正癸基硼酸 | 24464-63-9

• 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 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 正癸基硼酸
• 英文名称: decylboronic acid
• 英文别名: n-decylboronic acid；1-decylboronic acid
• CAS: 24464-63-9
• 化学式: C₁₀H₂₃BO₂
• 分子量: 186.102
• InChiKey: TUTSEMMBKGBUGD-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78°C
• 沸点：
  297.1±23.0 °C(Predicted)
• 密度：
  0.883±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解。避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 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：
  保持贮藏器密封，并将其放入一个紧密的容器中。存放在阴凉、干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
N-Decylboronic 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.
N-Decylboronic acid
Ingredient name:
CAS number: 24464-63-9

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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.
Store in closed vessels, under −20◦C.
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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H23BO2
Molecular weight: 186.1

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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：

  正癸基硼酸 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 1-乙酸基-1,2-苯碘酰-3-(1H)-酮 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 N-十一烷基腈
  参考文献：
  名称：

  Deboronative cyanation of potassium alkyltrifluoroborates via photoredox catalysis

  摘要：

  通过可见光光合还原催化，实现了烷基三氟硼酸酯的基团脱硼氰化反应，适用于具有广泛功能基团的化合物。

  DOI：

  10.1039/c6cc01530a
• 作为产物：
  描述：

  2-n-Decyl-1,3,2-dithiaborolan 在 H₂O 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 正癸基硼酸
  参考文献：
  名称：

  Hydroboration of alkenes and alkynes by 1,3,2-dithiaborolane

  摘要：

  DOI：

  10.1021/jo00440a009

文献信息

• Phthalocyanine Zinc‐catalyzed Hydroxylation of Aryl Boronic Acids under visible Light
  作者：Dong-Ping Luo、Yang-Feng Huang、Xiao-Yi Hong、Dingben Chen、Guo-Xing Li、Xiaobo Huang、Miaochang Liu、Wenxia Gao、Yun-Bing Zhou、Huayue Wu

  DOI：10.1002/adsc.201801276

  日期：——

  A visible‐light‐promoted aerobic oxidative hydroxylation of boronic acids using phthalocyanine zinc as an easily available photosensitizer has been developed. It provided a direct access to synthesize aliphatic alcohols and phenols from boronic acids. The advantages of this approach included the low catalyst loading (0.5 mol%), high efficient, the use of O2 as an oxygen source, wide substrate range

  已经开发了使用酞菁锌作为易用的光敏剂的可见光促进硼酸的好氧氧化羟基化反应。它提供了直接从硼酸合成脂族醇和酚的途径。该方法的优点包括催化剂负载量低（0.5 mol％），高效，使用O 2作为氧气源，底物范围宽，操作过程简单以及条件温和。
• Oxidation with air by ascorbate-driven quinone redox cycling
  作者：Gastón Silveira-Dorta、Diego M. Monzón、Fernando P. Crisóstomo、Tomás Martín、Víctor S. Martín、Romen Carrillo

  DOI：10.1039/c5cc01519g

  日期：——

  Transition metal-free oxidation with air at room temperature has been achieved by simply using ascorbate (vitamin C) and catalytic amounts of menadione (vitamin K3). A combination of the mentioned vitamins transforms atmospheric oxygen into hydrogen peroxide, which is able to oxidize arylboronic acids and other chemical moieties.

  只需使用抗坏血酸盐（维生素C）和催化量的甲萘醌（维生素K3），即可在室温下用空气实现无过渡金属的氧化。上述维生素的组合将大气中的氧气转化为过氧化氢，该过氧化氢能够氧化芳基硼酸和其他化学部分。
• Photoinduced hydroxylation of arylboronic acids with molecular oxygen under photocatalyst-free conditions
  作者：Yu-Ting Xu、Chen-Yuan Li、Xiao-Bo Huang、Wen-Xia Gao、Yun-Bing Zhou、Miao-Chang Liu、Hua-Yue Wu

  DOI：10.1039/c9gc02229e

  日期：——

  Photoinduced hydroxylation of boronic acids with molecular oxygen under photocatalyst-free conditions is reported, providing a green entry to a variety of phenols and aliphatic alcohols in a highly concise fashion. This new protocol features photocatalyst-free conditions, wide substrate scope and excellent functional group compatibility.

  据报道，在无光催化剂的条件下，硼酸与分子氧的光诱导羟基化反应，为绿色的苯酚和脂肪族醇的绿色合成提供了一种简洁的方法。该新协议具有无光催化剂的条件，广泛的底物范围和出色的官能团相容性。
• Sustainable oxidations with air mediated by gallic acid: potential applicability in the reutilization of grape pomace
  作者：Jimena Scoccia、Marcelle D. Perretti、Diego M. Monzón、Fernando P. Crisóstomo、Víctor S. Martín、Romen Carrillo

  DOI：10.1039/c5gc02966j

  日期：——

  Tannins like gallic acid and even grape pomace extract are able to perform oxidations with air thus unleashing an alternative method for reutilization and valorization of bio-wastes.

  单宁酸如没食子酸，甚至葡萄渣提取物都能够与空气进行氧化，从而释放出另一种方法来重新利用和回收生物废物。
• 无光催化剂条件下硼酸衍生物需氧羟基化反应制备醇和酚的方法
  申请人：温州大学

  公开号：CN110668921A

  公开（公告）日：2020-01-10

  本发明公开了一种无光催化剂条件下硼酸衍生物需氧羟基化反应制备醇和酚的方法，所述的硼酸衍生物为芳基硼酸或烷基硼酸，其所对应的目标化合物分别为酚类化合物和醇类化合物；该方法以硼酸衍生物为反应底物，在溶剂条件下，加入添加剂并在有氧和光照条件下发生羟基化反应，得到对应的目标化合物。本发明通过无光催化剂的芳基硼酸的需氧羟基化为酚类的合成提供一种新的策略。本发明首次公开了一种以三乙胺为添加剂，光催化芳基硼酸或烷基硼酸的无催化剂需氧羟基化的方法。本发明的优点是该新方法具有无光催化剂条件、广泛的底物范围和良好的官能团兼容性。