二环戊亚甲基二硫化四烷基秋兰姆 | 94-37-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 二环戊亚甲基二硫化四烷基秋兰姆
• 英文名称: bis(piperidinothiocarbonyl)disulfide
• 英文别名: piperidine-1-carbothioic dithioperoxyanhydride；N,N,N',N'-Bis-pentamethylenthiuramdisulfid；S,S'-bis(piperidinothiocarbonyl) disulfide；bis(piperidine-1-yl-thiocarbonyl)disulfide；bis(piperidin-1-ylthiocarbonyl)disulfide；bis(1-piperidinylthiocarbonyl)disulfide；Dipentamethylenethiuram disulfide；piperidine-1-carbothioylsulfanyl piperidine-1-carbodithioate
• CAS: 94-37-1
• 化学式: C₁₂H₂₀N₂S₄
• 分子量: 320.568
• InChiKey: KNBRWWCHBRQLNY-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  436.6±28.0 °C(Predicted)
• 密度：
  1.3550 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）
• 稳定性/保质期：
  在常温常压下稳定，避免与不相容材料及强氧化剂接触。与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

毒理性

• 副作用

皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24,S26,S37
• 危险类别码：
  R36/37/38,R43
• 海关编码：
  2933399090
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	Dicyclopentamethylenethiuram Disulfide 99+% Material Safety Data Sheet
Synonym:	Bis(piperidinothiocarbonyl) Disulfide
CAS:	94-37-1

Section 1 - Chemical Product MSDS Name:Dicyclopentamethylenethiuram Disulfide 99+% Material Safety Data Sheet
Synonym:Bis(piperidinothiocarbonyl) Disulfide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
94-37-1	Dicyclopentamethylenethiuram Disulfide	>99	202-328-1

Hazard Symbols: XI
Risk Phrases: 36/37/38 43

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin. May cause sensitization by skin contact.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 94-37-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: light beige
Odor: sulfide odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 113.00 - 116.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H20N2S4
Molecular Weight: 320.53

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 94-37-1: JO1585000 LD50/LC50:
CAS# 94-37-1: Oral, mouse: LD50 = 2870 mg/kg.
Carcinogenicity:
Dicyclopentamethylenethiuram Disulfide - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
R 43 May cause sensitization by skin contact.
Safety Phrases:
S 24 Avoid contact with skin.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 94-37-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 94-37-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 94-37-1 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

反应信息

• 作为反应物：
  描述：

  二环戊亚甲基二硫化四烷基秋兰姆 在 sodium hydroxide 、 硫酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-(5-Piperidin-1-yl-1,3,4-thiadiazol-2-yl)aniline
  参考文献：
  名称：

  Thioureidoquinazolin-4(3H)-ones

  摘要：

  3-(N',N'-Dialkylthioureido)quinazolin-4( prepared by the reaction of 3-aminoquinazolin-4(3H)-one with thiuram disulfides undergo the previously unknown acid-induced recyclization to give the corresponding 5-(2-aminophenyl)-2-dialkylamino-1,3,4-thiadiazoles. The structures of the products obtained were confirmed by IR and H-1 and C-13 NMR data. A plausible mechanism of the recyclization is discussed.

  DOI：

  10.1007/bf02496350
• 作为产物：
  描述：

  piperidine-1-carbodithioic acid 在 sodium chlorite 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 二环戊亚甲基二硫化四烷基秋兰姆
  参考文献：
  名称：

  A COMPARATIVE STUDY OF OXIDANTS ON THIOLS

  摘要：

  DOI：

  10.1080/00304949609356543

文献信息

• Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides
  作者：Tian-Tian Li、Xiang-Hai Song、Mei-Shuang Wang、Ning Ma

  DOI：10.1039/c4ra04628e

  日期：——

  Diverse disubstituted and trisubstituted thioureas were synthesized by the condensation of dithiocarbamate TEA (or DABCO) salts and amines using cerium ammonium nitrate (CAN) as a catalyst in high yields at room temperature. It is a one-pot method and it is unnecessary to isolate isothiocyanates. This reaction probably took place through nucleophilic addition of amines to isothiocyanates, which were generated by oxidative coupling of dithiocarbamates and the following decomposition of bis(aminothiocarbonyl)disulfides. When secondary amines and CS2 served as the reactants, bis(aminothiocarbonyl)disulfides were obtained via tandem nucleophilic addition/oxidative coupling reactions in moderate to excellent yields. In all the coupling reactions, the oxidant was air and CAN possibly acted as an SET catalyst.

  多种二取代和三取代硫脲通过二硫代氨基甲酸TEA（或DABCO）盐与胺在室温下使用硝酸铈铵（CAN）作为催化剂进行缩合反应，以高产率合成。这是一种一步法，无需分离异硫氰酸酯。该反应可能涉及胺对异硫氰酸酯的亲核加成，异硫氰酸酯是由二硫代氨基甲酸盐的氧化偶联以及随后双(氨基硫羰基)二硫化物的分解产生的。当使用二级胺和CS2作为反应物时，通过串联的亲核加成/氧化偶联反应，以中等至优异的产率获得了双(氨基硫羰基)二硫化物。在所有偶联反应中，氧化剂为空气，CAN可能作为单电子转移催化剂发挥作用。
• Carbon Tetrabromide Promoted Reaction of Amines with Carbon Disulfide: Facile and Efficient Synthesis of Thioureas and Thiuram Disulfides
  作者：Fushun Liang、Qun Liu、Jing Tan、Chengri Piao

  DOI：10.1055/s-0028-1083199

  日期：2008.11

  A novel carbon tetrabromide promoted one-pot reaction of amines and carbon disulfide under mild conditions has been developed, which provides a straightforward and efficient access to thioureas and thiuram disufides, depending on the nature of the amines employed. The promotion effect is explained as the transient formation of a sulfenyl bromide intermediate from dithiocarbamate and carbon tetrabromide

  已经开发出一种在温和条件下促进胺和二硫化碳的一锅反应的新型四溴化碳，根据所用胺的性质，它可以直接有效地获得硫脲和二硫化秋兰姆。促进作用被解释为在反应过程中由二硫代氨基甲酸酯和四溴化碳瞬时形成亚磺酰溴中间体。
• Role of disulfide linkage in action of bis(dialkylaminethiocarbonyl)disulfides as potent double-Edged microbicidal spermicide: Design, synthesis and biology
  作者：Nand Lal、Santosh Jangir、Veenu Bala、Dhanaraju Mandalapu、Amit Sarswat、Lalit Kumar、Ashish Jain、Lokesh Kumar、Bhavana Kushwaha、Atindra K. Pandey、Shagun Krishna、Tara Rawat、Praveen K. Shukla、Jagdamba P. Maikhuri、Mohammad I. Siddiqi、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.ejmech.2016.03.012

  日期：2016.6

  generally treated by Metronidazole and Fluconazole respectively. Poor vaginal efficacy, drug-resistance and non-spermicidal nature limit their use as topical microbicidal contraceptives. Bis(dialkylaminethiocarbonyl)disulfides (4–38) were designed as dually active, non-surfactant molecules capable of eliminating Trichomonas vaginalis and Candida strains as well as irreversibly immobilizing 100% human sperm

  滴虫病和念珠菌病是最常见的致病性生殖道感染，通常分别用甲硝唑和氟康唑治疗。阴道功效差，耐药性和非杀精性限制了它们作为局部杀微生物避孕药的使用。双（二烷基胺硫代羰基）二硫化物（4 – 38）被设计为具有双重活性的非表面活性剂分子，能够消除阴道毛滴虫和念珠菌菌株，并且能够以不可细胞毒性的剂量立即不可逆地固定100％人类精子，对人类宫颈上皮细胞和体外阴道菌群。化合物12，16，17它们的活性是非氧化酚9，OTC阴道杀精子剂的50倍，并且化合物12和17在兔模型中显示出显着的体内活性。最有前途的化合物17由于具有更高的活性和安全性以及显着的体内滴虫杀菌活性，已显示出有望进一步发展为双刃阴道杀微生物剂。二硫化物基团的作用是由于化学修饰过程中杀精子活性的丧失而确立的（39 – 56）。这些二硫化物可能靶向存在于人精子和滴虫的细胞膜上的巯基，如游离巯基的荧光标记所示。
• Development of an Improved Method for Conversion of Thiuram Disulfides into N,N-Dialkylcarbamoyl Halides and Derivatives
  作者：K. Adeppa、D. C. Rupainwar、Krishna Misra

  DOI：10.1080/00397910903537331

  日期：2010.12.22

  carbamoyl halides is reported. It consists of two steps: (1) reaction of carbon disulfide and a secondary amine in the presence of a polar organic solvent and oxygen to produce the corresponding tetraalkyl thiuram disulfides and (2) reaction of tetraalkyl thiuram disulfide with a halide in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halide.

  报道了一种制备 N,N-二取代氨基甲酰卤的简便方法。它由两个步骤组成：（1）二硫化碳和仲胺在极性有机溶剂和氧气存在下反应生成相应的四烷基秋兰姆二硫化物和（2）四烷基秋兰姆与卤化物在一种非质子有机溶剂，可产生相应的 N,N-二取代氨基甲酰卤。
• Zerovalent titanium–sulfur complexes. Novel dithiocarbamato derivatives of Ti(CO)₆: [Ti(CO)₄(S₂CNR₂)]⁻
  作者：Robert E. Jilek、Giovanna Tripepi、Eugenijus Urnezius、William W. Brennessel、Victor G. Young, Jr.、John E. Ellis

  DOI：10.1039/b700808b

  日期：——

  Oxidation of [Ti(CO)6]2− by thiuram disulfides, (R2NCS2)2, affords the first isolable mononuclear six-coordinate titanium(0) carbonyls, [Ti(CO)4(S2CNR2)]−, which have unusual trigonal prismatic geometries and chemical and spectral properties that are remarkably similar to those of the 18-electron and seven-coordinate anion [Ti(CO)4(η5-C5H5)]−.

  通过硫脲二硫化物（R2NCS2）2对[Ti(CO)6]2-进行氧化反应，得到了首批可分离的单核六配位零价钛羰基化合物[Ti(CO)4(S2CNR2)]-，这些化合物具有不寻常的三角棱柱几何结构，并且其化学和光谱特性与18电子、七配位的阴离子[Ti(CO)4(η5-C5H5)]-极为相似。

表征谱图