2-苯胺环己酮 | 4504-43-2

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-苯胺环己酮
• 英文名称: 2-(phenylamino)cyclohexanone
• 英文别名: 2-Anilinocyclohexanone；2-anilinocyclohexan-1-one
• CAS: 4504-43-2
• 化学式: C₁₂H₁₅NO
• mdl: MFCD00465146
• 分子量: 189.257
• InChiKey: AWMZFBYYIATTOW-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  346.0±35.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090
• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Anilinocyclohexanone
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 189,26 g/mol
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
No data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
No special environmental precautions required.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin 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.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
No special environmental precautions required.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation rate No data available
i) Flammability (solid, gas) No data available
j) Upper/lower No data available
flammability or
explosive limits
k) Vapour pressure No data available
l) Vapour density No data available
m) Relative density No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition No data available
temperature
q) Decomposition No data available
temperature
r) Viscosity No data available
s) Explosive properties No data available
t) Oxidizing properties No data available
Other safety information
No data available

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SECTION 10: Stability and reactivity
Reactivity
No data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
No data available
Skin corrosion/irritation
No data available
Serious eye damage/eye irritation
No data available
Respiratory or skin sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
Results of PBT and vPvB assessment
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
No data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2-苯胺环己酮 在 RuCl₂[(S)-XylSDP][(R,R)-DPEN] 、 potassium tert-butylate 、 氢气 作用下， 以 异丙醇 为溶剂， 20.0 ℃ 、1.01 MPa 条件下， 反应 6.0h， 以97%的产率得到(1S,2R)-2-(phenylamino)cyclohexanol
  参考文献：
  名称：

  钌催化的不对称加氢高对映选择性合成手性环状氨基醇和对苯二甲酸

  摘要：

  一个高效对映和非对映选择性合成的手性顺式-β- ñ -烷基/芳基氨基环醇已经由外消旋的不对称氢化实现α氨基经由DKR环酮催化通过将[RuCl 2（（小号）-Xyl-SDP） （（R，R）-DPEN）]。该反应的对映选择性分别达到99.9％ee的用99：1分的顺式-选择性。还开发了一种实用的催化方法，可合成水合所有四个异构体。

  DOI：

  10.1021/ol901605a
• 作为产物：
  描述：

  环己酮 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 对甲苯磺酸 、 丙酮 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-苯胺环己酮
  参考文献：
  名称：

  Synthesis of Multiple-Substituted Pyrroles via Gold(I)-Catalyzed Hydroamination/Cyclization Cascade

  摘要：

  A gold-catalyzed cascade hydroamination/cyclization reaction of alpha-amino ketones with alkynes to form substituted pyrroles has been developed. The method offers several advantages such as high regioselectivity with the tested cases, wide functional group tolerance, and easily accessible starting materials. The synthetic utility of the obtained pyrrole products was demonstrated by their efficient transformations to 2-vinylated pyrroles via gold-catalyzed intermolecular hydroarylation.

  DOI：

  10.1021/acs.orglett.5b01281

文献信息

• A Strategy to Construct <i>cis</i>-Hydrocarbazole via Nickel/Lewis Acid Dual-Catalyzed Arylcyanation
  作者：Hao Zhang、Peiqi Chen、Hesi Yang、Shiqiang Ma、Zemin Wang、Xingang Xie、Xiaolei Wang、Huilin Li、Xuegong She

  DOI：10.1021/acs.joc.9b03243

  日期：2020.3.6

  for the synthesis of cis-hydrocarbazole with a C3 quaternary carbon center has been developed through nickel/Lewis acid dual-catalyzed arylcyanation. A wide array of cis-hydrocarbazoles was accessed with high diastereoselectivities and atom economies in a good yield. The rich chemistry of the installed nitrile group was demonstrated in the preparation of tryptamine- and tryptophol-derived cis-hydrocarbazoles

  通过镍/路易斯酸双催化的芳基氰化反应，已经开发出一种具有C3季碳中心的顺式咔唑合成策略。以高非对映选择性和原子经济性获得了多种顺式-咔唑，并具有良好的收率。在制备由色胺和色胺醇衍生的顺式咔唑中已证明，已安装的腈基具有丰富的化学性质。
• Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines
  作者：Zhengwang Chen、Huiying Zeng、Hang Gong、Haining Wang、Chao-Jun Li

  DOI：10.1039/c5sc00941c

  日期：——

  A highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using sodium formate as hydrogen donor is described.

  一种高效的Pd催化的直接偶联方法，将酚类木质素模型单体和类似物与苯胺偶联，使用甲酸钠作为氢供体，生成环己胺。
• A Route to the C,D,E Ring System of the <i>Aspidosperma</i> Alkaloids
  作者：Geoffrey M. Giampa、Jian Fang、Matthias Brewer

  DOI：10.1021/acs.orglett.6b01674

  日期：2016.8.19

  A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis

  报道了一个短的合成序列，该序列导致了曲霉植物生物碱的C，D，E环亚基的形成。该路线基于环断裂/分子内的甲亚胺基内酯1，3-偶极环加成反应序列，该序列给出所需的三环产物为单一非对映异构体。显示了在路易斯酸存在下，γ-氨基-β-羟基-α-重氮羰基化合物会断裂，从而生成可以直接还原为相应胺的亚胺产物。
• Development of a generic activation mode: nucleophilic α-substitution of ketones via oxy-allyl cations
  作者：Mark N. Vander Wal、Andrew K. Dilger、David W. C. MacMillan

  DOI：10.1039/c3sc51266e

  日期：——

  Oxy-allyl cations have been known as transient electrophilic species since they were first proposed as intermediates in the Favorskii rearrangement in 1894. Since that time, they also have been used as a mode of activation for [4 + 3] cycloadditions in a variety of natural product syntheses. In this manuscript, we describe a method for the interception of oxy-allyl cations with a diverse range of common

  自从1894年氧-烯丙基阳离子首次被提出作为Favorskii重排的中间体以来，它就被称为瞬态亲电子物种。从那时起，它们还被用作多种[4 + 3]环加成反应的活化方式。天然产物合成。在此手稿中，我们描述了一种用于拦截具有各种范围的常见亲核试剂的氧-烯丙基阳离子的方法，从而证明了该中间体作为活化的一般模式的价值。这种简单，温和的室温规程允许形成各种高价值的碳-碳和碳-杂原子键，这些键很容易结合在一系列环状和非环状酮体系中。还描述了开发对映选择性催化变体的初步努力。
• Thieme Chemistry Journals Awardees – Where Are They Now? A Cascade Synthesis of 1,2,4-Triazin-3(2H)-ones Using Nitrogen-Substituted Isocyanates
  作者：André Beauchemin、Mohammed Dahab、Joshua Derasp

  DOI：10.1055/s-0036-1588099

  日期：——

  A cascade synthesis of 1,2,4-triazin-3(2H)-ones is reported from readily accessible α-amino ketones and phenyl carbazate as a masked N-isocyanate precursor. The mild protocol provides a simple route to products with substitution patterns which are difficult to form directly. This also presents the first N-isocyanate cascade requiring the use of acidic conditions, which accelerates formation of the

  据报道，1,2,4-triazin-3(2H)-ones 的级联合成来自容易获得的 α-氨基酮和苯甲酸苯酯作为掩蔽的 N-异氰酸酯前体。温和的协议为具有难以直接形成的替代模式的产品提供了一种简单的途径。这也呈现出需要使用酸性条件的第一个 N-异氰酸酯级联，这会加速腙中间体的形成和环化步骤。这种级联进一步强调了在形成高反应性 N-异氰酸酯中间体的反应中可以实现高度控制。