甲基-3-氨基-5-[4-(叔丁基)苯基]噻吩-2-羧酸 | 175201-46-4

• 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: 甲基-3-氨基-5-[4-(叔丁基)苯基]噻吩-2-羧酸
• 中文别名: 3-氨基-5-(4-叔丁基苯基)噻吩-2-羧酸甲酯；甲基-3-氨基-5-[4-(叔丁基)苯基]噻吩-2-羧酸,97
• 英文名称: methyl 3-amino-5-(4-(tert-butyl)phenyl)thiophene-2-carboxylate
• 英文别名: methyl 3-amino-5-(4-tert-butylphenyl)thiophene-2-carboxylate
• CAS: 175201-46-4
• 化学式: C₁₆H₁₉NO₂S
• mdl: MFCD00068155
• 分子量: 289.398
• InChiKey: UFMSMLSNDDSQKN-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.312
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Name:	Methyl 3-amino-5-[4-(tert-butyl)phenyl]thiophene-2-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	175201-46-4

Section 1 - Chemical Product MSDS Name:Methyl 3-amino-5-[4-(tert-butyl)phenyl]thiophene-2-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175201-46-4	Methyl 3-amino-5-[4-(tert-butyl)phenyl	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 175201-46-4: 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: pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 157 - 158 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: C16H19NO2S
Molecular Weight: 289

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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.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175201-46-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 3-amino-5-[4-(tert-butyl)phenyl]thiophene-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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 175201-46-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175201-46-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175201-46-4 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：

  甲基-3-氨基-5-[4-(叔丁基)苯基]噻吩-2-羧酸 在 对甲苯磺酸 、 sodium nitrite 、 copper(l) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以58%的产率得到methyl 3-chloro-5-(4-tert-butylphenyl)-thiophene-2-carboxylate
  参考文献：
  名称：

  芳基取代的噻吩并[3,2-b]噻吩衍生物的合成及其在N，S-异戊二烯结构中的应用

  摘要：

  Fiesselmann噻吩合成用于方便地构造噻吩并[3,2- b ]噻吩衍生物。因此，通过将5-或4-芳基-3-氯噻吩-2-羧酸酯分别与巯基乙酸甲酯缩合，得到新的5-或6-芳基-3-羟基噻吩并[3,2- b ]噻吩-2-羧酸酯。在叔丁醇钾存在下 所得酯的皂化以及中间酸的脱羧，得到相应的噻吩并[3,2 - b ]噻吩-3（2 H）-酮。后者的酮用于合成新的N，S-杂踪烷，即9 H -thieno [2'，3'：4,5] thieno [3,2- b吲哚是通过根据Fischer吲哚化反应用芳基肼处理而得到的。

  DOI：

  10.3762/bjoc.15.261
• 作为产物：
  描述：

  3-(4-Tert-butylphenyl)-3-chloroprop-2-enenitrile 、 巯基乙酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到甲基-3-氨基-5-[4-(叔丁基)苯基]噻吩-2-羧酸
  参考文献：
  名称：

  通过原位生成的3-氨基噻吩从3-氨基噻吩-2-羧酸酯一锅合成2-取代的噻吩并[3,2- b ]吲哚

  摘要：

  一种方便的协议，可使用易于获得的5-取代的3-氨基噻吩-2-羧酸酯一锅合成噻吩并[3,2- b ]吲哚，在C-2位带有芳香，噻吩-2-基或苯乙烯基片段Fischer吲哚化反应是在这项研究期间开发的。该方法的两个主要步骤是用氢氧化钠对起始的3-氨基酯进行皂化，然后在冰醋酸溶液中用芳基肼对粗制的3-氨基酸钠盐进行下一步处理。后面的步骤包括将游离的3-氨基噻吩-2-羧酸原位脱羧为3-氨基噻吩，并使其与芳基肼的酸促进反应，最初形成5-取代噻吩-3（2 H的芳基hydr））-平滑地导致吲哚化以提供所需的噻吩并[3,2- b ]吲哚。

  DOI：

  10.1016/j.tetlet.2019.151185

文献信息

• Palladium-catalyzed direct arylation using free NH2 substituted thiophene derivatives with inhibition of amination type reaction
  作者：Fazia Derridj、Karima Si Larbi、Julien Roger、Safia Djebbar、Henri Doucet

  DOI：10.1016/j.tet.2012.06.053

  日期：2012.9

  The palladium-catalyzed direct arylation at C2 or C5 of free NH2 substituted thiophene derivatives was found to proceed in moderate to high yields using a variety of aryl halides. The choice of potassium acetate as the base was found to be crucial to inhibit the amination reaction and to promote the direct arylation.

  发现使用各种芳基卤化物，钯催化的游离NH 2取代的噻吩衍生物在C2或C5处的直接芳基化反应以中等至高收率进行。发现选择乙酸钾作为碱对于抑制胺化反应和促进直接芳基化至关重要。
• [EN] THIENOPYRIMIDINE INHIBITORS OF ATYPICAL PROTEIN KINASE C<br/>[FR] INHIBITEURS DE TYPE THIÉNOPYRIMIDINE DE PROTÉINES KINASES C ATYPIQUES
  申请人：CANCER REC TECH LTD

  公开号：WO2013078126A1

  公开（公告）日：2013-05-30

  The present invention provides a compound of formula (I) or a salt thereof, wherein R1, R2, R3, R4, R5, R6, A, G, M, Q and X are as defined herein. A compound of formula (I) and its salts have a PKC inhibitory activity, and may be used to treat proliferative disorders.

  本发明提供了一种式（I）的化合物或其盐，其中R1、R2、R3、R4、R5、R6、A、G、M、Q和X如本文所定义。式（I）的化合物及其盐具有PKC抑制活性，并可用于治疗增生性疾病。
• Thienopyrimidine Inhibitors of Atypical Protein Kinase C
  申请人：Cancer Research Technology Limited

  公开号：US20140323435A1

  公开（公告）日：2014-10-30

  The present application provides a compound of formula (I) or a salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A, G, M, Q and X are as defined herein. A compound of formula (I) and its salts have aPKC inhibitory activity, and may be used to treat proliferative disorders.

  本申请提供了公式（I）的化合物或其盐，其中R1、R2、R3、R4、R5、R6、A、G、M、Q和X的定义如本文所述。公式（I）的化合物及其盐具有aPKC抑制活性，可用于治疗增殖性疾病。
• THIENOPYRIMIDINE AS INHIBITORS OF ATYPICAL PROTEIN KINASE C
  申请人：Cancer Research Technology Limited

  公开号：EP3048106A1

  公开（公告）日：2016-07-27

  The present invention provides a compound of formula (I) or a salt thereof, wherein R1, R2, R3, R4, R5, R6, A, G, M, Q and X are as defined herein. The compound of formula (I) and its salts has aPKC inhibitory activity, and may be used to treat proliferative disorders.

  本发明提供了一种式 (I) 的化合物 或其盐，其中 R1、R2、R3、R4、R5、R6、A、G、M、Q 和 X 如本文所定义。式（I）化合物及其盐具有 PKC 抑制活性，可用于治疗增殖性疾病。
• Thienopyrimidine inhibitors of atypical protein kinase C
  申请人：Cancer Research Technology Limited

  公开号：US10183950B2

  公开（公告）日：2019-01-22

  The present application provides a compound of formula (I) or a salt thereof, wherein R1, R2, R3, R4, R5, R6, A, G, M, Q and X are as defined herein. A compound of formula (I) and its salts have aPKC inhibitory activity, and may be used to treat proliferative disorders.

  本申请提供了一种式 (I) 的化合物 或其盐，其中 R1、R2、R3、R4、R5、R6、A、G、M、Q 和 X 如本文所定义。式（I）化合物及其盐具有 PKC 抑制活性，可用于治疗增殖性疾病。