2-醛基-5-甲氧基苯硼酸 | 40138-18-9

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-醛基-5-甲氧基苯硼酸
• 中文别名: 5-甲氧基-2-甲酰苯硼酸
• 英文名称: (2-formyl-5-methoxyphenyl)boronic acid
• 英文别名: 5-Methoxy-2-formylphenylboronic acid
• CAS: 40138-18-9
• 化学式: C₈H₉BO₄
• mdl: MFCD03001335
• 分子量: 179.968
• InChiKey: YISYHZMNRATPRA-UHFFFAOYSA-N

物化性质

• 熔点：
  155-160 °C
• 沸点：
  418.0±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT, KEEP COLD
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  将药品存放在阴凉干燥的地方密封保存。

SDS

Name:	5-Methoxy-2-Formylphenylboronic Acid Material Safety Data Sheet
Synonym:	None Known
CAS:	40138-18-9

Section 1 - Chemical Product MSDS Name:5-Methoxy-2-Formylphenylboronic Acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
40138-18-9	5-Methoxy-2-Formylphenylboronic Acid	ca. 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 40138-18-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H9BO4
Molecular Weight: 179.96

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat.
Incompatibilities with Other Materials:
Acids, oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, boron oxides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 40138-18-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Methoxy-2-Formylphenylboronic Acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 40138-18-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 40138-18-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 40138-18-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-醛基-5-甲氧基苯硼酸 在 N,N,4-三甲基苯胺 N-氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 以86%的产率得到2-羟基-4-甲氧基苯甲醛
  参考文献：
  名称：

  Mild and Rapid Hydroxylation of Aryl/Heteroaryl Boronic Acids and Boronate Esters with N-Oxides

  摘要：

  Aryl and heteroaryl boronic acids and boronate esters are rapidly, often within minutes, transformed into the corresponding phenols by N-oxides in an open flask at ambient temperature. This transformation has broad compatibility with a variety of functional groups.

  DOI：

  10.1021/ol301463c
• 作为产物：
  描述：

  4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 在 sodium periodate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.33h， 以50%的产率得到2-醛基-5-甲氧基苯硼酸
  参考文献：
  名称：

  3-(α-丙烯酸)苯并氧杂硼杂环化合物的设计和对映选择性合成以对抗碳青霉烯酶耐药性

  摘要：

  手性 3-取代苯并氧硼杂环被设计为碳青霉烯酶抑制剂，并通过不对称 Morita-Baylis-Hillman 反应有效合成。一些苯并氧杂硼杂环戊烯是临床相关碳青霉烯酶的有效抑制剂，并恢复含有这些酶的细菌中美罗培南的活性。晶体学分析验证了所提出的与碳青霉烯酶结合的机制，即以与其抗生素底物相关的方式。结果说明了基于结构的设计方法与不对称催化相结合如何有效地产生有效的β-内酰胺酶抑制剂，并为开发对抗碳青霉烯酶的药物提供了起点。

  DOI：

  10.1039/d1cc03026d

文献信息

• Modifying aroylhydrazone prochelators for hydrolytic stability and improved cytoprotection against oxidative stress
  作者：Qin Wang、Katherine J. Franz

  DOI：10.1016/j.bmc.2018.11.004

  日期：2018.12

  BSIH ((E)-N′-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)isonicotinohydrazide) is a prodrug version of the metal chelator SIH ((E)-N′-(2-hydroxybenzylidene)isonicotinohydrazide) in which a boronate group prevents metal chelation until reaction with hydrogen peroxide releases SIH, which is then available for sequestering iron(III) and inhibiting iron-catalyzed oxidative damage. While BSIH

  BSIH（（（E）-N '-（2-（4,4,5,5-tetramethyl-1,3,2-dioxaboroboro-2--2-yl）苄叉基）异烟肼）是金属螯合剂SIH（（E）-N'-（2-羟基亚苄基）异二十二酰肼）中的硼酸酯基团防止金属螯合，直到与过氧化氢反应释放出SIH，然后可用于螯合铁（III）和抑制铁催化的氧化损伤。虽然BSIH已显示出在氧化应激条件下有条件地靶向细胞螯合铁的前景，但由于BSIH以其水解产物异烟肼和2-甲酰基苯基硼酸作为平衡混合物存在于细胞培养基中的事实限制了SIH的产量。在当前的研究中，评估了几种BSIH类似物的水解稳定性，与H 2 O 2的反应结果以及螯合剂到螯合剂的转化效率。值得注意的是，对甲氧基衍生物（p-OMe）BSIH（（E）-N '-（5-甲氧基-2-（4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基）亚苄基）异烟肼基）和间位- ，第-double取代的（MD）BSIH（（ë）
• Direct One-Pot Synthesis of Naphthoxindoles from 4-Bromooxindoles by Suzuki-Miyaura Coupling and Aldol Condensation Reactions
  作者：Kyeong-Yong Park、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1002/ejoc.201301242

  日期：2014.1

  An efficient one-pot synthesis of naphthoxindoles by using 4-bromoindolin-2-ones and 2-formylphenylboronic acids has been developed. The coupling reaction proceeds in good to excellent yields under microwave irradiation through a Suzuki–Miyaura coupling and an aldol condensation cascade reaction. In addition, this protocol permits the facile construction of naphthoxindoles through an expanded scope

  使用 4-bromoindolin-2-ones 和 2-formylphenylboronic 酸有效地一锅合成萘并吲哚。在微波辐射下，通过 Suzuki-Miyaura 偶联和醇醛缩合级联反应，偶联反应以良好的产率进行。此外，该协议允许通过扩大的底物范围轻松构建萘并吲哚。
• [EN] PESTICIDAL COMPOSITIONS<br/>[FR] COMPOSITIONS PESTICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2011017504A1

  公开（公告）日：2011-02-10

  The present invention concerns novel heteroaryl-N-aryl thiosemicarbazones and their use in pest control, as insecticides and acaπcides This invention also includes preparation of the pesticide compositions containing the compounds, and methods of controlling insects using the compounds

  这项发明涉及新颖的杂环基-N-芳基硫脲类化合物及其在害虫控制中的应用，作为杀虫剂和杀螨剂。该发明还包括含有这些化合物的杀虫剂组合物的制备，以及利用这些化合物控制昆虫的方法。
• Rhodium-Catalyzed Enantioselective Intramolecular Hydroacylation of Trisubstituted Alkenes
  作者：Kirsten F. Johnson、Eugene A. Schneider、Brian P. Schumacher、Arkady Ellern、Joseph D. Scanlon、Levi M. Stanley

  DOI：10.1002/chem.201603880

  日期：2016.10.24

  We report the first examples of transition metal‐catalyzed enantioselective alkene hydroacylations with 1,1,2‐trisubstituted alkenes. DFT and mechanistic studies are consistent with a reaction pathway for these rhodium‐catalyzed processes including intramolecular alkene hydroacylation and α‐epimerization to generate highly enantioenriched, polycyclic architectures. This reaction sequence enables the

  我们报告了第一个用1,1,2-三取代烯烃进行过渡金属催化的对映选择性烯烃加氢酰化的例子。DFT和机理研究与这些铑催化过程的反应途径一致，这些过程包括分子内烯烃加氢酰化和α-表异构化以生成高度对映体富集的多环结构。该反应顺序使2-（环己-1-烯-1-基）苯甲醛的加氢酰化，以形成六氢-9- ħ芴-9-酮在中度到高的产率（68-91％）与高对映选择性（高达99％ee）和非对映选择性（通常> 20：1）。
• Macrocyclic hepatitis C serine protease inhibitors
  申请人：Miao Zhenwei

  公开号：US20050153877A1

  公开（公告）日：2005-07-14

  The present invention relates to compounds of Formula I, II or Ill, or a pharmaceutically acceptable salt, ester, or prodrug, thereof: wherein W is a substituted or unsubstituted heterocyclic ring system. The compounds inhibit serine protease activity, particularly the activity of hepatitis c virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis c virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明涉及式I、II或III的化合物，或其药用可接受的盐、酯或前药： 其中W是取代或未取代的杂环环系。这些化合物抑制丝氨酸蛋白酶活性，尤其是丙型肝炎病毒（HCV）NS3-NS4A蛋白酶的活性。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，并且还可用作抗病毒剂。本发明进一步涉及包含上述化合物的药物组合物，用于给患有HCV感染的对象进行给药。本发明还涉及通过给主体投药包含本发明化合物的药物组合物来治疗主体HCV感染的方法。