5-氟喹啉-4-醇 | 436-72-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 5-氟喹啉-4-醇
• 中文别名: 5-氟-4-喹唑酮；5-氟-4-喹唑啉酮；5-氟-4-羟基喹唑啉
• 英文名称: 5-fluoroquinazolin-4(3H)-one
• 英文别名: 5-Fluoro-4-hydroxyquinazoline；5-fluoro-3H-quinazolin-4-one
• CAS: 436-72-6
• 化学式: C₈H₅FN₂O
• mdl: MFCD00173674
• 分子量: 164.139
• InChiKey: UXEZULVIMJVIFB-UHFFFAOYSA-N

物化性质

• 熔点：
  238 °C
• 沸点：
  317.5±44.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存放在室温、干燥且密封的环境中。

SDS

Name:	5-Fluoroquinazolin-4-ol 97% Material Safety Data Sheet
Synonym:	5-Fluoro-4-hydroxyquinazolin
CAS:	436-72-6

Section 1 - Chemical Product MSDS Name:5-Fluoroquinazolin-4-ol 97% Material Safety Data Sheet
Synonym:5-Fluoro-4-hydroxyquinazolin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
436-72-6	5-Fluoroquinazolin-4-ol	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Harmful 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:

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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# 436-72-6: 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: off-white - yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 240 - 242 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: C8H5FN2O
Molecular Weight: 164

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 436-72-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Fluoroquinazolin-4-ol - 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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 22 Harmful 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.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 436-72-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 436-72-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 436-72-6 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：

  5-氟喹啉-4-醇 在 sodium hydride 作用下， 以 异丁酰胺 为溶剂， 反应 2.0h， 以82%的产率得到5-(2-(methylamino)ethoxy)quinazolin-4(3H)-one
  参考文献：
  名称：

  [EN] QUINAZOLINE DERIVATIVES
  [FR] DERIVES DE QUINAZOLINE

  摘要：

  Formula (I)的喹唑啉衍生物：其中取代基如文本中定义的那样，用于生产抗增殖效应，该效应通过在诸如人类等恒温动物中抑制erbB2受体酪氨酸激酶而产生。

  公开号：

  WO2005051923A1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 xylene 作用下， 生成 5-氟喹啉-4-醇
  参考文献：
  名称：

  AN ANTIMALARIAL ALKALOID FROM HYDRANGEA. XV. SYNTHESIS OF 5-, 6-, 7-, AND 8-DERIVATIVES WITH TWO IDENTICAL SUBSTITUENTS

  摘要：

  DOI：

  10.1021/jo01135a015

文献信息

• Design, Synthesis, and Potency of Pyruvate Dehydrogenase Complex E1 Inhibitors against Cyanobacteria
  作者：Yuan Zhou、Jiangtao Feng、Hongwu He、Leifeng Hou、Wen Jiang、Dan Xie、Lingling Feng、Meng Cai、Hao Peng

  DOI：10.1021/acs.biochem.7b00636

  日期：2017.12.12

  designed and synthesized. A part of 10, 17, and 21 displayed potent inhibition of Escherichia coli pyruvate dehydrogenase complex E1 (E. coli PDHc-E1) (IC50 = 2.12–18.06 μM) and good inhibition of Synechocystis sp. PCC 6803 (EC50 = 0.7–7.1 μM) and Microcystis sp. FACH 905 (EC50 = 3.7–7.6 μM). The algaecidal activity of these compounds positively correlated with their inhibition of E. coli PDHc-E1. In particular

  需要安全有效的除藻剂来控制具有农业和环境意义的藻类。四个系列（6，10，17，和21 29新的4-氨基嘧啶衍生物）的合理设计和合成。的一部分10，17，和21中显示的有效抑制大肠杆菌丙酮酸脱氢酶复合物E1（大肠杆菌PDHC-E1）（IC 50 = 2.12-18.06μM）和抑制良好的集胞藻属。PCC 6803（EC 50 = 0.7–7.1μM）和微囊藻。FACH 905（EC 50= 3.7–7.6μM）。这些化合物的杀藻活性与它们对大肠杆菌PDHc-E1的抑制作用正相关。特别是21l和10b表现出对PCC 6803的强效杀藻活性（分别为EC 50 = 0.7和0.8μM），其值是硫酸铜（EC 50 = 1.8μM）的2倍，并且表现最佳抑制蓝细菌PDHc-E1（IC 50分别为5.10和6.06μM ）。17h和21e是大肠杆菌的最佳抑制剂通过分子对接，定点诱变和酶促测定研究了PDHc
• Metal-Free C-2-H Alkylation of Quinazolin-4-ones with Alkanes via Cross-Dehydrogenative Coupling
  作者：Shuai Mao、Kaixiu Luo、Lu Wang、Hong-Yi Zhao、Andrea Shergalis、Minhang Xin、Nouri Neamati、Yi Jin、San-Qi Zhang

  DOI：10.1021/acs.orglett.9b00638

  日期：2019.4.5

  A practically useful approach for the cross-dehydrogenative coupling of quinazolin-4-one with simple nonactivated alkanes is reported. The products were smoothly formed under mild reaction conditions, within short reaction time at ambient temperature. The formation of new Csp3-Csp2 bonds occurred at the electron-poor C-2 position of quinazolin-4-one. The approach has the potential to be an important

  报道了一种用于喹唑啉-4-酮与简单的未活化烷烃的交叉脱氢偶联的实用方法。在温和的反应条件下，在环境温度下短的反应时间内，可以平稳地形成产物。新的Csp 3 -Csp 2键的形成发生在喹唑啉-4-one的电子贫乏的C-2位。该方法有可能成为高级合成中间体后期功能化的重要工具，并可能在药物化学中找到许多应用。
• Rhodium-Catalyzed Asymmetric N−H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (−)-Chaetominine
  作者：Yirong Zhou、Bernhard Breit

  DOI：10.1002/chem.201705059

  日期：2017.12.22

  An unprecedented asymmetric N−H functionalization of quinazolinones with allenes and allylic carbonates was successfully achieved by rhodium catalysis with the assistance of chiral bidentate diphosphine ligands. The high efficiency and practicality of this method was demonstrated by a low catalyst loading of 1 mol % as well as excellent chemo‐, regio‐, and enantioselectivities with broad functional

  通过手性双齿二膦配体的铑催化成功地实现了喹唑啉酮与丙二烯和烯丙基碳酸酯的前所未有的不对称NH键化。该方法的高效率和实用性通过1 mol％的低催化剂负载量以及出色的化学，区域和对映选择性以及广泛的官能团相容性得到证明。此外，这种新开发的策略被用作（-）-chaetominine的第一个对映选择性正式全合成中的关键步骤。
• Discovery of IACS-9779 and IACS-70465 as Potent Inhibitors Targeting Indoleamine 2,3-Dioxygenase 1 (IDO1) Apoenzyme
  作者：Matthew M. Hamilton、Faika Mseeh、Timothy J. McAfoos、Paul G. Leonard、Naphtali J. Reyna、Angela L. Harris、Alan Xu、Michelle Han、Michael J. Soth、Barbara Czako、Jay P. Theroff、Pijus K. Mandal、Jason P. Burke、Brett Virgin-Downey、Alessia Petrocchi、Dana Pfaffinger、Norma E. Rogers、Connor A. Parker、Simon S. Yu、Yongying Jiang、Stephan Krapp、Alfred Lammens、Graham Trevitt、Martin R. Tremblay、Keith Mikule、Keith Wilcoxen、Jason B. Cross、Philip Jones、Joseph R. Marszalek、Richard T. Lewis

  DOI：10.1021/acs.jmedchem.1c00679

  日期：2021.8.12

  Indoleamine 2,3-dioxygenase 1 (IDO1), a heme-containing enzyme that mediates the rate-limiting step in the metabolism of l-tryptophan to kynurenine, has been widely explored as a potential immunotherapeutic target in oncology. We developed a class of inhibitors with a conformationally constrained bicyclo[3.1.0]hexane core. These potently inhibited IDO1 in a cellular context by binding to the apoenzyme

  吲哚胺 2,3-双加氧酶 1 (IDO1) 是一种含血红素的酶，可介导l-色氨酸代谢为犬尿氨酸的限速步骤，已被广泛探索为肿瘤学中潜在的免疫治疗靶点。我们开发了一类具有构象受限的双环 [3.1.0] 己烷核心的抑制剂。这些通过与脱辅基酶结合在细胞环境中有效抑制 IDO1，如生化表征和 X 射线晶体学所阐明的那样。SKOV3 肿瘤模型有助于区分化合物，从而鉴定出 IACS-9779 ( 62 ) 和 IACS-70465 ( 71）。IACS-70465 具有出色的细胞效力、强大的药效学反应，并且在人体全血测定中比 linrodostat (BMS-986205) 更有效。IACS-9779 预测人类每日有效剂量低于 1 mg/kg 以维持对 IDO1 的抑制 > 90%，在啮齿动物毒理学和狗心血管研究中显示出可接受的安全范围，以支持推进人类发育的临床前安全性评估。
• Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis
  作者：Saurabh Sharma、Dhananjay Bhattacherjee、Pralay Das

  DOI：10.1039/c7ob03064a

  日期：——

  An oxidant, base and metal free methodology has been developed for the synthesis of various 2-substituted and non-substituted benzazoles, quinazolines and quinazolinones using oxalic/malonic acids as an in situ carbon source. This methodology is applicable for a wide range of substituted o-phenylenediamine, o-aminothiophenol, o-aminophenol and o-aminobenzamide containing various functional groups and

  已经开发了一种无氧化剂，无碱和无金属的方法，用于使用草酸/丙二酸作为原位碳源合成各种2-取代的和未取代的苯并恶唑，喹唑啉和喹唑啉酮。这种方法适用于宽范围取代的ö苯二胺，ö -aminothiophenol，ö氨基苯酚和ö -aminobenzamide含有各种官能团，并提供良好的成相应的产品的优良率。此外，简便的后处理程序，高产量和易于分离的产品是该方法的关键特征。所开发的方案也适用于苯并咪唑的克级合成。