4-己-1-炔基苯甲醛 | 175203-90-4

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醛(含缩醛,半缩醛)
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-己-1-炔基苯甲醛
• 英文名称: 4-(1-hexynyl)benzaldehyde
• 英文别名: 4-(hex-1-yn-1-yl)benzaldehyde；4-(1-hexyn-1-yl)benzaldehyde；4-hex-1-ynyl benzaldehyde；4-Hex-1-ynylbenzaldehyde
• CAS: 175203-90-4
• 化学式: C₁₃H₁₄O
• mdl: MFCD00276593
• 分子量: 186.254
• InChiKey: MDAJCLIURGBJKY-UHFFFAOYSA-N

物化性质

• 沸点：
  106 °C
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2912299000

SDS

Name:	4-Hex-1-ynylbenzaldehyde tech Material Safety Data Sheet
Synonym:
CAS:	175203-90-4

Section 1 - Chemical Product MSDS Name:4-Hex-1-ynylbenzaldehyde tech Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175203-90-4	4-Hex-1-ynylbenzaldehyde		unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 175203-90-4: 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: Liquid
Color: yellow
Odor: Not available.
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: C13H14O
Molecular Weight: 186

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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, reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175203-90-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hex-1-ynylbenzaldehyde - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 175203-90-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175203-90-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175203-90-4 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：

  4-己-1-炔基苯甲醛 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以82%的产率得到4-N-己基苯甲醛
  参考文献：
  名称：

  [EN] RATIONALLY DESIGNED LAWSONE DERIVATIVES AS ANTIMICROBIALS AGAINST MULTIDRUG-RESISTANT STAPHYLOCOCCUS AUREUS
  [FR] DÉRIVÉS DE LAWSONE CONÇUS DE MANIÈRE RATIONNELLE EN TANT QU'AGENTS ANTIMICROBIENS CONTRE STAPHYLOCOCCUS AUREUS MULTIRÉSISTANT AUX ANTIBIOTIQUES

  摘要：

  劳森的萘醌衍生物被发现对金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌（MRSA）有效。这类化合物通常在特定萘醌化合物的3位含有取代基团，即2-羟基-1,4-萘醌。这些衍生物中，被称为系列中化合物6c的一种展现出了与两种商业抗生素氧氟沙星和环丙沙星对两种甲氧西林敏感的金黄色葡萄球菌（MSSA；ATCC 29213和ATCC 6538）株的抗菌活性相当的强大抗菌活性。在两种对氧氟沙星和环丙沙星产生耐药性的MRSA（ATCC BAA-44和ATCC BAA-1717）株的情况下，6c的抗菌活性几乎可以与万古霉素和达托霉素相匹敌。此外，6c对万古霉素中间型和达托霉素非敏感型MRSA（ATCC 700699）株也有效。除了疗效外，与常规抗生素相比，6c的耐药性表现有了显著改善。

  公开号：

  WO2021041506A1
• 作为产物：
  描述：

  对溴苯甲醛 、 1-己炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以91%的产率得到4-己-1-炔基苯甲醛
  参考文献：
  名称：

  开发Hy提高1-氮杂三烯的6π-电环化反应的效率。

  摘要：

  与肟醚相比，具有更大的几何不稳定性，被用作克服Z-肟醚氮杂三烯不愿意进行电环化以合成硼酸化（杂芳族）吡啶和环稠合类似物的基础。这种现在可以以高收率获得以前难以获得的三和四取代的3-硼基吡啶。

  DOI：

  10.1021/acs.orglett.9b02455

文献信息

• [EN] RATIONALLY DESIGNED LAWSONE DERIVATIVES AS ANTIMICROBIALS AGAINST MULTIDRUG-RESISTANT STAPHYLOCOCCUS AUREUS<br/>[FR] DÉRIVÉS DE LAWSONE CONÇUS DE MANIÈRE RATIONNELLE EN TANT QU'AGENTS ANTIMICROBIENS CONTRE STAPHYLOCOCCUS AUREUS MULTIRÉSISTANT AUX ANTIBIOTIQUES
  申请人：UNIV KENT STATE OHIO

  公开号：WO2021041506A1

  公开（公告）日：2021-03-04

  Naphthoquinone derivatives of Lawsone have been found to be effective against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA). Such compounds generally contain a substituent group at the 3-position of a specific naphthoquinone compound, i.e. 2-hydroxy-1,4-naphthoquinone. One of these derivatives referred to as compound 6c in the series exhibits potent antimicrobial activity that is comparable to that of the two commercial antibiotics ofloxacin and ciprofloxacin against the two strains of methicillin sensitive Staphylococcus aureus (MSSA; ATCC 29213 and ATCC 6538). In the case of two strains of MRSA (ATCC BAA-44 and ATCC BAA-1717) that have developed drug resistance to both ofloxacin and ciprofloxacin, the antimicrobial activity of 6c can almost rival that of vancomycin and daptomycin. Furthermore, 6c is also effective against vancomycin-intermediate and daptomycin non-susceptible strain of MRSA (ATCC 700699). Besides the efficacy, 6c has a much improved drug resistance profile in comparison with the conventional antibiotics.

  劳森的萘醌衍生物被发现对金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌（MRSA）有效。这类化合物通常在特定萘醌化合物的3位含有取代基团，即2-羟基-1,4-萘醌。这些衍生物中，被称为系列中化合物6c的一种展现出了与两种商业抗生素氧氟沙星和环丙沙星对两种甲氧西林敏感的金黄色葡萄球菌（MSSA；ATCC 29213和ATCC 6538）株的抗菌活性相当的强大抗菌活性。在两种对氧氟沙星和环丙沙星产生耐药性的MRSA（ATCC BAA-44和ATCC BAA-1717）株的情况下，6c的抗菌活性几乎可以与万古霉素和达托霉素相匹敌。此外，6c对万古霉素中间型和达托霉素非敏感型MRSA（ATCC 700699）株也有效。除了疗效外，与常规抗生素相比，6c的耐药性表现有了显著改善。
• Aerobic Direct Dioxygenation of Terminal/Internal Alkynes to α‐Hydroxyketones by an Fe Porphyrin Catalyst
  作者：Kento Kimura、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1002/asia.202101019

  日期：2021.11.15

  The synthesis of α-hydroxyketones through the dioxygenation of alkynes is reported. The reaction is mediated by an Fe porphyrin complex and pinacolborane at room temperature under air as a green oxidant, furnishing α-hydroxyketones in up to 93% yields. The mild reaction conditions allow chemoselective oxidation with good functional group tolerance.

  报道了通过炔烃的双氧合合成 α-羟基酮。该反应由铁卟啉配合物和频哪醇硼烷在室温下作为绿色氧化剂介导，以高达 93% 的产率提供 α-羟基酮。温和的反应条件允许具有良好官能团耐受性的化学选择性氧化。
• Green Catalysts: Solid-Phase Peptide Carbene Ligands in Aqueous Transition-Metal Catalysis
  作者：Kasper Worm-Leonhard、Morten Meldal

  DOI：10.1002/ejoc.200800633

  日期：2008.11

  functionalized imidazolium ions containing a pyridine moiety and carboxylic acid functionality has been synthesized in solution. These compounds serve as N-heterocyclic carbene precursors and were attached to a dipeptide on solid support by means of standard peptide coupling techniques. Treatment with base generated the corresponding carbenes, which were directly complexed to palladium(II) and subsequently studied

  已经在溶液中合成了一系列含有吡啶部分和羧酸官能团的官能化咪唑鎓离子。这些化合物用作 N-杂环卡宾前体，并通过标准肽偶联技术连接到固体支持物上的二肽上。用碱处理产生相应的卡宾，它们直接与钯 (II) 络合，随后通过质谱和核磁共振光谱进行研究。负载型单卡宾催化剂7成功应用于Sonogashira和Suzuki交叉偶联反应，并以优异的收率分离出交叉偶联产物。双（卡宾）催化剂 8 成功应用于高产铃木交叉偶联反应的溶液中。此外，该催化剂被证明在水性介质中是稳定的，这使得铃木交叉偶联反应可以在水中进行。当负载型催化剂 7 被回收并在水中进行 Suzuki 交叉偶联反应的重复循环时，没有观察到催化活性的损失。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Exploring Bis(cyclometalated) Ruthenium(II) Complexes as Active Catalyst Precursors: Room-Temperature Alkene-Alkyne Coupling for 1,3-Diene Synthesis
  作者：Jing Zhang、Angel Ugrinov、Yong Zhang、Pinjing Zhao

  DOI：10.1002/anie.201402098

  日期：2014.8.4

  bis(cyclometalated) ruthenium(II) catalyst precursors for CC coupling reactions between alkene and alkyne substrates. The complex [(cod)Ru(3‐methallyl)2] reacts with benzophenone imine or benzophenone in a 1:2 ratio to form bis(cyclometalated) ruthenium(II) complexes (1). The imine‐ligated complex 1 a promoted room‐temperature coupling between acrylic esters and amides with internal alkynes to form 1,3‐diene

  描述了一类新的双（环金属化）钌 (II) 催化剂前体的开发，用于烯烃和炔烃底物之间的C  C 偶联反应。配合物 [(cod)Ru(3-methallyl) 2 ] 与二苯甲酮亚胺或二苯甲酮以 1:2 的比例反应形成双（环金属化）钌 (II) 配合物 ( 1 )。亚胺连接的配合物1a促进了丙烯酸酯和酰胺与内部炔烃之间的室温偶联，形成 1,3-二烯产物。提议的催化循环包括通过氧化环化、β-氢化物消除和C H 键还原消除形成C  C 键。这个 Ru II / Ru IV途径与观察到的1 a 的催化反应性一致，用于温和的尾对尾丙烯酸甲酯二聚反应和通过 [2+2] 降冰片烯/炔环加成形成环丁烯。
• Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes
  作者：Santiago Cañellas、John Montgomery、Miquel À. Pericàs

  DOI：10.1021/jacs.8b09677

  日期：2018.12.19

  The nickel-catalyzed synthesis of tetrasubstituted cyclobutenes from alkynes is reported. This transformation is uniquely promoted by the use of a primary aminophosphine, an unusual ligand in nickel catalysis. Mechanistic insights for this new transformation are provided, and postreaction modifications of the cyclobutene products to stereodefined cyclic and acyclic compounds are reported, including

  报道了镍催化从炔烃合成四取代环丁烯的方法。这种转化是通过使用伯氨基膦（镍催化中一种不常见的配体）来独特促进的。提供了这种新转化的机理见解，并报道了环丁烯产物对立体定义的环状和无环化合物的反应后修饰，包括表-特鲁昔酸的合成。