6,8-二氯-2-氧代-2H-苯并吡喃-3-羧酸 | 2199-86-2

• 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: 6,8-二氯-2-氧代-2H-苯并吡喃-3-羧酸
• 英文名称: 6,8-dichloro-2-oxo-2H-chromene-3-carboxylic acid
• 英文别名: 6,8-dichlorocoumarin-3-carboxylic acid；6,8-dichloro-2-oxochromene-3-carboxylic acid
• CAS: 2199-86-2
• 化学式: C₁₀H₄Cl₂O₄
• mdl: MFCD00047641
• 分子量: 259.045
• InChiKey: WJEHZKIVHXRVSR-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C
• 沸点：
  460.7±45.0 °C(Predicted)
• 密度：
  1.712±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38

SDS

Name:	6 8-Dichloro-2-oxo-2h-chromene-3-carboxylic acid Material Safety Data Sheet
Synonym:
CAS:	2199-86-2

Section 1 - Chemical Product MSDS Name:6 8-Dichloro-2-oxo-2h-chromene-3-carboxylic acid Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2199-86-2	6,8-Dichloro-2-oxo-2H-chromene-3-carbo		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.
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:
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:
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# 2199-86-2: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 198 - 200 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: C10H4Cl2O4
Molecular Weight: 259.04

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
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# 2199-86-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6,8-Dichloro-2-oxo-2H-chromene-3-carboxylic acid - 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# 2199-86-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2199-86-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2199-86-2 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：

  6,8-二氯-2-氧代-2H-苯并吡喃-3-羧酸 在 盐酸 、 二苯基磷酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 3-amino-6,8-dichloro-2H-chromen-2-one
  参考文献：
  名称：

  新2的合成ħ，4 ħ -苯并吡喃并[3,4- b ] yridine -1,3,5-三酮衍生物通过二氧化三碳

  摘要：

  新的2 ħ，4 ħ - [1]苯并吡喃并[3,4- b ]吡啶-1,3,5-三酮衍生物10A-F在以下三个步骤制备：新的第一制备ñ - （叔-通过香豆素-3-羧酸与二苯基磷酰叠氮化物的反应，然后将5a-f与气态氯化氢水解，得到相应的胺7a-（丁氧基羰基）-3-氨基-2 H -1-苯并吡喃-2-酮衍生物5a-f。f，最后在路易斯酸存在下，通过7a-f与亚氧化碳的反应制备10a-f。

  DOI：

  10.1002/jhet.5570350122
• 作为产物：
  描述：

  ethyl 6,8-dichloro-2-oxo-2H-chromene-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以91%的产率得到6,8-二氯-2-氧代-2H-苯并吡喃-3-羧酸
  参考文献：
  名称：

  羟基酪醇和香豆素结合物的合成及抗氧化活性

  摘要：

  抗氧化剂由于其许多健康益处而已成为人们广泛研究的主题。在这项工作中，合成了一系列新型的羟基酪醇和香豆素共轭物，并对其体外自由基清除，毒性和抗氧化机理进行了评估。在DPPH自由基和ABTS +自由基阳离子清除试验中，所有目标化合物14a–t均表现出比BHT，羟基酪醇和香豆素更好的自由基清除活性。结构-活性关系研究表明，香豆素环上羟基的数量和位置对于良好的抗氧化能力至关重要。此外，最有前途的化合物14q在正常的WI-38和GES细胞中，溶血试验显示的毒性比BHT弱，抗增殖作用较弱，并且H 2 O 2诱导的HepG2细胞活力增强。另外，14q降低了HepG2细胞的凋亡百分比，减少了ROS的产生和LDH的释放，并改善了H 2 O 2处理的HepG2细胞中的GSH和SOD水平。最后，在甲醇溶液中，14q比羟基酪醇具有更高的稳定性。这些结果表明，羟基酪醇和香豆素的结合物显示出更好的抗氧化能力，并且是发现新型潜在抗氧化剂的有效方法。

  DOI：

  10.1016/j.bioorg.2020.104427

文献信息

• Synthesis and Characterisation of Some New Hybrid Molecules Containing Thiophene, Triazole and Coumarin Rings under Microwave Conditions
  作者：Fatih Yilmaz

  DOI：10.3184/174751918x15314831778603

  日期：2018.7

  In this work, a new series of N‘-[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl}-2-oxo-2H-1-benzopyran-3-carbohydrazides (thiophene–triazole–coumarin hybrid molecules) was synthesised from the reaction of 2-[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide and 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-ones by using microwave irradiation

  在这项工作中，新系列的 N'-[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl ]乙酰}-2-oxo-2H-1-benzopyran-3-carbohydrazides（噻吩-三唑-香豆素杂化分子）由 2-[4-amino-5-oxo-3-(thiophen-2- yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide 和 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-ones 通过使用微波辐射和常规加热程序和它们的结果进行了比较。该反应使用非常少量的有机溶剂并且不使用催化剂进行。
• Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones <i>via</i> doubly decarboxylative Giese reaction
  作者：Marek Moczulski、Ewelina Kowalska、Elżbieta Kuśmierek、Łukasz Albrecht、Anna Albrecht

  DOI：10.1039/d1ra05914a

  日期：——

  Doubly decarboxylative, photoredox synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones is described. The reaction involves two independent decarboxylation processes: the first one initiating the cycle and the second completing the process. Visible light, photoredox catalyst, base, anhydrous solvent and inert atmosphere constitute the key parameters for the success of the developed

  描述了 4-取代-chroman-2-ones 和 2-取代-chroman-4-ones 的双脱羧、光氧化还原合成。该反应涉及两个独立的脱羧过程：第一个启动循环，第二个完成该过程。可见光、光氧化还原催化剂、碱、无水溶剂和惰性气氛构成了开发转化成功的关键参数。该协议证明适用于香豆素-3-羧酸和色酮-3-羧酸以及作为相应烷基自由基前体的N- (酰氧基) 邻苯二甲酰亚胺。
• Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
  作者：Mohammad Ali Zolfigol、Roya Ayazi-Nasrabadi、Saeed Baghery

  DOI：10.1039/c5ra14001c

  日期：——

  Green and straight-forward syntheses of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives using nano structure organocatalysts, namely 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid, have been developed.

  利用纳米结构有机催化剂，即2-氨基甲酰肼-1-磺酸和氨基甲酰磺酸，直接绿色合成4,4′-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物的方法已经被开发出来。

• Synthesis and Biological Evaluation of Some Succinimide Hybrid Molecules
  作者：Fatih Yılmaz、Emre Menteşe、Nimet Baltaş

  DOI：10.1134/s1068162019060402

  日期：2019.11

  In this study, a new series of succinimide hybrid molecules containing isothiocyanate, coumarin, isatin, and furan moieties was synthesized and screened for α-glucosidase and antioxidant activities. Preliminary results revealed that all molecules showed good α-glucosidase inhibition effectiveness. Antioxidant activities of the hybrid molecules were determined using cupric reducing antioxidant capacity

  在这项研究中，合成了一系列新的含有异硫氰酸酯、香豆素、靛红和呋喃部分的琥珀酰亚胺杂化分子，并筛选了 α-葡萄糖苷酶和抗氧化活性。初步结果表明，所有分子均表现出良好的α-葡萄糖苷酶抑制效果。使用铜还原抗氧化能力 (CUPRAC) 和铁还原抗氧化能力 (FRAP) 测定法测定杂交分子的抗氧化活性。还，通过使用 \documentclass[12pt]minimal} \usepackageamsmath} \usepackagewasysym} \usepackageamsfonts} \usepackageamssymb} \usepackageamsbsy} \usepackagemathrsfs} 测定合成化合物的自由基清除活性\usepackageupgreek} \setlength\oddsidemargin}-69pt} \begindocument}$$
• Synthesis and biological evaluation of some 1, <scp>3‐benzoxazol</scp> ‐2( <scp> <i>3H</i> </scp> )‐one hybrid molecules as potential antioxidant and urease inhibitors
  作者：Fatih Yilmaz、Emre Menteşe、Bahar Bilgin Sökmen

  DOI：10.1002/jhet.4165

  日期：2021.1

  A new series of 1,3‐benzoxazol‐2(3H)‐one hybrid compounds, including coumarin, isatin 1,3,4‐triazole and 1,3,4‐thiadiazole moieties, were synthesized and biologically evaluated for their antioxidant capacities and anti‐urease properties. The synthesized benzoxazole‐coumarin (6a–e) and benzoxazole‐isatin (10a–c) hybrids showed remarkable urease inhibitory activities with IC50 (μM), ranging from 0.0306 ± 0

  合成了一系列新的1,3-苯并恶唑-2（3H）-杂合化合物，包括香豆素，靛红1,3,4-三唑和1,3,4-噻二唑部分，并对其生物学性能进行了评估。抗脲酶特性。合成的苯并恶唑香豆素（6a–e）和苯并恶唑·isatin（10a–c）杂种表现出显着的脲酶抑制活性，IC 50（μM）为0.0306±0.0030至0.0402±0.0030，而标准硫脲的IC 50为0.5027 ±0.0293。合成的苯并恶唑-三唑（8a–c）和苯并恶唑–噻二唑（9a–c）杂种显示出对尿素酶的抑制活性与IC 50相似（μM），范围从0.3861±0.0379到0.5126±0.0345。评估了合成化合物的抗氧化活性，如还原力和ABTS（2,2'-叠氮基-双（3-乙基苯并噻唑啉-6-磺酸）二铵盐）清除自由基的活性。一些合成分子的ABTS自由基清除活性结果显示出比标准Trolox更高的活性，SC 50（μM）= 213.04±18