3,4-二苯胺基-3-环丁烯-1,2-二酮 | 33512-89-9

• 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: 3,4-二苯胺基-3-环丁烯-1,2-二酮
• 英文名称: 3,4-bis(phenylamino)cyclobut-3-ene-1,2-dione
• 英文别名: 2,4-Dianilino-3-cyclobuten-1,2-dion；N,N'-diphenylsquaramide；1.2-Bis-(N-phenylamid)-cyclobuten-3.4-dion；1.2-Dianilinocyclobuten-3.4-dion；1,2-Bis-anilino-cyclobutendion；Quadratsaeure-dianilid；3,4-Dianilinocyclobut-3-ene-1,2-dione
• CAS: 33512-89-9
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: CIDRCQIUUYZBSG-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C
• 沸点：
  410.7±55.0 °C(Predicted)
• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2924299090

SDS

Name:	3 4-Dianilinocyclobut-3-ene-1 2-dione 97% Material Safety Data Sheet
Synonym:
CAS:	33512-89-9

Section 1 - Chemical Product MSDS Name:3 4-Dianilinocyclobut-3-ene-1 2-dione 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
33512-89-9	3,4-Dianilinocyclobut-3-ene-1,2-dione	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful 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. Wash mouth out with 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.
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.
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:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 33512-89-9: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 270 deg C
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: C16H12N2O2
Molecular Weight: 264

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 33512-89-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Dianilinocyclobut-3-ene-1,2-dione - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 33512-89-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 33512-89-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 33512-89-9 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

反应信息

• 作为反应物：
  描述：

  3,4-二苯胺基-3-环丁烯-1,2-二酮 在 C₁₁H₁₂N₂P₂S₄ 作用下， 以 乙腈 为溶剂， 以66%的产率得到3,4-bis(phenylamino)cyclobut-3-ene-1,2-dithione
  参考文献：
  名称：

  Thiosquaramides: pH switchable anion transporters

  摘要：

  Thiosquaramides在脂质双分子层中显示出受pH控制的阴离子传输特性。

  DOI：

  10.1039/c4sc01629g
• 作为产物：
  描述：

  3-Anilino-4-(N,N'-diphenylureido)-3-cyclobuten-1,2-dion 在 乙醇 、 N,N-二甲基甲酰胺 作用下， 以85%的产率得到3,4-二苯胺基-3-环丁烯-1,2-二酮
  参考文献：
  名称：

  关于方酸与碳二亚胺的反应

  摘要：

  方酸 (5) 和碳二亚胺 2 得到：N-(2-羟基-3,4-二氧代-1-环丁烯基)-N, N'-二烷基脲 6 和 N, N'-二芳基-方酸二酰胺 8，其中 N -异丙基-N'-苯基碳二亚胺(2f)取决于反应条件N-(2-羟基-3,4-二氧-1-环丁烯基)-N'-异丙基-N-苯基脲(17)或3,4-二（3-异丙基-1-苯基脲基）-3-环丁烯-1,2-二酮（19）。

  DOI：

  10.1002/ardp.19853181203

文献信息

• Squaramide-Quaternary Ammonium Salt as an Effective Binary Organocatalytic System for Oxazolidinone Synthesis from Isocyanates and Epoxides
  作者：Ali Rostami、Amirhossein Ebrahimi、John Husband、Muhammad Usman Anwar、Rene Csuk、Ahmed Al-Harrasi

  DOI：10.1002/ejoc.202000153

  日期：2020.3.31

  organocatalyst for the atom‐economic conversion of a plethora of alkyl‐ and aryl‐substituted epoxides and isocyanates into oxazolidinones is described. A mechanism was proposed wherein the nucleophilic ring‐opening operation, and oxo‐ and carbamate‐anions stabilization occur cooperatively towards isocyanate fixation.

  探戈需要两个步骤：方酸-季铵盐是一种有效的二元有机催化剂，用于将大量烷基和芳基取代的环氧化物和异氰酸酯原子经济转化为恶唑烷酮。提出了一种机制，其中亲核开环操作以及氧代和氨基甲酸酯阴离子的稳定作用共同作用于异氰酸酯固定。
• Hydrogen‐Bond Catalysis of Imine Exchange in Dynamic Covalent Systems
  作者：Fredrik Schaufelberger、Karolina Seigel、Olof Ramström

  DOI：10.1002/chem.202001666

  日期：2020.12

  of dynamic covalent chemistry, with applications such as preparation of functional systems, dynamic materials, molecular machines, and covalent organic frameworks. However, acid catalysis is commonly needed for efficient equilibration of imine mixtures. Herein, it is demonstrated that hydrogen bond donors such as thioureas and squaramides can catalyze the equilibration of dynamic imine systems under

  亚胺键的可逆性已在动态共价化学领域得到了广泛的应用，例如功能体系的制备，动态材料，分子机器和共价有机骨架的制备。但是，为了有效平衡亚胺混合物，通常需要酸催化。在本文中，证明了在前所未有的温和条件下，氢键供体如硫脲和方酰胺可催化动态亚胺系统的平衡。催化作用发生在多种溶剂中，并且在许多敏感的添加剂的存在下，对于亚胺的复分解以及胺，肼和羟胺的转氨反应，显示出中等至良好的速率加速。此外，该催化剂易于固定，
• Hydrogen-Bonded Homoleptic Fluoride–Diarylurea Complexes: Structure, Reactivity, and Coordinating Power
  作者：Lukas Pfeifer、Keary M. Engle、George W. Pidgeon、Hazel A. Sparkes、Amber L. Thompson、John M. Brown、Véronique Gouverneur

  DOI：10.1021/jacs.6b07501

  日期：2016.10.12

  hydrogen bonding on the structure and reactivity of complexed fluoride is therefore important for catalysis and numerous other applications, such as anion supramolecular chemistry. Herein we disclose a detailed study examining the structure of 18 novel urea-fluoride complexes in the solid state, by X-ray and neutron diffraction, and in solution phase and explore the reactivity of these complexes as a

  在分析 5'-氟-5'-脱氧腺苷合酶的作用模式时，氢与氟化物的键合是一个关键的相互作用，该酶是唯一能够催化 F-形成 CF 键的酶。因此，进一步了解氢键对络合氟化物的结构和反应性的影响对于催化和许多其他应用（例如阴离子超分子化学）非常重要。在此，我们公开了一项详细的研究，通过 X 射线和中子衍射检查了 18 种新型尿素 - 氟化物复合物在固态下的结构，并在溶液相中探索了这些复合物作为 SN2 化学中的氟化物源的反应性。实验数据表明，结构、协调强度、尿素-氟化物复合物的反应性和反应性可通过修饰尿素受体上的取代基进行调节。尿素上芳基的哈米特分析表明，氟化物结合取决于 σp 和 σm 参数，对于缺电子尿素配体观察到更强的结合。定义的尿素氟化物复合物首次用作氟化物结合试剂，用于模型烷基溴的亲核取代。与已知的醇-氟化物配合物相比，该反应较慢，但 SN2 比 E2 更受青睐，其比例超过了文献中记录的用
• Amino Substituted Bisketenes:  Generation, Structure, and Reactivity
  作者：Nanyan Fu、Annette D. Allen、Shinjiro Kobayashi、Thomas T. Tidwell、Sinisa Vukovic、Selvananthan Arumugam、Vladimir V. Popik、Masaaki Mishima

  DOI：10.1021/jo062090h

  日期：2007.3.1

  factor of 7.5 × 104, and the bis(Me2N) bisketene 14 is the most reactive in ring closure that has been reported. Rate constants for ring closure of these and previously observed bisketenes vary by a factor of 1013. The dialkylamino bisketenes 16 (R = Me, n-Bu) with tethered substituents and restricted geometries are less reactive than the bis(Me2N) bisketene 14 by factors of 1700 and 540, respectively

  迄今为止，通过使用激光闪光光解法使相应的环丁二烯酮开环，已经生成了具有游离的（14）和束缚的（16）氨基取代基的未知的二氨基取代的双烯酮。通过红外或紫外光谱法测量氨基双烯酮回到环丁二烯的开环反应的时间分辨动力学，并给出一阶速率常数，其变化系数为7.5×10 4，而双（Me 2 N）据报道，双烯酮14在闭环中是反应性最强的。这些和先前观察到的双烯酮的闭环速率常数相差10 13倍。二烷基氨基双烯酮16（R = Me，具有束缚的取代基和受限制的几何形状的n- Bu）的反应性比双（Me 2 N）双烯酮14分别低1700和540倍。用DFT方法获得的计算结果表明，拴系的环丁二酮15中的角度应变会抑制双烯酮16的容易环化。
• Squaramides as Potent Transmembrane Anion Transporters
  作者：Nathalie Busschaert、Isabelle L. Kirby、Sarah Young、Simon J. Coles、Peter N. Horton、Mark E. Light、Philip A. Gale

  DOI：10.1002/anie.201200729

  日期：2012.4.27

  Square peg in a round ball: Squaramides are shown to be potent transmembrane anion transporters for both chloride and bicarbonate, performing better than the thiourea and urea analogues. Studies into the nature of this transport point to a mobile carrier mechanism, where the squaramide delivers the anion cargo across the lipid bilayer (see scheme, green sphere=anion). These drug‐like molecules provide

  圆球中的方钉：对于氯化物和碳酸氢盐，方胺被证明是有效的跨膜阴离子转运蛋白，其性能比硫脲和尿素类似物更好。对这种转运性质的研究指向一种移动载体机制，在这种机制中，方酸酰胺将阴离子货物输送通过脂质双层（请参阅方案，绿色球体=阴离子）。这些类药物分子为开发新一代阴离子转运系统提供了平台。