1,3-苯并二唑-5-基异硫氰酸酯 | 113504-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 1,3-苯并二唑-5-基异硫氰酸酯
• 中文别名: 5-异硫代氰酰基-1,3-苯并二氧代
• 英文名称: 5-isothiocyanato-benzo[1,3]dioxole
• 英文别名: 3,4-methylenedioxyphenyl isothiocyanate；5-isothiocyanatobenzo[d][1,3]dioxole；3,4-methylenedioxophenyl isothiocyanate；5-isothiocyanato-1,3-benzodioxole
• CAS: 113504-93-1
• 化学式: C₈H₅NO₂S
• mdl: MFCD00066321
• 分子量: 179.199
• InChiKey: UVVSPZKAEJHDCY-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  137 °C
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi,T
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  UN 2811
• 海关编码：
  2932999099
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 储存条件：
  保持冷静

SDS

Name:	1 3-Benzodioxol-5-yl isothiocyanate 97% Material Safety Data Sheet
Synonym:	3,4-Methylenedioxyphenyl isothiocynaat
CAS:	113504-93-1

Section 1 - Chemical Product MSDS Name:1 3-Benzodioxol-5-yl isothiocyanate 97% Material Safety Data Sheet
Synonym:3,4-Methylenedioxyphenyl isothiocynaat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
113504-93-1	1,3-Benzodioxol-5-yl isothiocyanate	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
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:

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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 foam, dry chemical, or carbon dioxide.

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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.
Store under an inert atmosphere.

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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# 113504-93-1: 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: tan
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C8H5NO2S
Molecular Weight: 179

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Amines, strong oxidizing agents, alcohols.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 113504-93-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,3-Benzodioxol-5-yl isothiocyanate - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
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 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 113504-93-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 113504-93-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 113504-93-1 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：

  1,3-苯并二唑-5-基异硫氰酸酯 在 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(3,4-亚甲基二氧苯基)-2-硫脲
  参考文献：
  名称：

  Design, Synthesis, X-ray Crystallographic Analysis, and Biological Evaluation of Thiazole Derivatives as Potent and Selective Inhibitors of Human Dihydroorotate Dehydrogenase

  摘要：

  Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

  DOI：

  10.1021/jm501127s
• 作为产物：
  描述：

  3,4-亚甲二氧基苯胺 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 16.0h， 生成 1,3-苯并二唑-5-基异硫氰酸酯
  参考文献：
  名称：

  2-氨基恶唑的微波介导合成

  摘要：

  开发了在 150 °C 下微波介导的 2-氨基恶唑合成，提供了具有多种官能团的产品。反应需要 5 分钟，并以中等至良好的收率提供具有简单沉淀的产物，无需重结晶或快速色谱法。

  DOI：

  10.1016/j.tetlet.2021.153555

文献信息

• Discovery of SHR1653, a Highly Potent and Selective OTR Antagonist with Improved Blood–Brain Barrier Penetration
  作者：Xin Li、Zhigao Zhang、Yang Chen、Hong Wan、Jiakang Sun、Bin Wang、Bingqiang Feng、Bing Hu、Xingxing Shi、Jun Feng、Lei Zhang、Feng He、Chang Bai、Lianshan Zhang、Weikang Tao

  DOI：10.1021/acsmedchemlett.9b00186

  日期：2019.6.13

  oxytocin receptor (OTR) plays a major role in the control of male sexual responses. Antagonists of the OTR have been reported to inhibit ejaculation in animal models and serve as a potential treatment for premature ejaculation (PE). Herein, we describe a novel scaffold featuring an aryl substituted 3-azabicyclo [3.1.0] hexane structure. The lead compound, SHR1653, was shown to be a highly potent OTR antagonist

  催产素受体（OTR）在控制男性性反应中起主要作用。据报道，在动物模型中，OTR的拮抗剂可抑制射精，并可作为早泄（PE）的潜在治疗方法。在这里，我们描述了一种新型的脚手架，其特征是芳基取代的3-氮杂双环[3.1.0]己烷结构。铅化合物SHR1653被证明是一种高效的OTR拮抗剂，相对于V 1A R，V 1B R和V 2 R表现出优异的选择性。该新型分子也显示出对整个物种都具有良好的药代动力学特征体内一样健壮在大鼠子宫收缩模型中的功效。有趣的是，SHR1653表现出出色的血脑屏障穿透性，可能对中枢神经系统相关PE的治疗有益。
• An automated, polymer-assisted strategy for the preparation of urea and thiourea derivatives of 15-membered azalides as potential antimalarial chemotherapeutics
  作者：Antun Hutinec、Renata Rupčić、Dinko Žiher、Kirsten S. Smith、Wilbur Milhous、William Ellis、Colin Ohrt、Zrinka Ivezić Schönfeld

  DOI：10.1016/j.bmc.2011.01.030

  日期：2011.3

  series of 15-membered azalide urea and thiourea derivatives has been synthesized and evaluated for their in vitro antimalarial activity against chloroquine-sensitive (D6), chloroquine/pyremethamine resistant (W2) and multidrug resistant (TM91C235) strains of Plasmodium falciparum. We have developed an effective automated synthetic strategy for the rapid synthesis of urea/thiourea libraries of a macrolide

  合成了一系列15元氮杂内酰胺脲和硫脲衍生物，并评估了它们对恶性疟原虫的氯喹敏感性（D6），氯喹/乙胺嘧啶抗性（W2）和多药耐药性（TM91C235）菌株的体外抗疟活性。我们已经开发出一种有效的自动化合成策略，用于大环内酯支架的尿素/硫脲库的快速合成。使用溶液相策略合成化合物，总收率为50–80％。大多数合成的化合物具有抑制作用。前三种化合物对所有三种菌株的效力比阿奇霉素高30-65倍，阿奇霉素具有抗疟疾活性。
• Synthesis and evaluation of new thiourea derivatives as antitumor and antiangiogenic agents
  作者：Wenjing Bai、Jianxin Ji、Qiang Huang、Wei Wei

  DOI：10.1016/j.tetlet.2020.152366

  日期：2020.10

  A series of novel thiourea derivatives were synthesized and evaluated by biological activities. Among them, compound 10e containing 3,5-bis(trifluoromethyl)phenyl moiety (R1) at the terminal thiourea and phenylamino (R2) at the terminal acyl position showed the best cytotoxic activities against seven cancer cell lines (NCI-H460, Colo-205, HCT116, MDA-MB-231, MCF-7, HepG2, PLC/PRF/5) and HUVECs. Moreover

  合成了一系列新型硫脲衍生物，并通过生物学活性对其进行了评估。其中，在末端硫脲处含有3,5-双（三氟甲基）苯基部分（R 1）在酰基末端具有苯氨基（R 2）的化合物10e对7种癌细胞系（NCI-H460， Colo-205，HCT116，MDA-MB-231，MCF-7，HepG2，PLC / PRF / 5）和HUVEC。此外，化合物10e适度抑制各种RTK，例如VEGFR2，VEGFR3和PDGFRβ。值得注意的是，在相同浓度下，10e对肿瘤形成和抗血管生成活性的抑制作用比索拉非尼和Regorafenib好得多。进一步的对接研究表明10e 可以作为癌症治疗的潜在候选人。
• [EN] CYANOGUANIDINES AND THEIR USE AS ANTIVIRAL AGENTS<br/>[FR] CYANOGUANIDINES ET LEUR UTILISATION COMME AGENTS ANTIVIRAUX
  申请人：ABBVIE INC

  公开号：WO2014005129A1

  公开（公告）日：2014-01-03

  This disclosure relates to: (a) compounds and salts thereof that, inter alia, inhibit RSV infection and/or replication; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.

  这份披露涉及：(a) 抑制RSV感染和/或复制的化合物及其盐，等等；(b) 用于制备这些化合物和盐的中间体；(c) 包含这些化合物和盐的组合物；(d) 制备这些中间体、化合物、盐和组合物的方法；(e) 使用这些化合物、盐和组合物的方法；以及(f) 包含这些化合物、盐和组合物的试剂盒。
• Design, Synthesis, and Structure−Activity Relationship of Substrate Competitive, Selective, and in Vivo Active Triazole and Thiadiazole Inhibitors of the c-Jun N-Terminal Kinase
  作者：Surya K. De、John L. Stebbins、Li-Hsing Chen、Megan Riel-Mehan、Thomas Machleidt、Russell Dahl、Hongbin Yuan、Aras Emdadi、Elisa Barile、Vida Chen、Ria Murphy、Maurizio Pellecchia

  DOI：10.1021/jm801503n

  日期：2009.4.9

  We report comprehensive structure−activity relationship studies on a novel series of c-Jun N-terminal kinase (JNK) inhibitors. The compounds are substrate competitive inhibitors that bind to the docking site of the kinase. The reported medicinal chemistry and structure-based optimizations studies resulted in the discovery of selective and potent thiadiazole JNK inhibitors that display promising in

  我们报告了一系列新型 c-Jun N 末端激酶 (JNK) 抑制剂的综合构效关系研究。这些化合物是与激酶对接位点结合的底物竞争性抑制剂。报道的药物化学和基于结构的优化研究导致发现了选择性和有效的噻二唑 JNK 抑制剂，这些抑制剂在胰岛素不敏感的小鼠模型中显示出有希望的体内活性。

表征谱图