2-溴-N-甲基苯胺 | 6832-87-7

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-溴-N-甲基苯胺
• 中文别名: N-甲基-邻溴苯胺；N-甲基-2-溴苯胺；N-甲基邻溴苯胺
• 英文名称: 2-bromo-N-methylaniline
• 英文别名: N-methyl-2-bromoaniline；o-bromo-N-methylaniline；N-methyl-o-bromoaniline
• CAS: 6832-87-7
• 化学式: C₇H₈BrN
• mdl: MFCD06798064
• 分子量: 186.051
• InChiKey: SMVIAQFTVWDWDS-UHFFFAOYSA-N

物化性质

• 沸点：
  107-109 °C/12 mmHg (lit.)
• 密度：
  1.589 g/mL at 25 °C (lit.)
• 闪点：
  219 °F
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S37,S39
• 危险类别码：
  R22
• 海关编码：
  2921420090
• WGK Germany：
  2
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  密闭保存

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 2-Bromo-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)
According to European Directive 67/548/EEC as amended.
Harmful if swallowed.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
Precautionary statement(s)
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)
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
Formula : C7H8BrN
Molecular Weight : 186,05 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
2-Bromo-N-methylaniline
6832-87-7 - - Acute Tox. 4; H302 -
Xn, 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
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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 contact with skin and eyes. Avoid inhalation of vapour or mist.
Normal measures for preventive fire protection.
Conditions for safe storage
Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully
resealed and kept upright to prevent leakage. Store in cool 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
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without
touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves
after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Eye protection
Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate
government standards such as NIOSH (US) or EN 166(EU).
Skin and body protection
Complete suit protecting against chemicals, The type of protective equipment must be selected according
to the concentration and amount of the dangerous substance at the specific workplace.
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 brown
Safety data
pH no data available
Melting point no data available
Boiling point 107 - 109 °C at 16 hPa - lit.
Flash point 103 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 1,589 g/cm3 at 25 °C
Water solubility no data available
Partition coefficient: log Pow: 2,607
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),
Hydrogen bromide gas

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Section 11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
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 Causes 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: Not 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
Harmful to aquatic life.
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional
waste disposal service to dispose of this material.
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
UN-Number: 3334 Class: 9
Proper shipping name: Aviation regulated liquid, n.o.s. (2-Bromo-N-methylaniline)

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：重要的医药中间体

反应信息

• 作为反应物：
  描述：

  2-溴-N-甲基苯胺 在 盐酸 、 potassium cyanide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 14.0h， 生成 (E)-2-(2-bromo-N-methylanilino)-4-phenylbut-2-enenitrile
  参考文献：
  名称：

  钯催化溴苯胺基丙烯腈的化学选择性分子内环化

  摘要：

  α-（o-溴苯胺基）丙烯腈1a-f和2a-e和α-（N-链烯基氨基）-β-（o-溴苯基）丙烷腈7a-c <和8a-c经历钯催化转化为o-（甲基氨基） ）苄腈12，邻-[（（烯基氨基）乙烯基]苄腈24a-c，N-烯基苯胺26b，26c，3-苯并ze庚因29a，29c，31a和32a，γ-咔啉36和吡咯并[3,2- b ]吲哚45该反应涉及将芳族钯分子内加成到氰基上，以及随后的过程，例如氰基基团的转位，水解，电环化，乙基基团的转移和氧化芳构化。提出了氰基钯催化芳基化的一般机理。

  DOI：

  10.1039/a702710i
• 作为产物：
  描述：

  N-甲基-N-亚硝基苯胺 在 N-溴代丁二酰亚胺(NBS) 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 水 、 叔丁醇 、 甲醇 为溶剂， 反应 13.0h， 以72%的产率得到2-溴-N-甲基苯胺
  参考文献：
  名称：

  Cp * Rh（iii）通过溶剂控制的区域选择性C–H官能化催化N-亚硝基苯胺的邻位卤化†

  摘要：

  我们提出了一种新颖，有效和区域选择性的方法，用于铑催化苯胺的直接C–H邻位卤化反应，其中涉及可移动的N-亚硝基导向基团。该方法反应条件温和，底物范围宽，官能团耐受性好，收率令人满意。为了维持高邻位选择性和转化率，增加溶剂的空间位阻是至关重要的。初步的机理研究表明，C–H活化可能参与速率测定步骤。

  DOI：

  10.1039/c8ob00601f

文献信息

• HETEROBICYCLIC COMPOUNDS
  申请人：Amgen Inc.

  公开号：US20130225552A1

  公开（公告）日：2013-08-29

  Heterobicyclic compounds of Formula (I): or a pharmaceutically-acceptable salt, tautomer, or stereoisomer thereof, as defined in the specification, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, Huntington's Disease, and the like.

  Formula (I)的杂环化合物： 或其药用可接受的盐、互变异构体或立体异构体，如规范中所定义，并含有它们的组合物，以及制备这种化合物的方法。本文还提供了通过抑制PDE10来治疗由此可治疗的疾病或疾病的方法，如肥胖症、非胰岛素依赖型糖尿病、精神分裂症、躁郁症、强迫症、亨廷顿病等。
• Nanoparticle mediated organic synthesis (NAMO-synthesis): CuI-NP catalyzed ligand free amidation of aryl halides
  作者：Atul Kumar、Ajay Kumar Bishnoi

  DOI：10.1039/c4ra06804a

  日期：——

  The first CuI-nanoparticle catalyzed ligand free synthesis of N-aryl amides from aryl halides and arylamides/cyclic amides has been developed. This methodology is further extended for the synthesis of nitrogen heterocycles such as benzimidazole, and quinazolinone via intermolecular amidation reaction followed by cyclization. TEM images of the CuI-NP catalyst showed spherical, well-dispersed particles

  已经开发了由CuI-纳米颗粒催化的从芳基卤化物和芳基酰胺/环状酰胺的N-芳基酰胺的无配体的合成。该方法进一步扩展用于通过分子间酰胺化反应然后环化来合成氮杂环，例如苯并咪唑和喹唑啉酮。CuI-NP催化剂的TEM图像显示球形，分散良好的颗粒，为反应性提供了较大的表面积，并具有良好的可回收性。
• Simple RuCl ₃ ‐catalyzed <i>N</i> ‐Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol
  作者：Naina Sarki、Vishakha Goyal、Nitin Kumar Tyagi、Puttaswamy、Anand Narani、Anjan Ray、Kishore Natte

  DOI：10.1002/cctc.202001937

  日期：2021.4.9

  readily available feedstock chemicals, highlighting synthetic value of this advanced N‐methylation reaction. Using this platform, we also attempted tandem reactions with selected nitroarenes to convert them into corresponding N‐methylated amines using MeOH under H2‐free conditions including transfer hydrogenation of nitroarenes‐to‐anilines and prepared drug molecules (e. g., benzocaine and butamben) as well

  甲醇是潜在的氢源和C 1合成子，在化学合成和能源技术中都有有趣的应用。在有机合成中有效利用这种简单的醇具有至关重要的意义，并引起了科学兴趣。本文中，我们报道了一种清洁且具有成本竞争力的方法，该方法使用甲醇作为C 1合成子和H 2源，通过使用相对便宜的RuCl 3 .xH 2 O作为无配体催化剂，对胺进行选择性N-甲基化。这种易于获得的催化剂可耐受各种包含缺电子基团和供电子基团的胺，并使它们转化为相应的N甲基化产品，产率中等至优异。此外，很少有市售的药剂（例如文拉法辛和丙咪嗪）是通过后期功能化从容易获得的原料化学品中成功合成的，从而突出了这种先进的N-甲基化反应的合成价值。在该平台上，我们还尝试与选定的硝基芳烃进行串联反应，以在H 2下使用MeOH将它们转化为相应的N甲基化胺。无条件的条件包括硝基芳烃到苯胺的转移氢化以及制备的药物分子（例如苯佐卡因和丁苯本）以及关键的医药中间体。我们进一步使
• 菲啶酮类化合物的合成方法
  申请人：洛阳师范学院

  公开号：CN104926723B

  公开（公告）日：2017-04-19

  本发明涉及菲啶酮类化合物的合成方法，取邻卤芳胺和芳基甲醇（或芳胺和邻卤芳基甲醇）、钌催化剂、钯盐、氮杂环咪唑盐和碱加入到有机溶剂中，在N2气保护下加热，通过氢转移反应和碳氢键活化反应一步生成菲啶酮类化合物，为合成具有生物活性的取代菲啶酮类衍生物提供了一个实用的方法，该方法操作简单，反应底物便宜范围广、产率高，具有重要的应用价值。
• Alkyltelluro Substitution Improves the Radical-Trapping Capacity of Aromatic Amines
  作者：Jia-fei Poon、Jiajie Yan、Vijay P. Singh、Paul J. Gates、Lars Engman

  DOI：10.1002/chem.201602377

  日期：2016.8.26

  The synthesis of a variety of aromatic amines carrying an ortho‐alkyltelluro group is described. The new antioxidants quenched lipidperoxyl radicals much more efficiently than α‐tocopherol and were regenerable by aqueous‐phase N‐acetylcysteine in a two‐phase peroxidation system. The inhibition time for diaryl amine 9 b was four‐fold longer than recorded with α‐tocopherol. Thiol consumption in the aqueous

  描述了带有邻烷基碲基的各种芳香胺的合成。新的抗氧化剂比α-生育酚更有效地淬灭脂质过氧自由基，并且可以在两相过氧化系统中被水相N-乙酰半胱氨酸再生。二芳基胺9b的抑制时间比α-生育酚的抑制时间长四倍。发现水相中的硫醇消耗与抑制时间成反比，硫醇的可用性是抗氧化剂保护持续时间的限制因素。拟议的过氧自由基淬灭机理涉及在溶剂笼中O原子从过氧原子转移到Te，然后H原子从胺转移到烷氧基。