(2,2'-二羟基-1,1'-联萘-3,3'-二基)二硼酸 | 957111-27-2

• 物质功能分类: 化学试剂 - 手性化学试剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (2,2'-二羟基-1,1'-联萘-3,3'-二基)二硼酸
• 中文别名: （S）-2,2'-二羟基-1,1'-联萘-3,3'-二硼酸
• 英文名称: 2,2'-dihydroxy-1,1'-binaphthyl-3,3'-diboronic acid
• 英文别名: (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid；[4-(3-borono-2-hydroxynaphthalen-1-yl)-3-hydroxynaphthalen-2-yl]boronic acid
• CAS: 957111-27-2
• 化学式: C₂₀H₁₆B₂O₆
• 分子量: 373.965
• InChiKey: JQGYHOADNLSJJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

安全信息

• 海关编码：
  2918290000

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-2,2’-Dihydroxy-1,1’-binaphthalene-3,3’-diboronic acid
Synonyms: (S)-2,2’-Dihydroxy-1,1’-binaphthyl-3,3’-diyldiboronic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (S)-2,2’-Dihydroxy-1,1’-binaphthalene-3,3’-diboronic acid
CAS number: 957111-27-2

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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.
Store in closed vessels.
Storage:

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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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C20H16B2O6
Molecular weight: 374.0

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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

制备方法与用途

(S)-2,2'-二羟基-1,1'-联萘-3,3'-二硼酸作为一种手性试剂，可在医药合成中发挥重要作用。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  S-1,1'-联-2-萘酚	1,1'-bi-2-naphthol	602-09-5	C20H14O2	286.33

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2,2',3,3'-四羟基-1,1'-联萘	rac-2,2',3,3'-tetrahydroxy-1,1'-binaphthyl	39215-21-9	C20H14O4	318.329

反应信息

• 作为反应物：
  描述：

  (2,2'-二羟基-1,1'-联萘-3,3'-二基)二硼酸 在 双氧水 、 sodium sulfate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  (S)-BINOL-based boronic ester fluorescence sensors for enantioselective recognition of α-phenylethylamine and phenylglycinol

  摘要：

  合成并开发了四种包含硼酸酯和(S)-1,1â²-双-2-萘酚（BINOL）分子的手性荧光传感器（S）-L1â4，用于对δ-苯乙胺和苯基甘氨醇对映体的对映选择性识别。传感器（S）-L1 对δ-苯乙胺和苯基甘氨醇的对映体都有明显的荧光淬灭反应。有趣的是，传感器(S)-L2 对(S)-δ-苯乙胺表现出显著的荧光增强 "urn-on "反应行为，但对苯甘氨醇对映体没有反应。对于(L)-和(D)-苯甘氨醇，(S)-L1的斯特恩-沃尔默常数（Ksv）值分别为0.63 Ã 103 L molâ1 和4.48 Ã 103 L molâ1，而(S)-L2的对映体荧光差异比（ef）值为4。(S)-L2可用作荧光传感器，对有机分子对映体进行简单而直接的视觉判别。相反，使用含有较大萘基或 8-甲氧基喹啉基取代基的 (S)-BINOL 基硼酯传感器 (S)-L3 和 (S)-L4 时，则无法观察到荧光对映体选择性识别反应。

  DOI：

  10.1039/c3ra45682j
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 以1.56 g的产率得到(2,2'-二羟基-1,1'-联萘-3,3'-二基)二硼酸
  参考文献：
  名称：

  (S)-BINOL-based boronic ester fluorescence sensors for enantioselective recognition of α-phenylethylamine and phenylglycinol

  摘要：

  合成并开发了四种包含硼酸酯和(S)-1,1â²-双-2-萘酚（BINOL）分子的手性荧光传感器（S）-L1â4，用于对δ-苯乙胺和苯基甘氨醇对映体的对映选择性识别。传感器（S）-L1 对δ-苯乙胺和苯基甘氨醇的对映体都有明显的荧光淬灭反应。有趣的是，传感器(S)-L2 对(S)-δ-苯乙胺表现出显著的荧光增强 "urn-on "反应行为，但对苯甘氨醇对映体没有反应。对于(L)-和(D)-苯甘氨醇，(S)-L1的斯特恩-沃尔默常数（Ksv）值分别为0.63 Ã 103 L molâ1 和4.48 Ã 103 L molâ1，而(S)-L2的对映体荧光差异比（ef）值为4。(S)-L2可用作荧光传感器，对有机分子对映体进行简单而直接的视觉判别。相反，使用含有较大萘基或 8-甲氧基喹啉基取代基的 (S)-BINOL 基硼酯传感器 (S)-L3 和 (S)-L4 时，则无法观察到荧光对映体选择性识别反应。

  DOI：

  10.1039/c3ra45682j

文献信息

• Syntheses of new chiral chimeric photo-organocatalysts
  作者：Jiyaun Lyu、Matteo Leone、Aurélie Claraz、Clémence Allain、Luc Neuville、Géraldine Masson

  DOI：10.1039/d1ra06885g

  日期：——

  A new family of chiral chimeric photo-organocatalysts derived from phosphoric acid were synthesized and their spectroscopic and electrochemical properties were investigated. Then, the ability of these photo-activable molecules to catalyse an asymmetric tandem electrophilic β-amination of enecarbamates was evaluated.

  合成了源自磷酸的一类新的手性嵌合光有机催化剂，并研究了它们的光谱和电化学性质。然后，评估了这些光活化分子催化烯氨基甲酸酯的不对称串联亲电β-氨基化的能力。
• (S)-BINOL-based boronic ester fluorescence sensors for enantioselective recognition of α-phenylethylamine and phenylglycinol
  作者：Jiemin Jiao、Guo Wei、Fei Li、Xuerong Mao、Yixiang Cheng、Chengjian Zhu

  DOI：10.1039/c3ra45682j

  日期：——

  Four chiral fluorescence sensors (S)-L1–4 incorporating boronic ester and (S)-1,1′-bi-2-naphthol (BINOL) moieties were synthesized and developed for the enantioselective recognition of α-phenylethylamine and phenylglycinol enantiomers. The sensor (S)-L1 shows an obvious fluorescence quenching “turn-off” response towards enantiomers of both α-phenylethylamine and phenylglycinol. Interestingly, the sensor (S)-L2 can exhibit remarkable fluorescent enhancement “turn-on” response behavior towards (S)-α-phenylethylamine, but shows no response towards phenylglycinol enantiomers. The Stern–Volmer constant (Ksv) values of (S)-L1 are 0.63 × 103 L mol−1 and 4.48 × 103 L mol−1 for (L)- and (D)-phenylglycinol, respectively, and the value of the enantiomeric fluorescence difference ratio (ef) of (S)-L2 is 4.6 for α-phenylethylamine, demonstrating that (S)-L2 could be used as a fluorescence sensor for simple and direct visual discrimination of organic molecule enantiomers. On the contrary, no fluorescence enantioselective recognition response could be observed when using the (S)-BINOL-based boronic ester sensors (S)-L3 and (S)-L4 incorporating bigger naphthyl or 8-methoxyquinolinyl substituent groups.

  合成并开发了四种包含硼酸酯和(S)-1,1â²-双-2-萘酚（BINOL）分子的手性荧光传感器（S）-L1â4，用于对δ-苯乙胺和苯基甘氨醇对映体的对映选择性识别。传感器（S）-L1 对δ-苯乙胺和苯基甘氨醇的对映体都有明显的荧光淬灭反应。有趣的是，传感器(S)-L2 对(S)-δ-苯乙胺表现出显著的荧光增强 "urn-on "反应行为，但对苯甘氨醇对映体没有反应。对于(L)-和(D)-苯甘氨醇，(S)-L1的斯特恩-沃尔默常数（Ksv）值分别为0.63 Ã 103 L molâ1 和4.48 Ã 103 L molâ1，而(S)-L2的对映体荧光差异比（ef）值为4。(S)-L2可用作荧光传感器，对有机分子对映体进行简单而直接的视觉判别。相反，使用含有较大萘基或 8-甲氧基喹啉基取代基的 (S)-BINOL 基硼酯传感器 (S)-L3 和 (S)-L4 时，则无法观察到荧光对映体选择性识别反应。