2,6-二甲氧基苄胺 | 20781-22-0

• 物质功能分类: 医药中间体
• 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: 2,6-二甲氧基苄胺
• 中文别名: 2,6-二甲氧基苯甲胺
• 英文名称: 2,6-Dimethoxybenzylamine
• 英文别名: (2,6-dimethoxyphenyl)methanamine
• CAS: 20781-22-0
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: XEKGMBAKVJAVAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  82 °C
• 沸点：
  108-110°C 1mm
• 密度：
  1.062±0.06 g/cm3(Predicted)
• 闪点：
  108-110°C/1mm
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会分解。应避免接触氧化物、酸以及空气。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2922299090
• 包装等级：
  III
• 危险类别：
  8
• 危险品运输编号：
  3259
• 危险性防范说明：
  P260,P264,P280,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P363,P405,P501
• 危险性描述：
  H314
• 储存条件：
  在干性保护气体中处理，并确保贮藏容器密封。存放于阴凉、干燥处，并使用紧密封装的容器。

SDS

Name:	2 6-Dimethoxybenzylamine Material Safety Data Sheet
Synonym:
CAS:	20781-22-0

Section 1 - Chemical Product MSDS Name:2 6-Dimethoxybenzylamine Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
20781-22-0	2,6-Dimethoxybenzylamine		unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Air sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Store under nitrogen.

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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# 20781-22-0: 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: distictive odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 108 - 110 deg C @1mmHg
Freezing/Melting Point: 71 - 73 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: C9H13NO2
Molecular Weight: 167.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, moisture, exposure to air.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 20781-22-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,6-Dimethoxybenzylamine - 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
Shipping Name: AMINES, SOLID, CORROSIVE, N.O.S.*
Hazard Class: 8
UN Number: 3259
Packing Group: III
IMO
Shipping Name: AMINES, SOLID, CORROSIVE, N.O.S.
Hazard Class: 8
UN Number: 3259
Packing Group: III
RID/ADR
Shipping Name: AMINES, SOLID, CORROSIVE, N.O.S.
Hazard Class: 8
UN Number: 3259
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 20781-22-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 20781-22-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 20781-22-0 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

制备方法与用途

用途

2,6-二甲氧基苄胺广泛应用于有机合成和医药中间体等领域。

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基苄胺 在 氢溴酸 、 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以87%的产率得到2,6-dihydroxybenzylamine hydrochloride
  参考文献：
  名称：

  Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases

  摘要：

  In order to obtain substrate-like inhibitors of copper amine oxidases (CAOs), a class of enzymes involved in important cellular processes as well as in crosslinking of elastin and collagen and removal of biogenic primary amines, we synthesized a set of benzylamine derivatives properly substituted at positions 2 and 6 and studied their biological activity towards some members of CAOs.With benzylamines 6, 7, 8 containing linear alkoxy groups we obtained reversible inhibitors of benzylamine oxidase (BAO), very active and selective toward diamine oxidase (DAO), lysyl oxidase (LO) and monoamine oxidase B (MAO B) characterized by a certain toxicity consequent to the crossing of the brain barrier. Poorly toxic, up to very active, reversible inhibitors of BAO, very selective toward DAO, LO and MAO B, were obtained with benzylamines 10, 11, 12 containing hydrophilic x-hydroxyalkoxy groups. With benzylamines 13, 14, 15, containing linear alkyl groups endowed with steric, but not conjugative effects for the absence of properly positioned oxygen atoms, we synthesized moderately active inhibitors of BAO reversible and selective toward DAO, LO and MAO B.The cross examination of the entire biological data brought us to the conclusion that the bioactive synthesized compounds most likely exert their physiological role of reversible inhibitors in consequence of the formation of a plurality of hydrogen bonds or hydrophobic non-covalent interactions with proper sites in the protein. Accordingly, the reported inhibitors may be considered as a set of research tools for general biological studies and the formation of enzyme complexes useful for X-ray structure determinations aimed at the design of more sophisticated inhibitors to always better modulate the protein activity without important side effects. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.037
• 作为产物：
  描述：

  2,6-二甲氧基苯甲腈 在 钾硼氢 作用下， 以 乙醇 、 水 为溶剂， 以72%的产率得到2,6-二甲氧基苄胺
  参考文献：
  名称：

  外消旋环丙烷和醛亚胺取代吡咯烷的动态动力学不对称合成：反应发展和机理见解

  摘要：

  通过外消旋供体-受体环丙烷和 (E)-醛亚胺的动态动力学不对称转化 (DyKAT)，实现了 2,5-顺式二取代吡咯烷的对映选择性制备。机理研究表明，醛亚胺或所得亚胺向 Z 几何结构的异构化不是提供观察到的 2,5-顺式二取代产物的途径。

  DOI：

  10.1021/ja1032277

文献信息

• Nickel-Catalyzed Enantioselective α-Alkenylation of <i>N</i>-Sulfonyl Amines: Modular Access to Chiral α-Branched Amines
  作者：Lun Li、Yu-Cheng Liu、Hang Shi

  DOI：10.1021/jacs.1c00622

  日期：2021.3.24

  α-branched amines are common structural motifs in functional materials, pharmaceuticals, and chiral catalysts. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we describe an atom-economical, modular method for a nickel-catalyzed enantioselective α-alkenylation of readily available linear N-sulfonyl amines

  手性α-支化胺是功能材料、药物和手性催化剂中常见的结构基序。因此，开发用于制备具有这些特权支架的化合物的有效方法是合成化学中的一项重要努力。在这里，我们描述了一种原子经济的模块化方法，用于镍催化的线性N 的对映选择性 α-烯基化-磺胺与炔烃可提供多种烯丙基胺，无需外源性氧化剂、还原剂或活化剂。该方法为构建手性α-支化胺以及α-氨基酰胺和β-氨基醇等衍生物提供了一个平台，这些衍生物可以方便地从新引入的烯烃中获得。鉴于该方法的通用性、多功能性和高原子经济性，我们预计它将具有广泛的合成效用。
• Novel S1P₁ Receptor Agonists – Part 1: From Pyrazoles to Thiophenes
  作者：Martin H. Bolli、Claus Müller、Boris Mathys、Stefan Abele、Magdalena Birker、Roberto Bravo、Daniel Bur、Patrick Hess、Christopher Kohl、David Lehmann、Oliver Nayler、Markus Rey、Solange Meyer、Michael Scherz、Gunther Schmidt、Beat Steiner、Alexander Treiber、Jörg Velker、Thomas Weller

  DOI：10.1021/jm4014373

  日期：2013.12.12

  identification of novel S1P1 receptor agonists, the pyrazole derivative 2 emerged as a hit structure. Medicinal chemistry efforts focused not only on improving the potency of the compound but in particular also on resolving its inherent instability issue. This led to the discovery of novel bicyclo[3.1.0]hexane fused thiophene derivatives. Compounds with high affinity and selectivity for S1P1 efficiently reducing

  通过旨在鉴定新型S1P 1受体激动剂的高通量筛选活动，吡唑衍生物2成为一种命中结构。药物化学工作不仅着重于提高化合物的效力，而且特别着重于解决其固有的不稳定性问题。这导致了新的双环[3.1.0]己烷稠合噻吩衍生物的发现。鉴定出对S1P 1具有高亲和力和选择性的化合物，可有效减少大鼠的淋巴细胞计数。例如，化合物85在S1P 1和S1P 3上的EC 50值为7和2880 nM。分别在大鼠和狗中具有良好的药代动力学特性，很好地分布在脑组织中，并且有效且剂量依赖性地降低了大鼠的淋巴细胞计数。自发性高血压大鼠口服给药后，S1P 1选择性化合物85仅对动物的苏醒阶段没有表现出对平均动脉压的影响，并且仅影响心率。
• Design, synthesis and biological evaluation of novel Pseudomonas aeruginosa DNA gyrase B inhibitors
  作者：Sridhar Jogula、Vagolu Siva Krishna、Nikhila Meda、Vadla Balraju、Dharmarajan Sriram

  DOI：10.1016/j.bioorg.2020.103905

  日期：2020.7

  In the present study, we attempted to develop a novel class of compounds active against Pseudomonas aeruginosa (Pa) by exploring the pharmaceutically well exploited enzyme targets. Since, lack of Pa gyrase B crystal structures, Thermus thermophilus gyrase B in complex with novobiocin (1KIJ) was used as template to generate model structure by performing homology modeling. Further the best model was

  在本研究中，我们试图通过探索药物上广泛使用的酶靶标来开发一类新型的对铜绿假单胞菌（Pausudoer aeruginosa）有活性的化合物。由于缺乏Pa促旋酶B晶体结构，因此将与新霉素（1KIJ）配合使用的Thermus thermophilus促旋酶B作为模板，通过进行同源性建模来生成模型结构。进一步验证了最佳模型，并使用内部数据库鉴定Pa DNA促旋酶B抑制剂，可用于高通量虚拟筛选，对接和动力学模拟。这项研究导致鉴定了针对Pa促旋酶超螺旋测定法的三个铅分子，IC50值在6.25-15.6 µM之间。Lead-1的优化和扩展产生了15种化合物。在合成的化合物中，六个化合物显示出比Lead-1（IC50 6.25 µM）更好的酶抑制作用。化合物13以最有潜力的化合物出现，表现出Pa促旋酶超螺旋的抑制作用，IC50为2.2 µM。在外排泵抑制剂存在下，MIC为8 µg / mL的体外Pa活性
• [EN] KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME<br/>[FR] INHIBITEURS DE KINASES ET PROCÉDÉ DE TRAITEMENT DU CANCER UTILISANT CEUX-CI
  申请人：UNIV HEALTH NETWORK

  公开号：WO2011123937A1

  公开（公告）日：2011-10-13

  The present teachings provide a compound represented by Strutural Formula (I): or a pharmaceutically acceptable salt thereof. Also described are a pharmaceutical composition and method of use thereof.

  本教学提供了一种由结构式(I)表示的化合物，或其药用可接受的盐。还描述了一种药物组合物及其使用方法。
• Inhibitors of 17Beta-Hydroxysteroid Dehydrogenases Type 1 and Type 2
  申请人：ELEXOPHARM GMBH

  公开号：US20160318895A1

  公开（公告）日：2016-11-03

  Provided herein are non-steroidal 17beta-hydroxysteroid dehydrogenase type 1 and type 2 (17β-HSD1 and 17β-HSD2) inhibitors, their production and use, especially for the treatment and for prophylaxis of hormone-related diseases.

  提供的是非甾体的17β-羟基类固醇脱氢酶1型和2型（17β-HSD1和17β-HSD2）抑制剂，它们的生产和应用，尤其是用于治疗和预防激素相关疾病。

表征谱图