2-氯-4-硫代氰酰基苯胺 | 3226-47-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-氯-4-硫代氰酰基苯胺
• 英文名称: 2-chloro-4-thiocyanatoaniline
• 英文别名: 2-Chlor-4-thiocyanato-anilin；(4-amino-3-chlorophenyl) thiocyanate
• CAS: 3226-47-9
• 化学式: C₇H₅ClN₂S
• mdl: MFCD04614735
• 分子量: 184.649
• InChiKey: TZBOJMWJGHBCEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Chloro-4-thiocyanatoaniline
Synonyms: 4-Amino-3-chlorophenylthiocyanate

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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-Chloro-4-thiocyanatoaniline
CAS number: 3226-47-9

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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: C7H5ClN2S
Molecular weight: 184.6

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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, sulfur oxides.

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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-氯-4-硫代氰酰基苯胺 在 盐酸 、 sodium sulfide 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 生成 2-氯-4-巯基苯胺
  参考文献：
  名称：

  发现 ABBV-3373，一种抗 TNF 糖皮质激素受体调节剂免疫学抗体药物偶联物

  摘要：

  使用收敛合成路线以实现多个多样性点，对一系列糖皮质激素受体调节剂（GRM）的效力、选择性和体外药物特性进行了分析。尽管涵盖了大范围的多样性，但对非缀合小分子的分析并不理想，并且使用 MP-Ala-Ala 连接子将它们与小鼠抗肿瘤坏死因子 (TNF) 抗体缀合。对所得抗体药物偶联物 (ADC) 的筛选可以更好地评估功效和物理特性，从而强化了对完整 ADC 进行结构-活性关系研究的必要性。在测量生物标志物的急性小鼠接触超敏反应模型中筛选 DAR4 ADC，以确保足够的治疗窗口。在慢性小鼠关节炎模型中，小鼠抗 TNF GRM ADC 在单剂量 10 mg/kg ip 持续 30 天以上后有效。未缀合的有效负载和小鼠替代抗 TNF ADC 的数据确定了有效负载17，该有效负载 17 与人抗 TNF 抗体缀合，并以 ABBV-3373 的形式进入临床。

  DOI：

  10.1021/acs.jmedchem.2c01579
• 作为产物：
  描述：

  1-(1-propylsulfonic)-3-methylimidazolium thiocyanate 、 邻氯苯胺 在 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以85%的产率得到2-氯-4-硫代氰酰基苯胺
  参考文献：
  名称：

  使用新型布朗斯台德酸性离子液体对芳香族和杂芳香族化合物进行区域硫代氰化反应。

  摘要：

  描述了一种方便的程序，用于制备1-（1-丙磺酸基）-3-甲基咪唑鎓硫氰酸盐作为新型的布朗斯台德酸性离子液体硫氰化剂和高效的多相催化剂。该催化剂用于在温和的H2O2和EtOH：H2O（1：1 v / v）的氧化剂存在下对吲哚，苯胺，吡咯及其衍生物（芳族和杂芳族有机化合物）进行区域选择性硫氰化。这些反应在温和且简单的条件下进行，从而以高产率和短反应时间提供区域选择性产物。

  DOI：

  10.2174/1386207319666160709191851

文献信息

• Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
  作者：Trimbak B. Mete、Tushar M. Khopade、Ramakrishna G. Bhat

  DOI：10.1016/j.tetlet.2016.12.043

  日期：2017.2

  An expedient direct and regioselective thiocyanation of phenols, anilines and heterocycles is described. Transformation is realized via the direct CH functionalization under transition metal free conditions at ambient temperature in excellent yields. Method proved to be monoselective and variety of functional groups tolerated the reaction conditions. The practicality of the protocol is demonstrated

  描述了酚，苯胺和杂环的方便的直接和区域选择性的硫氰化。通过在无过渡金属条件下于环境温度下直接C H官能化以优异的收率实现转化。方法被证明是单选择性的，并且各种官能团都能耐受反应条件。该协议的实用性在PPARδ激动剂前体的克级合成中得到了很好的证明。
• A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions
  作者：Xing Zhang、Chenguang Wang、Hong Jiang、Linhao Sun

  DOI：10.1039/c8ra04407d

  日期：——

  A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell without the use of any catalyst or oxidant.

  已开发出一种针对富电子芳烃的低成本高效的硫氰化和硒氰化策略，在不使用任何催化剂或氧化剂的情况下，在不分隔电池中的恒定电流电解条件下进行。
• Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics
  作者：Huanfeng Jiang、Wentao Yu、Xiaodong Tang、Jianxiao Li、Wanqing Wu

  DOI：10.1021/acs.joc.7b01122

  日期：2017.9.15

  A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O2 as the oxidant. The combination of Cu(OTf)2, N,N,N′,N′-tetramethylethylenediamine (TMEDA) and BF3·Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group

  以O 2为氧化剂，开发了铜与KSCN之间的铜催化需氧氧化反应。Cu（OTf）2，N，N，N '，N'-四甲基乙二胺（TMEDA）和BF 3 ·Et 2 O的组合提供了有效的催化体系，以优异的收率提供了取代的硫氰化产物和2-氨基苯并噻唑。对于强吸电子基团和给电子基团，该反应还具有良好的官能团耐受性。
• Visible light thiocyanation of <i>N</i>-bearing aromatic and heteroaromatic compounds using Ag/TiO₂ nanotube photocatalyst
  作者：Mona Hosseini-Sarvari、Zeinab Hosseinpour、Mehdi Koohgard

  DOI：10.1039/c8nj03128b

  日期：——

  nanotubes (Ag/TNT) were synthesized via simple hydrothermal process, and this photocatalyst was successfully exploited in thiocyanation reactions at room temperature under visible light irradiation. Four classes of important heterocyclic compounds including indole, aniline, pyrrole and 2-amino thiazole derivatives via Ag/TNT treated with ammonium thiocyanate formed the corresponding thiocyano compounds

  本研究通过简单的水热法合成了Ag / TiO 2纳米管（Ag / TNT），并在室温下可见光照射下成功地将该光催化剂用于硫氰化反应。四类重要的杂环化合物，包括吲哚，苯胺，吡咯和2-氨基噻唑衍生物通过用硫氰酸铵处理的Ag / TNT以中等至极好的收率形成了相应的硫氰基化合物。Ag纳米颗粒（主要沉积在TNT的表面）对包含硫原子的吸收物种的等离子特性和催化性能是反应进行的关键因素。首次报道的这种有效，简单和通用的方案在可见光下提供了苯胺，吡咯和2-氨基噻唑衍生物的硫氰化反应。通过应用空气分子氧作为低成本和环境友好的末端氧化剂，反应通过自由基途径进行。
• DDQ-promoted thiocyanation of aromatic and heteroaromatic compounds
  作者：Hamid R Memarian、Iraj Mohammadpoor-Baltork、Kobra Nikoofar

  DOI：10.1139/v07-092

  日期：2007.11.1

  Thiocyanation of various aromatic and heteroaromatic compounds has been achieved using ammonium thiocyanate in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in methanol solution at room temperature and under reflux condition. The rate of reaction is influenced by the electron-donor ability of the aromatic nucleus.Key words: amines, DDQ, indoles, thiocyanation.

  在室温和回流条件下，在 2,3-二氯-5,6-二氰基苯醌（DDQ）存在的甲醇溶液中，使用硫氰酸铵实现了各种芳香族和杂芳香族化合物的硫氰化反应。反应速率受芳香核电子供体能力的影响。

表征谱图