4,5-双(2-氰乙基硫代)-1,3-二硫醇-2-硫酮 | 132765-35-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 4,5-双(2-氰乙基硫代)-1,3-二硫醇-2-硫酮
• 英文名称: 4,5-bis((2-cyanoethyl)thio)-1,3-dithiole-2-thione
• 英文别名: 4,5-bis(2-cyanoethylthio)-1,3-dithiol-2-thione；4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiole-2-thione；4,5-Bis(2-cyanoethylthio)-1,3-dithiole-2-thione；3-[[5-(2-cyanoethylsulfanyl)-2-sulfanylidene-1,3-dithiol-4-yl]sulfanyl]propanenitrile
• CAS: 132765-35-6
• 化学式: C₉H₈N₂S₅
• mdl: MFCD01096160
• 分子量: 304.506
• InChiKey: DRMGXZWMQXEMKB-UHFFFAOYSA-N

物化性质

• 熔点：
  81.0 to 85.0 °C
• 沸点：
  512.8±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险等级：
  6.1
• 海关编码：
  2930909090
• 危险品运输编号：
  UN 2811
• 储存条件：
  | 室温 干燥 |

SDS

4,5-Bis(2-cyanoethylthio)-1,3-dithiole-2-thione Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: 4,5-Bis(2-cyanoethylthio)-1,3-dithiole-2-thione

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Category 3
Acute toxicity (Oral)
Acute toxicity (Dermal) Category 3
Category 3
Acute toxicity (Inhalation)
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements
Pictograms or hazard symbols
Signal word Danger
Hazard statement Toxic by inhalation, in contact with skin and if swallowed
Causes skin irritation
Causes serious eye irritation
Precautionary statements
[Prevention] Avoid breathing.
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
[Response]
breathing. Call a POISON CENTER or doctor/physician.
IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Rinse
mouth.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Remove/Take off immediately all contaminated clothing.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.

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Section 2. HAZARDS IDENTIFICATION
[Storage] Store in a well-ventilated place. Keep container tightly closed.
Store locked up.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): 4,5-Bis(2-cyanoethylthio)-1,3-dithiole-2-thione
>98.0%(LC)
Percent:
CAS Number: 132765-35-6
Chemical Formula: C9H8N2S5

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Call a POISON CENTER or doctor/physician.
Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
Skin contact:
soap and water. Call a POISON CENTER or doctor/physician.
Rinse cautiously with water for several minutes. Remove contact lenses, if present
Eye contact:
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Immediately call a POISON CENTER or doctor/physician. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep
protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should
emergency procedures: be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a closed system if possible. Use a local exhaust if dust or aerosol will be
generated.
Avoid contact with skin, eyes and clothing.
Advice on safe handling:
Storage
Keep container tightly closed. Store in a cool, dark and well-ventilated place.
Storage conditions:
Store locked up.

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Section 7. HANDLING AND STORAGE
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Hand protection: Impervious gloves.
Eye protection: Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Solid
Physical state (20°C):
Form: crystal - powder
Color: Reddish yellow - Deep yellow red
Odor: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
Upper: No data available
Density: No data available
Solubility: Soluble in : Acetonitrile

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Stability:
Reactivity: No special reactivity has been reported.
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulphur oxides
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobillity in soil
log Pow: No data available

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Section 12. ECOLOGICAL INFORMATION
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
6.1: Toxic substance.
Hazards Class:
UN-No: 2811
Proper shipping name: Toxic solid, organic, n.o.s.
Packing group: III

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4,5-双(2-氰乙基硫代)-1,3-二硫醇-2-硫酮 在 cesium hydroxide 、 亚磷酸三乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 Diethyl 2-[6-[[2-[4,5-bis[(8-ethoxy-7-ethoxycarbonyl-8-oxooctyl)sulfanyl]-1,3-dithiol-2-ylidene]-5-(8-ethoxy-7-ethoxycarbonyl-8-oxooctyl)sulfanyl-1,3-dithiol-4-yl]sulfanyl]hexyl]propanedioate
  参考文献：
  名称：

  Arborol 功能化四硫富瓦烯衍生物：合成和薄膜形成

  摘要：

  报道了一系列新型四硫富瓦烯衍生物的合成，这些四硫富瓦烯衍生物的四个侧链终止于亲水性酰胺醇 (arborol) 基团，例如四硫富瓦烯衍生物 15。这些 arborol 衍生物中的一些通过从甲醇溶液旋涂到固体上形成薄膜支持如玻璃、ITO 涂层玻璃和黄金。随着分子外围醇取代基数量的增加，薄膜的质量显着提高。光吸收光谱表明这些薄膜的氧化掺杂可以通过化学和电化学方式实现。观察紫外/可见吸收光谱中的低能带（λmax = 820 nm 拖尾至约 1300 nm) 和这些掺杂薄膜中中等水平的电导率 (σrt ≈ 10−4 S cm−1) 强烈表明存在显着程度的超分子有序，TTF 核呈 π-π 堆叠。据我们所知，这是第一次在具有电活性核心单元的分子 arborol 系统中实现半导体行为。这项工作为使用 TTF-arborols 的旋涂膜作为光电器件中的半导体电荷传输层提供了前景。(© Wiley-VCH Verlag

  DOI：

  10.1002/ejoc.200300286
• 作为产物：
  描述：

  bis(tetraetylammonium) bis(thioxo-1,3-dithiole-4,5-dithiolato)zincate(II) 生成 4,5-双(2-氰乙基硫代)-1,3-二硫醇-2-硫酮
  参考文献：
  名称：

  两种新的不对称四硫富瓦烯衍生物的合成，结构和电化学性能

  摘要：

  两个新的不对称四硫富富瓦烯（TTF）衍生物2,3-双（氰基乙硫基）-6,7-（甲基-乙二硫基）四硫富瓦烯（6a）和2,3-双（氰基乙硫基）-6,7-（环戊二硫基）四硫富富瓦烯（已经通过NMR，MS，IR和元素分析制备并表征了图6b）。分子结构已经通过X射线晶体学确定。通过在二氯甲烷溶液中的循环伏安法研究了它们的氧化还原特性，每种化合物显示出两个可逆的单电子氧化还原对。

  DOI：

  10.1002/jhet.5570420515

文献信息

• Structures of sulfur-rich dithiolate-gold(I) complexes and their oxidation
  作者：Tatsuya Ryowa、Motohiro Nakano、Hatsue Tamura、Gen-etsu Matsubayashi

  DOI：10.1016/j.ica.2004.03.048

  日期：2004.9

  [NMe 4 ][Au(PEt 3 )(C 3 S 5 )], [NMe 4 ][Au(PPh 3 )(C 3 S 5 )], [NMe 4 ][Au(PEt 3 )(C 8 H 4 S 8 )], [N-methylpyridinium][Au(PPh 3 )(C 8 H 4 S 8 )] [(PEt 3 )Au-C 3 S 5 -Au(PEt 3 )], and [(PEt 3 )Au-C 8 H 4 S 8 -Au(PEt 3 i)] [C 3 S 2 - 5 =4,5-disulfanyl-1,3-dithiole-2-thionate(2-); C 8 H 4 S 2 - 8 =2-(4,5-ethylenedithio)-1,3-dithiole-2-ylidene}-1,3-dithiole-4,5-dithionate(2-)] were prepared. They exhibited

  [NMe 4] [Au（PEt 3）（C 3 S 5）]，[NMe 4] [Au（PPh 3）（C 3 S 5）]，[NMe 4] [Au（PEt 3）（C 8 H 4 S 8）]，[N-甲基吡啶] [Au（PPh 3）（C 8 H 4 S 8）] [（PEt 3）Au-C 3 S 5 -Au（PEt 3）]和[（PEt 3 ）Au-C 8 H 4 S 8 -Au（PEt 3 i）] [C 3 S 2-5 = 4,5-二硫烷基-1,3-二硫代-2-硫代酸酯（2-）; 制备C 8 H 4 S 2-8 ＝ 2-（4，5-亚乙基二硫代）-1，3-二硫代-2-亚基} -1，3-二硫代-4，5-二硫代（2-）]。由于在二氯甲烷中在-0.30至+0.21 V（vs. Ag / Ag +）处以二硫醇盐配体为中心的氧化作用，因此它们显示出了第一氧化电位。它们与碘或7,7,8,8-四氰基-对-喹二甲烷（T
• Dithiolene dimetallic molybdenum(v) complexes displaying intraligand charge transfer (ILCT) emission
  作者：David Recatalá、Artem L. Gushchin、Rosa Llusar、F. Galindo、Konstantin A. Brylev、Maxim R. Ryzhikov、Noboru Kitamura

  DOI：10.1039/c3dt51102b

  日期：——

  terminal oxygen atom and the two sulfur atoms of the bifunctional dithiolene ligand. This arrangement leaves two nitrogen atoms on each side which coordinate to two Re atoms in the 22− tetrametallic complex. Compound 3 has a distorted tetrahedral structure defined by two carbon atoms of the methyl groups and two sulfur atoms of the dithiolene ligand. The luminescence properties of all three complexes in

  双功能 二硫代烯配体已配位到沫V（O）（μ-S 2）的Mo V（O）单元，得到[沫2 ö 2（μ-S）2（BPyDTS 2）2 ] 2 2 - （1 2-） （BPyDTS 2（2-双-（2-吡啶基）亚甲基-1,3-二硫代烯）阴离子。的反应1 2-钼二聚体pentacarbonylchlorothenium（我），得到一个复合tetrametallic式[沫2 ö 2（μ-S）2（BPyDTS 2）2 的Re（CO）3氯} 2 ] 2-（2 2 −）。还已经制备了单体（CH 3）2 Sn（BPyDTS 2）（3）锡络合物用于比较目的。在（Et 4 N）2 [ 1]，两个金属原子处于由两个桥连的硫原子，一个末端氧原子和两个双官能团的两个硫原子限定的方形金字塔配位环境中 二硫代烯配体。这种排列在每侧留下两个氮原子，这些氮原子与2 2-四金属配合物中的两个Re原子配位。化合物3具有扭曲的四面体
• TTFs nonsymmetrically fused with alkylthiophenic moieties
  作者：Rafaela A L Silva、Bruno J C Vieira、Marta M Andrade、Isabel C Santos、Sandra Rabaça、Dulce Belo、Manuel Almeida

  DOI：10.3762/bjoc.11.71

  日期：——

  Two new dithiolene ligand precursors, containing fused TTF and alkyl thiophenic moieties 3,3'-[2-(5-(tert-butyl)thieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-tbtdt, 1), and 3,3'-[2-(5-methylthieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-mtdt, 2), were synthesized and characterized. The electrochemical properties of these electronic donors were studied by cyclic voltammetry (CV) in dichloromethane. Both compounds show two quasi-reversible oxidation processes, versus Ag/AgCl, typical of TTF donors at E¹_1/2 = 279 V and E²_1/2 = 680 V for 1 and E¹_1/2 = 304 V and E²_1/2 = 716 V in the case of 2. The single-crystal X-ray structure of 1 and of a charge transfer salt of 2, (α-mtdt)[Au(mnt)₂] (3), are reported.

  两种新的二硫烯配体前体，含有融合的TTF和烷基噻吩基团3,3'-[2-(5-(叔丁基)噻吩[2,3-d][1,3]二硫烯-2-基亚甲基)-1,3-二硫杂环戊二烯-4,5-二基]双[硫代二基]}二丙腈(α-tbtdt，1)，和3,3'-[2-(5-甲基噻吩[2,3-d][1,3]二硫烯-2-基亚甲基)-1,3-二硫杂环戊二烯-4,5-二基]双[硫代二基]}二丙腈(α-mtdt，2)，已合成并表征。通过二氯甲烷中的循环伏安法（CV）研究了这些电子给体的电化学性质。两种化合物均显示出两个准可逆氧化过程，相对于Ag/AgCl，在E¹_1/2 = 279 V和E²_1/2 = 680 V的情况下，1的典型TTF给体，以及在2的情况下，E¹_1/2 = 304 V和E²_1/2 = 716 V。报道了1的单晶X射线结构和2的电荷转移盐(α-mtdt)[Au(mnt)₂] (3)。
• Thiolated π-Extended Tetrathiafulvalenes:  Versatile Multifunctional π-Systems
  作者：Christian A. Christensen、Andrei S. Batsanov、Martin R. Bryce

  DOI：10.1021/jo062199p

  日期：2007.2.1

  Derivatives of 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (ex-TTF) have been synthesized by a new synthetic methodology, viz., direct phosphite-mediated cross-couplings of anthraquinone with 1,3-dithiole-2-thione derivatives. These ex-TTFs bear one, two, or four cyanoethyl-protected thiol groups on the dithiole rings. Deprotection (NaOMe, MeOH, DMF, 20 °C) and trapping of the transient

  通过一种新的合成方法，即直接亚磷酸酯介导的蒽醌交叉偶联，合成了9,10-双（1,3-二硫醇-2-亚基）-9,10-二氢蒽（ex-TTF）的衍生物1,3-二硫代-2-硫酮衍生物。这些ex-TTF在二硫环上带有一个，两个或四个氰乙基保护的硫醇基。脱保护（NaOMe，MeOH，DMF，20°C）并用亲电试剂捕获瞬态硫醇盐，得到了新的前TTF三聚体19，二聚环烷22和25，四（羟乙硫基）衍生物23和应变环烷24。已经通过循环伏安法研究了溶液的氧化还原特性。对于化合物19，22，以及每个25个ex-TTF单元表现为一个独立的2电子氧化还原系统，分别产生单个，准可逆的6、4和4电子波。由于24中的短桥阻碍了伴随氧化的构象变化，因此24（0→2+波）的E ox值与其前驱体15的E ox值正移了290 mV 。23 ·2.5MeOH，23 ·1.5MeCN，24 ·CH 2 Cl 2和24 ·1.5CH 2
• New Multi(tetrathiafulvalene) Dendrimers
  作者：Christian A. Christensen、Martin R. Bryce、Jan Becher

  DOI：10.1055/s-2000-8203

  日期：——

  The convergent synthesis of multi(TTF) dendrimers with glycol chains as the branches is reported. Key methodology in the iterative steps involves nucleophilic displacement of reactive halides by transient TTF-thiolate anions. Core units in the dendrimers are 1,3,5-trisubstituted benzene, TTF and hexa-substituted benzene, providing three-, four- and six-directional cores, respectively. Cyclic voltammetry (CV) and thin layer CV studies establish that the TTF redox chemistry is retained in the dendrimer structures, with clean sequential formation of multi(cation radical) and multi(dication) species upon electrochemical oxidation.

  报告了以乙二醇链为分支的多(TTF)树枝状大分子的聚合合成方法。迭代步骤中的关键方法涉及利用瞬态TTF-硫醇盐阴离子对活性卤化物进行亲核取代。树枝状大分子的核心单元分别为1,3,5-三取代苯、TTF和六取代苯，提供了三向、四向和六向的核心结构。循环伏安法(CV)和薄层CV研究表明，树枝状大分子结构中保留了TTF的氧化还原化学，通过电化学氧化可以清晰地依次形成多(阳离子自由基)和多(二阳离子)物种。