4-氯-6-氟-2H-苯并吡喃-3-甲醛 | 105799-69-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 4-氯-6-氟-2H-苯并吡喃-3-甲醛
• 英文名称: 4-chloro-6-fluoro-2H-benzo[1,2-b]pyran-3-carboxaldehyde
• 英文别名: 1-chloro-7-fluoro-3,4-dihydronaphthalene-2-carbaldehyde；4-chloro-6-fluoro-2H-chromene-3-carbaldehyde
• CAS: 105799-69-7
• 化学式: C₁₀H₆ClFO₂
• mdl: MFCD00084953
• 分子量: 212.608
• InChiKey: RBLLNXBYFXPIPW-UHFFFAOYSA-N

物化性质

• 熔点：
  84-88 °C (lit.)
• 沸点：
  332.6±42.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  常温常压下稳定，应避免与强氧化剂和空气接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 危险类别码：
  R36/37/38
• 海关编码：
  2913000090
• 安全说明：
  S26,S37/39

SDS

Name:	4-Chloro-6-fluoro-2H-chromene-3-carbaldehyde 97% Material Safety Data Sheet
Synonym:	4-Chloro-6-fluoro-2H-benzopyran-3-carboxaldehyd
CAS:	105799-69-7

Section 1 - Chemical Product MSDS Name:4-Chloro-6-fluoro-2H-chromene-3-carbaldehyde 97% Material Safety Data Sheet
Synonym:4-Chloro-6-fluoro-2H-benzopyran-3-carboxaldehyd

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
105799-69-7	4-Chloro-6-fluoro-2H-chromene-3-carbal	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.
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:
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# 105799-69-7: 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: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 84 - 86 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: C10H6ClFO2
Molecular Weight: 213

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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, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 105799-69-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Chloro-6-fluoro-2H-chromene-3-carbaldehyde - 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.

---

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# 105799-69-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 105799-69-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 105799-69-7 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：

  4-氯-6-氟-2H-苯并吡喃-3-甲醛 在 sodium ethanolate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 8-氟-4H-噻吩并[3,2-c]色烯-2-羧酸
  参考文献：
  名称：

  4H-Thieno[3,2-c]chromene based inhibitors of Notum Pectinacetylesterase

  摘要：

  A group of small molecule thienochromenes inhibitors of Notum Pectinacetylesterase are described. We developed SAR on three series based on carbon, oxygen and sulfur replacement of the 5-position. In each series, highly potent Notum Pectinacetylesterase inhibitors were identified. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.038
• 作为产物：
  描述：

  6-氟-4-二氢色原酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 2.0h， 生成 4-氯-6-氟-2H-苯并吡喃-3-甲醛
  参考文献：
  名称：

  Jagath Reddy; Latha; Pallavi, Heterocyclic Communications, 2003, vol. 9, # 5, p. 453 - 456

  摘要：

  DOI：

文献信息

• Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection
  作者：Wolfram Wilk、Andrea Nören-Müller、Markus Kaiser、Herbert Waldmann

  DOI：10.1002/chem.200901797

  日期：2009.11.9

  of natural products that has more than 100 members and displays diverse biological activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biology‐oriented synthesis (BIOS). We have presented a solid‐phase synthesis of isomerically pure cycloocta[b]indoles by employing the Pictet–Spengler reaction and the Dieckmann cyclization as key steps

  巨线构成一类天然产物，具有100多个成员，并显示出多种生物活性。这些化合物具有环八[ b ]吲哚支架，代表了面向生物学的合成（BIOS）的有趣目标结构。我们通过采用Pictet-Spengler反应和Dieckmann环化作为关键步骤，提出了异构体纯净的环八[ b ]吲哚的固相合成。通过使用各种其他多样化的程序，例如固相上的Pd催化的Sonogashira或Suzuki偶联，对该反应序列的范围进行了更详细的研究，因此，例如，可以生成10个取代的环辛基[ b]。]吲哚衍生物。最后，通过还原和皂化作用评估了环八[ b ]吲哚骨架的固溶相修饰，从而进一步扩大了固相合成的范围。
• A Clean Conversion of Aldehydes to Nitriles Using a Solid-Supported Hydrazine
  作者：Ian R. Baxendale、Steven V. Ley、Helen F. Sneddon

  DOI：10.1055/s-2002-25333

  日期：——

  A polymer-supported hydrazine reagent has been ap- plied to the conversion of a range of aldehydes to nitriles, providing a clean and efficient route to more diverse building blocks for com- binatorial chemistry programmes.

  聚合物负载的肼试剂已被应用于将一系列醛类转化为腈类，为组合化学程序提供了一条清洁、有效的途径，以构建更加多样化的构建模块。
• Robenidine Analogues as Gram-Positive Antibacterial Agents
  作者：Rebecca J. Abraham、Andrew J. Stevens、Kelly A. Young、Cecilia Russell、Anastasia Qvist、Manouchehr Khazandi、Hui San Wong、Sam Abraham、Abiodun D. Ogunniyi、Stephen W. Page、Ryan O’Handley、Adam McCluskey、Darren J. Trott

  DOI：10.1021/acs.jmedchem.5b01797

  日期：2016.3.10

  also accommodated a CH2OH moiety (75; 2,2′-bis[1-(4-chlorophenyl)-2-hydroxyethylidene]carbonimidic dihydrazide). Analogues 1, 27 (2,2′-bis[4-(1,1-dimethylethyl)phenyl]methylene}carbonimidic dihydrazide), and 69 (2,2′-bis[1-(4-chlorophenyl)ethylidene]carbonimidic dihydrazide hydrochloride) were active against 24 clinical MRSA and MSSA isolates. No dose-limiting cytotoxicity at ≥2× MIC or hemolysis at

  Robenidine 1（2,2'-双[（4-氯苯基）亚甲基]羰基二酰肼）具有抗MRSA和VRE的活性，MIC分别为8.1和4.7μM。SAR显示4-F（8），3-F（9），3-CH 3（22）和4-C（CH 3）3（27）（23.7–71μM）和用3-Cl（3），4-CH 3（21）和4-CH（CH 3）2（26）（8.1-13.0μM）。亚胺碳烷基化确定了一个甲基/乙基结合口袋，该口袋也可以容纳CH 2 OH部分（75; 2,2'-双[1-（4-氯苯基）-2-羟基亚乙基]亚氨基二酰肼。类似物1，27（2,2'-双[4-（1,1-二甲基乙基）苯基]亚甲基}肼carbonimidic）和69（2,2'-双[1-（4-氯苯基）亚乙基] carbonimidic盐酸二酰肼）对24种临床MRSA和MSSA分离物具有活性。在≥2xMIC时未观察到剂量限制的细胞毒性，在≥8xMIC时未观察到溶血。
• α-C–H Functionalization of π-Bonds Using Iron Complexes: Catalytic Hydroxyalkylation of Alkynes and Alkenes
  作者：Yidong Wang、Jin Zhu、Austin C. Durham、Haley Lindberg、Yi-Ming Wang

  DOI：10.1021/jacs.9b11716

  日期：2019.12.18

  functionalization of C-H bonds enables streamlined and sustainable solutions to problems in synthetic organic chemistry. In this Communication, we disclose an iron-based catalytic system for the functionalization of propargylic and allylic C-H bonds. Inexpensive and readily-available cyclopentadienyliron(II) dicarbonyl complexes were employed as catalysts for a novel deprotonative activation mode for C-H functionalization

  发现基于地球丰富的过渡金属的催化体系用于 CH 键的功能化，为合成有机化学中的问题提供了简化和可持续的解决方案。在本通讯中，我们公开了一种用于炔丙基和烯丙基 CH 键功能化的铁基催化系统。廉价且容易获得的环戊二烯基 (II) 二羰基配合物被用作 CH 官能化的新型去质子活化模式的催化剂，这种方法允许不饱和结构单元与芳基醛和其他羰基亲电子试剂直接结合，以提供一系列不饱和的在操作简单和官能团耐受反应条件下的醇偶联产物。
• Synthesis and in Silico Study of Novel Benzisoxazole‐Chromene Derivatives as Potent Inhibitors of Acetylcholinesterase: Metal‐Free Site‐Selective C−N Bond Formation <i>via</i> Aza‐Michael Reaction
  作者：Grace Victoria Govada、Sabbasani Rajasekhara Reddy

  DOI：10.1002/cbdv.202300573

  日期：2023.8

  An efficient metal-free approach for site selective C−N coupling reaction of benzo[d]isoxazole and 2H-chromene derivatives has been designed and developed against AchE. This nitrogen containing organo-base promoted methodology, which is both practical and environmentally friendly, provides an easy and suitable pathway for synthesizing Benzisoxazole-Chromene (BC) possessing poly heteroaryl moieties

  针对 AchE，设计并开发了一种有效的无金属方法，用于苯并[d]异恶唑和 2 H-色烯衍生物的位点选择性 CN 偶联反应。这种含氮有机碱促进的方法既实用又环保，为合成具有多杂芳基部分的苯并异恶唑-色烯（BC）提供了一种简单且合适的途径。将合成的 BC 衍生物4 a – n对接至 AChE 的活性位点，以获得对化合物结合模式的更多了解。其中，化合物4a和4l对 AChE 抑制表现出有效的活性和高选择性。最终对接结果表明，化合物4l与AChE的结合能最低，为-11.2260 kcal/mol。合成的BC类似物将成为促进药物化学研究中适当研究的潜在候选者。