4-溴-3-羟基噻吩-2-羧酸甲酯 | 95201-93-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 4-溴-3-羟基噻吩-2-羧酸甲酯
• 中文别名: 4-溴-3-羟基噻吩-2-甲酸甲酯
• 英文名称: methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate
• 英文别名: methyl 4-bromo-3-hydroxythiophene-2-carboxylate；methyl 4-bromo-3-hydroxy-2-thiophenecarboxylate
• CAS: 95201-93-7
• 化学式: C₆H₅BrO₃S
• 分子量: 237.074
• InChiKey: UFTXASQYKJFRKI-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80°C
• 沸点：
  247.9±35.0℃ (760 Torr)
• 密度：
  1.803±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  103.7±25.9℃
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与酸、碱、还原剂或氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  密封储存于阴凉、干燥的库房。应远离氧化剂、还原剂和酸性物质。

SDS

Name:	Methyl 4-bromo-3-hydroxythiophene-2-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	95201-93-7

Section 1 - Chemical Product MSDS Name:Methyl 4-bromo-3-hydroxythiophene-2-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
95201-93-7	Methyl 4-bromo-3-hydroxythiophene-2-ca	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 95201-93-7: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 79 - 80 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H5BrO3S
Molecular Weight: 237

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acid chlorides.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 95201-93-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 4-bromo-3-hydroxythiophene-2-carboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 95201-93-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 95201-93-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 95201-93-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-溴-3-羟基噻吩-2-羧酸甲酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三氟甲磺酸酐 、 caesium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 3-(3-aminophenyl)-5-morpholin-4-yl-thieno[3,2-b]pyran-7-one
  参考文献：
  名称：

  被设计为下一代PI3K抑制剂的5-Morpholino-7 H -thieno [3,2 - b ] pyran-7-ones的合成及基于癌干细胞的活性

  摘要：

  磷脂酰肌醇-3-激酶（PI3K）通路在多种肿瘤中的失调使PI3K成为抑制的共识靶标，目前临床试验中已使用15种以上的抑制剂进行了说明。我们先前的工作是建立在早期的首创的多激酶抑制剂LY294002的基础上的，导致了唯一的PI3K血管靶向PI3K抑制剂前药SF1126，该药物现已完成I期临床试验。该抑制剂具有比其酶促效力应赋予的更多的体内活性，该酶促效力通常远低于其他临床阶段的PI3K抑制剂。我们着手探索保留了这些特性并同时展现出对PI3K更高效力的支架。这项工作导致发现了5-morpholino-7 H -thieno [3,2- b] pyran-7-one系统作为潜在的PI3K抑制剂新化合物类别的基础，对PI3K具有增强的效力。这些化合物的合成和基于癌症干细胞的活性在本文中报道。

  DOI：

  10.1021/jm301522m
• 作为产物：
  描述：

  2-氯-3-氧代-2,3-二氢-2-噻吩羧酸甲酯 在 氢溴酸 、 溶剂黄146 作用下， 生成 4-溴-3-羟基噻吩-2-羧酸甲酯
  参考文献：
  名称：

  4,5-未取代的3-羟基吡咯烷基/ 3-羟基噻吩-2-基-羧酸盐的区域选择性和有效卤化

  摘要：

  取代的杂环，例如吡咯和噻吩，在药物和材料科学领域中很常见。在这里，我们研究了4,5-未取代的3-羟基吡咯-2-基-羧酸盐和4,5-未取代的烷基3-羟基噻吩-2-基-羧酸盐在不同卤化条件下的反应性，这是由于它们作为结构单元的兴趣。生物活性化合物和材料的合成。我们在本文中描述了在普通条件下用普通卤化剂对3-羟基吡咯和3-羟基噻吩进行区域选择性单卤代反应。研究了卤化的选择性。发现了用于单溴化和单氯化的最佳一步反应条件。最后，我们观察到用N溴化-溴琥珀酰亚胺（NBS）发生在杂环的C4位，而用SO 2 Cl 2氯化则生成C5卤代衍生物。

  DOI：

  10.1016/j.tetlet.2017.05.025

文献信息

• Thienopyranones as kinase inhibitors
  申请人：SignalRx Pharmaceuticals, Inc.

  公开号：US09550790B2

  公开（公告）日：2017-01-24

  The invention relates to compounds of formula I (or pharmaceutically acceptable salts thereof) as defined herein, pharmaceutical compositions thereof, and their use in manufactures and methods for modulating biological processes including inhibition of kinase activity such as PI-3 kinase.

  本发明涉及式I化合物（或其药用可接受的盐），如本文所述，其药物组合物，及其在制造和调节生物过程，包括抑制激酶活性如PI-3激酶的方法中的用途。
• 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
  申请人：Schering Corporation

  公开号：US20040106794A1

  公开（公告）日：2004-06-03

  There are disclosed compounds of the formula 1 or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  这里公开了用于治疗诸如急性和慢性炎症性疾病以及癌症的趋化因子介导疾病的公式1化合物或其药用可接受的盐或溶剂。
• N-1H-tetrazol-5-yl-2-thiophene carboxamides,
  申请人：Warner-Lambert Company

  公开号：US04748183A1

  公开（公告）日：1988-05-31

  The present invention is for compounds having the formula of N-1H-tetrazol-5-yl-2-thiophenecarboxamides, N-1H-tetrazol-5-yl-2-pyrrolecarboxamides, N-1H-tetrazol-5-yl-2-furancarboxamides or analogs of each of the carboxamides. The compounds are useful for the treatment of allergic or inflammatory conditions or diseases. Thus, pharmaceutical compositions and methods of use are also the invention. Processes of preparation for the compounds are also the invention.

  本发明涉及具有N-1H-四唑-5-基-2-噻吩羧酰胺、N-1H-四唑-5-基-2-吡咯羧酰胺、N-1H-四唑-5-基-2-呋喃羧酰胺或每种羧酰胺的类似物的化合物。这些化合物可用于治疗过敏或炎症性疾病。因此，药物组合物和使用方法也属于本发明。制备这些化合物的方法也是本发明的一部分。
• Novel thiophene-, pyrrole-, furan-, and benzene carboxamidotetrazoles as potential antiallergy agents
  作者：Michael D. Mullican、Roderick J. Sorenson、David T. Connor、David O. Thueson、John A. Kennedy、Mary Carol Conroy

  DOI：10.1021/jm00111a039

  日期：1991.7

  The synthesis and antiallergic activity of a series of novel thiophene-, pyrrole-, furan-, and benzenecarboxamidotetrazoles are described. A number of compounds inhibit the release of histamine from anti-IgE-stimulated human basophils. Optimal inhibition is exhibited in compounds with a 3-alkoxy, a 4-halo, and a 5-methyl, 5-methoxy, or 5-bromo on a thiophene-2-carboxamidotetrazole.

  描述了一系列新型噻吩，吡咯，呋喃和苯甲酰胺四唑的合成和抗过敏活性。许多化合物抑制组胺从抗IgE刺激的人类嗜碱细胞释放。在噻吩-2-羧酰胺基四唑上具有3-烷氧基，4-卤代和5-甲基，5-甲氧基或5-溴的化合物中表现出最佳抑制作用。
• Thienopyranones as Kinase and Epigenetic Inhibitors
  申请人：SignalRx Pharmaceuticals, Inc.

  公开号：US20150344494A1

  公开（公告）日：2015-12-03

  The invention relates to methods of treating diseases including but not limited to, cancer non-cancer proliferative disease, sepsis, autoimmune disease, viral infaction, atheroscleosis, Type 1 or 2 diabetes, obesity, inflammatory disease, or Myc-depenent disorder including by modulating biological processes by the inhibition of PI3 kinase and/or bromodomain protein binding to substrates composing the administration of a compound(s) of Formula I-IX (or pharmaceutically acceptable salts thereof) as defined herein.

  这项发明涉及治疗疾病的方法，包括但不限于癌症、非癌性增生性疾病、败血症、自身免疫疾病、病毒感染、动脉粥样硬化、1型或2型糖尿病、肥胖症、炎症性疾病或Myc依赖性疾病，通过调节生物过程，通过抑制PI3激酶和/或溴结构域蛋白与构成给药的底物结合的生物过程，包括使用本文所定义的化合物的给药（或其药学上可接受的盐）的I-IX式。