对二氨基偶氮苯 | 538-41-0

• 物质功能分类: 化学试剂 - 有机试剂 - 偶氮、重氮化合物
• 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: 对二氨基偶氮苯
• 中文别名: 4,4’-偶氮二苯胺；4,4'-偶氮二苯胺；4,4"-偶氮二苯胺
• 英文名称: 4,4'-Diaminoazobenzene
• 英文别名: 4,4'-azodianiline；4-[(4-aminophenyl)diazenyl]aniline
• CAS: 538-41-0
• 化学式: C₁₂H₁₂N₄
• 分子量: 212.254
• InChiKey: KQIKKETXZQDHGE-UHFFFAOYSA-N

物化性质

• 熔点：
  245 °C
• 沸点：
  342.09°C (rough estimate)
• 密度：
  1.2046 (rough estimate)
• 溶解度：
  可溶于DMSO（少许）、乙酸乙酯（少许）
• 稳定性/保质期：

  按要求保存是不会发生分解或者反应的，远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  T
• 安全说明：
  S28A,S45
• 危险类别码：
  R40,R25
• 海关编码：
  2927000090
• RTECS号：
  BW7450000
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN 2811
• 储存条件：
  请将密封保存，并放置在通风、干燥的地方。

SDS

Name:	4 4 -Azodianiline 95% (Titr.) Material Safety Data Sheet
Synonym:	4,4'-Azobisbenzenamine; 4,4'-Diaminoazobenzene
CAS:	538-41-0

Section 1 - Chemical Product MSDS Name:4 4 -Azodianiline 95% (Titr.) Material Safety Data Sheet
Synonym:4,4'-Azobisbenzenamine; 4,4'-Diaminoazobenzene

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
538-41-0	4,4'-Azodianiline	95	208-690-7

Hazard Symbols: T
Risk Phrases: 25 40

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic if swallowed. Limited evidence of a carcinogenic effect.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Methemoglobinemia is characterized by dizziness, drowsiness, headache, shortness of breath, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), rapid heart rate and chocolate-brown colored blood. Overexposure may cause methemoglobinemia.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Methemoglobinemia is characterized by dizziness, drowsiness, headache, shortness of breath, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), rapid heart rate and chocolate-brown blood. Inhalation of aniline causes anoxia due to the formation of methemoglobin.
Chronic:
May cause methemoglobinemia, which is characterized by chocolate-brown colored blood, headache, weakness, dizziness, breath shortness, cyanosis (bluish skin due to deficient oxygenation of blood), rapid heart rate, unconsciousness and possible death.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
For methemoglobinemia, administer oxygen alone or with Methylene Blue depending on the methemoglobin concentration in the blood.
Antidote: Methylene blue, alone or in combination with oxygen is indicated as a treatment in nitrite induced methemoglobinemia.

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 538-41-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: almost white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 245 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: >285 deg C
Solubility in water: slightly soluble in water
Specific Gravity/Density:
Molecular Formula: C12H12N4
Molecular Weight: 212.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, temperatures above 250C, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 538-41-0: BW7450000 LD50/LC50:
Not available.
Carcinogenicity:
4,4'-Azodianiline - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 25 Toxic if swallowed.
R 40 Limited evidence of a carcinogenic effect.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 538-41-0: No information available.
Canada
CAS# 538-41-0 is listed on Canada's NDSL List.
CAS# 538-41-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 538-41-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

类别：有毒物品

毒性分级：高毒

急性毒性：

• 静脉注射 - 小鼠 LD50: 180 毫克/公斤

可燃性危险特性：

• 可燃；燃烧时产生有毒氮氧化物烟雾

储运特性：

• 通风、低温干燥储存
• 应与库房食品原料分开存放

灭火剂：

• 干粉、泡沫、沙土、二氧化碳、雾状水

反应信息

• 作为反应物：
  描述：

  对二氨基偶氮苯 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 以90%的产率得到4,4'-Diazido-azobenzol
  参考文献：
  名称：

  Light-driven nanofiber and nanoring morphological transformations in organogels based on an azobenzene-bridged biscalix[4]arene

  摘要：

  一个以偶氮苯桥联的双卡利克斯[4]芳烃有机凝胶（1）在不同有机溶剂中的形态可以在纳米纤维和纳米环之间以及封闭和开放形态的囊泡之间进行光可逆转换。

  DOI：

  10.1039/c7cc07172h
• 作为产物：
  描述：

  对硝基乙酰苯胺 在 盐酸 、 sodium perborate hexahydrate 、 水 、 硼酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 对二氨基偶氮苯
  参考文献：
  名称：

  从合成二胺和水杨醛轻松，温和，方便地制备和表征一些新型席夫碱配体

  摘要：

  通过在温和的反应条件下将水杨醛与合成的各种伯二胺缩合，可以制备出一些新颖的席夫碱配体。从低成本的可商购材料开始，以高收率合成所用的芳族二胺。在这些反应中，希夫碱产品具有优异的收率和适当的反应时间。这些配体的结构已通过IR，1 H NMR和13 C NMR技术表征。关键词：席夫碱，水杨醛，制备，配体，二胺牛。化学 Soc。埃塞俄比亚。2015，29（1），117-122 DOI：http://dx.doi.org/10.4314/bcse.v29i1.10

  DOI：

  10.4314/bcse.v29i1.10

文献信息

• [EN] ENCAPSULATES<br/>[FR] PRODUITS ENCAPSULÉS
  申请人：PROCTER & GAMBLE

  公开号：WO2013022949A1

  公开（公告）日：2013-02-14

  The present application relates to encapsulates, compositions, products comprising such encapsulates, and processes for making and using such encapsulates. Such encapsulates comprise a core comprising a perfume and a shell that encapsulates said core, such encapsulates may optionally comprise a parametric balancing agent, such shell comprising one or more azobenzene moieties.

  本申请涉及封装体、组合物、包含这种封装体的产品，以及制备和使用这种封装体的方法。这种封装体包括一个包含香水的核心和封装该核心的壳，这种封装体可以选择性地包含一个参数平衡剂，该壳包括一个或多个偶氮苯基团。
• Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities
  作者：C. Karunakaran、R. Venkataramanan

  DOI：10.1007/s11696-018-0599-z

  日期：2019.2

  azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion

  偶氮苯被广泛用于纺织品和皮革的染色，通过调节环中的取代基，可以获得鲜艳的色彩。在这里，我们报道了在温和条件下，使用过硼酸钠（SPB）和催化量的Na 2 MoO 4由市售苯胺以高收率制备大量的偶氮苯。冰醋酸是首选的溶剂，苯胺到偶氮苯的转化率是零，相对于SPB，Na 2 MoO 4来说，是一阶和一阶和苯胺。根据动力学级数，紫外可见光谱和循环伏安图，提出了转化机理。在20–50°C时约50个苯胺的反应速率及其能量和活化熵分别符合等动力学或Exner关系和补偿效应。然而，由迄今为止采用的方法推导的反应速率不能符合哈米特相关性。通过改进的计算获得的分子苯胺的特定反应速率符合哈米特关系。因此，这项工作提出了一种方便，廉价，无害的制备大量偶氮苯的方法，
• Cucurbit[7]uril Complexation Drives Thermal<i>trans</i>-<i>cis</i>-Azobenzene Isomerization and Enables Colorimetric Amine Detection
  作者：Jing Wu、Lyle Isaacs

  DOI：10.1002/chem.200901522

  日期：2009.11.2

  Complexation of yellow diaminoazobenzenes 1 and 3 inside cucurbit[7]uril (CB[7]) results in the formation of purple‐colored CB[7]⋅cis‐1⋅2 H+ and CB[7]⋅cis‐3⋅2 H+ complexes, respectively. The high binding affinity and selectivity displayed by CB[7] toward 1 and 3 pays the >10 kcal mol−1 thermodynamic cost for this isomerization. We investigated the behavior of these complexes as a function of pH and

  黄色diaminoazobenzenes络合1和3内葫芦[7]脲（CB [7]）导致紫色CB [7]的形成⋅顺- 1⋅ 2小时+和CB [7] ⋅顺- 3⋅ 2 H +配合物。CB [7]对1和3表现出的高结合亲和力和选择性为该异构化支付了> 10 kcal mol -1的热力学成本。我们研究了这些复合物的行为作为pH的函数和观察到的大的P ķ一个位移和高pH响应性，其是葫芦的特性[n ] uril分子容器。显着的黄色到紫色的变化被用于构建生物活性胺4 – 10的指示剂位移测定。该指标置换测定是能够量化伪麻黄碱（的5在Sudafed片剂在5-350μ）内容中号范围。
• Photo-control of peptide conformation on a timescale of seconds with a conformationally constrained, blue-absorbing, photo-switchable linker
  作者：Andrew A. Beharry、Oleg Sadovski、G. Andrew Woolley

  DOI：10.1039/b810533b

  日期：——

  Azobenzene derivatives can be used to reversibly photo-regulate conformation and activity when introduced as intramolecular bridges in peptides and proteins. Here we report the design, synthesis, and characterization of an azobenzene derivative that absorbs between 400-450 nm in aqueous solution to produce the cis isomer, and relaxes back to the trans isomer with a half-life of a few seconds at room

  当偶氮苯衍生物作为分子内桥引入到肽和蛋白质中时，可用于可逆地光调节构象和活性。在这里，我们报道了偶氮苯衍生物的设计，合成和表征，该偶氮苯衍生物在水溶液中吸收400-450 nm之间以产生顺式异构体，并在室温下以几秒钟的半衰期松弛回到反式异构体。在反式形式中，接头可以跨越大约25 A的距离，因此它可以桥接间隔为i，i + 15的Cys残基。偶氮苯交联剂从反式转换为顺式导致肽的螺旋含量降低，其中连接子通过间隔在i，i + 15和i，i + 14位的Cys残基连接，Cys的螺旋含量没有变化残基间隔为i，i + 11和Cys残基位于i，i + 7的肽中的螺旋含量增加。在存在10 mM还原型谷胱甘肽的情况下，偶氮苯交联剂在24小时后继续进行光开关。因此，这种交联剂设计扩展了生化系统中对肽和蛋白质结构进行快速光控的可能性。
• Photoswitching a molecular catalyst to regulate CO₂ hydrogenation
  作者：Nilusha Priyadarshani、Bojana Ginovska、J. Timothy Bays、John C. Linehan、Wendy J. Shaw

  DOI：10.1039/c5dt01649e

  日期：——

  the amines of diaminoazobenzene, creating a complex consisting of a rhodium bound to a photo-responsive tetradentate ligand. The photo-induced cis–trans isomerization of the azobenzene-containing complexes imposes structural changes on these complexes, as evidenced by NMR studies. We found that the CO2 hydrogenation activity for the β-Ala bound rhodium complex is 40% faster at 27 °C with the light on

  受自然界利用生理刺激调节催化能力的启发，将偶氮苯掺入Rh（bis）二膦CO 2氢化催化剂中，以光引发结构变化以调节所得的催化活性。铑结合的二膦配体（P（Ph 2）-CH 2 -N（R）-CH 2 -P（Ph 2））包含非天然氨基酸的末端胺，R-基团为β-丙氨酸（β-丙氨酸）或γ-氨基丁酸（GABA）。对于含有β-Ala和GABA的复合物，氨基酸的羧酸都与二氨基偶氮苯的胺偶联，形成由结合到光响应性四齿配体上的铑组成的复合物。光致顺式– NMR研究证明，含偶氮苯的配合物的反式异构化使这些配合物发生结构变化。我们发现，CO 2为β丙氨酸加氢活性结合的铑配合物是在27℃下与所述光40％的速度上，即在偶氮苯顺-conformation（TOF = 16号-1）时相比，该复合物在反式构象中为暗色和偶氮苯（TOF = 11 s -1）。相反，含γ-氨基丁酸的铑配合物与顺式或反式的偶氮苯具有相同的速率（TOF〜17