2-氨基苯硼酸频哪醇酯 | 191171-55-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 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-氨基苯硼酸频哪醇酯
• 中文别名: 2-氨基苯硼酸频那醇酯；2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯胺；2-(4,4,5,5-四甲基-1,3,2-二恶硼烷)苯胺；2-氨基苯硼酸嚬哪醇酯；2-(4,4,5,5-四甲基-1，3，2-二恶硼烷）苯胺
• 英文名称: 2-anilineboronic acid pinacol ester
• 英文别名: 2-aminophenylboronic acid pinacol ester；2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline；2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylamine；2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine；2-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline；2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline；2-aminophenylboronic acid pinacolate ester；pinacol (2-aminophenyl)boronate；2-aminophenylpinacolboronate；2-aminophenylpinacolborane；o-aminophenyl boronic acid pinacol ester；anthranilate pinacol ester
• CAS: 191171-55-8
• 化学式: C₁₂H₁₈BNO₂
• mdl: MFCD02179448
• 分子量: 219.091
• InChiKey: ZCJRWQDZPIIYLM-UHFFFAOYSA-N

物化性质

• 熔点：
  63-68 °C (lit.)
• 沸点：
  125°C/1.5mmHg(lit.)
• 密度：
  1.05±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：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  保存方法：密封、阴凉、通风干燥处。

SDS

Name:	2-(4 4 5 5-Tetramethyl-1 3 2-dioxaborolan-2-yl)aniline Material Safety Data Sheet
Synonym:	2-Aminophenylboronic acid pinacol este
CAS:	191171-55-8

Section 1 - Chemical Product MSDS Name:2-(4 4 5 5-Tetramethyl-1 3 2-dioxaborolan-2-yl)aniline Material Safety Data Sheet
Synonym:2-Aminophenylboronic acid pinacol este

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
191171-55-8	2-(4,4,5,5-Tetramethyl-1,3,2-dioxaboro	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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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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:
Keep refrigerated. (Store below 4C/39F.) Store in a tightly closed container. Store in a dry area.

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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# 191171-55-8: 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: Crystalline powder
Color: cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 62 - 64 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C12H18BNO2
Molecular Weight: 219.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, boron oxides.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 191171-55-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 191171-55-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 191171-55-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 191171-55-8 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

制备方法与用途

概述

氨基硼酸频那醇酯作为药物和有机发光材料（LED）合成的中间体，目前多侧重于该类化合物的应用。

用途

2-氨基苯硼酸频哪醇酯是一种酯类衍生物，用作有机试剂。

反应信息

• 作为反应物：
  描述：

  2-氨基苯硼酸频哪醇酯 在 Oxone 、 potassium phosphate 、 2-萘硼酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-氨基苯酚
  参考文献：
  名称：

  通过硼酸选择性相转移实现芳基有机硼系统的化学选择性氧化†

  摘要：

  我们报道了含有两个可氧化硼基团的芳基有机硼系统的直接化学选择性布朗型氧化。碱性双相反应条件能够在硼酸频哪醇 (BPin) 酯存在下选择性形成硼酸三羟基硼酸酯并进行相转移，同时避免形态平衡。光谱研究验证了有机硼物质的碱促进相选择性辨别。这种现象在多种有机硼化合物中普遍存在，也可用于反转传统的保护基策略，使 BMIDA 物质能够在通常更具反应性的 BPin 底物上进行化学选择性氧化。我们还证明了二硼酸系统的选择性氧化具有可先验预测的化学选择性。该方法的实用性通过化学选择性氧化亲核试剂偶联的开发来例证。

  DOI：

  10.1039/c6sc04014d
• 作为产物：
  描述：

  2-硝基苯基硼酸 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-氨基苯硼酸频哪醇酯
  参考文献：
  名称：

  Self-Activation and 1,8-Stereoinduction in a Boronate-substituted Dienophile

  摘要：

  发现邻硼代苯胺亲双烯体 4 与环戊二烯的 [4+2] 环加成反应比其对位异构体 8 和未取代的衍生物 6 进行得更快，从而证实了在 4 的情况下，通过内部配位的自激活是有效的。 手性硼酸酯衍生物9和10提供了小水平的远程1,8-立体诱导。这些结果表明，二烷氧基硼酸酯可以作为弱的内路易斯酸，并在环加成反应中活化含羰基的官能团。

  DOI：

  10.1055/s-2002-20470
• 作为试剂：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 1-苯基甲基-2,4-哌啶二酮 、 异氰酸苯酯 在 三乙胺 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 2-氨基苯硼酸频哪醇酯 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  通过二碘化钐介导的碳二亚胺还原环化合成 2-亚氨基二氢吲哚

  摘要：

  报道了一种使用二碘化钐 (SmI2) 合成 2-亚氨基二氢吲哚的方法。在叔丁醇的存在下，处理带有 α,β-不饱和羰基部分的碳二亚胺...

  DOI：

  10.1246/cl.2012.44

文献信息

• Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from <i>N</i> -Ts-Anilines and Styrenes
  作者：So Won Youn、Tae Yun Ko、Young Ho Jang

  DOI：10.1002/anie.201702205

  日期：2017.6.1

  A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly

  建立了N -Ts-苯胺和苯乙烯之间Pd催化的分子间氧化环。该方法使用容易获得的，具有良好的官能团耐受性和高区域选择性和效率的起始原料，为各种3-芳基吲哚提供了一种简单而稳健的方法。从该方法获得的产物的进一步精制提供了获得高度官能化且结构多样的吲哚的途径，例如3-（吲哚-3-基）咔唑，1,9-二氢吡咯并-[2,3-b]咔唑和3 '-芳基-3,5'-联吲哚。
• Diastereoselective Intramolecular Carbamoylketene/Alkene [2 + 2] Cycloaddition: Enantioselective Access to Pyrrolidinoindoline Alkaloids
  作者：Takaaki Araki、Tsukasa Ozawa、Hiromasa Yokoe、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1021/ol303204v

  日期：2013.1.4

  A novel and highly diastereoselective intramolecular carbamoylketene/alkene [2 + 2] cycloaddition has been developed, and the methodology was successfully applied to the enantioselective syntheses of (−)-esermethole and Takayama’s intermediate for (+)-psychotrimine.

  已开发出一种新颖的，高度非对映选择性的分子内氨基甲酰基乙烯酮/烯烃[2 + 2]环加成反应，该方法已成功地应用于（-）-乙二胺和高山的（+）-精神三胺中间体的对映选择性合成。
• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20150259357A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , R 2 , R 3 , R 3 ′, L, W, and V are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention

  本发明涉及式（I）的化合物，或其形式，其中环A，R1，R2，R3，R3'，L，W和V如本文所定义，可用作FLAP调节剂。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
  作者：Kai Chen、Shuai Zhang、Pei He、Pengfei Li

  DOI：10.1039/c5sc04521e

  日期：——

  A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions...

  发现了在低温下，水溶液中芳基碘化物和溴化物的快速，化学选择性和无金属的CB键形成反应。该反应适合间歇和连续流动条件...
• [EN] BIPHENYL SUBSTITUTED 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDENEAMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDÈNE-AMINE À SUBSTITUTION BIPHÉNYLE
  申请人：NOVARTIS AG

  公开号：WO2011157787A1

  公开（公告）日：2011-12-22

  The invention relates to new derivatives of formula (I), wherein the substituents are as defined in the specification; to processes for the preparation of such derivatives; pharmaceutical compositions comprising such derivatives; such derivatives as a medicament; such derivatives for the treatment of one or more IGF-1 R mediated disorders or diseases.

  这项发明涉及公式（I）的新衍生物，其中取代基如规范中所定义；制备这种衍生物的方法；包括这种衍生物的药物组合物；将这种衍生物用作药物；将这种衍生物用于治疗一个或多个IGF-1 R介导的疾病。