6-碘-1,4-苯并二氧烷 | 57744-67-9

• 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: 6-碘-1,4-苯并二氧烷
• 中文别名: 3,4-亚乙基二氧基碘苯；3,4-亚乙二氧基碘苯
• 英文名称: 6-iodo-1,4-benzodioxane
• 英文别名: 6-iodo-2,3-dihydrobenzo[b][1,4]dioxine；3,4-ethylenedioxyiodobenzene；6-iodo-2,3-dihydro-1,4-benzodioxine；6-iodo-2,3-dihydrobenzo[1,4]dioxine
• CAS: 57744-67-9
• 化学式: C₈H₇IO₂
• 分子量: 262.047
• InChiKey: HZTMYTXWFHBHDC-UHFFFAOYSA-N

物化性质

• 沸点：
  98 °C
• 密度：
  1.872 g/cm3
• 闪点：
  100-102°C/0.25mm
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会发生分解，也未发现有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2932999099
• 包装等级：
  II
• 危险类别：
  8
• 危险品运输编号：
  1760
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将贮藏器密封保存，在阴凉、干燥处存放，并确保工作环境有良好的通风或排气设施。

SDS

Name:	6-Iodo-2 3-dihydro-1 4-benzodioxine 97% Material Safety Data Sheet
Synonym:	3,4-Ethylenedioxyiodobenzen
CAS:	57744-67-9

Section 1 - Chemical Product MSDS Name:6-Iodo-2 3-dihydro-1 4-benzodioxine 97% Material Safety Data Sheet
Synonym:3,4-Ethylenedioxyiodobenzen

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
57744-67-9	6-Iodo-2,3-dihydro-1,4-benzodioxine	97%	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.

---

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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable 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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 57744-67-9: 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: Liquid
Color: light purple
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 100 - 102 deg C @0.2mmHg
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: Not available.
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H7IO2
Molecular Weight: 262

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 57744-67-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Iodo-2,3-dihydro-1,4-benzodioxine - 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# 57744-67-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 57744-67-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 57744-67-9 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：

  6-碘-1,4-苯并二氧烷 在 水 、 sodium formate 、 palladium diacetate 、 1,2-双(二苯基膦)乙烷 作用下， 以 二甲基亚砜 为溶剂， 生成 1,4-苯并二恶烷-6-甲醛
  参考文献：
  名称：

  由芳基卤和醛的钯催化合成的叔丁基胩使用甲酸盐作为氢化物供体†

  摘要：

  通过使用叔丁基异氰化物作为C 1资源和甲酸盐作为氢化物供体，无需任何其他碱，就已经实现了芳烃卤化物的高效一锅钯催化的芳基卤化物的加氢甲酰化反应。反应条件温和，易于操作且毒性较低，该反应可耐受各种官能团，产率中等至优异。

  DOI：

  10.1039/c4ra16388e
• 作为产物：
  描述：

  6-氨基-1,4-苯并二氧杂环 在 盐酸 、 sodium nitrite 、 potassium iodide 作用下， 以 水 为溶剂， 反应 0.5h， 以94.22%的产率得到6-碘-1,4-苯并二氧烷
  参考文献：
  名称：

  三苯胺供体中甲氧基的数量，位置和形状对染料敏化太阳能电池性能的影响

  摘要：

  四个新的有机光敏剂（SH-11〜14介绍了甲氧基作为附加给体）被合成，并在染料敏化太阳能电池中使用。设计染料的目的是通过对-/邻-和对-/间-和间-和对-基引入的甲氧基的数量，位置和形状，研究对染料光物理性质和电池光伏性能的影响。-三苯胺供体上的-（开环或闭环）位置。甲氧基的引入导致吸收光谱的红移，并增加了染料的摩尔消光系数。由于空间位阻的增加，它们的引入减少了TiO 2表面吸附的染料量。随着数量的增加，开路电压值降低。综上所述，具有闭环形状的染料（SH-14）在AM 1.5G条件下显示出最佳的转换效率，为6.01％（在相同条件下，N719染料的转换率为7.59％）。

  DOI：

  10.1016/j.dyepig.2014.09.014

文献信息

• Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
  作者：Jian-Hua Liang、Liang Yang、Si Wu、Si-Si Liu、Mark Cushman、Jing Tian、Nuo-Min Li、Qing-Hu Yang、He-Ao Zhang、Yun-Jie Qiu、Lin Xiang、Cong-Xuan Ma、Xue-Meng Li、Hong Qing

  DOI：10.1016/j.ejmech.2017.05.025

  日期：2017.8

  discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。
• Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
  作者：Yajun Liu、Jihye Kim、Heesun Seo、Sunghyouk Park、Junghyun Chae

  DOI：10.1002/adsc.201400941

  日期：2015.7.6

  single‐step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2‐ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high

  利用铜（II）催化剂和1,2-乙二硫醇开发了一种高效的过渡金属催化的从芳基卤化物单步合成芳基硫醇的方法。关键特征是使用现成的试剂，简单的操作以及相对温和的反应条件。该新协议显示了广泛的底物范围，具有出色的官能团相容性。由芳基卤化物直接以高收率制备各种芳基硫醇。此外，芳基硫醇原位用于合成更高级的分子，例如二芳基硫醚和苯并噻吩。
• Copper-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Aryl Iodides and Bromides
  作者：Rui Shang、Yao Fu、Yan Wang、Qing Xu、Hai-Zhu Yu、Lei Liu

  DOI：10.1002/anie.200904916

  日期：2009.11.23

  For copper only: The decarboxylative cross‐coupling of readily accessible and nonvolatile potassium polyfluorobenzoates with aryl iodides and bromides using a copper catalyst provides polyfluorobiaryls and polyfluorostilbenes in excellent yields (see scheme). Mechanistic analyses are reported for the title reaction.

  仅适用于铜：使用铜催化剂，易于获得且不挥发的多氟苯甲酸钾与芳基碘化物和溴化物的脱羧交叉偶联可提供极佳的收率的多氟联芳基和多氟苯磺酸酯（请参见方案）。报告了标题反应的机理分析。
• [¹¹C]CO₂ to [¹¹C]CO conversion mediated by [¹¹C]silanes: a novel route for [¹¹C]carbonylation reactions
  作者：Carlotta Taddei、Salvatore Bongarzone、Abdul Karim Haji Dheere、Antony D. Gee

  DOI：10.1039/c5cc02095f

  日期：——

  A novel chemical methodology is described for the conversion of [¹¹C]CO₂ to [¹¹C]CO via silane derivatives. The released [¹¹C]CO is used for radiosynthetic applications.

  描述了一种新颖的化学方法，通过硅烷衍生物将[¹¹C]CO₂转化为[¹¹C]CO。释放的[¹¹C]CO用于放射合成应用。

• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。