2-hydroxy-5-bromobenzaldoxime | 82486-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-5-bromobenzaldoxime
• 英文别名: 5-bromosalicylaldehyde oxime；5-bromosalicylaldoxime；5-bromo-2-hydroxybenzaldehyde oxime；5-Bromo-2-hydroxybenzaldoxime；4-bromo-2-(hydroxyiminomethyl)phenol
• CAS: 82486-43-9
• 化学式: C₇H₆BrNO₂
• 分子量: 216.034
• InChiKey: YSDJVLAQRCCLPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2-hydroxybenzaldehyde Oxime
Synonyms: 4-Bromo-2-[(1E)-(hydroxyimino)methyl]phenol

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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: 5-Bromo-2-hydroxybenzaldehyde Oxime
CAS number: 82486-43-9

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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.
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: C7H6BrNO2
Molecular weight: 216.0

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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 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-hydroxy-5-bromobenzaldoxime 在 咪唑 、 碘苯二乙酸 、 Cu(AAOPD) 作用下， 以 乙腈 为溶剂， 反应 0.2h， 以85%的产率得到5-溴水杨醛
  参考文献：
  名称：

  Co（AAOPD）和Cu（AAOPD）Schiff碱催化剂在氧化肟和羧酸衍生物中的作用研究

  摘要：

  肟和羧酸衍生物在医学，制药，农业工业中具有广泛的用途。因此，它们对这些领域具有重大影响。钴和镍基团的碱促进基团或（RC = N-）基团。检查了它们的肟和羧酸的氧化过程。该过程是绝对选择性的，在该过程中，肟以高收率转化为醛和酮衍生物，而在醛基上没有更多的氧化过程。在这种机理下，大量的各种肟转化为羰基。然而，获得的结果表明，由于具有较高的速度和收率，在存在碱助剂如Co（AAOPD）和Cu（AAOPD）的情况下，肟和羧酸的氧化过程。为了进一步评估反应进程和通过不同的方法鉴定产物，使用了以下方法：

  DOI：

  10.13005/ojc/280228
• 作为产物：
  描述：

  5-溴水杨醛 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.15h， 以83%的产率得到2-hydroxy-5-bromobenzaldoxime
  参考文献：
  名称：

  醛-肟转化的一种通用的绿色机械化学途径。

  摘要：

  探索了使用羟胺和NaOH进行醛-肟转化的稳健，简便和无溶剂的机械化学途径。该方法适用于装饰有一系列取代基的芳族和脂族醛。

  DOI：

  10.1039/c2cc36315a

文献信息

• [EN] GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES<br/>[FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE POUR LE TRAITEMENT DE MALADIES
  申请人：BIOMARIN PHARM INC

  公开号：WO2015042397A1

  公开（公告）日：2015-03-26

  Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

  本文描述了一种I式化合物，制备这种化合物的方法，含有这种化合物的药物组合物和药物，以及使用这种化合物治疗或预防与葡萄糖酰胺合成酶（GCS）相关的疾病或症状的方法。
• An efficient synthesis of oxazolines <i>via</i> a cascade reaction between azaoxyallyl cations and 1,2-benzisoxazoles
  作者：Li Sun、Yi Liu、Yankai Wang、Yuanyuan Li、Zhiwen Liu、Tao Lu、Wenhai Li

  DOI：10.1039/c9ob01366k

  日期：——

  A formal [3 + 2] cycloaddition reaction between the C and O terminals of azaoxyallyl cations formed in situ and 1,2-benzisoxazoles has been realized. This one-pot cycloaddition method provided an effective and practical pathway to synthesize oxazoline in good yields under mild conditions. The title products exhibited unique fluorescence properties.

  已经实现了在原位形成的氮杂烯丙基阳离子的C和O末端与1,2-苯并恶唑之间的正式[3 + 2]环加成反应。这种一锅法环加成法为在温和条件下以高收率合成恶唑啉提供了有效而实用的途径。标题产物表现出独特的荧光性质。
• A stereoselective synthesis of symmetrical and unsymmetrical bibenzo[e][1,3]oxazine-2,2′-dione derivatives induced by low-valent titanium reagent
  作者：Guo-Lan Dou、Fang Sun、Da-Qing Shi

  DOI：10.1016/j.tet.2012.03.122

  日期：2012.6

  unsymmetrical bibenzo[e][1,3]oxazine-2,2′-dione derivatives were synthesized by the reaction of various o-hydroxy Schiff bases and triphosgene induced by low-valent titanium reagent (TiCl4/Sm). A variety of substrates can participate in the process with good yields. The present method provides a useful preparation of 3,3′,4,4′-tetrahydro-4,4′-bibenzo[e][1,3]oxazine-2,2′-dione derivatives, which cannot be

  低价钛试剂（TiCl 4 / Sm）诱导的各种邻羟基席夫碱与三光气反应合成了一系列对称和不对称的联苯并[ e ] [1,3]恶嗪-2,2'-二酮衍生物。）。多种底物可以高收率参与该过程。本方法提供了有用的3,3'，4,4'-四氢-4,4'-联苯并[ e ] [1,3]恶嗪-2,2'-二酮衍生物的制备方法，否则无法制备。反应的机理表明一锅参与还原，偶联和环化。
• Heterogeneous Catalytic Method for the Conversion of Aldoximes into Nitriles Using Molecular Sieve Modified with Copper(II)
  作者：Árpád Kiss、Zoltán Hell

  DOI：10.1080/00397911.2012.667861

  日期：2013.7.3

  Abstract A simple heterogeneous metal-catalyzed method was developed for the transformation of aldoximes into nitriles. Molecular sieve (4 Å) modified with copper(II) proved to be an efficient catalyst for the conversion. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file. GRAPHICAL ABSTRACT

  摘要 开发了一种简单的多相金属催化方法将醛肟转化为腈。经铜 (II) 改性的分子筛 (4 Å) 被证明是转化的有效催化剂。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• METHODS OF FORMING IMINES, IMINE-RELATED AND IMINE-DERIVED COMPOUNDS USING GREEN SOLVENTS
  申请人：Research Foundation for the State University of New York

  公开号：US20210323911A1

  公开（公告）日：2021-10-21

  The present disclosure relates to using green solvents to synthesize an array of imines, imine-related and imine-derived compounds in an efficient and eco-friendly matter, satisfying green chemistry requirements. Reaction embodiments are performed using solvents, such as ethyl lactate and dimethyl isosorbide, which are both individually characterized as green. In embodiments, solvents include lactic whey and/or water as co-solvents. In these green solvents, the synthesis process discussed herein can produce up to quantitative yields of product at room temperature in a short duration. Embodiments include a method of forming an imine, imine-related or imine-derived compound product. In embodiments, the methods include mixing an aldehyde reactant with a nucleophilic/nitrogen-containing reactant in a green solvent at a temperature between negative twenty degrees Celsius (−20° C.) and positive fifty degrees Celsius (50° C.); stirring the mixture; and forming an imine, imine-related or imine-derived compound product.

  本公开涉及使用绿色溶剂在高效且环保的条件下合成一系列亚胺、亚胺相关和亚胺衍生化合物，满足绿色化学要求。反应实施例使用乳酸乙酯和异山梨醇二甲醚等溶剂进行，这两种溶剂均被单独界定为绿色。在实施例中，溶剂包括乳清和/或水作为共溶剂。在这些绿色溶剂中，所讨论的合成过程可以在室温下在短时间内产生高达定量产物收率。实施例包括形成亚胺、亚胺相关或亚胺衍生化合物产品的方法。在实施例中，方法包括在负二十摄氏度（-20°C）和正五十摄氏度（50°C）之间的温度下，在绿色溶剂中混合醛反应物和亲核/含氮反应物；搅拌混合物；形成亚胺、亚胺相关或亚胺衍生化合物产品。