6-氨基-5-溴烟酸甲酯 | 180340-70-9

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-氨基-5-溴烟酸甲酯
• 中文别名: 5-溴-6-氨基烟酸甲酯
• 英文名称: methyl 6-amino-5-bromonicotinate
• 英文别名: methyl 6-amino-5-bromopyridine-3-carboxylate；6-amino-5-bromo-nicotinic acid methyl ester
• CAS: 180340-70-9
• 化学式: C₇H₇BrN₂O₂
• 分子量: 231.049
• InChiKey: LNTAAMVZKGYIIA-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168
• 沸点：
  323.7±37.0 °C(Predicted)
• 密度：
  1.662±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Methyl 6-amino-5-bromonicotinate
Product Name:
Synonyms: Methyl 2-amino-3-bromo-5-pyridinecarboxylate; Methyl 2-amino-3-bromopyridine-5-carboxylate

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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.
Methyl 6-amino-5-bromonicotinate
Ingredient name:
CAS number: 180340-70-9

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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: C7H7BrN2O2
Molecular weight: 231.0

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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

制备方法与用途

6-氨基-5-溴烟酸甲酯是一种羧酸酯类衍生物，主要用作医药中间体。

反应信息

• 作为反应物：
  描述：

  6-氨基-5-溴烟酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 1-丙基磷酸酐 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  通过肽偶联剂丙基膦酸酐（T3P）介导的Pictet-Spengler反应选择性合成5,6-二氢菲啶，5,6-二氢苯并[ c ] [1,8]萘啶及其完全芳构化的类似物

  摘要：

  已开发出一种新方法，用于通过丙基膦酸酐（T3P）介导的Pictet-Spengler反应选择性合成5，6-二氢菲啶，5，6-二氢苯并[ c ] [1,8]萘啶及其完全芳构化的类似物。使用毒性较小且易于获得的T3P的方法通常似乎更灵活，更有效地制备5，6-二氢菲啶衍生物，并且与制备吡啶的常规方法相辅相成。

  DOI：

  10.1016/j.tetlet.2012.09.034
• 作为产物：
  描述：

  6-氨基烟酸甲酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 以69.1 %的产率得到6-氨基-5-溴烟酸甲酯
  参考文献：
  名称：

  通过可扩展的工艺开发建立二氢氮杂吲哚羧酸四元立体中心

  摘要：

  由于其独特的性质，二氢氮杂吲哚是活性药物成分的重要片段，并且在制药工业中引起了极大的兴趣。在这篇手稿中，一种可扩展且经济的合成复杂 ( R )-2-(4-氟苯基)-2-甲基-2,3-二氢-1 H-吡咯并[2,3- b ]吡啶-的方法描述了公斤级的5-羧酸( R )-1 。该合成是通过第二代合成策略进行的，该策略不依赖手性超临界流体色谱分离，而手性超临界流体色谱分离是成本最高的因素。通过系统的化学拆分筛选，我们发现化合物( R )-1可以以高(>99%)的对映体过量被分离出来。此外，第一次拆分过程中的母液可回收，将S-异构体外消旋成( R )-1和( S ) -1混合物，可用于额外的化学拆分过程。贵重的钯 (Pd) 络合物可以从 20 mol% 减少到 1 mol%，并且可以在内部安全地制备长交付周期的构件。通过一锅法工艺开发减少分离步骤，有效合成高级中间体。经过二-对-甲苯甲酰-d-酒石酸

  DOI：

  10.1021/acs.oprd.3c00231

文献信息

• Tricyclic benzazepine vasopressin antagonists
  申请人：American Cyanamid Company

  公开号：US05532235A1

  公开（公告）日：1996-07-02

  Tricyclic compound of the general Formula I: ##STR1## as defined herein which exhibit antagonist activity at V.sub.1 and/or V.sub.2 receptors and exhibit in vivo vasopressin antagonist activity, methods for using such compounds in treating diseases characterized by excess renal reabsorption of water, and process for preparing such compounds.

  通用式I的三环化合物：##STR1##，如本文所定义，在V.sub.1和/或V.sub.2受体表现出拮抗活性，并在体内表现出抗利尿素拮抗活性，使用这类化合物治疗以肾脏过度重吸水为特征的疾病的方法，以及制备这类化合物的方法。
• [EN] BICYCLIC HYDROXAMIC ACIDS USEFUL AS INHIBITORS OF MAMMALIAN HISTONE DEACETYLASE ACTIVITY<br/>[FR] ACIDES HYDROXAMIQUES BICYCLIQUES UTILES COMME INHIBITEURS DE L'ACTIVITÉ HISTONE DÉSACÉTYLASE CHEZ LE MAMMIFÈRE
  申请人：KANCERA AB

  公开号：WO2017108282A1

  公开（公告）日：2017-06-29

  A compound of formula (Ia) or (Ib) or a pharmaceutically acceptable salt thereof. The compound is an inhibitor of a histone deacetylase, and as such is useful in terepy, e.g. in the treatment of autoimmune disorders, mental disorders, neurodegenerative disorders, and hyperproliferative disorders.

  化合物的化学式（Ia）或（Ib）或其药学上可接受的盐。该化合物是组蛋白去乙酰化酶的抑制剂，因此在治疗自身免疫性疾病、精神障碍、神经退行性疾病和过度增生性疾病等方面非常有用。
• [EN] PROTEIN KINASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE KINASE ET LEUR UTILISATION
  申请人：MERCK SERONO SA

  公开号：WO2009108670A1

  公开（公告）日：2009-09-03

  Disclosed are benzonaphthyridinyl derivative compounds and analogs thereof, pharmaceutical compositions comprising such compounds and processes for preparing the same. The compounds are useful in the treatment of diseases amenable to kinase signal transduction inhibition, regulation or modulation.

  揭示了苯并萘啶衍生物化合物及其类似物，包括含有这些化合物的药物组合物以及制备这些化合物的方法。这些化合物在治疗对激酶信号传导抑制、调节或调控敏感的疾病中很有用。
• Tricyclic thieno-azepine vasopressin antagonists
  申请人：American Cyanamid Company

  公开号：US05654297A1

  公开（公告）日：1997-08-05

  This invention relates to new bicyclic non-peptide vasopressin antagonists which are useful in treating conditions where decreased vasopressin levels are desired, such as in congestive heart failure, in disease conditions with excess renal water reabsorption and in conditions with increased vascular resistance and coronary vasoconstriction.

  这项发明涉及新的双环非肽抗利尿素拮抗剂，可用于治疗需要降低加压素水平的情况，例如充血性心力衰竭、伴有肾脏过度水分重吸收的疾病情况以及伴有增加血管阻力和冠状动脉收缩的情况。
• [EN] CARBOXY SUBSTITUTED (HETERO) AROMATIC RING DERIVATIVES AND PREPARATION METHOD AND USES THEREOF<br/>[FR] DÉRIVÉS DE CYCLE (HÉTÉRO) AROMATIQUE SUBSTITUÉS PAR CARBOXY ET PROCÉDÉS DE PRÉPARATION ET UTILISATIONS ASSOCIÉS
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2017036404A1

  公开（公告）日：2017-03-09

  Carboxy-substituted (hetero)aryl derivatives, pharmaceutical compositions comprising these compounds, and methods of preparing such compounds and compositions are provided. The compounds or compositions are useful in inhibiting xanthine oxidase and urate anion transporter 1, and also can be used in the treatment or prevention of diseases associated with high blood uric acid level in mammals, especially humans.

  提供了含有羧基取代的(杂)芳基衍生物、包括这些化合物的药物组合物，以及制备这些化合物和组合物的方法。这些化合物或组合物在抑制黄嘌呤氧化酶和尿酸阴离子转运蛋白1方面具有用途，并且还可用于治疗或预防与高血尿酸水平有关的疾病，特别是人类。