四甲基四硒富瓦烯 | 55259-49-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硒化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物
• 中文名称: 四甲基四硒富瓦烯
• 中文别名: 四甲基四硒酸富烯
• 英文名称: tetramethyltetraselenafulvalene
• 英文别名: 2-(4,5-dimethyl-1,3-diselenol-2-ylidene)-4,5-dimethyl-1,3-diselenole
• CAS: 55259-49-9
• 化学式: C₁₀H₁₂Se₄
• mdl: MFCD00011507
• 分子量: 448.045
• InChiKey: YMWLPMGFZYFLRP-UHFFFAOYSA-N

物化性质

• 熔点：
  273-275 °C (dec.) (lit.)
• 沸点：
  338.8±42.0 °C(Predicted)
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.38
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  T,N
• 安全说明：
  S20/21,S28,S45
• 危险类别码：
  R23/25,R33
• WGK Germany：
  3
• 海关编码：
  2901299090
• 危险品运输编号：
  UN 3283 6.1/PG 2
• 包装等级：
  II
• 危险类别：
  6.1(a)
• 危险标志：
  GHS06,GHS08,GHS09
• 危险性描述：
  H301 + H331,H373,H410
• 危险性防范说明：
  P261,P273,P301 + P310,P311,P501
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	Tetramethyltetraselenafulvalene Material Safety Data Sheet
Synonym:
CAS:	55259-49-9

Section 1 - Chemical Product MSDS Name:Tetramethyltetraselenafulvalene Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
55259-49-9	Tetramethyltetraselenafulvalene		unlisted

Hazard Symbols: T
Risk Phrases: 23/25 33

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation and if swallowed. Danger of cumulative effects.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
Poison by ingestion.
Inhalation:
Toxic if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under nitrogen.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 55259-49-9: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear a chemical apron.
Respirators:
A NIOSH/MSHA approved air purifying dust or mist respirator or European Standard EN 149.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 265 - 270 deg C (de
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H12Se4
Molecular Weight: 447.924

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, selenium/selenium oxides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 55259-49-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tetramethyltetraselenafulvalene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/25 Toxic by inhalation and if swallowed.
R 33 Danger of cumulative effects.
Safety Phrases:
S 20/21 When using do not eat, drink or smoke.
S 28A After contact with skin, wash immediately with
plenty of water.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 55259-49-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 55259-49-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 55259-49-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：该物质及其盐和电荷转移复合物展现出超导性。关于TMTSF及相关有机金属电子供体的化学特性，可参考《Frontiers in Solid State Science》的相关综述。

反应信息

• 作为反应物：
  描述：

  四甲基四硒富瓦烯 在 tricaprylmethylammonium perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 tetramethyltetraselenafulvalenium-perchlorate
  参考文献：
  名称：

  分离为纳米粒子的四种分子超导体

  摘要：

  (TMTSF)2PF6 和 (TMTSF)2ClO4 Bechgaard 盐、(BEDT-TTF)2I3 和 TTF[Ni(dmit)2]2 [TMTSF = 四甲基四硒富瓦烯；BEDT-TTF = 双（乙二硫）四硫富瓦烯；TTF = 四硫富瓦烯；dmit = 1,3-dithiole-2-thione-4,5-dithiolate] 是最受欢迎的分子超导体之一。它们以纳米粒子的形式生长，表现出与本体一致的特性。颗粒的形状、大小和均匀性取决于稳定剂和合成条件。我们报告了最近研究的条件 (i) 生产 35 nm 的 β-(BEDT-TTF)2I3 纳米粒子，(ii) 将粒径减小到 10-15 nm 的 TTF[Ni(dmit)2]2 (TMTSF)2ClO4 为 3–5 nm，以及 (iii) 将 (TMTSF)2PF6 的生长持续时间从几天延长到一小时。最后，我们报告了 (TMTSF)2ClO4

  DOI：

  10.1002/ejic.201402007
• 作为产物：
  描述：

  4,5-二甲基-2-硒氧代-1,3-二硒醚 在 三甲氧基磷 作用下， 以90%的产率得到四甲基四硒富瓦烯
  参考文献：
  名称：

  High-yield synthesis of tetramethyltetraselenafulvalene (TMTSF) avoiding the use of gaseous hydrogen selenide

  摘要：

  DOI：

  10.1021/jo00151a024

文献信息

• Stable molecular metals based on a novel unsymmetrical diselenadithiafulvalene
  作者：Shuji Aonuma、Yoshinori Okano、Hiroshi Sawa、Reizo Kato、Hayao Kobayashi

  DOI：10.1039/c39920001193

  日期：——

  Novel unsymmetrical π-electron donors have been synthesized and electrical conductivities of their radical cation salts have been studied: among them 4,5-ethylenedithio-4′,5′-(isopropylidenemethylenedithio)diselenadithiafulvalene salts are all metallic down to 4.2 K, and exhibit two-dimensional nature in the anisotropy of the conductivity.

  新型不对称π电子供体已被合成，并研究了其自由基阳离子盐的电导率：其中，4,5-乙烯二硫-4′,5′-(异丙基亚甲基二硫)二硒二硫富瓦烯盐在4.2 K下均呈现金属特性，并在电导率的各向异性中展现出二维特性。
• New fulvalenium salts of bis(dicarbollide) cobalt and iron: Synthesis, crystal structure and electrical conductivity
  作者：Olga N. Kazheva、Grigorii G. Alexandrov、Andrey V. Kravchenko、Vladimir A. Starodub、Igor B. Sivaev、Irina A. Lobanova、Vladimir I. Bregadze、Lev I. Buravov、Oleg A. Dyachenko

  DOI：10.1016/j.jorganchem.2007.07.034

  日期：2007.10

  New radical cation salts (BEDT-TTF)2[3,3′-Co(1,2-C2B9H11)2] (1), (BEDT-TTF)2[8-I-3,3′-Co(1,2-C2B9H10)(1′,2′-C2B9H11)] (2), (BMDT-TTF)[3,3′-Co(1,2-C2B9H11)2] (3) and (TMTSF)2[3,3′-Fe(1,2-C2B9H11)2] (4) were synthesized and their crystal structures and electrical conductivities were determined. Compound 4 is isostructural to the earlier reported Co analogue. All the radical cation salts synthesized are

  新的自由基阳离子盐（BEDT-TTF）2 [3,3'-Co（1,2-C 2 B 9 H 11）2 ]（1），（BEDT-TTF）2 [8- I -3,3' -Co（1,2-C 2 B 9 H 10）（1'，2'-C 2 B 9 H 11）]（2），（BMDT-TTF）[3,3'-Co（1,2- C 2 B 9 H 11）2 ]（3）和（TMTSF）2 [3,3'-Fe（1,2-C 2 B 9 H 11）2合成了（4），并确定了它们的晶体结构和电导率。化合物4与较早报道的Co类似物同构。合成的所有自由基阳离子盐都是半导体。
• Preparation and properties of tetrathiafulvalene (ttf) and tetramethyltetraselenafulvalene salts of tin(IV) halide anions and X-ray crystal structure of [ttf]3[SnCl6]
  作者：Kensuke Kondo、Gen-etsu Matsubayashi、Toshio Tanaka、Hiroshi Yoshioka、Kazumi Nakatsu

  DOI：10.1039/dt9840000379

  日期：——

  [ttf]3[SnX6], [ttf]3[SnMe2Cl4], or [tmtsf][SnMe2Cl3]. Electrical resistivities of these salts as compacted samples fall in the range 1.6 × 101–9.9 × 104Ω cm at 25 °C. The stacking of the ttf and tmtsf moieties is discussed on the basis of electronic reflectance spectra. A single-crystal X-ray analysis of the salt [ttf]3[SnCl6] has revealed a layer structure consisting of ttf trimers. The tetragonal crystal

  四硫富瓦烯（ttf）与MeCN中的SnX 4（X = Cl或Br ）反应生成[ttf] 2 [SnX 6 ]。通过tmtsf与SnCl 4在MeCN中的反应，也可以得到相应的四甲基四硒富勒烯（tmtsf）盐，为乙腈溶剂化物[tmtsf] 2 [SnCl 6 ]· MeCN。另一方面，在SnX 6 2–（X = Cl或Br）或[SnMe 2 Cl 3 ] –在MeCN或CHCl 2 CH 2 Cl存在下对ttf和tmtsf进行电结晶得到[ttf] 3 [SnX 6 ]，[ttf] 3 [SnMe2 Cl 4 ]或[tmtsf] [SnMe 2 Cl 3 ]。这些盐作为压实的样品电阻率落在范围1.6×10 1 -9.9×10 4，在25Ω厘米℃。在电子反射光谱的基础上讨论了ttf和tmtsf部分的堆叠。盐[ttf] 3 [SnCl 6 ]的单晶X射线分析显示了由ttf三聚体组成的层结构。四方晶体，空间群P
• π-Bonded molecular wires: self-assembly of mixed-valence cation-radical stacks within the nanochannels formed by inert tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anions
  作者：Sergiy V. Rosokha、Charlotte L. Stern、Jeremy T. Ritzert

  DOI：10.1039/c3ce41719k

  日期：——

  A series of mixed-valence cation-radical salts D(n+1) TFPBn, where D is a planar organic donor of about 0.7 to 0.9 nm wide and 1.1 to 1.3 nm long (e.g., tetramethyltetraselenafulvalene, octamethylanthracene, octamethylbiphenylene, perylene) and TFPB is a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anion, were crystallized and characterized via single-crystal X-ray analyses and UV–vis-NIR-IR measurements

  一系列混合价阳离子自由基盐D （n +1） TFPB n，其中D是约0.7至0.9 nm宽，1.1至1.3 nm长的平面有机供体（例如，四甲基四硒富勒烯，八甲基蒽，八甲基联苯，per ）和TFPB是四[3,5-双（三氟甲基）苯基]硼酸盐阴离子，进行了结晶化和表征通过单晶X射线分析和UV-vis-NIR-IR测量。所有这些盐都显示了位于由庞大的惰性阴离子形成的纳米通道内的π堆叠的部分氧化的供体的一维阵列（由于平面有机阳离子自由基及其母体分子的自组装而产生）。π堆内基本平行的烃部分以〜3.4–3.6Å的平面间距分布。由于混合价阵列中的分子间相互作用，所有这些盐在NIR至IR范围（8000–1500 cm -1）中均显示出强烈的吸收带）具有低HOMO / LUMO间隙的导电有机材料的特性。量子力学计算提供了介于0.1 eV至0.3 eV之间的相邻物种之间的电子耦合元件。这些值大于用于电子转移的相
• Charge transfer salts obtained with organic donors (TTF, TMTTF, TMTSF, and BEDT-TTF) and tetracyanometallate planar dianions [M(CN)_42–, M = Pt^II, Ni^II]
  作者：Lahcène Ouahab、Jean Padiou、Daniel Grandjean、Chantal Garrigou–Lagrange、Pierre Delhaes、Mustapha Bencharif

  DOI：10.1039/c39890001038

  日期：——

  The electrochemical preparations, X-ray crystal structures, d.c. conductivities and optical absorption of new charge transfer salts of general formula (Dx)2+C2–, where D indicates an organic donor and C a planar tetracyanometallate dianion, are presented.

  介绍了通式（D x）2+ C 2–的新型电荷转移盐的电化学制备，X射线晶体结构，直流电导率和光吸收，其中D表示有机供体，C表示平面四氰基金属阴离子。

表征谱图