3-乙酰基-6,8-二氯-2H-色烯-2-酮 | 2199-91-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3-乙酰基-6,8-二氯-2H-色烯-2-酮
• 英文名称: 3-acetyl-6,8-dichloro-2H-1-benzopyran-2-one
• 英文别名: 3-acetyl-6,8-dichloro-2H-chromen-2-one；3-acetyl-6,8-dichlorocoumarin；3-acetyl-6,8-dichloro-coumarin；3-Acetyl-6,8-dichlor-cumarin；6.8-Dichlor-3-acetyl-cumarin；3-acetyl-6,8-dichlorochromen-2-one
• CAS: 2199-91-9
• 化学式: C₁₁H₆Cl₂O₃
• mdl: MFCD00087010
• 分子量: 257.073
• InChiKey: HCEPIRHGFPRDGG-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 沸点：
  462.6±45.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2932209090

SDS

Name:	3-Acetyl-6 8-dichloro-2H-chromen-2-one 97% Material Safety Data Sheet
Synonym:	3-Acetyl-6,8-dichlorocoumarin
CAS:	2199-91-9

Section 1 - Chemical Product MSDS Name:3-Acetyl-6 8-dichloro-2H-chromen-2-one 97% Material Safety Data Sheet
Synonym:3-Acetyl-6,8-dichlorocoumarin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2199-91-9	3-Acetyl-6,8-dichloro-2H-chromen-2-one	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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:
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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:
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# 2199-91-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 171 - 173 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: C11H6Cl2O3
Molecular Weight: 257.07

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2199-91-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Acetyl-6,8-dichloro-2H-chromen-2-one - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 2199-91-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2199-91-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2199-91-9 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：

  3-乙酰基-6,8-二氯-2H-色烯-2-酮 在 溴 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 1.0h， 以61%的产率得到3-(2-bromoacetyl)-6,8-dichloro-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of derivatives of phosphorus- and nitrogen-containing coumarins

  摘要：

  DOI：

  10.1007/bf02219466
• 作为产物：
  描述：

  C₁₁H₅Cl₃O₃ 在 copper(l) iodide 、 potassium carbonate 、 异丙醇 作用下， 反应 12.0h， 以83%的产率得到3-乙酰基-6,8-二氯-2H-色烯-2-酮
  参考文献：
  名称：

  异丙醇中CuI对芳香族α-和β-卤代羰基化合物的区域选择性加氢脱卤

  摘要：

  在碱性条件下，使用CuI在异丙醇中开发了一种有效的且对区域选择性的芳香族α-和β-卤代羰基化合物进行加氢脱卤的方法。该反应体系可有效还原氯，溴和碘基团，并以羰基化合物形式提供高收率（最高97％）。该方法是环境友好的，并且显示出对多种电子富和取代基的优异耐受性。

  DOI：

  10.1002/ejoc.201801385

文献信息

• Oxidant controlled regioselective mono- and di-functionalization reactions of coumarins
  作者：Arghya Banerjee、Sourav Kumar Santra、Nilufa Khatun、Wajid Ali、Bhisma K. Patel

  DOI：10.1039/c5cc06200d

  日期：——

  C-3 alkylation of coumarins has been accomplished using cycloalkanes/alkylbenzenes and Fe^III/DTBP while C-4 cycloalkylation–C-3 peroxidation has been achieved using AcOH/TBHP.

  香豆素的C-3烷基化已经通过使用环烷烃/烷基苯和Fe^III/DTBP实现，而C-4环烷基化-C-3过氧化已经通过使用AcOH/TBHP实现。
• Copper(<scp>i</scp>)-promoted cycloalkylation–peroxidation of unactivated alkenes via sp³C–H functionalisation
  作者：Arghya Banerjee、Sourav Kumar Santra、Aniket Mishra、Nilufa Khatun、Bhisma K. Patel

  DOI：10.1039/c4ob01962h

  日期：——

  been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide (TBHP) and internal conjugated alkenes possessing electron-withdrawing groups (EWGs). This process installs C–O and C–C bonds via sp3 C–H functionalisation with concomitant generation of two stereocentres. This regioselective radical addition of coumarin system is opposite to that of styrene.

  通过三组分反应，开发了一种由铜（I）促进的环烷基化-过氧化策略，该反应涉及环烷烃，叔丁基氢过氧化物（TBHP）和具有吸电子基团（EWG）的内部共轭烯烃。此过程通过sp 3 C–H功能化安装了C–O和C–C键，并同时生成了两个立体中心。香豆素系统的这种区域选择性自由基加成与苯乙烯相反。
• An Approach to the Synthesis of 2-Acylchromeno[3,4-c]pyrrol-4(2H)-one Derivatives via a Sequential Three-Component Reaction
  作者：Abdolali Alizadeh、Rashid Ghanbaripour、Long-Guan Zhu

  DOI：10.1055/s-0033-1339521

  日期：——

  An efficient synthesis of 2-acylchromeno[3,4-c]pyrrol-4(2H)-one derivatives by a three-component reaction of salicylaldehydes, β-keto esters, and p-toluenesulfonylmethyl isocyanide is reported.

  报道了通过水杨醛、β-酮酯和对甲苯磺酰基甲基异氰化物的三组分反应有效合成 2-酰基色基 [3,4-c] 吡咯-4(2H)-one 衍生物。
• A facile one-pot, three-component synthesis of a new series of thiazolyl pyrazole carbaldehydes: In vitro anticancer evaluation, in silico ADME/T, and molecular docking studies
  作者：Srikanth Mamidala、R Kowshik Aravilli、Gondru Ramesh、Shaik Khajavali、Raju Chedupaka、Vijjulatha Manga、Rajeswar Rao Vedula

  DOI：10.1016/j.molstruc.2021.130356

  日期：2021.7

  A series of thiazolyl pyrazole carbaldehydes (4a-n) were synthesized by conventional method using thiosemicarbazide, substituted phenacyl bromides, substituted 3-acetylcoumarins, and Vilsmeyer-Hack reagent. Structures of all the synthesized compounds were confirmed by spectral (1H & 13C NMR, FTIR, Mass) and analytical data. The target compounds were screened for their in vitro anticancer activity.

  使用硫代氨基脲，取代的苯甲酰溴，取代的3-乙酰香豆素和Vilsmeyer-Hack试剂，通过常规方法合成了一系列噻唑基吡唑甲醛（4a-n）。通过光谱（1 H和13 C NMR，FTIR，Mass）和分析数据确认所有合成化合物的结构。筛选目标化合物的体外抗癌活性。从结果可知，化合物4m已经显示出对所有测试的细胞系显着的抗增殖活性。此外，还进行了计算机模拟ADME / T，以为未来的抗癌药物发现计划设定有效的潜在候选人。针对秋水仙碱对β-微管蛋白的结合位点进行了分子对接研究，其结果与体外抗癌数据一致。
• PhI(OAc) 2 mediated an efficient Knoevenagel reaction and their synthetic application for coumarin derivatives
  作者：Danish Khan、Sayeed Mukhtar、Meshari A. Alsharif、Mohammed Issa Alahmdi、Naseem Ahmed

  DOI：10.1016/j.tetlet.2017.07.018

  日期：2017.8

  A phenyliododiacetate (PhI(OAc)2) mediated an efficient and novel protocol for the Knoevenagel reaction has been successfully accomplished. A base free, simple and straightforward method afforded wide substrate scope and good functional group tolerance, having high yields (80–92%) under environmentally benign and mild reaction conditions.

  已成功完成了碘二苯乙酸苯酯（PhI（OAc）2）介导的Knoevenagel反应的有效和新颖的协议。一种无碱，简单，直接的方法可提供较宽的底物范围和良好的官能团耐受性，在环境温和和温和的反应条件下具有较高的收率（80-92％）。