吩恶噻-4-硼酸 | 100124-07-0

• 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 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 吩恶噻-4-硼酸
• 中文别名: 4-吩恶噻硼酸
• 英文名称: phenoxathiin-4-boronic acid
• 英文别名: phenoxathiin-4-ylboronic acid
• CAS: 100124-07-0
• 化学式: C₁₂H₉BO₃S
• mdl: MFCD01605731
• 分子量: 244.079
• InChiKey: IIENVBUXFRSCLM-UHFFFAOYSA-N

物化性质

• 熔点：
  162-167 °C
• 沸点：
  457.5±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  <b> <p></p> </b>

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P352,P280,P305+P351+P338
• 危险性描述：
  H319,H315,H335
• 储存条件：
  0-6°C

SDS

Name:	Phenoxathiin-4-Boronic Acid Material Safety Data Sheet
Synonym:	None Known
CAS:	100124-07-0

Section 1 - Chemical Product MSDS Name:Phenoxathiin-4-Boronic Acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
100124-07-0	Phenoxathiin-4-Boronic 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# 100124-07-0: 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: C12H9BO3S
Molecular Weight: 244.07

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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:
Oxidizing agents, acids, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide, boron oxides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 100124-07-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Phenoxathiin-4-Boronic 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# 100124-07-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 100124-07-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 100124-07-0 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

化学性质

吩恶噻-4-硼酸通常为白色或淡黄色固体，可溶于许多有机溶剂如乙醇、二甲基甲酰胺和二氯甲烷，并且稍溶于水。它具有羧酸类物质的通性，可以发生酯化反应。

用途

吩恶噻-4-硼酸作为有机合成中的重要试剂和中间体，在多种化学反应中发挥重要作用，例如Suzuki反应、Stille反应和Negishi反应等；此外，它还广泛用于合成各种有机杂环化合物。

合成方法

将吩恶噻-4-碘或吩恶噻-4-溴与亚砜进行反应，生成吩恶噻-4-亚砜酰卤化物；随后再与三苯基硼反应，形成吩恶噻-4-硼酸三苯基酯；最后通过水解反应得到吩恶噻-4-硼酸。

反应信息

• 作为反应物：
  描述：

  吩恶噻-4-硼酸 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 C₁₈H₂₂NO₃P 、 氢气 、 碘 、 palladium diacetate 、 sodium hydroxide 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 甲苯 、 正丁醇 为溶剂， 20.0~100.0 ℃ 、4.14 MPa 条件下， 反应 14.5h， 生成 1-benzyl-2-(phenoxathiin-4-yl)piperidine
  参考文献：
  名称：

  吡啶鎓盐不对称氢化对映选择性合成α-(杂)芳基哌啶及其机理

  摘要：

  报道了 α-芳基和 α-杂芳基哌啶的对映选择性合成。关键步骤是取代的N-苄基吡啶鎓盐的铱催化不对称氢化。一系列 α-杂芳基哌啶获得了高达 99.3:0.7 er 的高水平对映选择性。DFT 计算支持吡啶还原的外层解离机制。值得注意的是，最终烯胺中间体的初始质子化决定了转化的立体化学结果，而不是所得亚胺中间体的氢化物还原。

  DOI：

  10.1021/acs.orglett.8b00067
• 作为产物：
  描述：

  二苯醚 在 aluminum (III) chloride 、 正丁基锂 、 sulfur 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 吩恶噻-4-硼酸
  参考文献：
  名称：

  化合物及包含它的有机电子元件

  摘要：

  本发明涉及一种化合物及包含它的有机电子元件。本发明的化合物用于以有机发光元件为代表的有机电子元件，能够降低有机电子元件的驱动电压，提高光效率，并且利用化合物的热稳定性而提高元件的寿命特性。

  公开号：

  CN107325090B

文献信息

• Nickel-Catalyzed Alkyl–Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes
  作者：Amberly B. Sanford、Taylor A. Thane、Tristan M. McGinnis、Pan-Pan Chen、Xin Hong、Elizabeth R. Jarvo

  DOI：10.1021/jacs.0c01330

  日期：2020.3.18

  3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also

  两个 Csp3-X 键的交叉亲电偶联反应仍然具有挑战性。在此，我们报告了分子内镍催化的 1,3-二醇衍生物的交叉亲电偶联反应。值得注意的是，这种转化用于合成一系列单和 1,2-二取代的烷基环丙烷，包括衍生自萜烯、类固醇和醛醇产品的那些。此外，对映体富集的环丙烷是由脯氨酸催化和埃文斯羟醛反应的产物合成的。还描述了将 1,3-二醇直接转化为环丙烷的过程。计算和实验数据与镍催化机制一致，该机制始于二级中心的立体氧化加成。
• ATM inhibitors
  申请人：Kudos Pharmaceuticals Ltd

  公开号：US20040002492A1

  公开（公告）日：2004-01-01

  The application concerns a compound of formula I: 1 wherein one of P and Q is O, and the other of P and Q is CH, where there is a double bond between whichever of Q and P is CH and the carbon atom bearing the R 3 group; Y is either O or S; R 1 and R 2 are independently hydrogen, an optionally substituted C 1-7 alkyl group, C 3-20 heterocyclyl group, or C 5-20 aryl group, or may together form an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; R 3 is a phenyl or pyridyl group, attached by a first bridge group selected from —S—, —S(═O)—, —S(═O) 2 —, —O—, —NR N — and CR C1 R C2 — to an optionally substituted C 5-20 carboaryl group, the phenyl or pyridyl group and optionally substituted C 5-20 carboaryl group being optionally further linked by a second bridge group, so as to form an optionally substituted C 5-7 ring, the phenyl or pyridyl group being further optionally substituted.

  该应用涉及一种具有以下式I的化合物：其中P和Q中的一个是O，另一个是CH，Q和P中的CH之一之间存在双键，并且带有R3基团的碳原子；Y可以是O或S；R1和R2独立地是氢、可选择地取代的C1-7烷基、C3-20杂环基团或C5-20芳基，或者可以一起形成具有4至8个环原子的可选择地取代的杂环环；R3是苯基或吡啶基团，通过第一桥基团连接到一个可选择地取代的C5-20碳芳基团，该苯基或吡啶基团和可选择地取代的C5-20碳芳基团可以进一步通过第二桥基团连接，从而形成一个可选择地取代的C5-7环，苯基或吡啶基团可以进一步选择性地取代。
• 6-Alkyl-, 6-aryl- or 6-hetaryl-7-deazapurine ribonucleosides as inhibitors of human or MTB adenosine kinase and potential antimycobacterial agents
  作者：Pavla Perlíková、Petr Konečný、Petr Nauš、Jan Snášel、Ivan Votruba、Petr Džubák、Iva Pichová、Marián Hajdúch、Michal Hocek

  DOI：10.1039/c3md00232b

  日期：——

  Title 6-alkyl-, 6-aryl- and 6-hetaryl-7-deazapurine ribonucleosides previously known as nanomolar cytostatics were found to be potent inhibitors of either human or mycobacterial (MTB) adenosine kinase (ADK). Several new derivatives bearing bulky substituents at position 6 were non-cytotoxic but selectively inhibited MTB ADK. However, most of the nucleosides (ADK inhibitors) as well as their octadecylphosphate prodrugs were inactive in the whole cell assay of inhibition of Mycobacterium bovis growth. 6-Methyl-7-deazapurine ribonucleoside was found to be a potent antimycobacterial agent.

  标题：6-烷基、6-芳基和6-杂芳基-7-脱氮嘌呤核糖核苷，先前被称为纳摩尔级的细胞抑制剂，被发现是强效的人类或分枝杆菌（MTB）腺苷激酶（ADK）抑制剂。一些在6位带有大体积取代基的新衍生物无细胞毒性，但能选择性地抑制MTB ADK。然而，大多数核苷（ADK抑制剂）及其十八烷基磷酸前药在抑制牛分枝杆菌生长的整体细胞试验中均无活性。6-甲基-7-脱氮嘌呤核糖核苷被发现是一种强效的抗分枝杆菌剂。
• Room Temperature Aryl Trifluoromethylation via Copper-Mediated Oxidative Cross-Coupling
  作者：Todd D. Senecal、Andrew T. Parsons、Stephen L. Buchwald

  DOI：10.1021/jo1023377

  日期：2011.2.18

  A method for the room temperature copper-mediated trifluoromethylation of aryl and heteroaryl boronic acids has been developed. This protocol is amenable to normal benchtop setup and reactions typically require only 1−4 h. Proceeding under mild conditions, the method tolerates a range of functional groups, allowing access to a variety of trifluoromethylarenes.

  已开发出一种用于室温铜介导的芳基和杂芳基硼酸三氟甲基化的方法。该协议适用于正常的台式设置，反应通常只需要 1-4 小时。该方法在温和条件下进行，可耐受一系列官能团，从而可以使用各种三氟甲基芳烃。
• Modular Synthesis of 5-Substituted Furan-2-yl C-2′-Deoxyribonucleosides and Biaryl Covalent Base-Pair Analogues
  作者：Jan Bárta、Lenka Slavětínská、Blanka Klepetářová、Michal Hocek

  DOI：10.1002/ejoc.201000726

  日期：——

  A modular and efficient synthesis of 5-(hetero)arylfuran C-2'-deoxyribonucleosides was developed. Friedel-Crafts C-glycosidation of 2-bromofuran with toluoyl-protected methyl 2'-deoxyribofuranoside in the presence of BF 3 ·Et 2 O gave 5-bromofuran C-nucleosides, which were used as key intermediates for Stille or Suzuki coupling with (hetero)arylstannanes or boronic acids to afford a series of 5-(hetero)arylfuran

  开发了一种模块化和高效的 5-(杂) 芳基呋喃 C-2'-脱氧核糖核苷合成方法。在 BF 3 ·Et 2 O 存在下，2-溴呋喃与甲苯甲酰基保护的甲基 2'-脱氧呋喃核糖苷的 Friedel-Crafts C-糖苷化得到 5-溴呋喃 C-核苷，其用作 Stille 或 Suzuki 偶联的关键中间体 (杂）芳基锡烷或硼酸以提供一系列 5-（杂）芳基呋喃 C-核苷。5-硼呋喃 C-核苷通过溴呋喃与双（频哪醇二硼）的 Suzuki 偶联或通过 Ir 催化的呋喃 C-H 硼酸化制备，并用于与 5-溴杂芳基 C-核苷交叉偶联以提供新的共价类似物核苷对。标题 5-arylfuran C-nucleosides 具有有趣的荧光特性，可用于生物分子的荧光标记。