烷基化剂和亲核试剂，提供了相同的产物。甲氧基羰基取代的杂环水解为游离酸，可用于进一步转化。
• Biphenyl derivatives substituted by an aromatic or heteroaromatic radical and pharamaceutical and cosmetic compositions containing same
  申请人：Galderma Research & Development

  公开号：US06316009B1

  公开（公告）日：2001-11-13

  “Biphenyl derivatives substituted with an aromatic or heteroaromatic radical, and pharmaceutical and cosmetic compositions containing them” in which: Ar represents an aromatic or a heteroaromatic radical optionally substituted, in particular, with an alkyl or a carboxyl group, R2 and R3 represent, in particular, H or alkyl, or R2 and R3, taken together, form a 5- or 6-membered ring, R4 and R5 represent, in particular, H or halogen, R6 represents, in particular, H or lower alkyl, and the salts of the compounds of formula (I). These compounds can be used in particular in the treatment of dermatological complaints associated with a keratinization disorder, and for combating ageing of the skin.

  含有芳香或杂环芳基取代的联苯衍生物，以及含有它们的药用和化妆品组合物，其中：Ar代表一个芳香或杂环芳基，可选地取代，特别是与烷基或羧基取代，R2和R3代表特别是H或烷基，或者R2和R3一起形成一个5-或6-成员环，R4和R5代表特别是H或卤素，R6代表特别是H或较低的烷基，以及具有化合物的盐的化合物。这些化合物可以用于特别是治疗与角化不良有关的皮肤疾病，并用于对抗皮肤衰老。
• 具有苯并环烷烃配体的金属配合物及其应用
  申请人：瑞声科技（南京）有限公司

  公开号：CN108948097A

  公开（公告）日：2018-12-07

  本发明属于电致发光材料技术领域，公开了一种具有苯并环烷烃配体的金属配合物及其应用。本发明所提供的金属配合物的通式结构为M(Lx)m(Ly)n，在该种金属配合物的结构中，由于卞位活泼氢被烷基取代，且在辅助配体或者在吡啶基团中引入了更多的芳基或烷基基团，从而降低了分子平面堆积的可能性，增强了材料的稳定性，提高了器件寿命。
• Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides
  作者：Marc Magre、Josep Cornella

  DOI：10.1021/jacs.1c11463

  日期：2021.12.29

  A Bi-catalyzed synthesis of sulfonyl fluorides from the corresponding (hetero)aryl boronic acids is presented. We demonstrate that the organobismuth(III) catalysts bearing a bis-aryl sulfone ligand backbone revolve through different canonical organometallic steps within the catalytic cycle without modifying the oxidation state. All steps have been validated, including the catalytic insertion of SO2

  介绍了由相应的（杂）芳基硼酸双催化合成磺酰氟。我们证明了带有双芳基砜配体骨架的有机铋（III）催化剂在催化循环中通过不同的规范有机金属步骤旋转，而不会改变氧化态。所有步骤都已经过验证，包括将 SO 2催化插入Bi-C 键，从而形成结构独特的 O 键亚磺酸铋复合物。该催化方案为各种芳基和杂芳基硼酸提供了出色的收率，显示出广泛的官能团耐受性。