5-溴-2-甲酰基苯甲酸甲酯 | 1016163-89-5

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 5-溴-2-甲酰基苯甲酸甲酯
• 英文名称: methyl 5-bromo-2-formylbenzoate
• CAS: 1016163-89-5
• 化学式: C₉H₇BrO₃
• 分子量: 243.057
• InChiKey: ZYGJVCDDZZSSEE-UHFFFAOYSA-N

物化性质

• 沸点：
  337.2±32.0 °C(Predicted)
• 密度：
  1.566±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  储存条件为2-8°C，并需保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 5-bromo-2-formylbenzoate
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: Methyl 5-bromo-2-formylbenzoate
CAS number: 1016163-89-5

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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: C9H7BrO3
Molecular weight: 243.1

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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

制备方法与用途

用途

5-溴-2-甲酰基苯甲酸甲酯是一种酯类有机物，常被用作医药中间体。

反应信息

• 作为反应物：
  描述：

  5-溴-2-甲酰基苯甲酸甲酯 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 5-bromo-2-formyl-N,N-dimethylbenzamide
  参考文献：
  名称：

  [EN] CARBAMATE COMPOUNDS AND OF MAKING AND USING SAME
  [FR] COMPOSÉS DE CARBAMATE ET LEUR PRÉPARATION ET UTILISATION

  摘要：

  本公开提供了可能是MAGL和/或ABHD6的调节剂的化合物和组合物，以及它们作为药用剂的用途，它们的制备过程，以及包括所公开化合物作为至少一种活性剂的药物组合物。该公开还提供了一种治疗有需要的患者的方法，其中患者患有疼痛、实体肿瘤癌和/或肥胖等症状，包括给予公开的化合物或组合物。

  公开号：

  WO2013103973A1
• 作为产物：
  描述：

  苯酞 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硫酸 、 水 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 5-溴-2-甲酰基苯甲酸甲酯
  参考文献：
  名称：

  An Indium-Mediated Allylative/Transesterification DFT-Directed Approach to Chiral C₍₃₎-Functionalized Phthalides

  摘要：

  A one-pot synthesis of chiral C-(3)-substituted phthalides via an indium-mediated allylation/transesterification reaction is described. The development of this reaction was facilitated through the applied use of DFT calculations to rationalize the stereoselection of a chiral In-mediated process. It was discovered that the enantiomeric excess of this reaction depended upon the steric size, chain length, and substitution of the aldehyde employed.

  DOI：

  10.1021/ol301566f

文献信息

• [EN] CARBAMATE COMPOUNDS AND OF MAKING AND USING SAME<br/>[FR] COMPOSÉS CARBAMATES ET LEUR PROCÉDÉ DE FABRICATION ET D'UTILISATION
  申请人：ABIDE THERAPEUTICS

  公开号：WO2013142307A1

  公开（公告）日：2013-09-26

  Provided herein are carbamate compounds which may be useful in the treatment of, for example, pain, solid tumors and/or obesity.

  本文提供的是可能在治疗疼痛、实体肿瘤和/或肥胖等方面有用的氨基甲酸酯化合物。
• Cobalt(<scp>ii</scp>)-catalyzed benzylic oxidations with potassium persulfate in TFA/TFAA
  作者：Tianlei Li、Jishun Li、Zihao Zhu、Weidong Pan、Song Wu

  DOI：10.1039/c9ra03346g

  日期：——

  A cobalt-catalyzed C(sp3)–H oxygenation reaction to furnish aldehyde was herein reported. This transformation demonstrated high chemo-selectivity, and tolerated various methylarenes bearing electron-withdrawing substituents. This reaction provided rapid access to diverse aldehydes form methylarenes. Notably, TFA/TFAA was used for the first time as a mixed solvent in cobalt-catalyzed oxygenation of

  本文报道了钴催化的 C(sp 3 )-H 氧化反应以提供醛。这种转化表现出高化学选择性，并耐受各种带有吸电子取代基的甲基芳烃。该反应提供了从甲基芳烃中快速获得各种醛的途径。值得注意的是，TFA/TFAA 首次作为混合溶剂用于钴催化的苄基亚甲基氧化反应。
• Highly Enantioselective Synthesis of 2,3-Dihydro-1<i>H</i>-imidazo[2,1-<i>a</i>]isoindol-5(9b<i>H</i>)-ones via Catalytic Asymmetric Intramolecular Cascade Imidization–Nucleophilic Addition–Lactamization
  作者：Yuwei He、Chuyu Cheng、Bin Chen、Kun Duan、Yue Zhuang、Bo Yuan、Meisan Zhang、Yougui Zhou、Zihong Zhou、Yu-Jun Su、Rihui Cao、Liqin Qiu

  DOI：10.1021/ol5031603

  日期：2014.12.19

  2-diamine with methyl 2-formylbenzoate catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones with high yields and excellent enantioselectivities. This strategy has been shown to be quite general toward various methyl 2-formylbenzoates.

  手性磷酸催化N 1-烷基乙烷-1,2-二胺与2-甲酰基苯甲酸甲酯的高对映选择性催化不对称分子内级联酰亚胺化-亲核加成-内酰胺化是制备具有医学意义的手性2,3-手性化合物的第一种有效方法二氢-1 H-咪唑并[2,1- a ] isoindol-5（9b H）-具有高收率和优异的对映选择性。已经显示出该策略对于各种2-甲酰基苯甲酸甲酯是相当普遍的。
• Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones
  作者：Masaaki Yohda、Yasunori Yamamoto

  DOI：10.1039/c5ob01661d

  日期：——

  Ruthenium/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to methyl 2-formylbenzoates afforded chiral 3-aryl-isobenzofuranones. [RuCl2(p-cymene)]2/Me-BIPAM and RuCl2(PPh3)3/Me-BIPAM catalyst systems tolerate a variety of functional groups and give high yields with high enantioselectivities.

  钌/ Me-BIPAM催化将芳基硼酸不对称加成到2-甲酰基苯甲酸甲酯中，得到手性3-芳基-异苯并呋喃酮。[RuCl 2（对-cymene）] 2 / Me-BIPAM和RuCl 2（PPh 3）3 / Me-BIPAM催化剂体系可耐受多种官能团，并具有高对映选择性和高收率。
• Synthesis of Chiral 3-Substituted Phthalides by a Sequential Organocatalytic Enantioselective Aldol-Lactonization Reaction. Three-Step Synthesis of (<i>S</i>)-(−)-3-Butylphthalide
  作者：Haoyi Zhang、Shilei Zhang、Lu Liu、Guangshun Luo、Wenhu Duan、Wei Wang

  DOI：10.1021/jo902118x

  日期：2010.1.15

  enantioenriched “privileged” scaffold. As a result of the sensitive nature of substrate structures of an organocatalytic enantioselective aldol reaction, after extensive optimization of reaction conditions, catalyst l-prolinamide alcohol IV is identified as the best promoter. Interestingly, it is found that in this reaction, addition of an acid additive PhCO2H can significantly enhance reaction efficiency with

  易于构建重要分子框架的有效方法的开发是有机合成的重要目标。手性3-取代的邻苯二甲酸酯广泛分布在大量具有广泛，有效和潜在发展前景的生物活性的天然产物中。在这项研究中，我们发现了2-甲酰基苯甲酸酯与酮/醛的前所未有的有机催化不对称醛醇内酯化反应，可方便地构建对映体富集的“特权”支架。由于有机催化对映选择性醛醇缩合反应的底物结构的敏感性质，在广泛优化反应条件后，催化剂1-脯氨酰胺醇IV被确定为最佳启动子。有趣的是，发现在该反应中，添加酸添加剂PhCO 2 H可以显着提高反应效率，而该方法仅使用低至2.5mol％的IV。此外，由于反应条件对顺序的羟醛-内酯化过程敏感，而又不影响对映选择性和外消旋作用，因此在存在K 2 CO 3的情况下，必须除去催化剂以用于随后的容易的内酯化反应。醛醇内酯化方法是制备具有高对映选择性的合成上和生物学上重要的3-取代的邻苯二甲酸酯的有力方法。报道了3-丁基邻苯二甲酸酯的天然产物的三步催化不对称合成。