2,3-二氢-1,4-苯并二氧-6-基异硫氰酸酯 | 141492-50-4

• 物质功能分类: 化学试剂 - 有机试剂 - 氰酸酯/异氰酸酯
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: 2,3-二氢-1,4-苯并二氧-6-基异硫氰酸酯
• 英文名称: 6-isothiocyanato-2,3-dihydrobenzo[b][1,4]dioxine
• 英文别名: 6-isothiocyanato-2,3-dihydrobenzo[1,4]dioxine；6-isocyanato-2,3-dihydrobenzo[1,4]dioxine；3,4-ethylenedioxyphenylisothiocyanate；1,4-benzodioxin-6-yl isothiocyanate；2,3-dihydro-6-isothiocyanato-benzo[b][1,4]dioxine；2,3-dihydro-6-isothiocyanato-1,4-benzodioxin；6-Isothiocyanato-2,3-dihydro-1,4-benzodioxine
• CAS: 141492-50-4
• 化学式: C₉H₇NO₂S
• mdl: MFCD00175465
• 分子量: 193.226
• InChiKey: KALNNFRLHRAJNK-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64°C
• 沸点：
  329.2±41.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 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
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R20/21/22
• 海关编码：
  2932999099
• 危险品运输编号：
  UN 2923
• 储存条件：
  室温

SDS

Name:	2 3-Dihydro-1 4-benzodioxin-6-yl isothiocyanate 97% Material Safety Data Sheet
Synonym:	3,4-(Ethylenedioxy)phenyl isothiocyanat
CAS:	141492-50-4

Section 1 - Chemical Product MSDS Name:2 3-Dihydro-1 4-benzodioxin-6-yl isothiocyanate 97% Material Safety Data Sheet
Synonym:3,4-(Ethylenedioxy)phenyl isothiocyanat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
141492-50-4	2,3-Dihydro-1,4-benzodioxin-6-yl isoth	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 nitrogen.

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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# 141492-50-4: 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: 62 - 64 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: C9H7NO2S
Molecular Weight: 193

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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:
Strong oxidizing agents, acids, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, 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# 141492-50-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3-Dihydro-1,4-benzodioxin-6-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 LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
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# 141492-50-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 141492-50-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 141492-50-4 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：

  2,3-二氢-1,4-苯并二氧-6-基异硫氰酸酯 在 吡啶 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 20.0h， 生成 3-[5-(2,3-dihydro-1,4-benzodioxin-6-ylamino)-4-methyl-1,2,4-triazol-3-yl]-N-(3,5-dimethoxyphenyl)pyridin-2-amine
  参考文献：
  名称：

  1,2,4-三唑类化合物作为一类新型有效的微管蛋白聚合抑制剂的合成与构效关系。

  摘要：

  一种新型的含有三唑的化学系列显示抑制微管蛋白聚合并导致细胞周期停滞在EC（50）值在一位数纳摩尔范围内的A431癌细胞。结合实验表明，这类代表性的活性化合物与秋水仙碱竞争其在微管蛋白上的结合位点。本文描述了三唑衍生物的合成和结构-活性关系研究。

  DOI：

  10.1016/j.bmcl.2005.08.056
• 作为产物：
  描述：

  6-氨基-1,4-苯并二氧杂环 在 乙基溴化镁 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2,3-二氢-1,4-苯并二氧-6-基异硫氰酸酯
  参考文献：
  名称：

  异硫氰酸芳基酯的新合成†

  摘要：

  伯芳族胺很容易转化为芳基-1,2,3-二噻唑2和衍生的氰基硫代甲酰苯胺6，两者在热THF中被乙基溴化镁迅速裂解，得到相应的异硫氰酸酯。转换2→6→ArNCS可以作为“一锅法”操作执行。在热THF中，通过氰基硫代甲酰苯胺6 ，氢化钠中的亚胺2也更缓慢地转化为异硫氰酸酯。在2，6-二甲基吡啶中在微波辐射下，苯胺6向异硫氰酸酯的转化要快得多。提出了用于这些反应的机制。

  DOI：

  10.1039/a707801c

文献信息

• Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents
  作者：Masao Yoshida、Ichiro Hayakawa、Noriyuki Hayashi、Toshinori Agatsuma、Youko Oda、Fumie Tanzawa、Shiho Iwasaki、Kumiko Koyama、Hidehiko Furukawa、Shinichi Kurakata、Yuichi Sugano

  DOI：10.1016/j.bmcl.2005.05.077

  日期：2005.7

  cytotoxicity against tumorigenic cell lines, 2,6-dichloro-N-[2-(cyclopropanecarbonylamino)benzothiazol-6-yl]benzamide (13b) was designed and synthesized as a biologically stable derivative containing no nitro group. The highly potent derivative 13b exhibited excellent in vivo inhibitory effect on tumor growth.

  基于2-甲基-4-硝基-2H-吡唑-3-羧酸[2-（环己烷羰基氨基）苯并噻唑-6-基]酰胺（1），该化合物对致瘤细胞系2,6-二氯-将N- [2-（环丙烷羰基氨基）苯并噻唑-6-基]苯甲酰胺（13b）设计并合成为不含硝基的生物稳定衍生物。高效衍生物13b对肿瘤生长表现出优异的体内抑制作用。
• 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。
• Piperazinyl derivatives and methods of treating central nervous system
  申请人：Novo Nordisk A/S

  公开号：US05246935A1

  公开（公告）日：1993-09-21

  Piperazinyl derivatives of the general formula I ##STR1## wherein R.sup.1 represents substituted phenyl, 1- or 2-diazanaphthyl, azadiazanaphtyl or diazanaphtyl groups; n is 1, 2, 3 or 4; X is --O-- or ##STR2## wherein R.sup.2 is hydrogen, C.sub.1-6 -alkyl or C.sub.3-8 -cycloalkyl; Y is .dbd.O or .dbd.S or .dbd.NZ wherein Z is hydrogen, C.sub.1-6 -alkyl or --CN and R.sup.3 is selected from a group consisting of various structures have been found to exhibit high affinity for various receptor subtypes including the 5-HT.sub.2 receptor, the 5-HT.sub.1A receptor, the alpha.sub.1 receptor the dopamine receptor or a combination of these and may therefore be useful for treating CNS system, cardiovascular system and gastrointestinal disorders.

  通式I的吡哌啉衍生物 其中R.sup.1代表取代苯基，1-或2-二氮杂萘基，氮杂萘基或二氮杂萘基；n为1、2、3或4；X为--O--或 其中R.sup.2为氢、C.sub.1-6-烷基或C.sub.3-8-环烷基；Y为.dbd.O、.dbd.S或.dbd.NZ，其中Z为氢、C.sub.1-6-烷基或--CN，R.sup.3从一组中选择，该组包括各种结构已被发现对各种受体亚型表现出高亲和力，包括5-HT.sub.2受体，5-HT.sub.1A受体，alpha.sub.1受体，多巴胺受体或这些受体的组合，因此可能对治疗中枢神经系统，心血管系统和胃肠道疾病有用。
• [EN] GALACTOPYRANOSYL DERIVATIVES USEFUL AS MEDICAMENTS<br/>[FR] DÉRIVÉS DE GALACTOPYRANOSYLE UTILES EN TANT QUE MÉDICAMENTS
  申请人：UNIV GENT

  公开号：WO2014001204A1

  公开（公告）日：2014-01-03

  This invention relates to carbamate-containing or thiocarbamate-containing galacto-pyranosyl compounds useful as therapeutic agents and being represented by the structural formula (II), wherein: X is O or S, R is selected from the group consisting of C1-8 alkyl, C3-10 cycloalkyl, aryl-C1-4 alkyl, heterocyclyl-C1-4 alkyl, cycloalkyl-C1-4 alkyl, aryl and heterocyclyl, wherein R is optionally substituted with one or more R9; R2, R3, R4, R6 and R7 are independently selected from the group consisting of hydroxyl and protected hydroxyl groups; R5 is selected from the group consisting C6-30 alkyl and arylalkyl; R8 is C6-30 alkyl; and each R9 is independently selected from the group consisting of halogen, hydroxy, trifluoromethyl, trifluoromethoxy, C1-8 alkoxy, C1-6 alkyl, cyano, methylthio, phenyl, phenoxy, chloromethyl, dichloromethyl, chloro-difluoromethyl, acetyl, nitro, benzyl, heterocyclyl and di-C1-4 alkyl-amino, or a pharmaceutically acceptable salt thereof.

  这项发明涉及含有碳酸酯或硫代碳酸酯的半乳糖基化合物，可作为治疗剂，并由结构式（II）表示，其中：X为O或S，R从以下组中选择：C1-8烷基、C3-10环烷基、芳基-C1-4烷基、杂环基-C1-4烷基、环烷基-C1-4烷基、芳基和杂环基，其中R可选择性地被一个或多个R9取代；R2、R3、R4、R6和R7独立地选自羟基和保护羟基基团；R5选自C6-30烷基和芳基烷基；R8为C6-30烷基；每个R9独立地选自卤素、羟基、三氟甲基、三氟甲氧基、C1-8烷氧基、C1-6烷基、氰基、甲硫基、苯基、苯氧基、氯甲基、二氯甲基、氯二氟甲基、乙酰基、硝基、苄基、杂环基和二C1-4烷基氨基，或其药用可接受盐。
• New syntheses of aryl isothiocyanates from N-arylimino-1,2,3-dithiazoles
  作者：Thierry Besson、Jérôme Guillard、Charles W. Rees、Michel Thérisod

  DOI：10.1039/a700551b

  日期：——

  Treatment of N-arylimino-1,2,3-dithiazoles 2 with ethylmagnesium bromide (2 equiv.) gives the corresponding aryl isothiocyanates 13, providing a very mild two-step conversion of ArNH 2 into ArNCS avoiding hazardous reagents; alternatively the iminodithiazoles 2 can be converted into cyanothioformanilides 11 which rapidly give the same isothiocyanates with 1 equiv. of the Grignard reagent.

  用溴化乙基镁（2当量）处理N-芳基亚胺-1,2,3-硫二唑2，可以得到相应的芳基异硫氰酸酯13，提供了一种非常温和的两步反应，将ArNH₂转化为ArNCS，避免了使用有害试剂；另外，亚胺硫二唑2还可以转化为氰硫酰胺11，这些化合物与1当量的格氏试剂迅速生成相同的异硫氰酸酯。