4,4'-二(三氟甲基)-2,2'-二硝基二苯基二硫醚 | 860-39-9

• 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: 4,4'-二(三氟甲基)-2,2'-二硝基二苯基二硫醚
• 中文别名: 4,4'-双(三氟甲基)-2,2'-二硝基二苯基二硫醚
• 英文名称: bis(2-nitro-4-trifluoromethylphenyl) disulfide
• 英文别名: Bis-(2-nitro-4-trifluormethyl-phenyl)-disulfid；Bis-<4-trifluormethyl-2-nitrophenyl>-disulfid；Disulfide, bis[2-nitro-4-(trifluoromethyl)phenyl]；2-nitro-1-[[2-nitro-4-(trifluoromethyl)phenyl]disulfanyl]-4-(trifluoromethyl)benzene
• CAS: 860-39-9
• 化学式: C₁₄H₆F₆N₂O₄S₂
• 分子量: 444.335
• InChiKey: YDCXWQUDQRHVHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  157-160°C
• 沸点：
  426.6±45.0 °C(Predicted)
• 密度：
  1.6554 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

安全信息

• 危险等级：
  TOXIC
• 危险品标志：
  T
• 危险类别码：
  R23/24/25
• 危险品运输编号：
  UN 2811
• 海关编码：
  2930909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Nitro-4-trifluoromethylphenyl disulfide
2-Nitro-1-{[2-nitro-4-(trifluoromethyl)phenyl]disulfanyl}-4-(trifluoromethyl)benzene
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-Nitro-4-trifluoromethylphenyl disulfide
CAS number: 860-39-9

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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: C14H6F6N2O4S2
Molecular weight: 444.3

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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 fluoride, 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

制备方法与用途

类别：有毒物质
毒性分级：高毒
急性毒性：腹腔-小鼠 LD50: 50 毫克/公斤
可燃性危险特性：受热排放有毒氮氧化物、硫氧化物和氟化物蒸汽
储运特性：通风、干燥、防晒
灭火剂：沙土、水、泡沫和二氧化碳

反应信息

• 作为反应物：
  描述：

  4,4'-二(三氟甲基)-2,2'-二硝基二苯基二硫醚 在 盐酸 、 tin 作用下， 生成 2-氨基-4-(三氟甲基)苯硫酚盐酸盐
  参考文献：
  名称：

  Synthesis of 6-trifluoromethyl-4h-1,4-benzothiazines as possible anticancer agents

  摘要：

  DOI：

  10.1016/s0022-1139(00)85084-8
• 作为产物：
  描述：

  4-氯-3-硝基三氟甲苯 在 sodium disulfide 作用下， 生成 4,4'-二(三氟甲基)-2,2'-二硝基二苯基二硫醚
  参考文献：
  名称：

  2-硝基苯基硫代酸酯中的构象偏爱和超分子聚集：二硫化物和硫代磺酸酯。

  摘要：

  在每个不对称取代的二硫化物2-硝基-4'-甲基二苯基二硫化物中，C（13）H（11）NO（2）S（2）（1），2-硝基-4'-氯二苯基二硫化物中，C（12 ）H（8）ClNO（2）S（2）（2），2，4-二硝基-4'-甲基二苯基二硫化物，C（13）H（10）N（2）O（4）S（2）（ 3）和2,4-二硝基苯基-2'-甲氧羰基甲基二硫化物C（9）H（8）N（2）O（6）S（2）（4）以及两个对称取代的二硫化物bis（ 2-硝基苯基）二硫化物C（12）H（8）N（2）O（4）S（2）（5）和双（2-硝基-4-三氟甲基苯基）二硫化物C（14）H（6 ）F（6）N（2）O（4）S（2）（6），2-硝基基团与相邻的芳基环基本共面，并且远离硝化芳基环的S原子也基本与共面基和transoid硝基。在S-（2-硝基苯基）2-硝基苯硫代磺酸盐中，C（12）H（8）N（2）O（6）S（2）（7），在不对称单元

  DOI：

  10.1107/s0108768100007114

文献信息

• Electrophilic additions to alkenes, part V. Substituent effects on the rates of reaction of arylsulphenyl chlorides with cyclohexene
  作者：C. Brown、D. R. Hogg

  DOI：10.1039/j29680001262

  日期：——

  The rates of addition of a series of 4-substituted 2-nitrobenzenesulphenyl chlorides to cyclohexene in acetic acid solution increase with increasing electron-release from the 4-substituent, and a value of –0·715 is obtained for the reaction constant, ρ+, at 25°. The ρ+ correlation is in agreement with the mechanism proposed for this reaction, which postulates an episulphonium ion rather than an open

  一系列4-取代的2-硝基苯磺酰氯在乙酸溶液中向环己烯的添加速率随着从4-取代基释放的电子的增加而增加，反应常数ρ +为–0·715。，在25°。ρ +相关性与针对该反应提出的机理相吻合，该机理假定是上s离子而不是开放碳离子作为阳离子中间体。相对反应速率遵循中间epi磺酸盐离子的预期稳定性顺序。与其他亲电试剂相反，亲电原子上初始正电荷的大小在确定相对反应速率时并不重要。
• Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines
  作者：Masahiro Teramoto、Takumi Mizuno、Mitsutaka Imoto、Motonori Takeda、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1055/a-1430-5100

  日期：2021.7

  sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical

  这项研究旨在开发基于氧化还原环化的绿色和可持续的先进合成方法。元素硫显示出在不存在过渡金属催化剂和溶剂的情况下，通过氧化还原环化作用，可以由2,2'-二硝基二苯基二硫化物和苄基胺促进2-取代的苯并噻唑的高效合成。以良好至优异的产率获得2-取代的苯并噻唑。该合成方法是高度原子经济的，不需要任何外部氧化剂和/或还原剂。
• ORGANIC SULFUR COMPOUNDS: PART I. BENZOTHIAZINE HYDROXAMIC ACIDS AND RELATED COMPOUNDS
  作者：R. T. Coutts、H. W. Peel、Elizabeth M. Smith

  DOI：10.1139/v65-449

  日期：1965.12.1

  2H-1,4-Benzothiazine hydroxamic acids of type V (see Table I) are readily prepared by reducing suitably substituted (o-nitrophenylthio)acetates (II, R″ = Me or Et) by means of sodium borohydride and palladium–charcoal. The ester precursors can be prepared by the interaction of o-nitrothiophenols and α-bromoesters, but such a method is limited in scope. Diethyl bromomalonate, for example, reacts atypically

  V 型 2H-1,4-苯并噻嗪异羟肟酸（见表 I）可通过硼氢化钠和钯-木炭还原适当取代的（邻硝基苯硫基）乙酸盐（II，R″ = Me 或 Et）来制备。酯前体可以通过邻硝基苯硫酚和α-溴酯的相互作用来制备，但这种方法的范围有限。例如，溴丙二酸二乙酯与邻硝基苯硫酚的反应异常。酯前体通过相应酸的 Fischer-Speier 酯化 (II, R" = H) 更好地制备，而这些酸又是 α-巯基酸对合适的邻氯-（或溴-）硝基苯进行亲核攻击的产物. 这种通用的制备方法在两种情况下都失败了。邻氯硝基苯或4-氯-3-硝基甲苯与α-巯基异丁酸反应时，
• Fluorinated tricyclic neuroleptics with prolonged action: 3-Fluoro-8-trifluoromethyl derivatives of 10-(4-methylpiperazino)- and 10-[4-(2-hydroxyethyl)piperazino]-10,11-dihydrodibenzo-[b,f]thiepin
  作者：Karel Šindelář、Miroslav Ryska、Jiří Holubek、Emil Svátek、Jiřina Metyšová、Jiří Protiva、Miroslav Protiva

  DOI：10.1135/cccc19810118

  日期：——

  A reaction of (4-fluoro-2-iodophenyl)acetic acid with 4-(trifluoromethyl)thiophenol gave the acid VIII which was cyclized with the reagent consisting from methanesulphonic acid and phosphorus pentoxide and afforded the methanesulphonic enol ester XIX. The alkaline hydrolysis resulted in 3-fluoro-8-trifluoromethyldibenzo[b,f]thiepin-10(11H)-one (XVI) which was transformed via the alcohol XXIV to the chloro derivative XXV. Substitution reactions with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine resulted in the title compounds IV and V. These products are very potent cataleptic neuroleptic agents with a prolongation of duration of the effects comparable to that of isofloxythepin and tefluthixol. A series of further synthetic experiments aimed at alternative syntheses of the acid VIII and the ketone XVI; their results were mostly not of use for preparative purpose but they led to isolation and characterization of a series of interesting heterocyclic products (XVII, XVIII, XXII, XXIII, XXIX-XXXI, XXXVI-XXXIX).

  (4-氟-2-碘苯基)乙酸与4-(三氟甲基)硫代苯酚反应，生成酸VIII，然后与由甲磺酸和五氧化二磷组成的试剂环化，生成甲磺酸烯基酯XIX。碱性水解产生3-氟-8-三氟甲基二苯并[bf]噻吩-10(11H)-酮(XVI)，通过醇XXIV转化为氯衍生物XXV。与1-甲基哌嗪和1-(2-羟乙基)哌嗪的取代反应产生IV和V。这些产物是非常有效的猫病性镇静剂，其效果持续时间延长，与异氟沙替平和替氟西乐相当。一系列进一步的合成实验旨在寻找酸VIII和酮XVI的替代合成方法；它们的结果大多数并没有用于制备目的，但导致了一系列有趣的杂环产物(XVII、XVIII、XXII、XXIII、XXIX-XXXI、XXXVI-XXXIX)的分离和表征。
• One-Pot Synthesis and Asymmetric Oxidation of 2-Nitro-4-(Trifluoromethyl)Benzene Containing Sulfides
  作者：Konstantin S. Rodygin、Svetlana A. Rubtsova、Alexander V. Kutchin、Pavel A. Slepukhin

  DOI：10.1080/10426507.2010.547893

  日期：2011.9.1

  method for the preparation of 2-nitro-4-(trifluoromethyl)benzene containing sulfides from 1,1′-disulfanediylbis[2-nitro-4-(trifluoromethyl)benzene] is proposed. The corresponding enantiomerically enriched sulfoxides with up to 78% enantiomeric excess are prepared by the asymmetric oxidation of sulfides using a modified Sharpless method. The yield of sulfoxides is shown to decrease with an increase in

  摘要 提出了一种由1,1'-二硫烷二基双[2-硝基-4-(三氟甲基)苯]制备含硫化物2-硝基-4-(三氟甲基)苯的高效一锅法。相应的对映体富集亚砜具有高达 78% 的对映体过量，通过使用改进的 Sharpless 方法对硫化物进行不对称氧化来制备。显示亚砜的产率随着脂肪族基团体积的增加和烃部分对硫原子的诱导作用的降低而降低。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要