6-喹喔啉羰酰氯 | 258503-93-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酰卤化物
• 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: 6-喹喔啉羰酰氯
• 英文名称: quinoxaline-6-carbonyl chloride
• CAS: 258503-93-4
• 化学式: C₉H₅ClN₂O
• 分子量: 192.605
• InChiKey: UTEQROVYZDJSOO-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 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：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R34
• 海关编码：
  2933990090
• 危险品运输编号：
  UN 3261
• 储存条件：
  储存条件：密封避光，存放在2-8°C的环境中。

SDS

Name:	6-Quinoxalinecarbonyl chloride 97% Material Safety Data Sheet
Synonym:
CAS:	258503-93-4

Section 1 - Chemical Product MSDS Name:6-Quinoxalinecarbonyl chloride 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
258503-93-4	6-Quinoxalinecarbonyl chloride	97%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Store under an inert atmosphere.

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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# 258503-93-4: 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: beige
Odor: characteristic odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
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:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H5ClN2O
Molecular Weight: 192.61

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, bases.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 258503-93-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Quinoxalinecarbonyl chloride - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
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 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 258503-93-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 258503-93-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 258503-93-4 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-喹喔啉羰酰氯 在 lithium tri-butoxyaluminohydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 6.5h， 以73%的产率得到喹喔啉-6-甲醛
  参考文献：
  名称：

  [EN] AZOLIDINONE-VINYL FUSED-BENZENE DERIVATIVES
  [FR] DERIVES DE BENZENE A FUSION AZOLIDINONE-VINYLE

  摘要：

  本发明涉及式(I)的噁唑烷二酮-乙烯融合苯衍生物，用于治疗和/或预防自身免疫性疾病和/或炎症性疾病、心血管疾病、神经退行性疾病、细菌或病毒感染、肾脏疾病、血小板聚集、癌症、移植排斥或肺部损伤。式(I)中，A、X、Y、Z、R1、R2和n如描述中所述。

  公开号：

  WO2004007491A1
• 作为产物：
  描述：

  3,4-二氨基苯甲酸 在 氯化亚砜 、 sodium docusate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 6-喹喔啉羰酰氯
  参考文献：
  名称：

  Synthesis, Crystal Structure and Biological Activity of Two Triketone-Containing Quinoxalines as HPPD Inhibitors

  摘要：

  采用片段拼接策略，以3,4-二氨基苯甲酸和取代环己二酮为起始材料，设计了两种新的含三酮基喹啉衍生物。通过红外、1H和13C NMR、高分辨质谱和X射线衍射对两种化合物进行了表征。3-羟基-5-甲基-2-(喹啉-6-羰基)环己-2-烯-1-酮(6a)在三斜晶系中结晶，空间群Pī，a=7.9829(2) Å，b=8.1462(2) Å，c=10.7057(3) Å，α=84.3590(10)°，β=89.7760(10)°，γ=87.4190(10)°，Z=2，V=692.12(3) Å3，F(000)=296，Dc=1.335 Mg/m3，μ(MoKα)=0.095 mm–1，R=0.0683和wR=0.1983。3-羟基-5,5-二甲基-2-(3-乙氧基喹啉-6-羰基)环己-2-烯-1-酮(6b)在单斜晶系中结晶，空间群P21/c，a=10.1554(6) Å，b=9.6491(6) Å，c=17.7645(10) Å，β=90.784(2)°，Z=4，V=1740.59(18) Å3，F(000)=720，Dc=1.299 Mg/m3，μ(MoKα)=0.092 mm–1，R=0.0462和wR=0.1235。物理化学性质比较和ADMET预测表明，化合物6a与商业除草剂美索托芬具有类似的性质。分子对接结果表明，6a与AtHPPD之间的相互作用类似于美索托芬。此外，扩展的芳香环系统和额外的烷基与周围残基形成更多的相互作用。对AtHPPD抑制和除草活性的检查表明，6a具有与美索托芬类似的抑制值，并且对稗草的抑制效果更好。

  DOI：

  10.17344/acsi.2022.7516

文献信息

• Piperazine and homopiperazine compounds
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20030153556A1

  公开（公告）日：2003-08-14

  Compounds are provided having a piperazine or homopiperazine ring which are useful in the treatment of thrombosis.

  提供了具有哌嗪或同源哌嗪环的化合物，这些化合物在治疗血栓症方面很有用。
• Synthesis and Biological Evaluation of 4(5)-(6-Alkylpyridin-2-yl)imidazoles as Transforming Growth Factor-β Type 1 Receptor Kinase Inhibitors
  作者：Dae-Kee Kim、Yoojeung Jang、Ho Soon Lee、Hyun-Ju Park、Jakyung Yoo

  DOI：10.1021/jm070129k

  日期：2007.6.1

  A series of 4(5)-(6-alkylpyridin-2-yl)imidazoles 13a-p, 17a, and 17b have been synthesized and evaluated for ALK5 inhibitory activity in an enzyme assay and in cell-based luciferase reporter assays. The quinoxalinyl analogue 13e inhibited ALK5 phosphorylation with an IC50 of 0.012 muM and showed more than 90% inhibition at 0.05 muM in a luciferase reporter assay using HaCaT cells transiently transfected

  已经合成了一系列4（5）-（6-烷基吡啶-2-基）咪唑13a-p，17a和17b，并在酶测定法和基于细胞的萤光素酶报告基因测定法中评估了ALK5抑制活性。喹喔啉基类似物13e抑制ALK5磷酸化，IC5​​0为0.012μM，在萤光素酶报告基因测定中，使用瞬时转染了p3TP-luc报告基因构建体的HaCaT细胞，在0.05μM处显示90％以上的抑制作用。通过柔性对接研究生成的13e的结合模式表明13e通过形成几个紧密的相互作用而很好地适合于ALK5的活性位点腔。
• Synthesis and biological evaluation of 5-(pyridin-2-yl)thiazoles as transforming growth factor-β type1 receptor kinase inhibitors
  作者：Dae-Kee Kim、Joon Hun Choi、Young Jae An、Ho Soon Lee

  DOI：10.1016/j.bmcl.2008.01.084

  日期：2008.3

  A series of 5-(pyridin-2-yl)thiazoles (14a-l and 15a-l) has been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 3-[[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)thiazol-2-ylamino]methyl]benzamid e (15i) and 3-[[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)thiazol-2-ylamino]methyl]benzamide (15k) showed more than 95% inhibition at 0.1

  已经合成了一系列5-（吡啶-2-基）噻唑（14a-1和15a-1），并在基于细胞的荧光素酶报告基因分析中评估了其对ALK5的抑制活性。其中，3-[[5-（6-甲基吡啶-2-基）-4-（喹喔啉-6-基）噻唑-2-基氨基]甲基]苯甲酰胺e（15i）和3-[[5-（6使用瞬时转染p3TP- luc报告基因构建体和ARE荧光素酶报告基因构建体。
• Palladium‐Catalyzed Decarbonylative Difluoromethylation of Acid Chlorides at Room Temperature
  作者：Fei Pan、Gregory B. Boursalian、Tobias Ritter

  DOI：10.1002/anie.201811139

  日期：2018.12.17

  Methods for the direct synthesis of difluoromethylated arenes are sparse, despite the importance of the difluoromethyl group in medical, agro‐, and materials chemistry. A palladium‐catalyzed decarbonylative cross‐coupling reaction of acid chlorides with a difluoromethyl zinc reagent is achieved to access difluoromethylated compounds. The transformation proceeds at room temperature and shows broad functional

  尽管二氟甲基在医学，农业和材料化学中很重要，但直接合成二氟甲基化的芳烃的方法很少。酰基氯与二氟甲基锌试剂的钯催化脱羰交叉偶联反应可实现二氟甲基化化合物的访问。该转化在室温下进行并显示出宽泛的官能团耐受性，因此提供了用于广泛范围的芳族羧酸的脱羰二氟甲基化的通用且有效的方法。
• A phase-switch purification approach for the expedient removal of tagged reagents and scavengers following their application in organic synthesis
  作者：Jason Siu、Ian R. Baxendale、Russell A. Lewthwaite、Steven V. Ley

  DOI：10.1039/b503778f

  日期：——

  In this paper we wish to report on a variety of expedient chemical transformations and purifications achieved via a generic ‘catch and release’ methodology, based on a synthetically inert bipyridyl chelating tag that can be selectively captured with a resin-bound copper(II) species. Utilising this approach we are able to derive many of the same benefits associated with both solid phase synthesis and supported reagent methods.

  本文旨在报道通过一种基于合成不活跃的双吡啶螯合标签的通用“捕获与释放”方法，实现的一系列便捷的化学转化和纯化。该方法可以选择性地利用树脂结合的铜(II)物种来捕获双吡啶螯合标签。采用这种方法，我们能够获得与固相合成和支持试剂法相关的许多相同益处。