N-甲基-3-甲氧基苯胺 | 14318-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-甲基-3-甲氧基苯胺
• 中文别名: 3-甲氧基-N-甲基苯胺；N-甲基-间茴香胺
• 英文名称: 3-methoxy-N-methylaniline
• 英文别名: N-methyl-3-methoxyaniline；N-methyl-m-anisidine；3-methoxy-N-methylbenzenamine
• CAS: 14318-66-2
• 化学式: C₈H₁₁NO
• mdl: MFCD05665953
• 分子量: 137.181
• InChiKey: ZFMZSZMUFWRAOG-UHFFFAOYSA-N

物化性质

• 沸点：
  239-240 °C(lit.)
• 密度：
  1.049 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24,S36/37
• 危险类别码：
  R22,R43
• 海关编码：
  2922299090
• WGK Germany：
  2
• 危险性防范说明：
  P261,P264,P270,P272,P280,P301+P312+P330,P302+P352,P305+P351+P338,P333+P313,P337+P313,P501
• 危险性描述：
  H302,H317,H320
• 储存条件：
  贮存于阴凉处，并保持容器密闭，在干燥且通风良好之处存放。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 3-Methoxy-N-methylaniline

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Acute toxicity, Oral (Category 4)
Eye irritation (Category 2)
Skin sensitization (Category 1)
According to European Directive 67/548/EEC as amended.
May cause sensitization by skin contact. Harmful if swallowed.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
Harmful if swallowed.
May cause an allergic skin reaction.
Causes serious eye irritation.
Precautionary statement(s)
Wear protective gloves.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Hazard symbol(s)
Xn Harmful
R-phrase(s)
R43 May cause sensitization by skin contact.
R22 Harmful if swallowed.
S-phrase(s)
S37/39 Wear suitable gloves and eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Synonyms : N-Methyl-m-anisidine
Formula : C8H11NO
Molecular Weight : 137,18 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
N-Methyl-m-anisidine
14318-66-2 238-259-9 - Acute Tox. 4; Eye Irrit. 2; Skin -
Sens. 1; H302, H317, H319
Xn, R43 - R22
For the full text of the H-Statements mentioned in this Section, see Section 16.

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Section 4. FIRST AID MEASURES
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing give artificial respiration Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed
containers for disposal.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid inhalation of vapour or mist.
Normal measures for preventive fire protection.
Conditions for safe storage
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with
multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to
engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Hand protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Handle with gloves.
Eye protection
Face shield and safety glasses
Skin and body protection
Choose body protection according to the amount and concentration of the dangerous substance at the
work place.
Hygiene measures
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form liquid
Colour colourless
Safety data
pH no data available
Melting point no data available
Boiling point 239 - 240 °C - lit.
Flash point > 110 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 1,049 g/cm3 at 25 °C
Water solubility no data available
Partition coefficient: log Pow: 1,698
n-octanol/water

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx)

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Section 11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
Skin corrosion/irritation
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
May cause allergic skin reaction.
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: no data available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Product
Observe all federal, state, and local environmental regulations. Contact a licensed professional waste
disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
Not dangerous goods

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Section 15. REGULATORY INFORMATION

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-甲基-3-甲氧基苯胺 在 Co(dmgH)(dmgH₂)Cl₂ 、 (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以94%的产率得到间氨基苯甲醚
  参考文献：
  名称：

  反向电子转移的最小化使得仲苯胺难以捉摸的 sp3 C−H 官能化

  摘要：

  苯胺是光诱导电子转移中最常用的一类底物。 N,N-二烷基衍生物能够通过氧化然后去质子化使 N 原子产生自由基 α。然而，由于快速反电子转移（BET），这种方法对于单取代苯胺来说难以捉摸。在这里，我们证明了在外源烷基胺存在的情况下使用光氧化还原催化可以最大限度地减少 BET。这种方法协同帮助苯胺 SET 氧化，然后加速随后的去质子化。通过这种方式，现在可以生成 α-苯胺烷基自由基，并且这些物质可以在一般意义上用于实现不同的 sp 3 C−H 官能化。

  DOI：

  10.1002/anie.202100051
• 作为产物：
  描述：

  N-(3-甲氧基苯基)-N-甲基甲酰胺 在 盐酸 作用下， 反应 1.0h， 以80%的产率得到N-甲基-3-甲氧基苯胺
  参考文献：
  名称：

  荧光染料的合成。九。新的4-羟基香豆素，4-羟基-2-喹诺酮类，2 H，5 H-吡喃并[3,2- c ]苯并吡喃-2,5-二酮和2 H，5 H-吡喃并[3,2- c ]喹啉-2,5-二酮†

  摘要：

  由适当的酚或苯胺合成了7位取代的4-羟基香豆素（2a-e）和4-羟基-2-喹诺酮（2f-i），并使用三乙氧基甲烷和苯胺将其转化为烯胺3。3与腈4a-h的缩合反应生成2 H，5 H-吡喃并[3,2- c ]苯并吡喃-2,5-二酮（5a-r）或2 H，5 H-吡喃并[3,2- c ]喹啉-2,5-二酮（5s-x），显示出自发的和受激的荧光，最大值介于418和549 nm之间。7a，b（由2d，e和3-氧代丁酸乙酯合成）的荧光光谱证明了5中的吸电子3取代基的显着影响，与化合物21-r相比，其最大值急剧转变为蓝色。。

  DOI：

  10.1002/jhet.5570170204

文献信息

• BENZOTHIOPHENE INHIBITORS OF RHO KINASE
  申请人：Kahraman Mehmet

  公开号：US20080021026A1

  公开（公告）日：2008-01-24

  The present invention relates to compounds and methods which may be useful as inhibitors of Rho kinase for the treatment or prevention of disease.

  本发明涉及化合物和方法，这些化合物和方法可能作为Rho激酶的抑制剂在治疗或预防疾病方面有用。
• Asymmetric α-arylation of amino acids
  作者：Daniel J. Leonard、John W. Ward、Jonathan Clayden

  DOI：10.1038/s41586-018-0553-9

  日期：2018.10

  α-aryl amino acids and their derivatives are valuable precursors to bioactive molecules10,11. Here we describe the synthesis of quaternary α-aryl amino acids from enantiopure amino acid precursors by α-arylation without loss of stereochemical integrity. Our approach relies on the temporary formation of a second stereogenic centre in an N′-arylurea adduct12 of an imidazolidinone derivative6 of the precursor

  季氨基酸，其中带有氨基和羧基的 α-碳也带有两个碳取代基，作为肽构象和生物活性的修饰剂以及作为药用重要化合物的前体具有重要作用 1,2。与在该 α-碳上的对映选择性烷基化（有多种方法 3-8）相比，在 α-碳上一般对映选择性引入芳基取代基在合成上具有挑战性 9。尽管如此，由此产生的 α-芳基氨基酸及其衍生物是生物活性分子 10,11 的有价值的前体。在这里，我们描述了通过 α-芳基化从对映纯氨基酸前体合成季 α-芳基氨基酸而不损失立体化学完整性。我们的方法依赖于在前体氨基酸的咪唑啉酮衍生物 6 的 N'-芳基脲加合物中临时形成第二个立体中心，并使用容易获得的对映体纯氨基酸作为前体和不对称的来源。它避免使用有价值的过渡金属，并能够用富电子、贫电子和杂环取代基进行芳基化。产物的任一对映异构体都可由单一氨基酸前体形成。该方法实用且可扩展，并提供了生产数克数量的 α-芳基化季铵氨基酸的机会。该方法
• CO2 as a C1-building block for the catalytic methylation of amines
  作者：Olivier Jacquet、Xavier Frogneux、Christophe Das Neves Gomes、Thibault Cantat

  DOI：10.1039/c3sc22240c

  日期：——

  A novel catalytic reaction has been designed to utilize, for the first time, CO2 as a C1 feedstock in the synthesis of N-methylamines. Simple zinc catalysts, based on commercially available zinc salts and ligands, prove highly efficient in promoting both a 6 electron reduction of carbon dioxide and the formation of a C–N bond, using hydrosilanes and amines.

  设计了一种新型催化反应，首次利用二氧化碳作为C1原料，在N-甲基胺的合成中发挥了作用。基于商业可获得的锌盐和配体，简便的锌催化剂表现出高效的特点，能够促进二氧化碳的6电子还原以及使用氢硅烷和胺的C-N键的形成。
• Hydroarylation of Alkenes Using Anilines in Hexafluoroisopropanol
  作者：Ignacio Colomer

  DOI：10.1021/acscatal.0c00872

  日期：2020.6.5

  one to modulate bioactive molecules. This work reports a method for the selective functionalization of anilines using hexafluoroisopropanol (HFIP) as a solvent to promote an acid-catalyzed hydroarylation of olefins. Mechanistic experiments revealed that HFIP both protonates the alkene and selectively enables anilines toward the electrophilic aromatic substitution. This powerful strategy has been applied

  迫切需要提供用于小分子选择性功能化的新方法，因为例如将分子多样性安装在所需位置可允许人们调节生物活性分子。这项工作报告了一种使用六氟异丙醇（HFIP）作为溶剂来促进烯烃的酸催化加氢芳基化的苯胺选择性官能化的方法。机理实验表明，HFIP既可以使烯烃质子化，又可以选择性地使苯胺实现亲电芳族取代。这种强大的策略已应用于化学控制和区域控制的消炎性甲芬那酸的功能化。
• [EN] BICYCLIC HETEROCYCLE DERIVATIVES AND USE THEREOF AS GPR119 MODULATORS<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES BICYCLIQUES ET LEUR UTILISATION EN TANT QUE MODULATEURS DE GPR119
  申请人：SCHERING CORP

  公开号：WO2009143049A1

  公开（公告）日：2009-11-26

  The present invention relates to Bicyclic Heterocycle Derivatives of formula (I), compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of GPR1 19 in a patient.

  本发明涉及公式（I）的双环杂环衍生物，包含双环杂环衍生物的组合物，以及使用双环杂环衍生物治疗或预防患者的肥胖、糖尿病、代谢紊乱、心血管疾病或与GPR119活性相关的疾病的方法。