3a,6a-二苯基甘脲 | 5157-15-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 3a,6a-二苯基甘脲
• 中文别名: 二苯基甘脲；3A,6A-二苯基八氢咪唑并[4,5-D]咪唑-2,5-二酮；3a,6a-二苯基八氢咪唑并[4,5-d]咪唑-2,5-二酮
• 英文名称: 3a,6a-diphenylglycoluril
• 英文别名: 1,5-diphenyl-2,4,6,8-tetraazabicyclo[3.3.0]octan-3,7-dione；3a,6a-diphenylperhydroimidazo[4,5-d]imidazole-2,5-dione；3α,6α-diphenylglycoluril；diphenylglycoluril；3a,6a-diphenyl-tetrahydro-imidazo[4,5-d]imidazole-2,5-dione；3a,6a-Diphenyl-tetrahydro-imidazo[4,5-d]imidazol-2,5-dion；GLYCOLURIL, 3a,6a-DIPHENYL-；3a,6a-diphenyl-1,3,4,6-tetrahydroimidazo[4,5-d]imidazole-2,5-dione
• CAS: 5157-15-3
• 化学式: C₁₆H₁₄N₄O₂
• 分子量: 294.313
• InChiKey: WUDVGTHXCLJVJN-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C
• 沸点：
  677.1±55.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微加热）、乙醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Glycoluril, 3a,6a-diphenyl-
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 5157-15-3
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Formula : C16H14N4O2
Molecular weight : 294,31 g/mol
CAS-No. : 5157-15-3
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
No data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx)
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
No special environmental precautions required.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
No special environmental precautions required.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation rate No data available
i) Flammability (solid, gas) No data available
j) Upper/lower No data available
flammability or
explosive limits
k) Vapour pressure No data available
l) Vapour density No data available
m) Relative density No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition No data available
temperature
q) Decomposition No data available
temperature
r) Viscosity No data available
s) Explosive properties No data available
t) Oxidizing properties No data available
Other safety information
No data available

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SECTION 10: Stability and reactivity
Reactivity
No data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - No data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
No data available
Skin corrosion/irritation
No data available
Serious eye damage/eye irritation
No data available
Respiratory or skin sensitisation
No data available
Germ cell mutagenicity
No data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
No data available
Specific target organ toxicity - single exposure
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
No data available
Persistence and degradability
No data available
Bioaccumulative potential
No data available
Mobility in soil
No data available
Results of PBT and vPvB assessment
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
No data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  3a,6a-二苯基甘脲 在 sodium hydroxide 、 对甲苯磺酸 作用下， 生成 5,7,12,13b,13c,14-hexahydro-1,4,8,11-tetrahydroxy-13b,13c-diphenyl-6H,13H-5a,6a,12a,13a-tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13-dione
  参考文献：
  名称：

  用于合成有机主体的新型凹面积木

  摘要：

  自然宿主通常包含一个空腔或裂缝，其内凹表面与客体的凸表面相匹配2最近，已经设计了模仿此特征的合成宿主（cavitand ~ ~ ~ ）。）^^ 如果新的和更复杂的主客体系统是要开发，必须有通用且易于访问的构建块。在这里，我们描述了满足这些要求的新型构建块 2。化合物 2 包含两个稠合的 2-咪唑烷酮环，其两侧是两个邻二甲苯单元。其整体形状为凹面，其凸面被两个苯基取代基屏蔽。证明了 2 在三个新空腔酸的合成中的应用。二苯基甘脲 (la) 5a 在 Me 2 SO 0 中用多聚甲醛和 NaOH 处理，得到四 (羟基甲基) 衍生物 1b (85%)。5b 在苯中用 4 当量对甲苯磺酸回流 1b 得到 2a，产率为 35%。类似地，用过量的氢醌或1,4-二甲氧基苯在1,2-二氯乙烷中处理1b，分别得到2b（75%）和2c（50%）。分子模型表明 2 的邻二甲苯单元可以具有向上 (u) 或向下 (d)

  DOI：

  10.1021/ja00237a064
• 作为产物：
  描述：

  3a,7a-diphenyltetrahydroimidazo<4,5-d>imidazole-2,5-dithione 在 tetrabromoglycoluril 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以90%的产率得到3a,6a-二苯基甘脲
  参考文献：
  名称：

  Oxidation of Thioamides to Amides with Tetrachloro- and Tetrabromoglycolurils

  摘要：

  Tetrabromo- and tetrachloroglycolurils have been shown to act as good oxidants capable of converting thioamides to the corresponding amides. This approach offers such advantages as good yields (81-99%), short reaction times (10-25 min), simple workup procedure, and environmental safety.

  DOI：

  10.1134/s1070428019120108
• 作为试剂：
  描述：

  二碳酸二叔丁酯 、 对氨基苯甲酸 在 3a,6a-二苯基甘脲 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到N-BOC-4-氨基苯甲酸
  参考文献：
  名称：

  使用二苯基甘氨酰脲作为有机催化剂的脂肪族/芳香族/杂环胺的高效化学选择性N-叔丁氧基羰基化

  摘要：

  已经描述了使用二苯基甘脲作为有机催化剂进行多种胺的化学选择性N-叔丁氧基羰基化的有效方法。第一次，使用核磁共振研究支持的密度泛函理论（DFT）计算，提出了一种可能的N-叔丁氧羰基化机理。在不形成副产物如脲，恶唑烷酮，异氰酸酯和N，N-二-Boc衍生物的情况下，形成了有机催化剂的可重复使用性和观察到所需的N-Boc保护的胺，这使本方案成为人们所希望的。

  DOI：

  10.1016/j.tet.2020.131223

文献信息

• [EN] PROCESS FOR THE PREPARATION OF IODIDES<br/>[FR] PROCÉDÉ DE PRÉPARATION D'IODURES
  申请人：TECHNION R & D FOUNDATION LTD

  公开号：WO2011154953A1

  公开（公告）日：2011-12-15

  This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.

  这项发明涉及利用N-碘酰胺从相应的羧酸制备高产量的烷基或芳基碘化物的过程。
• Rapid and scalable synthesis of chiral porphyrin cage compounds
  作者：Pieter J. Gilissen、Anne Swartjes、Bram Spierenburg、Jeroen P.J. Bruekers、Paul Tinnemans、Paul B. White、Floris P.J.T. Rutjes、Roeland J.M. Nolte、Johannes A.A.W. Elemans

  DOI：10.1016/j.tet.2019.07.009

  日期：2019.8

  An improved and scalable synthetic route to chiral porphyrin cage compounds, which will be used as catalytic machines for the encoding of information into polymers, has been developed. The porphyrin cage was made chiral by introducing one or two nitro groups on its xylylene sidewalls. This nitration was performed with fuming nitric acid at low temperature and occurred in a highly regioselective fashion

  已经开发出一种改进的，可扩展的合成手性卟啉笼化合物的合成途径，该途径将用作催化信息，将信息编码到聚合物中。通过在二甲苯侧壁上引入一个或两个硝基，使卟啉笼呈手性。该硝化在低温下用发烟硝酸进行，并且以高度区域选择性的方式发生。后者被认为是笼状化合物腔体内硝基阳离子结合的结果，该反应将反应引导至侧壁。然而，用硝酸或硝鎓盐[NO 2 ] [BF 4 ]对卟啉笼化合物进行1 H NMR滴定。]揭示了硝化氮离子的主客体结合对反应选择性的影响可以忽略不计。相反，卟啉的质子化起重要作用，因为它防止环被氧化，从而使硝化作用指向侧壁。
• Synthesis of some novel tetraimidazolium salts derived from diphenyl- and dimethylglycolurils
  作者：Mohammad Rahimizadeh、Esmaeel Rezaei Seresht、Neda Golari、Mehdi Bakavoli

  DOI：10.1007/s00706-007-0805-0

  日期：2008.6

  diphenyl- and dimethylglycolurils were synthesized. Sequential treatment of these compounds with imidazole, methyl iodide, and sodium tetrafluoroborate gave their corresponding tetra imidazolium salts. Some of these compounds because of their low melting points can be registered as a potential and new class of ionic liquids.

  合成了几种基于二苯基和二甲基甘脲的新四溴化合物。用咪唑，碘甲烷和四氟硼酸钠依次处理这些化合物，得到它们相应的四咪唑鎓盐。这些化合物中的一些由于其低熔点而可以被注册为潜在的新型离子液体。
• Preparation of Several Active <i>N</i>-Chloro Compounds from Trichloroisocyanuric Acid
  作者：Ahmad Khoramabadi-zad、Azam Shiri

  DOI：10.1055/s-0029-1216889

  日期：——

  N-chlorosaccharin, N-chlorosuccinimide, N-chlorophthalimide, N,N′-dichlorophenobarbital, and N,N′-dichlorobarbital were synthesized by chlorination with trichloroisocyanuric acid under mild reaction conditions at room temperature. This method is clean, fast, and efficient; the yields are also good to excellent. chlorinated compounds - imides - amides - halogenation - trichloroisocyanuric acid

  已经开发了一种非常简单的方法来制备几种在有机合成，工业和医学中具有广泛应用的活性N-氯化合物。Tetrachloroglycolurils，氯胺T，Ñ -chlorosaccharin，Ñ氯琥珀酰亚胺，Ñ -chlorophthalimide，Ñ，Ñ '-dichlorophenobarbital，和Ñ，Ñ通过氯化，在室温下温和反应条件下三氯异氰尿酸合成-dichlorobarbital'。这种方法干净，快速，高效；产量也不错到极好。 氯化化合物-酰亚胺-酰胺-卤化-三氯异氰尿酸
• Condensation reactions of benzils with ureas in ethylene glycol
  作者：Chang Kiu Lee、Sun Hee Kim、Yong Bun Kim

  DOI：10.1002/jhet.5570330403

  日期：1996.7

  Reactions of benzils and urea in ethylene glycol at 180° for 1-2 hours gave 2,4,5-triaryloxazoles as major products and bicyclic imidazoimidazole-2,5-diones as minor products. N-Methylurea and N-phenylurea gave the oxazoles under similar conditions. The solvent seemed to assist the formation of oxazole by eliminating the isocyanate components as ethylene glycol biscarbamates.

  苯甲醚和脲在乙二醇中于180°反应1-2小时，得到的主要产物为2,4,5-三芳基恶唑，次要的产物为双环咪唑并咪唑-2,5-二酮。N-甲基脲和N-苯基脲在类似条件下得到恶唑。该溶剂似乎通过消除异氰酸酯组分（如乙二醇双氨基甲酸酯）来帮助恶唑的形成。

表征谱图