4-羟基-4-二甲氨基偶氮苯 | 2496-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 4-羟基-4-二甲氨基偶氮苯
• 中文别名: 4-二甲氨基-4’-羟基偶氮苯；4-羟基-4'-二甲氨基偶氮苯
• 英文名称: 4-hydroxy-4'-(N,N-dimethylamino)azobenzene
• 英文别名: 4-hydroxy-4'-dimethylaminoazobenzene；4'-Hydroxy-4-dimethylamino-azobenzol；4'-Dimethylamino-4-hydroxy-azobenzol；N,N-dimethyl-4-amino-4'-hydroxyazobenzene；4-[[4-(dimethylamino)phenyl]diazenyl]phenol
• CAS: 2496-15-3
• 化学式: C₁₄H₁₅N₃O
• mdl: MFCD00059624
• 分子量: 241.293
• InChiKey: CQKQINNUKSBEQR-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  430.5±30.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2927000090

SDS

4-Hydroxy-4'-dimethylaminoazobenzene Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4-Hydroxy-4'-dimethylaminoazobenzene

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 4
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Harmful if swallowed
Precautionary statements:
[Prevention] Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
[Response]
Rinse mouth.
Dispose of contents/container through a waste management company authorized by
[Disposal]
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4-Hydroxy-4'-dimethylaminoazobenzene
Percent: >98.0%(LC)(T)
CAS Number: 2496-15-3
Synonyms: 4-(4-Dimethylaminophenylazo)phenol
Chemical Formula: C14H15N3O

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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. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
4-Hydroxy-4'-dimethylaminoazobenzene

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Section 4. FIRST AID MEASURES
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: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
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 under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
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:
Colour: Yellow red - Deep red
No data available
Odour:
4-Hydroxy-4'-dimethylaminoazobenzene

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:200°C
Boiling point/range: No data available
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] No data available

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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:
No data available
IARC =
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
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
UN-No: Not listed
4-Hydroxy-4'-dimethylaminoazobenzene

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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：

  4-羟基-4-二甲氨基偶氮苯 在 吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  [18F]Flotaza 的开发和评估，用于死后人类阿尔茨海默病大脑中的 Aβ 斑块成像

  摘要：

  阿尔茨海默病 (AD) 中β淀粉样蛋白 (Aβ) 积累的正电子发射断层扫描 (PET) 研究已显示出临床实用性。本研究的目的是开发和评估新型氟 18 放射性示踪剂 [ 18 F]Flotaza (2-{2-[2-[ 18 F]氟乙氧基]乙氧基}乙氧基)-4′- N , N -二甲基氨基偶氮苯），用于 Aβ 斑块成像。亲核[ 18 F]氟化物用于[ 18 F]flotaza的一步放射合成。使用由前扣带回 (AC) 和胼胝体 (CC) 组成的死后人类 AD 脑组织，Flotaza 对人类 Aβ 斑块的结合亲和力 Ki = 1.68 nM，对 Tau 蛋白的结合亲和力较弱 (>10 -5 M)。[ 18 F]Flotaza 的放射合成非常有效，放射化学产率很高 (>25%)，比活性 >74 GBq/μmol。所有 AD 受试者的脑切片均采用抗 Aβ 免疫染色呈阳性。在所有 6 名受试者中，灰质 AC

  DOI：

  10.1016/j.bmcl.2021.128164
• 作为产物：
  描述：

  N,N-二甲基-4-亚硝基苯胺 在 氢氧化钾 、 乙醇 、 硫酸 作用下， 生成 4-羟基-4-二甲氨基偶氮苯
  参考文献：
  名称：

  319.缩合的Ñ -phenylhydroxylamine与NN二甲基p -nitrosoaniline。衍生自氧化偶氮化合物p -dimethylaminoazobenzene

  摘要：

  DOI：

  10.1039/jr9520001722

文献信息

• Non-linear optical materials containing molybdenum or tungsten mononitrosyl redox centres: diaromatic azo derivatives
  作者：Benjamin J. Coe、Jean-Dominic Foulon、Thomas A. Hamor、Christopher J. Jones、Jon A. McCleverty、David Bloor、Graham H. Cross、Tony L. Axon

  DOI：10.1039/dt9940003427

  日期：——

  following compounds have been prepared: [M(NO)L(X)nEC6H3(R-3)[NNC6H3(R′-3)(R″-4)-4]}2 – n][L = tris(3,5-dimethylpyrazolyl)hydroborate; R″=(η5-C5H4)Fe(η5-C5H5), E = O, R = R′= H, M = Mo, X = Cl or I, n= 0 or 1; E = NH, R = R′= H, n= 1, M = Mo or W, X = Cl; E = NH, R = Me, R′= H, n= 1, M = Mo, X = F, Cl, Br, I or OC6H11; M = W, X = Cl; E = NH, R = R′= Me, n= 1, M = Mo, X = Cl or I; M = W, X = Cl; R″= NMe2

  已制备以下化合物：[M（NO）L（X）n EC 6 H 3（R-3）[N NC 6 H 3（R'-3）（R''-4）-4]} 2 – n ] [L =三（3,5-二甲基吡唑基）氢硼酸盐；R“=（η 5 -C 5 H ^ 4）的Fe（η 5 -C 5 H ^ 5）中，E = O，R = R'= H，M =钼，X = Cl或I，ñ = 0或1; E ＝ NH，R ＝ R′＝ H，n＝ 1，M ＝ Mo或W，X ＝ Cl。E ＝ NH，R ＝ Me，R′＝ H，n＝ 1，M ＝ Mo，X ＝ F，Cl，Br，I或OC 6 H 11；E ＝ NH，R ＝ Me，R ＝ H，n＝ 1，M ＝ Mo，X ＝ F，Cl，Br，I或OC 6 H 11。M = W，X = Cl；E = NH，R = R′= Me，n= 1，M = Mo，X = Cl或I；M = W，X = Cl；R” ＝ NMe 2，E
• Boronic acids as molecular inks for surface functionalization of polyvinyl alcohol substrates
  作者：Ryuhei Nishiyabu、Miku Tomura、Tomo Okade、Yuji Kubo

  DOI：10.1039/c8nj00992a

  日期：——

  Boronic acids are proposed to be used as molecular inks for surface functionalization of polyvinyl alcohol substrates using marker pen applicators.

  硼酸被建议用作分子墨水，用于使用记号笔涂抹器对聚乙烯醇基材进行表面官能化。

• Orthogonal Light-Induced Self-Assembly of Nanoparticles using Differently Substituted Azobenzenes
  作者：Debasish Manna、Thumu Udayabhaskararao、Hui Zhao、Rafal Klajn

  DOI：10.1002/anie.201502419

  日期：2015.10.12

  surfaces of metallic nanoparticles with differently substituted azobenzenes, it is possible to modulate the wavelength of light at which the self‐assembly of these nanoparticles is induced. Exposing a mixture of two types of nanoparticles, each functionalized with a different azobenzene, to UV or blue light induces the selective self‐assembly of only one type of nanoparticles. Irradiation with the

  精确控制复杂混合物中所选成分的自组装是一个具有挑战性的目标，实现这一点对于制造新型纳米材料非常重要。本文表明，通过用不同取代的偶氮苯修饰金属纳米颗粒的表面，可以调节诱导这些纳米颗粒自组装的光的波长。将两种类型的纳米颗粒（分别用不同的偶氮苯官能化）的混合物暴露于紫外线或蓝光下，仅会诱导一种类型的纳米颗粒的选择性自组装。另一波长的辐射会触发聚集体的分解，并同时引发另一种类型的纳米粒子的自组装。通过将两种类型的偶氮苯置于相同的纳米粒子上，
• Fine-Tuning the Electronic Properties of Azo Chromophore-Incorporated Perylene Bisimide Dyads
  作者：Tankut Türel、Suresh Valiyaveettil

  DOI：10.1021/acs.joc.0c01166

  日期：2020.8.21

  Perylene bisimide (PBI) and azo-compounds are fascinating molecules with interesting optical properties. Here, we combine the two chromophores to prepare nonconjugated and conjugated stable azo-PBI dyes. The detailed structural characterization, comparison of properties, and solid-state self-assembly of the compounds are discussed. The incorporation of azo groups at the bay side of PBI led to significant

  ylene双酰亚胺（PBI）和偶氮化合物是具有有趣光学特性的引人入胜的分子。在这里，我们结合两个生色团，以制备非共轭和共轭的稳定偶氮PBI染料。讨论了化合物的详细结构表征，性质比较和固态自组装。与模型PBI（M 1和M 2）相比，在PBI的海湾一侧引入偶氮基团导致光学性能发生重大变化。所有新的偶氮-PBI均显示出光诱导的异构化，这引起了分解和荧光增强。结合有胺的偶氮PBI（3和6）将氯金酸还原成金纳米颗粒。当前的研究提供了一种简单的合成策略，并比较了共轭和非共轭偶氮PBI的性质，这可能在光电器件中有用。
• Photoisomerization and Mesophase Formation in Azo-Ionic Liquids
  作者：Olivier Renier、Guillaume Bousrez、Kathrin Stappert、Magdalena Wilk-Kozubek、Brando Adranno、Hanwen Pei、Eike T. Spielberg、Volodymyr Smetana、Anja-Verena Mudring

  DOI：10.1021/acs.cgd.9b01018

  日期：2020.1.2

  Ionic liquids present a versatile, highly tunable class of soft functional materials. Aside from being low melting salts, they can be endowed with additional functionalities. In N-alkylimidazolium halides, which are a prominent class of ionic liquids (ILs), the imidazolium cation was linked via an ether-bridge to an azobenzene unit in order to obtain photoresponsive materials through photoinduced trans-cis

  离子液体代表了一种通用的，高度可调的软功能材料。除了是低熔点盐以外，它们还可以具有其他功能。在离子液体（ILs）的一类突出的卤化N-烷基咪唑鎓盐中，咪唑鎓阳离子通过醚桥与偶氮苯单元相连，以便通过光诱导的反式-顺式异构化获得光敏材料。偶氮苯单元又被供电子或吸电子基团如甲基，叔丁基，甲氧基，N，N改性-二甲基氨基和硝基，以研究它们对光异构化和相行为的影响。另外，使咪唑鎓具有长的烷基链使得该材料在熔化成各向同性液体之前有可能形成液晶（LC）中间相。所有研究的化合物均符合离子液体的标准，并且除硝基化合物外，所有化合物均显示出近晶中间相的形成，并逐渐熔化成各向同性的液体。具有最大的脂族取代基叔丁基的化合物显示出最低的熔点，最大的中间相窗口和有效的光化学反式转化率（> 90％）。总之，通过空间和电子方式调节IL的阳离子部分，可以开发出一种可光开关的室温液晶，并可以获得光响应性离子液体的设计指南。