N,N-二(1-萘基)尿素 | 607-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N,N-二(1-萘基)尿素
• 中文别名: N,N-二-(1-萘)脲
• 英文名称: 1,3-dinaphthalen-1-ylurea
• 英文别名: Urea, N,N'-di-1-naphthalenyl-
• CAS: 607-56-7
• 化学式: C₂₁H₁₆N₂O
• 分子量: 312.371
• InChiKey: OAXACVUBJMHKTD-UHFFFAOYSA-N

物化性质

• 熔点：
  285-298 °C
• 沸点：
  452.29°C (rough estimate)
• 密度：
  1.1624 (rough estimate)
• 稳定性/保质期：
  在常温常压下保持稳定，但应避免与不相容的材料接触。此外，它会与强氧化剂发生反应。

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	N N -Di-(1-naphthyl)urea Material Safety Data Sheet
Synonym:
CAS:	607-56-7

Section 1 - Chemical Product MSDS Name:N N -Di-(1-naphthyl)urea Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
607-56-7	N,N'-Di-(1-naphthyl)urea		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 607-56-7: 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: Powder
Color: white - grey
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 285 - 298 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: Insoluble.
Specific Gravity/Density:
Molecular Formula: C21H16N2O
Molecular Weight: 312.37

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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:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 607-56-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N,N'-Di-(1-naphthyl)urea - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 607-56-7: No information available.
Canada
CAS# 607-56-7 is listed on Canada's NDSL List.
CAS# 607-56-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 607-56-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  丙醇 、 N,N-二(1-萘基)尿素 在 choline chloride * 2ZnCl2 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 以77%的产率得到1-propyl (naphthalene-1-yl)carbamate
  参考文献：
  名称：

  尿素作为安全的羰基来源，可与具有有效且可循环利用的溶剂/催化剂体系的深共熔溶剂（DESs）合成氨基甲酸酯†

  摘要：

  由尿素开发了一种简单，有效和环保的一锅法合成伯，N-单和N-二取代的氨基甲酸酯。相应的氨基甲酸酯是在120°C下，在18小时内且在深共熔溶剂作为可循环催化体系的情况下产生的。该催化剂可以重复使用几次，而不会降低其活性。为了证明这种方法的实用性，人们对各种醇和酚进行了研究，以发现中，高收率的各种氨基甲酸酯衍生物。

  DOI：

  10.1039/c8nj02624f
• 作为产物：
  描述：

  1-萘异硫氰酸酯 在 copper(I) oxide 、 二叔丁基过氧化物 、 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 15.0h， 以12%的产率得到N,N-二(1-萘基)尿素
  参考文献：
  名称：

  二叔丁基过氧化物（DTBP）介导的从水中异硫氰酸酯合成对称的N，N'-二取代脲/硫脲基序

  摘要：

  ABATRACT 已经开发了一种从异硫氰酸酯在水中的自缩合反应直接得到N , N '-二取代脲/硫脲的方法。这种访问容忍了芳环上的多种官能团，为N , N '-二取代脲/硫脲提供了一种实用且环境友好的工艺，从安全且易于获得的起始材料以中等至优异的产率。还提出了尿素脱硫自缩合反应的合理机理，并借助中间体研究的 ESI 质谱分析证明了二叔丁基过氧化物 (DTBP) 和铜催化剂在本策略中的作用。

  DOI：

  10.1080/00397911.2021.2001017

文献信息

• Ground-State Conformational Equilibrium and Photochemical Behavior of Syn and Anti <i>N</i>,<i>N</i><i>‘</i>-Dimethyl-<i>N</i>,<i>N</i><i>‘</i>-di-1-naphthylurea Protophanes
  作者：Todd L. Kurth、Frederick D. Lewis

  DOI：10.1021/ja034311w

  日期：2003.11.1

  The structure, spectroscopy, and photochemistry of N,N'-dimethyl-N,N'-di-1-naphthylurea have been investigated and compared to the properties of the corresponding secondary diarylurea N,N'-di-1-naphthylurea and the tertiary mono arylurea N,N,N'-trimethyl-N'-1-naphthylurea. The crystal structures and solution NMR spectra of the tertiary and secondary dinaphthylureas establish that they adopt folded

  研究了 N,N'-二甲基-N,N'-di-1-naphthylurea 的结构、光谱和光化学，并与相应的仲二芳基脲 N,N'-di-1-naphthylurea 和叔单芳基脲 N,N,N'-三甲基-N'-1-萘脲。叔二萘脲的晶体结构和溶液 NMR 谱表明它们在固态和溶液中分别采用折叠 (E,E) 和扩展 (Z,Z) 结构。在溶液中，叔 E,E-二萘脲作为顺式和反式构象的混合物存在，被约 14 kcal/mol，由变温 (1) H NMR 光谱测定。对基态势能面的计算探索表明，顺式和反式构象异构体相互转化的最低能量途径需要同时围绕氮-萘和氮-羰基单键旋转。由于萘环之间的激子相互作用，叔联萘脲表现出蓝移吸收和红移发射。二级二萘脲和单萘脲具有典型的类萘单体吸收和荧光光谱。双指数荧光衰减分配给三级联萘脲的两个构象异构体。荧光衰减时间的非线性拟合为两个构象异构体的单线态衰减提供了激活参数。衰变过程归
• Palladium-Catalyzed Aromatic Azidocarbonylation
  作者：Fedor M. Miloserdov、Vladimir V. Grushin

  DOI：10.1002/anie.201200078

  日期：2012.4.10

  Aryl iodides smoothly react with NaN3 and CO in the presence of a Pd/Xantphos catalyst to give aroyl azides (ArCON3) in 75–92 % yield. The reaction occurs under mild reaction conditions (1 atm, 20–50 °C) and exhibits high functional‐group tolerance. (Xantphos=9,9‐dimethyl‐4,5‐bis(diphenylphosphino)xanthene)

  在Pd / Xantphos催化剂存在下，芳基碘化物与NaN 3和CO平稳反应，以75-92％的收率得到芳基叠氮化物（ArCON 3）。该反应在温和的反应条件下（1 atm，20–50°C）发生，并且具有很高的官能团耐受性。（Xantphos = 9,9-二甲基-4,5-双（二苯基膦基）x吨）
• Diacetamides—I
  作者：A. Kornhauser、D. Keglević

  DOI：10.1016/0040-4020(62)80018-0

  日期：1962.1

  The action of boiling acetic anhydride on β-ureidesters, β-N-carbonyl esters and β-amino-esters was studied. It was shown that no cyclization of β-ureidoesters occurred and that N,N-diacetyl and N-acetyl-β-aminoesters were the reaction products in all three cases. A satisfactory separation of these compounds by chromatography was achieved and their physical properties determined. The mechanism of the

  研究了乙酸酐沸腾对β-脲酯，β-N-羰基酯和β-氨基酯的作用。结果表明，没有发生β-脲基酯的环化，并且在所有三种情况下，N，N-二乙酰基和N-乙酰基-β-氨基酯都是反应产物。通过色谱法令人满意地分离了这些化合物，并确定了它们的物理性质。简要讨论了反应机理。
• Transition-metal-free synthesis of thiazolidin-2-ones and 1,3-thiazinan-2-ones from arylamines, elemental sulfur and CO₂
  作者：Chuan-Kun Ran、Lei Song、Ya-Nan Niu、Ming-Kai Wei、Zhen Zhang、Xiao-Yu Zhou、Da-Gang Yu

  DOI：10.1039/d0gc03723k

  日期：——

  feedstocks in one reaction. Herein, we report the first utilization of both elemental sulfur and CO2 in a multi-component reaction to generate valuable thiazolidin-2-ones and 1,3-thiazinan-2-ones. Under transition-metal-free reaction conditions, a variety of easily available arylamines react with elemental sulfur and CO2 (1 atm) to give functional thiazolidin-2-ones and 1,3-thiazinan-2-ones in moderate to good

  在绿色化学中，将废物转化为珍宝非常重要。但是，由于反应性低，特别是在一个反应​​中同时利用两种非反应性原料，因此难以有效地实现。在此，我们报告了在多组分反应中首次利用元素硫和CO 2生成有价值的噻唑烷二-2-酮和1,3-噻嗪南-2-酮。下过渡金属无反应条件，多种容易获得的芳基胺的与元素硫和CO反应2（1大气压）至以良好的产率得到官能噻唑烷-2-酮和1,3-噻嗪烷-2-酮在中度经由C–H键功能化。该策略的突出特点是高步经济性，可在一个反应​​中生成三个键并具有良好的官能团耐受性。
• Pd/C-Catalyzed Domino Synthesis of Urea Derivatives Using Chloroform as the Carbon Monoxide Source in Water
  作者：Liang Wang、Hao Wang、Guiqing Li、Shuliang Min、Fangyuan Xiang、Shiqi Liu、Waigang Zheng

  DOI：10.1002/adsc.201800954

  日期：2018.12.3

  A Pd/C‐catalyzed domino synthesis of symmetrical and unsymmetrical ureas from aryl iodides, sodium azide, amines and CHCl3 in water has been developed. This reaction proceeds with sequential carbonylation, Curtius rearrangement and nucleophilic addition. CHCl3 serves as a convenient and safe alternation of CO gas in the presence of KOH. A series of urea derivatives were obtained in moderate to good

  已经开发了一种Pd / C催化由水中的芳基碘化物，叠氮化钠，胺和CHCl 3合成对称和不对称脲的多米诺骨牌。该反应以顺序的羰基化，Curtius重排和亲核加成进行。在KOH存在下，CHCl 3可作为一种方便，安全的CO气体替代气体。以中等至良好的产率获得了具有良好的官能团耐受性的一系列脲衍生物。此外，连续六次运行后，Pd / C催化剂很容易被回收，催化活性略有下降。