3-氨基-4-甲基苯甲酸乙酯 | 41191-92-8

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 3-氨基-4-甲基苯甲酸乙酯
• 中文别名: 3-氨基-对甲苯酸乙酯
• 英文名称: ethyl 3-amino-4-methylbenzoate
• 英文别名: 3-amino-4-methylbenzoic acid ethyl ester
• CAS: 41191-92-8
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD01926538
• 分子量: 179.219
• InChiKey: MCNBNDUVWQEKNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  48.6-50.1℃
• 沸点：
  105°C/0.2mmHg(lit.)
• 密度：
  1.103±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Ethyl 3-Amino-4-methylbenzoate Revision number: 5.3
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Ethyl 3-Amino-4-methylbenzoate

Revision number: 5.3

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Ethyl 3-Amino-4-methylbenzoate
Percent: >98.0%(GC)(T)
CAS Number: 41191-92-8
Synonyms: 3-Amino-4-methylbenzoic Acid Ethyl Ester , Ethyl 3-Amino-p-toluate , 3-Amino-p-
toluic Acid Ethyl Ester
Chemical Formula: C10H13NO2
Ethyl 3-Amino-4-methylbenzoate

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Ethyl 3-Amino-4-methylbenzoate

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Colour: White - Very pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:51°C
Boiling point/range: 105°C/0.03kPa
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Methanol

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Ethyl 3-Amino-4-methylbenzoate

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Section 14. TRANSPORT INFORMATION
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-氨基-4-甲基苯甲酸乙酯 在 盐酸 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 生成 尼罗替尼
  参考文献：
  名称：

  一种尼洛替尼的制备方法及其中间体

  摘要：

  本发明公开了一种尼洛替尼的制备方法及其中间体。该方法包括下述步骤：在溶剂中，在无机碱的作用下，将化合物D或化合物D的盐酸盐，与化合物SM3进行如下所示的反应得到化合物E尼洛替尼即可。本发明的尼洛替尼的制备方法反应简单易操作，所用试剂安全环保，副反应少，反应时间短。

  公开号：

  CN109666023B
• 作为产物：
  描述：

  4-甲基-3-硝基苯甲酸 在 palladium 10% on activated carbon 、 甲酸铵 、 对甲基苯甲酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 3-氨基-4-甲基苯甲酸乙酯
  参考文献：
  名称：

  一种制备N-(5-羧基-2-甲基苯基)-4-(3-吡啶)-2-嘧啶胺的方法

  摘要：

  本发明公开了一种制备N‑(5‑羧基‑2‑甲基苯基)‑4‑(3‑吡啶)‑2‑嘧啶胺的方法，具体包括一下步骤：步骤1，该合成路线以3‑硝基‑4‑甲基苯甲酸为起始原料经乙酯化反应生成化合物2；步骤2，化合物2的硝基经钯碳氢化还原反应生成化合物3；步骤3，化合物3与腈胺水溶液反应，再经盐基互换得到化合物4；步骤4，化合物4与化合物6环合得到化合物7；步骤5，化合物7在碱性的作用下水解生成化合物8即N‑(5‑羧基‑2‑甲基苯基)‑4‑(3‑吡啶)‑2‑嘧啶胺，本发明方法克服了现有技术存在的反应时间长、收率低、成本高、不利于工业化生产的缺陷，提供了一种收率高，环保经济十分适合工业化生产的制备方法。

  公开号：

  CN112745300A

文献信息

• Investigations into the Potential Role of Metabolites on the Anti-Leukemic Activity of Imatinib, Nilotinib and Midostaurin
  作者：Paul W. Manley

  DOI：10.2533/chimia.2019.561

  日期：——

  The efficacy and side-effects of drugs do not just reflect the biochemical and pharmacodynamic properties of the parent compound, but often comprise of cooperative effects between the properties of the parent and active metabolites. Metabolites of imatinib, nilotinib and midostaurin have been synthesised and evaluated in assays to compare their properties as protein kinase inhibitors with the parent drugs. The N-desmethyl-metabolite of imatinib is substantially less active than imatinib as a BCR-ABL1 kinase inhibitor, thus providing an explanation as to why patients producing high levels of this metabolite show a relatively low response rate in chronic myeloid leukaemia (CML) treatment. The hydroxymethylphenyl and N-oxide metabolites of imatinib and nilotinib are only weakly active as BCR-ABL1 inhibitors and are unlikely to play a role in the efficacy of either drug in CML. The 3-(R)-HO-metabolite of midostaurin shows appreciable accumulation following chronic drug administration and, in addition to mutant forms of FLT3, potently inhibits the PDPK1 and VEGFR2 kinases (IC50 values

  药物的功效和副作用不仅仅反映了母化合物的生化和药效特性，而且通常包括母化合物和活性代谢物之间的协同效应。已经合成和评估了伊马替尼、尼洛替尼和米多斯他林的代谢物，以比较它们作为蛋白激酶抑制剂的特性与母药的区别。伊马替尼的N-去甲基代谢物作为BCR-ABL1激酶抑制剂的活性明显低于伊马替尼，这解释了为什么产生高水平该代谢物的患者在慢性髓细胞白血病（CML）治疗中显示相对较低的反应率。伊马替尼和尼洛替尼的羟甲基苯和N-氧代谢物作为BCR-ABL1抑制剂的活性很弱，不太可能在CML中发挥作用。米多斯他林的3-(R)-HO-代谢物在长期用药后显示出明显的积累，并且除了FLT3的突变形式外，还强力抑制PDPK1和VEGFR2激酶（IC50值

• Synthesis of Symmetric Diester-Functionalised Tröger's Base Analogues
  作者：M. Delower H. Bhuiyan、Kai-Xian Zhu、Paul Jensen、Andrew C. Try

  DOI：10.1002/ejoc.201000086

  日期：2010.8

  The yields of ester-functionalised Troger's base analogues are dramatically improved by incorporating an electron-donating group on the aromatic ring and/or enhancing solubility of the aniline unit. In addition to 2,8-diester compounds, 1,7-, 3,9- and 4,10-diester-functionalised Troger's base analogues have been prepared for the first time.

  通过在芳环上加入给电子基团和/或提高苯胺单元的溶解度，酯官能化的 Troger 碱类似物的产率得到显着提高。除了 2,8-二酯化合物外，1,7-、3,9- 和 4,10-二酯官能化的 Troger 碱类似物也是首次制备。
• Synthesis of substituted 2-alkylquinolines by visible-light photoredox catalysis
  作者：Yousheng Mei、Jie Liu、Lei Wang、Pinhua Li

  DOI：10.1039/c9ob02259g

  日期：——

  The condensation of anilines and alkenyl ethers has been demonstrated by employing visible-light photoredox catalysis. The resulting method enables the synthesis of substituted 2-alkylquinolines under mild and simple conditions with good substrate scope and high yields.

  苯胺和烯基醚的缩合已通过可见光光氧化还原催化得到证实。所得方法能够在温和而简单的条件下以良好的底物范围和高收率合成取代的2-烷基喹啉。
• Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations
  作者：Yeming Ju、Di Miao、Ruiyang Yu、Sangho Koo

  DOI：10.1039/c4ob02441a

  日期：——

  One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(III)/Co(II) catalysts and the Paal–Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl

  一锅合成呋喃，噻吩和吡咯是通过使用Mn（III）/ Co（II）催化剂进行氧化脱乙酰作用以及1,5-二羰基化合物的Paal-Knorr反应完成的，该反应是通过乙酰乙酸乙酯的共轭加成制备的α，β-不饱和羰基化合物。衍生自乙酰乙酸乙酯和邻硝基苄基溴化物的β-酮酸酯的氧化脱乙酰基和还原环化有效地产生了各种取代的吲哚。
• 아세토아세틱 에스테르를 이용한 퓨란, 티오펜, 피롤의 합성방법
  申请人：Myongji University Industry and Academia Cooperation Foundation 명지대학교 산학협력단(220050139720) BRN ▼135-82-11060

  公开号：KR20160024702A

  公开（公告）日：2016-03-07

  본 발명은 아세토아세틱 에스테르를 이용한 퓨란, 티오펜, 피롤의 합성방법에 관한 것으로, 더욱 상세하게는 아세토아세틱 에스테르 화합물을 알파,베타-불포화 카르보닐 화합물에 첨가시켜 얻어지는 1,5-디카르보닐 화합물에 망간(III)/코발트(II) 촉매를 이용한 탈아세틸화 반응을 적용하여 1,4-디카로보닐 화합물을 합성한 다음, 여기에 Paal-Knorr 합성법을 이용하여 퓨란, 티오펜, 피롤을 합성하는 방법에 관한 것이다. 본 발명에 따르면, Paal-Knorr 합성에 필요한 1,4-디카르보닐 화합물을 효율적으로 용이하게 합성할 수 있으며 상기 1,5-디카르보닐 화합물로부터 상기 산화 반응(탈아세틸화 반응)과 Paal-Knorr 합성법을 연계하여 한 반응 용기에서 두 반응을 순차적으로 진행하는 퓨란, 티오펜, 및 피롤의 원-포트 합성방법을 제공할 수 있다.

  本发明涉及使用乙酰乙酸酯合成呋喃、噻吩和吡咯的方法，更详细地说，涉及将乙酰乙酸酯化合物加入α，β-不饱和羰基化合物中得到的1,5-二羰基化合物，然后利用锰(III)/钴(II)催化剂进行脱乙酰化反应合成1,4-二羰基化合物，然后使用Paal-Knorr合成方法合成呋喃、噻吩和吡咯的方法。根据本发明，可以高效地合成Paal-Knorr合成所需的1,4-二羰基化合物，并且可以通过将1,5-二羰基化合物与氧化反应（脱乙酰化反应）和Paal-Knorr合成方法结合，在同一反应容器中依次进行两个反应，从而提供呋喃、噻吩和吡咯的一锅法合成方法。