3,3'-二氨基联苯胺 | 91-95-2

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,3'-二氨基联苯胺
• 中文别名: 3,3’-二氨基联苯胺；3,3',4,4'-四氨基联苯；3,3',4,4'-联苯四胺；3,3"-二氨基联苯胺；3,3",4,4"-联苯四胺；3,3'-二氨基联苯胺(DAB)；3,3-二氨基联苯二胺
• 英文名称: 3,3',4,4'-tetraaminobiphenyl
• 英文别名: 3,3'-diaminobenzidine；3,3’-diaminobenzidine；DAB；3,3′-diaminobenzidine；4-(3,4-diaminophenyl)benzene-1,2-diamine
• CAS: 91-95-2
• 化学式: C₁₂H₁₄N₄
• mdl: MFCD00007725
• 分子量: 214.27
• InChiKey: HSTOKWSFWGCZMH-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C(lit.)
• 沸点：
  344.41°C (rough estimate)
• 密度：
  1.1726 (rough estimate)
• 闪点：
  12 °C
• 溶解度：
  水中的溶解度0.55克/升
• 物理描述：
  DryPowder
• 自燃温度：
  560 °C
• 稳定性/保质期：
  稳定性较差，易受潮和光照影响。避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  4

ADMET

毒理性

• 暴露途径

该物质可以通过吸入其气溶胶和通过摄入的方式，以危险的数量被人体吸收。

The substance can be absorbed into the body in hazardous amounts by inhalation of its aerosol and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 眼睛症状

Redness.

Redness.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 毒性数据

LCLo（大鼠）= 260 毫克/立方米/4小时

LCLo (rat) = 260 mg/m3/4hr

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37,S36/37/39,S45
• 危险类别码：
  R22,R40,R36/37/38
• WGK Germany：
  1
• 海关编码：
  2921590090
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  DV8750000
• 危险标志：
  GHS07,GHS08
• 危险性描述：
  H302,H319,H341,H350
• 危险性防范说明：
  P201,P280,P301 + P312 + P330,P305 + P351 + P338,P308 + P313,P337 + P313
• 储存条件：
  本品应密封、阴凉处保存，并避免光照。

SDS

Name:	3 3 -Diaminobenzidine 99% Material Safety Data Sheet
Synonym:	3,3',4,4'-Biphenyltetramine; 3,3',4,4'-Tetraaminobiphenyl
CAS:	91-95-2

Section 1 - Chemical Product MSDS Name:3 3 -Diaminobenzidine 99% Material Safety Data Sheet
Synonym:3,3',4,4'-Biphenyltetramine; 3,3',4,4'-Tetraaminobiphenyl

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
91-95-2	3,3'-Diaminobenzidine	99	202-110-6

Hazard Symbols: XN
Risk Phrases: 22 36/37/38 40

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin. Limited evidence of a carcinogenic effect.Light sensitive.Hygroscopic (absorbs moisture from the air).
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes irritation with burning pain, itching, and redness.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood). Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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.
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:
Treat symptomatically and supportively.
Antidote: None reported.

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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 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 or absorb material, then place into a suitable clean, dry, closed 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. Store protected from light.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture. Store protected from light.

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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# 91-95-2: United States OSHA: (Cancer suspect agent - see 29 CFR 1910.1010) (listed under Benzidine).
France - VME: (listed as benzidine): 0.001 ppm VME; 0.008 mg/m3 V Germany: 0.003 ppm TWA; 0.03 mg/m3 TWA (inhalable fraction) Germany: Skin absorber 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:
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: Crystalline powder
Color: brown
Odor: odorless
pH: 7 (1g/l aq. soln.)
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 176.00 - 180.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature: > 400 deg C
Solubility in water: 0.55 g/l (20 c)
Specific Gravity/Density:
Molecular Formula: C12H14N4
Molecular Weight: 214.27

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures. Light sensitive.
Hygroscopic: absorbs moisture or water from the air.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat, exposure to moist air or water.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, ammonia.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 91-95-2: DV8750000 LD50/LC50:
CAS# 91-95-2: Oral, mouse: LD50 = 1834 mg/kg.
Carcinogenicity:
3,3'-Diaminobenzidine - California: carcinogen, initial date 2/27/87 (listed as Benzidine).
NTP: Known carcinogen (listed as Benzidine).
IARC: Group 1 carcinogen (listed as Benzidine).
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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
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# 91-95-2: 2
Canada
CAS# 91-95-2 is listed on Canada's NDSL List.
CAS# 91-95-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 91-95-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

3，3′-二氨基联苯胺在各研究领域中的用途十分广泛。目前主要作为单体用于制备耐高温树脂和纤维材料等。而在分析领域中其应用并不多见，主要用于分光光度法测定硒的含量。

简介

3，3'-二氨基联苯胺是一种具有挥发性的发酵产物，因其具有特殊香气而被广泛应用于食品添加剂中。尽管它有显著的生化和毒理特性，宜人的香气可能让人忽视其对人体健康的潜在危害。该化合物目前主要作为单体用于制备耐高温树脂和纤维材料等，在分析领域中的应用则较少，主要用于分光光度法测定硒的含量。

用途

用作耐高温聚合物的单体。

生产方法

1. 以3，3`-二氯联苯胺为原料：在铜催化剂作用下与氨反应而得。
2. 以联苯胺为原料：
   • 首先与乙酸反应生成联苯二乙酰胺，
   • 再与硝酸反应生成3，3`-二硝基联苯二乙酰胺，
   • 在硫酸水溶液中水解生成3，3`-二硝基联苯胺，
   • 最后用硫化钠还原或催化加氢还原而得。

类别

有毒物品；

毒性分级

中毒；

急性毒性

• 口服-大鼠：LD50: 3000 毫克/公斤
• 口服-小鼠：LD50: 1834 毫克/公斤

可燃性危险特性

可燃；燃烧产生有毒氮氧化物烟雾。

储运特性

库房通风低温干燥。

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：

  3,3'-二氨基联苯胺 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 1H,1'H-5,5'-bibenzotriazole
  参考文献：
  名称：

  水性介质中超声降解二氨基联苯胺

  摘要：

  通过使用500 kHz高频超声（US），在空气气氛下在pH 2下处理3,3'-二氨基联苯胺（DAB）。280 nm处DAB吸收的US效应是在43和141 kHz上构成的，用于检测荧光。当使用100 W的US功率时，DAB吸收带会随着曝光时间而降低。值得注意的是，仅在141和500 kHz下出现了在350 nm – 500 nm处的新吸收宽带。同样，当在370nm激发时，测量处理过的DAB的荧光光谱。美国暴露时间的增加导致在478 nm处出现较宽的发射带，表明在500 kHz的美国暴露下会产生1H，1'H-5,5'-联苯并三唑（BBT）。通过NMR光谱确认该产物为由NH 2形成的三嗪环。DAB中的质子，是由于在美国水介质中以500 kHz的频率形成了亚硝酸根离子。因此，DAB降解而形成BBT。

  DOI：

  10.1016/j.ultsonch.2018.11.007
• 作为产物：
  描述：

  N-(4-(4-乙酰氨基-3-硝基苯基)-2-硝基苯基)乙酰胺 在 镍 硫酸 、 氢气 作用下， 生成 3,3'-二氨基联苯胺
  参考文献：
  名称：

  Symmetric bis-benzimidazoles: new sequence-selective DNA-binding molecules

  摘要：

  我们设计了一系列具有头对头取向的双苯并咪唑化合物，作为序列特异性 DNA 结合剂；寡核苷酸复合物的晶体学分析与 DNase I 标记相结合，证实了双苯并咪唑核心基团的最佳预测位点是 5′-AATT 四碱基对序列；这种序列特异性会抑制 A/T 位点的转录，可能是这些头对头双苯并咪唑具有细胞毒性和抗肿瘤作用的原因。

  DOI：

  10.1039/a901074b
• 作为试剂：
  描述：

  α-苯乙胺 在 agarose 3,3'-二氨基联苯胺 、 ammonia borane 、 Aspergillus niger monoamine oxidase-N mutant 作用下， 生成 D-α-methylbenzylamine
  参考文献：
  名称：

  Deracemization of��-Methylbenzylamine Using an Enzyme Obtained by In Vitro Evolution

  摘要：

  DOI：

  10.1002/1521-3773(20020902)41:17<3177::aid-anie3177>3.0.co;2-p

文献信息

• Materials and Complexes for the Delivery of Biologically-Active Materials to Cells
  申请人：Hart Stephen Lewis

  公开号：US20100184831A1

  公开（公告）日：2010-07-22

  The invention provides a peptide derivative of formula A-B-C wherein A is a polycationic nucleic acid-binding component; B is a spacer element peptide that is susceptible to cleavage within a cell; and C is a cell surface receptor binding component. The invention also provides a lipid derivative of general formula (I): (PEG) q -Linker-Spacer-Cationic headgroup-carbon skeleton-(hydrophobic chain) o wherein: the Linker is a group susceptible to cleavage within a cell; the Spacer is a group linking the Linker to the Cationic headgroup; q denotes the number of PEG chains and q=1, 2 or 3; o denotes the number of hydrophobic chains and o=1, 2 or 3; the carbon skeleton is a group linking the hydrophobic chains to the cationic headgroup. The peptide and lipid derivatives find use in non-viral gene delivery systems.

  该发明提供了一个公式为A-B-C的肽衍生物，其中A是多阳离子核酸结合组分；B是易在细胞内被裂解的间隔元素肽；C是细胞表面受体结合组分。该发明还提供了一个一般公式(I)的脂质衍生物：(PEG)q-连接物-间隔物-阳离子头基-碳骨架-(疏水链)o，其中：连接物是易在细胞内被裂解的基团；间隔物是连接连接物和阳离子头基的基团；q表示PEG链的数量，q=1、2或3；o表示疏水链的数量，o=1、2或3；碳骨架是将疏水链连接到阳离子头基的基团。这些肽和脂质衍生物可用于非病毒基因传递系统。
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2018006063A1

  公开（公告）日：2018-01-04

  Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

  用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。
• Expeditious and Efficient Synthesis of Benzoxazoles, Benzothiazoles, Benzimidazoles Catalyzed by Ga(OTf)3 under Solvent-Free Conditions
  作者：Juyan Liu、Qian Liu、Wei Xu、Weilu Wang

  DOI：10.1002/cjoc.201180310

  日期：2011.8

  new and efficient method for the synthesis of benzoxazoles, benzothiazoles, benzimidazoles from reactions of o‐substituted aminoaromatics with orthoesters in the presence of catalytic amounts of Ga(OTf)3 under solvent‐free conditions is presented. The remarkable features of this new protocol are high conversion, very short reaction times, cleaner reaction profiles under solvent‐free conditions, straight

  提出了在无溶剂条件下，在催化量的Ga（OTf）3存在下，由邻位取代的氨基芳烃与原酸酯反应合成苯并恶唑，苯并噻唑，苯并咪唑的新方法。该新方案的显着特征是高转化率，非常短的反应时间，在无溶剂条件下更干净的反应曲线，直接的程序以及使用相对无毒的催化剂。
• [EN] BI-1H-BENZIMIDAZOLES AS HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010017401A1

  公开（公告）日：2010-02-11

  The present disclosure relates to compounds, compositions and methods for the treatment of Hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及化合物、组合物和治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。
• Effect of multiple H-bonding on the properties of polyimides containing the rigid rod groups
  作者：Xiaoye Ma、Chuanqing Kang、Wenhui Chen、Rizhe Jin、Haiquan Guo、Xuepeng Qiu、Lianxun Gao

  DOI：10.1002/pola.27808

  日期：2016.2.15

  To investigate the influence of hydrogen bonding on the properties of polyimides (PIs) containing rigid rod‐like groups, five symmetrical diamines containing benzimidazole, benzoxazole, and hydroxy group were synthesized, and then a series of PIs were prepared. Results showed that hydroxyl‐containing poly(benzoxazole imide)s possess higher glass transition temperature (Tg) and dimensional stabilities

  为了研究氢键对含有刚性棒状基团的聚酰亚胺（PI）性能的影响，合成了五个对称的含苯并咪唑，苯并恶唑和羟基的二胺，然后制备了一系列PI。结果表明，含羟基的聚（苯并恶唑酰亚胺）比相应的聚（苯并恶唑酰亚胺）具有更高的玻璃化转变温度（T g）和尺寸稳定性。此外，相应的聚苯并咪唑酰亚胺表现出最好的性能，例如最高的T g，最高的char产量和最高的尺寸稳定性。苯并咪唑的氢键作用对PIs性能的影响强于羟基。在400°C热处理后，在交联结构中形成了含羟基的聚苯并恶唑酰亚胺。©2015 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2016，54，570-581

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