4-硝基查耳酮 | 1222-98-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硝基化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 4-硝基查耳酮
• 中文别名: 2-(4-硝基苯亚甲基)苯乙酮；4-硝基查尔酮
• 英文名称: 4-nitrochalcone
• 英文别名: 3-(4-nitrophenyl)-1-phenylprop-2-en-1-one；p-nitrochalcone；4-nitrobenzalacetophenone；3-(4-nitrophenyl)-1-phenyl-2-propen-1-one
• CAS: 1222-98-6
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: WDZGGAFMGIOIQS-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C (lit.)
• 沸点：
  396.45°C (rough estimate)
• 密度：
  1.1934 (rough estimate)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应。请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• WGK Germany：
  2
• 海关编码：
  2914700090
• RTECS号：
  FL7075500
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉干燥处。同时，确保工作环境具有良好的通风或排气设施。

SDS

Name:	4-Nitrochalcone 99% Material Safety Data Sheet
Synonym:	None
CAS:	1222-98-6

Section 1 - Chemical Product MSDS Name:4-Nitrochalcone 99% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1222-98-6	4-Nitrochalcone	99	214-949-5

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. 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.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid breathing dust.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 1222-98-6: 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 minimize contact with skin.
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: Crystals
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 158-160 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C15H11NO3
Molecular Weight: 253.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: May occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1222-98-6: FL7075500 LD50/LC50:
CAS# 1222-98-6: Oral, mouse: LD50 = >3 gm/kg.
Carcinogenicity:
4-Nitrochalcone - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1222-98-6: No information available.
Canada
CAS# 1222-98-6 is listed on Canada's NDSL List.
CAS# 1222-98-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1222-98-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

药物成分（用于研究实验）

反应信息

• 作为反应物：
  描述：

  4-硝基查耳酮 在 Amberlyst A-26 (OH^- form) 、 双氧水 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以91%的产率得到[3-(4-硝基苯基)-2-环氧乙烷基]苯基-甲酮
  参考文献：
  名称：

  AMBERLYST A-26 支持的过氧化物对 α,β-不饱和酮的温和和方便的环氧化

  摘要：

  描述了使用由 (35%) 过氧化氢和 amberlyst A-26(OH-) 原位制备的 amberlyst A-26 负载的氢过氧化物将 α,β-不饱和酮环氧化成相应的环氧酮。反应在室温下进行，相应的环氧化物以极好的收率分离。

  DOI：

  10.1081/scc-100104010
• 作为产物：
  描述：

  3-(4-nitrophenyl)-1-phenylprop-2-en-1-ol 在 benzyltriphenylphosphonium peroxodisulfate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以80%的产率得到4-硝基查耳酮
  参考文献：
  名称：

  苄基三苯基鏻过二硫酸盐 (PhCH2PPh3)2S2O8：一种温和且廉价的试剂，可在非水和非质子条件下有效氧化有机化合物

  摘要：

  苄基三苯基鏻过二硫酸盐是一种易于制备且稳定的试剂。在非质子和非水条件下，在有机溶剂中可用作氧化剂。该试剂氧化...

  DOI：

  10.1246/bcsj.71.1649

文献信息

• PCN Pincer Palladium(II) Complex Catalyzed Enantioselective Hydrophosphination of Enones: Synthesis of Pyridine-Functionalized Chiral Phosphine Oxides as NC_sp³O Pincer Preligands
  作者：Xin-Qi Hao、Juan-Juan Huang、Tao Wang、Jing Lv、Jun-Fang Gong、Mao-Ping Song

  DOI：10.1021/jo5015307

  日期：2014.10.17

  A series of chiral PCN pincer Pd(II) complexes VI–XIII with aryl-based aminophosphine–imidazoline or phosphinite–imidazoline ligands were synthesized and characterized. They were examined as enantioselective catalysts for the hydrophosphination of enones. Among them, complex IX, which features a Ph2PO donor as well as an imidazoline donor with (4S)-phenyl and N-Tol-p groups, was found to be the optimal

  合成并表征了一系列具有芳基氨基膦-咪唑啉或次膦酸酯-咪唑啉配体的手性PCN夹心Pd（II）配合物VI - XIII。他们被检查为烯酮氢磷酸化的对映选择性催化剂。其中，具有Ph 2 PO供体以及具有（4S）-苯基和N- Tol- p基团的咪唑啉供体的配合物IX被认为是最佳催化剂。因此，在2–5 mol％的络合物IX存在下各种各样的烯酮与二芳基膦平稳地反应，以高收率得到对映体选择性高达98％ee的相应手性膦衍生物。尤其是，对于Pd中心具有强配位能力的杂芳基物质，例如含2-噻吩基，2-呋喃基和2-吡啶基的烯酮，也是当前催化体系的合适底物。例如，用二苯基膦将2-烯酰基吡啶进行氢磷酸化，然后用H 2 O 2氧化以高收率得到具有良好或优异的对映选择性的相应的吡啶官能化的手性氧化膦（10个实施例，至多95％ee）。此外，已经证明，所获得的含吡啶的氧化膦在与PdCl 2的反应中作为三齿配体，通过C sp 3
• Nitrogen-enriched porous carbon supported Pd-nanoparticles as an efficient catalyst for the transfer hydrogenation of alkenes
  作者：Jie Li、Xin Zhou、Ning-Zhao Shang、Cheng Feng、Shu-Tao Gao、Chun Wang

  DOI：10.1039/c8nj03656j

  日期：——

  g-C3N4 as a nitrogen source and a self-sacrificial template. The prepared Pd@NPC exhibited superior catalytic activity and chemoselectivity for the catalytic transfer hydrogenation of alkenes under mild conditions with formic acid as a hydrogen donor. Moreover, the catalyst displays high structure stability, and can be reused for five runs without any significant decrease of its catalytic activity and

  将超细钯纳米颗粒固定在富氮多孔碳纳米片（NPC）上，该碳纳米片是用gC 3 N 4作为氮源和自牺牲模板制备的。所制得的Pd @ NPC在温和条件下，以甲酸为氢供体，对烯烃进行催化转移加氢显示出优异的催化活性和化学选择性。而且，该催化剂显示出高的结构稳定性，并且可以重复使用五次而不会显着降低其催化活性和明显的Pd浸出。这项工作提供了一种简便可行的方法来制造富氮碳纳米片，并构造高级钯负载的多相催化剂以实现高催化活性。
• Catalytic asymmetric hydrogenation using a [2.2]paracyclophane based chiral 1,2,3-triazol-5-ylidene–Pd complex under ambient conditions and 1 atmosphere of H₂
  作者：Ayan Dasgupta、Venkatachalam Ramkumar、Sethuraman Sankararaman

  DOI：10.1039/c5ra03021h

  日期：——

  Chiral 1,2,3-triazol-5-ylidene–Pd complexes with the planar chiral [2.2]paracyclophane wing tip group have been synthesized and structurally characterized. The complex with a labile acetonitrile co-ligand is an excellent catalyst for chemoselective hydrogenation of alkynes and alkenes and enantioselective hydrogenation of prochiral alkenes at ambient conditions and 1.0 atmosphere of H2.

  具有平面手性[2.2]对环环糊精翼尖基团的手性1,2,3-三唑-5-亚烷基-Pd配合物已经合成并在结构上进行了表征。具有不稳定的乙腈共配体的配合物是在环境条件和1.0大气压的H 2下炔烃和烯烃的化学选择性加氢和前手性烯烃的对映选择性加氢的极佳催化剂。
• Synthesis of γ-Sulfur-Substituted Ketones via Rh(II)/Sc(III) a Cocatalyzed Three-Component Reaction of Diazo Compounds with Thiophenols and Enones
  作者：Guolan Xiao、Chaoqun Ma、Xiang Wu、Dong Xing、Wenhao Hu

  DOI：10.1021/acs.joc.7b03074

  日期：2018.4.20

  A facile method for the synthesis of γ-sulfur-substituted ketones is developed via a Rh(II)/Sc(III) cocatalyzed three-component reaction of diazo compounds with thiophenols and enones. With this method, different γ-sulfur-substituted ketones were obtained in moderate to high yields with good diastereoselectivities.

  通过Rh（II）/ Sc（III）共催化重氮化合物与硫酚和烯酮的三组分反应，开发了一种简便的合成γ-硫取代的酮的方法。用这种方法，可以以中等到高产率获得具有良好非对映选择性的不同的γ-硫取代的酮。
• Zinc phthalocyanine with PEG-400 as a recyclable catalytic system for selective reduction of aromatic nitro compounds
  作者：Upendra Sharma、Neeraj Kumar、Praveen Kumar Verma、Vishal Kumar、Bikram Singh

  DOI：10.1039/c2gc35452g

  日期：——

  for the first time. The present catalytic system was successfully employed for the reduction of carbonyl and ester compounds to corresponding alcohols and reductive amination of benzaldehydes with primary amines to form corresponding secondary amines. Remarkable advantages of the present catalytic method include low loading of metal, avoidance of toxic ligands and high isolated yields. The catalyst was

  建立了带有PEG-400的酞菁锌作为催化体系，用于将芳香族硝基化合物化学和区域选择性还原为相应的胺。很好地耐受各种可还原的官能团，例如酸，酰胺，酯，卤素，内酯，腈，N-苄基，O-苄基，羟基和杂环。由O直接合成苯并三唑-二硝基苯是首次获得的。本催化体系已成功地用于将羰基和酯化合物还原成相应的醇，以及将苯甲醛与伯胺还原胺化以形成相应的仲胺。本催化方法的显着优点包括金属的低负载，避免有毒的配体和高的分离产率。催化剂可循环使用多达四次，而不会损失任何选择性和活性。