1,2-双(5-溴吡啶-2-基)二硫 | 872273-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1,2-双(5-溴吡啶-2-基)二硫
• 英文名称: 1,2-bis(5-bromopyridin-2-yl)disulfane
• 英文别名: bis-(5-bromo-[2]pyridyl)-disulfide；2,2'-bis(5-bromopyridyl)disulfide；5-bromo-2-[(5-bromopyridin-2-yl)disulfanyl]pyridine
• CAS: 872273-36-4
• 化学式: C₁₀H₆Br₂N₂S₂
• 分子量: 378.111
• InChiKey: WURUVZBYROJMDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 储存条件：
  存储条件：2-8°C，密封于干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1,2-Bis(5-bromopyridin-2-yl)disulfane
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: 1,2-Bis(5-bromopyridin-2-yl)disulfane
CAS number: 872273-36-4

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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: C10H6Br2N2S2
Molecular weight: 378.1

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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 bromide, 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：

  1,2-双(5-溴吡啶-2-基)二硫 在 potassium fluoride 、 氯化镍二甲氧基乙烷 、 碘苯二乙酸 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 silver fluoride 、 氯 、 4,4'-二叔丁基-2,2'-二吡啶 、 lithium hydroxide 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 74.0h， 生成
  参考文献：
  名称：

  Ni / Ir催化的S取代硫代乳酸与杂芳基溴化物的光氧化还原脱羧偶联：磺基草醚及其SF5类似物的短合成

  摘要：

  Metallaphotoredox交叉偶联反应最近成为构建C（sp 2）-C（sp 3）烷基链与芳族系统（包括缺乏电子的杂芳基）之间的键，这些键已知是挑战性的偶合伙伴。在本文中，我们公开了易于获得的S取代硫代乳酸与缺电子的杂芳基溴的Ni / Ir催化的光氧化还原脱羧偶联，这导致形成简单但不易获得的带有烷基硫醚侧链的杂芳烃。为了证明该偶联反应的实际应用，我们已经证明了它在一步合成最近销售的杀虫剂Sulfoxaflor的关键中间体的合成中以及SF 5 -Sulfoxaflor的短合成中的有效性。

  DOI：

  10.1002/chem.201701627
• 作为产物：
  描述：

  5-溴-2-氯吡啶 在 硫脲 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 为溶剂， 反应 42.0h， 以28%的产率得到1,2-双(5-溴吡啶-2-基)二硫
  参考文献：
  名称：

  Ni / Ir催化的S取代硫代乳酸与杂芳基溴化物的光氧化还原脱羧偶联：磺基草醚及其SF5类似物的短合成

  摘要：

  Metallaphotoredox交叉偶联反应最近成为构建C（sp 2）-C（sp 3）烷基链与芳族系统（包括缺乏电子的杂芳基）之间的键，这些键已知是挑战性的偶合伙伴。在本文中，我们公开了易于获得的S取代硫代乳酸与缺电子的杂芳基溴的Ni / Ir催化的光氧化还原脱羧偶联，这导致形成简单但不易获得的带有烷基硫醚侧链的杂芳烃。为了证明该偶联反应的实际应用，我们已经证明了它在一步合成最近销售的杀虫剂Sulfoxaflor的关键中间体的合成中以及SF 5 -Sulfoxaflor的短合成中的有效性。

  DOI：

  10.1002/chem.201701627

文献信息

• Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base
  作者：Tanmay Chatterjee、Brindaban C. Ranu

  DOI：10.1039/c3ra41996g

  日期：——

  An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields.

  在没有任何催化剂、共氧化剂、溶剂或碱的情况下，通过球磨中性氧化铝（研磨辅助剂），实现了硫醇到二硫化物的有效有氧化学选择性氧化。多种功能化的二芳基、二杂芳基和二烷基二硫化物以高产率获得。
• Hypervalent Iodine(III)-Promoted Metal-Free S-H Activation: An Approach for the Construction of S-S, S-N, and S-C Bonds
  作者：Eakkaphon Rattanangkool、Watanya Krailat、Tirayut Vilaivan、Preecha Phuwapraisirisan、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1002/ejoc.201402180

  日期：2014.8

  thiols with (diacetoxyiodo)benzene (DIB) has been explored in the preparation of symmetrical disulfides and sulfenamides. Disulfides can be produced in excellent yields (75–95 %) upon treatment of thiols with DIB. The reaction was complete in less than five minutes at room temperature. Aliphatic, aromatic, and heteroaromatic thiols are compatible with this transformation. Moreover, heteroaromatic disulfides

  在对称二硫化物和次磺酰胺的制备中，已经探索了用（二乙酰氧基碘）苯 (DIB) 活化硫醇的硫原子。用 DIB 处理硫醇后，二硫化物可以以极好的收率 (75–95%) 产生。在室温下反应在不到五分钟内完成。脂肪族、芳香族和杂芳香族硫醇与这种转化相容。此外，从杂芳族硫醇获得的杂芳族二硫化物在碱存在下进一步与亲核胺反应，以一锅法以相当到良好的产率（43-90%）提供相应的次磺酰胺。该方法成功地扩展到吲哚作为一种代表性的富电子芳香化合物，从而可以在一锅中成功构建 S-C 键。
• IF₅ affects the final stage of the Cl–F exchange fluorination in the synthesis of pentafluoro-λ⁶-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents
  作者：Benqiang Cui、Mikhail Kosobokov、Kohei Matsuzaki、Etsuko Tokunaga、Norio Shibata

  DOI：10.1039/c7cc02802d

  日期：——

  A difficult chlorine–fluorine (Cl–F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-λ6-sulfanyl-(hetero)arenes having electron-withdrawing substituents has now been elucidated through the use of iodine pentafluoride. A major side-reaction of C–S bond cleavage was sufficiently inhibited by the potential interaction between F and I with a halogen bonding.

  在五氟λ的制备的最后阶段甲难以氯-氟（CL-F）交换氟化反应6具有吸电子取代基-sulfanyl-（杂）芳烃现已通过使用五氟化碘的阐明。F和I与卤素键之间的潜在相互作用充分抑制了CS键断裂的主要副反应。
• Silver-induced self-immolative Cl–F exchange fluorination of arylsulfur chlorotetrafluorides: synthesis of arylsulfur pentafluorides
  作者：Benqiang Cui、Shichong Jia、Etsuko Tokunaga、Norimichi Saito、Norio Shibata

  DOI：10.1039/c7cc07222h

  日期：——

  A novel strategy for the synthesis of arylsulfur pentafluorides by silver carbonate-induced Cl–F exchange fluorination of arylsulfur chlorotetrafluorides is reported. This fluorination does not require any exogenous fluoride sources. Rather, the reaction proceeds via the self-immolation of the substrate Ar-SF4Cl.

  报道了一种通过碳酸银诱导的芳基硫代四氟化氯的Cl-F交换氟化合成芳基五氟化硫的新策略。这种氟化不需要任何外来的氟化物源。而是，反应通过基板Ar-SF 4 Cl的自焚而进行。
• AgBF₄-Mediated Chlorine-Fluorine Exchange Fluorination for the Synthesis of Pentafluorosulfanyl (Hetero)arenes
  作者：Kazuhiro Tanagawa、Zhengyu Zhao、Norimichi Saito、Norio Shibata

  DOI：10.1246/bcsj.20210109

  日期：2021.6.15

  We report a new protocol to form pentafluorosulfanyl (hetero)arenes via chlorine-fluorine exchange of (hetero)aryl tetrafluorosulfanyl chlorides by AgBF4. The method enables access to electron-deficient SF5(hetero)arenes, which are targets that are difficult to synthesize. Two advantages of AgBF4 are its ease of handling and stability. This would be a general transformation protocol.

  我们报告了一个新的协议，通过AgBF 4的（杂）芳基四氟硫烷基氯的氯氟交换，形成五氟硫烷基（杂）芳烃。该方法使得能够接近缺乏电子的SF 5（杂）芳烃，这是难以合成的目标。AgBF 4的两个优点是易于处理和稳定。这将是一个通用的转换协议。