2,6-二氯-1,4-苯二胺 | 609-20-1

• 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: 2,6-二氯-1,4-苯二胺
• 中文别名: 2,6-二氯对苯二胺；2,6-二氯-1,4-亚苯基二胺
• 英文名称: 2,6-dichloro-p-phenylenediamine
• 英文别名: 2,6-dichloro-1,4-phenylenediamine；2,6-dichlorobenzene-1,4-diamine
• CAS: 609-20-1
• 化学式: C₆H₆Cl₂N₂
• mdl: MFCD00025369
• 分子量: 177.033
• InChiKey: HQCHAOKWWKLXQH-UHFFFAOYSA-N

物化性质

• 熔点：
  122-127 °C
• 沸点：
  291.88°C (rough estimate)
• 密度：
  1.4668 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  2,6-dichloro-p-phenylenediamine appears as gray, microcrystalline powder or solid. (NTP, 1992)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

代谢

2,6-二氯-4-硝基苯胺（DCNA）被种植在处理过的土壤中的莴苣和番茄的根部吸收，并转运到叶片，在叶片中它迅速降解为极性代谢物。瞬时代谢物2,6-二氯-p-苯二胺未被检测到。

2,6-DICHLORO-4-NITROANILINE DCNA WAS ABSORBED BY ROOTS OF LETTUCE & TOMATOES GROWN IN TREATED SOIL & WAS TRANSLOCATED TO LEAVES, WHERE IT UNDERWENT RAPID DEGRADATION TO POLAR METABOLITES. TRANSIENT METABOLITES 2,6-DICHLORO-P-PHENYLENEDIAMINE WAS NOT DETECTED.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性的证据有限。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：2,6-二氯对苯二胺

IARC Carcinogenic Agent:2,6-Dichloro-para-phenylenediamine

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第39卷：(1986年)某些用于塑料和橡胶的化学品

IARC Monographs:Volume 39: (1986) Some Chemicals Used in Plastics and Elastomers

来源:International Agency for Research on Cancer (IARC)

毒理性

• 副作用

高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为次要毒性效应。

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

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

安全信息

• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2921519090
• 安全说明：
  S26
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P201,P202,P261,P264,P270,P280,P281,P285,P301+P312+P330,P304+P341,P305+P351+P338,P308+P313,P337+P313,P342+P311,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H302,H319,H334,H351
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,6-Dichloro-1,4-phenylenediamine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2,6-Dichloro-1,4-phenylenediamine
CAS number: 609-20-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H6Cl2N2
Molecular weight: 177.0

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,6-二氯-1,4-苯二胺 生成 1,2,3,5-四氯苯
  参考文献：
  名称：

  The Character of the Diazonium Group.¹ A New Method of Preparing Mixed Disazo Dyestuffs²

  摘要：

  DOI：

  10.1021/ja01338a034
• 作为产物：
  描述：

  1,3-二氯-2,5-二硝基苯 在 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 120.0 ℃ 、5.0 MPa 条件下， 反应 15.0h， 以92%的产率得到2,6-二氯-1,4-苯二胺
  参考文献：
  名称：

  用于硝基芳烃选择性加氢生成苯胺的纳米级 Fe2O3 基催化剂

  摘要：

  更轻的加氢催化剂 酶已经发展到可以使用丰富的金属（如铁、钴和镍）进行氧化还原催化。然而，合成催化通常依赖于这些元素的稀有、较重的亲戚：钌、铑、铱、钯和铂（参见布洛克的观点）。弗里德菲尔德等人。(p. 1076) 使用高通量筛选表明，通过使用为贵金属开发的传统配体，可以激活正确的钴前体以进行不对称氢化催化。左等人。(p. 1080) 专注于铁，展示了一种高效的不对称转移氢化催化剂，它使用经过仔细机理研究后合理设计的配体。贾加迪什等人。(p. 1073) 制备了负载铁催化剂，可选择性地将芳环上的硝基取代基还原为胺，从而促进广泛的苯胺衍生物的制备。氧化铁催化剂在许多其他敏感化学取代基的存在下选择硝基进行还原。[另请参阅 Bullock 的观点] 苯胺（精细化工、农用化学品和制药行业的关键中间体）的生产依赖于贵金属催化剂，该催化剂在其他易于还原的官能团存在的情况下选择性地氢化芳基硝基。在此，我们报告了方便且稳定的氧化铁

  DOI：

  10.1126/science.1242005

文献信息

• Cobalt-based nanoparticles prepared from MOF–carbon templates as efficient hydrogenation catalysts
  作者：Kathiravan Murugesan、Thirusangumurugan Senthamarai、Manzar Sohail、Ahmad S. Alshammari、Marga-Martina Pohl、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1039/c8sc02807a

  日期：——

  resulting nanoparticles create stable and reusable catalysts for selective hydrogenation of functionalized and structurally diverse aromatic, heterocyclic and aliphatic nitriles, and as well as nitro compounds to primary amines (>65 examples). The synthetic and practical utility of this novel non-noble metal-based hydrogenation protocol is demonstrated by upscaling several reactions to multigram-scale

  用于工业相关氢化反应的高效和选择性纳米结构催化剂的开发继续是化学研究的实际目标。尤其是腈和硝基芳烃的氢化对于伯胺的生产非常重要，伯胺构成了高级化学品，生命科学分子和材料的重要原料和关键中间体。在这里，我们报道了石墨烯壳包封的Co 3 O 4的制备-和钴-纳米颗粒通过碳上对苯二甲酸钴对苯二甲酸MOF的模板合成和随后的热解而负载在碳上。所得的纳米颗粒产生稳定且可重复使用的催化剂，用于官能化和结构多样的芳族，杂环和脂肪族腈以及硝基化合物选择性氢化为伯胺（> 65实例）。这种新型的基于非贵金属的氢化方案的合成和实用性通过将数种反应的规模扩大到数克规模并回收催化剂得到了证明。
• Facile protocol for reduction of nitroarenes using magnetically recoverable CoM_0.2Fe_1.8O₄ (M = Co, Ni, Cu and Zn) ferrite nanocatalysts
  作者：Ankita Goyal、Surbhi Kapoor、Pankaj Samuel、Vinod Kumar、Sonal Singhal

  DOI：10.1039/c5ra07190a

  日期：——

  stoichiometric ratio. The catalytic efficiency of the synthesized ferrite samples was explored for the reduction of nitrophenols. Cu substituted cobalt ferrite nanoparticles (CoCu0.2Fe1.8O4) possessed excellent catalytic activity while CoM0.2Fe1.8O4 (M = Co, Ni and Zn) were inactive for the same. The substrate scope of the developed protocol was also evaluated for the reduction of various CH3-, NH2-,

  使用溶胶-凝胶法制备了过渡金属掺杂的钴铁氧体（CoM 0.2 Fe 1.8 O 4（M = Co，Ni，Cu，Zn））纳米粒子。将获得的铁氧体纳米粒子在400°C下进行退火，并使用傅里叶变换红外光谱（FT-IR），X射线衍射（XRD），高分辨率透射电子显微镜（HR-TEM），振动样品磁法（VSM）进行表征能量色散X射线（EDX）和扫描透射电子显微镜（STEM）。在FT-IR光谱中，观察到1000-400 cm -1范围内的两个谱带，对应于四面体和八面体位置的M-O键。XRD图谱证实形成了具有Fd m的立方尖晶石结构空间群。HR-TEM分析显示，所有合成的铁氧体纳米粒子的粒度均为20–30 nm，为准球形。从HR-TEM获得的分别对应于（2 2 0），（3 1 1），（4 0 0）和（5 1 1）晶格的晶格晶面间距为0.29、0.25、0.21和0.16nm。与XRD数据完全一致。EDX-S
• Robust and economic reduction protocol employing immensely stable and leach-proof magnetically separable nanocomposites
  作者：Ankita Goyal、Sonal Singhal

  DOI：10.1039/c6ra17387j

  日期：——

  Metals stabilized over modified magnetic ferrite nanoparticles (M@Dop@CoFe₂O₄) have been established as very stable, magnetically recyclable and leach-proof competent catalysts for the reduction of nitroarenes.

  金属稳定在改性磁性铁氧体纳米颗粒（M@Dop@CoFe2O4）上被证实为非常稳定、可磁回收和不易溶解的高效催化剂，用于还原硝基芳烃。
• Method for the control of cattle grubs employing a phenylene
  申请人：American Cyanamid Company

  公开号：US04137310A1

  公开（公告）日：1979-01-30

  There is provided a method for controlling the larvae of heel flies which parasitize ruminants and other warm-blooded animals by administering to said animals an effective amount of an unsubstituted or substituted phenylene bis[imino(thio)carbonyl]diphosphor(thio)amidic acid ester.

  提供了一种控制寄生在反刍动物和其他温血动物身上的踵蝇幼虫的方法，该方法是向这些动物投与一定量未取代或取代的苯基双[亚硫(硫)羰基]二磷(硫)酰胺酸酯。
• Multinuclear half metallocene catalyst and method for preparing syndiotactic polystyrene using the same
  申请人：LG Chem Ltd.

  公开号：EP1777230A1

  公开（公告）日：2007-04-25

  Diclosed is a multinuclear transition metal half metallocene catalyst having a multinuclear half metallocene structure in which a transition metal of groups 3 to 10 on periodic table is connected to a cycloalkandienyl group or its derivative group on a side and also connected to phenol or phenolamine compound having a plurality of binding sites on another side. The metallocene catalyst is useful to produce syndiotatic styrene polymer having superior steroreguality, high melting point and broad molecular weight distribution with high activity together with a small amount of a cocatalyst. Further disclosed is a method for preparing styrene polymers using the same catalyst.

  披露了一种多核过渡金属半茂金属烯催化剂，其具有多核半茂金属烯结构，其中周期表3至10族的过渡金属连接到一个环戊二烯基团或其衍生物基团一侧，并且连接到另一侧具有多个结合位点的酚或酚胺化合物。这种茂金属烯催化剂可用于生产具有优越的立体构型、高熔点和宽分子量分布的顺反式苯乙烯聚合物，同时还需要少量的共催化剂。还公开了一种使用相同催化剂制备苯乙烯聚合物的方法。

表征谱图