2-溴-6-乙氧基萘 | 66217-19-4

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-溴-6-乙氧基萘
• 中文别名: 6-乙氧基-2-溴萘
• 英文名称: 2-ethoxy-6-bromo-naphthalene
• 英文别名: 2-ethyloxy-6-bromonaphthalene；2-bromo-6-ethoxy-naphthalene；2-bromo-6-ethoxynaphthalene；6-bromo-2-ethoxynaphthalene；ethyl-(6-bromo-[2]naphthyl)-ether；Aethyl-(6-brom-[2]naphthyl)-aether
• CAS: 66217-19-4
• 化学式: C₁₂H₁₁BrO
• mdl: MFCD01568865
• 分子量: 251.123
• InChiKey: FXVYIQCXQULCKL-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  337.8±15.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。储存地点需远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Bromo-6-ethoxynaphthalene
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.
2-Bromo-6-ethoxynaphthalene
Ingredient name:
CAS number: 66217-19-4

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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.
Storage: Store in closed vessels.

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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: C12H11BrO
Molecular weight: 251.1

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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, hydrogen bromide.

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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：

  2-溴-6-乙氧基萘 在 叔丁基锂 、 碘 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Organoaluminum-Mediated Direct Cross-Coupling Reactions

  摘要：

  AbstractWe present a direct cross‐coupling reaction between arylaluminum compounds (ArAlMe2⋅LiCl) and organic halides RX (R=aryl, alkenyl, alkynyl; X=I, Br, and Cl) without any external catalyst. The reaction takes place smoothly, simply upon heating, thereby enabling the efficient and chemo‐/stereoselective formation of biaryl, alkene, and alkyne coupling products with broad functional group compatibility.

  DOI：

  10.1002/anie.201412249
• 作为产物：
  描述：

  1,6-二溴-2-萘酚 在 盐酸 、 tin(ll) chloride 作用下， 生成 6-溴-2-萘酚 、 2-溴-6-乙氧基萘
  参考文献：
  名称：

  InterProScan – an integration platform for the signature-recognition methods in InterPro

  摘要：

  摘要：InterProScan是一种工具，用于将给定的蛋白质序列与InterPro成员数据库的蛋白质标志进行扫描，目前包括PROSITE、PRINTS、Pfam、ProDom和SMART。标志数据库的数量及其相关的扫描工具以及进一步的细化程序使问题变得复杂。InterProScan被设计为具有可扩展性和可扩展性的系统，具有稳健的内部架构。

  可用性：基于Perl的InterProScan实现可从EBI ftp服务器（ftp://ftp.ebi.ac.uk/pub/software/unix/iprscan/）获取，基于SRS的InterProScan可根据请求提供。我们提供公共网络界面（http://www.ebi.ac.uk/interpro/scan.html）以及电子邮件提交服务器（[e-mail]）。

  联系人：[e-mail]

  * 应该向谁通讯。

  DOI：

  10.1093/bioinformatics/17.9.847

文献信息

• Modular Synthesis of Di- and Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors
  作者：Ian de Toledo、Thiago A. Grigolo、James M. Bennett、Jonathan M. Elkins、Ronaldo A. Pilli

  DOI：10.1021/acs.joc.9b01844

  日期：2019.11.1

  A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol

  基于酮氧化，采用催化HBr和DMSO，然后通过咪唑与醛的缩合反应，开发了一种单罐模块化方法，用于合成2,4（5）-二取代的咪唑。该方法提供了二十九个二取代的NH-咪唑（23％-85％的产率）。通过采用这种氧化-缩合方案，然后在咪唑环中进行溴化和Suzuki偶联，得到三取代的NH-咪唑（23％-69％，三步法），实现了三步合成20种激酶抑制剂的过程。该方法还用于合成已知抑制剂GSK3037619A。
• Naphthalene derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06573289B1

  公开（公告）日：2003-06-03

  A composition containing a compound of the formula: wherein A is a nitrogen-containing heterocyclic group which may be substituted, R1 is a hydrogen atom, hydrocarbon group which may be substituted, or monocyclic aromatic heterocyclic group which may be substituted, R2 is a hydrogen atom or a lower alkyl group which may be substituted, R3, R4, R5, R6, R7, R8 and R9 are independently a hydrogen atom, a hydrocarbon group which may be substituted, a hydroxy group which may be substituted, a thiol group which may be substituted, an amino group which may be substituted, an acyl group or a halogen atom, a salt thereof or a prodrug thereof has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  包含以下公式化合物的组合物： 其中A是可被取代的含氮杂环基团，R1是氢原子、可被取代的烃基团或可被取代的单环芳族杂环基团，R2是氢原子或可被取代的低级烷基团，R3、R4、R5、R6、R7、R8和R9独立地是氢原子、可被取代的烃基团、可被取代的羟基、可被取代的硫醇基、可被取代的氨基、酰基或卤素原子，其盐或前药对类固醇C17,20-裂解酶具有抑制作用，并且对于例如预防治疗原发恶性肿瘤、其转移和复发等是有用的。
• Steroid complexation by cyclophane receptors in aqueous solution: Substrate selectivity, enthalpic driving force for cavity inclusion, and enthalpy-entropy compensation
  作者：Blake R. Peterson、Peter Wallimann、Daniel R. Carcanague、François Diederich

  DOI：10.1016/0040-4020(94)00905-a

  日期：1995.1

  of lithocholic acid is ≈ 2 kcal/mol more stable than the complex of deoxycholic acid. Steroid complexation by 1 is enthalpically driven, and complexation thermodynamics follows a strong enthalpy-entropy compensation relationship. Cyclophane 2 with 4 quaternary ammonium centers shows a much higher non-aggregated water-solubility than 1 with its two quaternary centers and forms stable steroid inclusion

  报道了由两个萘基苯基甲烷间隔基形成的两个新型环烷受体的合成，表征和类固醇结合特性。Cyclophane 1与胆汁酸，皮质类固醇和雄激素类固醇形成包合物，在一系列结构相似的胆汁酸衍生物中，特定的官能团溶剂化作用可产生高结合选择性：石胆酸的复合物比该复合物稳定≈2 kcal / mol脱氧胆酸。焓驱动1的类固醇络合，并且络合热力学遵循强的焓-熵补偿关系。Cyclophane 2与4季铵中心的非聚集水溶解度比具有两个季铵中心的1高得多，并且在纯水中形成稳定的类固醇包合复合物。阴离子类固醇与2的配合物可通过非极性相互作用和离子配对而稳定。
• Heteroaryl-Substituted Naphthalenes and Structurally Modified Derivatives:  Selective Inhibitors of CYP11B2 for the Treatment of Congestive Heart Failure and Myocardial Fibrosis
  作者：Marieke Voets、Iris Antes、Christiane Scherer、Ursula Müller-Vieira、Klaus Biemel、Catherine Barassin、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1021/jm0503704

  日期：2005.10.1

  a novel strategy for the treatment of congestive heart failure and myocardial fibrosis. In this study the synthesis and biological evaluation of heteroaryl-substituted naphthalenes and quinolines (1-31) is described. Key step for the preparation of the compounds was a Suzuki cross-coupling. Activity of the compounds was determined in vitro using human CYP11B2 and selectivity was evaluated toward the

  最近，我们提出抑制醛固酮合酶（CYP11B2）作为一种治疗充血性心力衰竭和心肌纤维化的新策略。在这项研究中，描述了杂芳基取代的萘和喹啉（1-31）的合成和生物学评估。制备化合物的关键步骤是铃木交叉偶联。使用人CYP11B2在体外确定化合物的活性，并评估对人类固醇生成酶CYP11B1，CYP19和CYP17的选择性。已鉴定出大量的CYP11B2高活性和选择性抑制剂。活性最高的抑制剂是6-氰基化合物8（IC50 = 3 nM），显示出竞争性的抑制类型（K（i）值= 1.9 nM）。发现6-乙氧基衍生物5是最具选择性的CYP11B2抑制剂（IC50 = 12 nM； K（i）值= 8 nM; CYP11B1 IC50 = 5419 nM；选择性因子= 451），显示没有对人CYP3A4（50 nM）和CYP2D6（20 nM）的抑制作用。使用我们的同源性建模的CYP11B2结构与所选化合物进行了
• Design of an extremely high birefringence nematic liquid crystal based on a dinaphthyl-diacetylene mesogen
  作者：Yuki Arakawa、Shunpei Nakajima、Sungmin Kang、Masayuki Shigeta、Gen-ichi Konishi、Junji Watanabe

  DOI：10.1039/c2jm32448b

  日期：——

  We designed dinaphthyl-diacetylene-based nematic liquid crystals with alkoxy tails (DNDA–OCm) and evaluated their birefringence (Δn). Actual measurements of pure target compounds showed that DNDA–OC2 had the highest value of 0.62 at 550 nm at Tc + 10 °C.

  我们设计了基于二萘并二炔并含有烷氧基尾链（DNDA–OCm）的向列型液晶，并评估了它们的折射率各向异性（Δn）。对目标纯化合物的实际测量显示，在Tc + 10 °C和550 nm波长下，DNDA–OC2具有最高的Δn值，达到0.62。