6-氯苯并噁唑 | 227197-72-0

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 6-氯苯并噁唑
• 中文别名: 6-氯-1,3-苯并恶唑；6-氯苯并恶唑
• 英文名称: 6-chlorobenzoxazole
• 英文别名: 6-chlorobenzo[d]oxazole；6-chloro-1,3-benzoxazole
• CAS: 227197-72-0
• 化学式: C₇H₄ClNO
• mdl: MFCD09027437
• 分子量: 153.568
• InChiKey: JJOOKXUUVWIARB-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  226.3±13.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：室温、密封、干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Chloro-1,3-benzoxazole
Synonyms:

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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: 6-Chloro-1,3-benzoxazole
CAS number: 227197-72-0

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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, refrigerated.
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: C7H4ClNO
Molecular weight: 153.6

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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, nitrogen oxides, hydrogen chloride.

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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

6-氯苯并噁唑可用作医药合成中间体。若吸入此物质，请立即将患者移至新鲜空气处；如皮肤受到污染，应脱去受污染的衣物，并用肥皂水和清水彻底清洗皮肤；如果眼睛接触到该物质，应翻开眼睑，用流动清水或生理盐水冲洗，并立即就医；若误食，则需立即漱口，禁止催吐，并尽快就医。

反应信息

• 作为反应物：
  描述：

  6-氯苯并噁唑 在 三氯化铝 、 氯 作用下， 以 三氯氧磷 为溶剂， 以94%的产率得到2,6-二氯苯并噁唑
  参考文献：
  名称：

  Method for producing chlorobenzoxazolene

  摘要：

  本发明涉及一种制备式(I)的氯代苯并噁唑的方法，其中R1、R2和R4如权利要求1所定义，在情况(a)中R3＝H、卤素、CN、NO2、C1-C5烷基、C1-C5烷氧基、芳基或芳氧基，其中最后4个基团中的每一个都是未取代的或取代的，或在情况(b)中R3＝氯，其包括在酸性催化剂存在下，用氯化试剂与式(II)的苯并噁唑反应，其中R1、R2和R4如式(I)所定义，在情况(a)中R3如式(I)所定义，在情况(b)中R3为氢，以给出单氯代产物(I)，或在情况(b)中使用过量的氯化试剂以给出二氯代产物(I)，其中R3＝氯。

  公开号：

  US06274739B1
• 作为产物：
  描述：

  2-氨基-5-氯苯酚 、 原甲酸三乙酯 生成 6-氯苯并噁唑
  参考文献：
  名称：

  CuCl光催化苯并恶唑的C-H胺化

  摘要：

  苯并恶唑与胺的直接偶联是通过可见光照射和CuCl催化实现的。以空气为氧化剂，在温和条件下成功合成了多种胺化苯并恶唑。

  DOI：

  10.1039/d2ob00687a

文献信息

• Copper-Catalyzed Oxidative Amination of Benzoxazoles via C−H and C−N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources
  作者：Shengmei Guo、Bo Qian、Yinjun Xie、Chungu Xia、Hanmin Huang

  DOI：10.1021/ol1030298

  日期：2011.2.4

  method for oxidative amination of azoles with tertiary amines via copper-catalyzed C−H and C−N bond activation has been developed. This protocol can be performed in the absence of external base and only requires atmospheric oxygen as oxidant. The catalyst system is very simple and efficient, which opens a new way for using tertiary amines as nitrogen group sources for C−N bond formation reactions.

  通过铜催化的CH和CN键活化作用，开发了一种高效，概念上新颖的用叔胺氧化唑类胺的方法。该方案可以在不存在外部碱的情况下进行，并且仅需要大气中的氧气作为氧化剂。催化剂体系非常简单和高效，这为使用叔胺作为C-N键形成反应的氮源提供了新途径。
• [EN] FUSED HETEROCYCLIC COMPOUNDS AS OREXIN RECEPTOR MODULATORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS EN TANT QUE MODULATEURS DE RÉCEPTEUR D'OREXINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011050202A1

  公开（公告）日：2011-04-28

  Certain disubstituted 3,8-diaza-bicyclo[4.2.0]octane and 3,6-diazabicyclo [3.2.0]heptane are described, which are useful as orexin inhibitors. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

  某些二取代的3,8-二氮杂双环[4.2.0]辛烷和3,6-二氮杂双环[3.2.0]庚烷被描述为俄雷昔蛋白抑制剂。这些化合物可能在制药组合物和治疗由俄雷昔蛋白活性介导的疾病状态、紊乱和病况的方法中有用，比如失眠。
• Catalyst- and Reagent-Free Electrochemical Azole C−H Amination
  作者：Youai Qiu、Julia Struwe、Tjark H. Meyer、João C. A. Oliveira、Lutz Ackermann

  DOI：10.1002/chem.201802832

  日期：2018.9.3

  Catalyst‐ and chemical oxidant‐free electrochemical azole C−H aminations were accomplished via cross‐dehydrogenative C−H/N−H functionalization. The catalyst‐free electrochemical C−H amination proved feasible on azoles with high levels of efficacy and selectivity, avoiding the use of stoichiometric oxidants under ambient conditions. Likewise, the C(sp3)−H nitrogenation proved viable under otherwise

  不含催化剂和化学氧化剂的电化学唑CH胺的胺化反应是通过交叉脱氢CH / NH官能化完成的。事实证明，无催化剂的电化学CH氨基化反应对具有高水平的效率和选择性的唑类是可行的，避免了在环境条件下使用化学计量的氧化剂。同样，C（sp 3）-H氮化在其他相同条件下也被证明是可行的。脱氢CHH胺的作用范围很广，包括环状和非环状脂肪胺以及苯胺，并且使用可持续的电力作为唯一的氧化剂。
• Palladium-Catalyzed <i>sp</i>² and <i>sp</i>³ C–H Bond Activation and Addition to Isatin toward 3-Hydroxy-2-oxindoles
  作者：Gang-Wei Wang、An-Xi Zhou、Jun-Jiao Wang、Rong-Bin Hu、Shang-Dong Yang

  DOI：10.1021/ol402494e

  日期：2013.10.18

  The first Pd(II)-catalyzed C–H addition to isatins by direct sp2/sp3 C–H bond activation for the construction of 3-substituted-3-hydroxy-2-oxindoles is reported. The bidentate nitrogen ligands were found to promote this reaction. Specifically, the preliminary bioassay indicated that 3-(5-chlorobenzoxazole)-3-hydroxy-N-benzyl-2-oxindole (2w) is a new inhibitor of human kidney cancer and hepatocellular

  据报道，通过直接的sp 2 / sp 3 C-H键活化，Pd（II）催化的CHs可以直接形成3-取代的3-羟基-2-羟基吲哚，并通过直接的sp 2 / sp 3的CH键活化。发现双齿氮配体促进该反应。具体地，初步的生物测定表明3-（5-氯苯并恶唑）-3-羟基-N-苄基-2-氧吲哚（2w）是人肾癌和肝细胞癌细胞的新抑制剂。而且，该反应体系表现出很大的官能团耐受性，并且不需要导向基团，额外的碱或添加剂。
• Amination of Benzoxazoles and 1,3,4-Oxadiazoles Using 2,2,6,6-Tetramethylpiperidine-N-oxoammonium Tetrafluoroborate as an Organic Oxidant
  作者：Sebastian Wertz、Shintaro Kodama、Armido Studer

  DOI：10.1002/anie.201104735

  日期：2011.11.25

  No transition metals are necessary to convert benzoxazoles and 1,3,4‐oxadiazoles into the corresponding pharmacologically interesting 2‐aminated heterocycles by formal direct C(2)‐amination using tetramethylpiperidine‐N‐oxoammonium tetrafluoroborate (TEMPO+BF4−) as an oxidant (see scheme; TEMP=2,2,6,6‐tetramethylpiperidine; TfOH=trifluoromethanesulfonic acid).

  没有过渡金属是必要通过正式直接C（2）使用-amination到tetramethylpiperidine-苯并恶唑和1,3,4-恶二唑转化成相应的药理学上感兴趣的2-胺化杂环Ñ -oxoammonium四氟硼酸盐（TEMPO + BF 4 - ），为氧化剂（参见方案; TEMP = 2,2,6,6-四甲基哌啶; TfOH =三氟甲磺酸）。