水杨醛腙 | 3291-00-7

• 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 - 酚类
• 中文名称: 水杨醛腙
• 中文别名: 2-羟基苯甲醛肼酮
• 英文名称: 2-(hydrazonomethyl)phenol
• 英文别名: salicylaldehyde hydrazone；2-hydroxybenzaldehyde hydrazone；Benzaldehyde, 2-hydroxy-, hydrazone；2-methanehydrazonoylphenol
• CAS: 3291-00-7
• 化学式: C₇H₈N₂O
• mdl: MFCD00007626
• 分子量: 136.153
• InChiKey: MYUNWHTZYXUCIK-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C(lit.)
• 沸点：
  292.1±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2928000090
• 储存条件：
  低于25℃保存

SDS

Name:	Salicylaldehyde hydrazone 98% Material Safety Data Sheet
Synonym:	2-Hydroxybenzaldehyde hydrazone; Salicylhydrazone; Salicylic aldehyde hydrazone; Salicylidene hydrazone; Salzone
CAS:	3291-00-7

Section 1 - Chemical Product MSDS Name:Salicylaldehyde hydrazone 98% Material Safety Data Sheet
Synonym:2-Hydroxybenzaldehyde hydrazone; Salicylhydrazone; Salicylic aldehyde hydrazone; Salicylidene hydrazone; Salzone

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3291-00-7	Benzaldehyde, 2-hydroxy-, hydrazone	98	221-953-0

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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
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. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion. 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. Clean up spills immediately, observing precautions in the Protective Equipment section. 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# 3291-00-7: 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 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: Flakes
Color: slightly yellow - shiny
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 96-99 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: C7H8N2O
Molecular Weight: 136.15

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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, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3291-00-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Benzaldehyde, 2-hydroxy-, hydrazone - 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
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# 3291-00-7: No information available.
Canada
CAS# 3291-00-7 is listed on Canada's NDSL List.
CAS# 3291-00-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3291-00-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

在三颈烧瓶中依次加入30 mL乙醇、10 mL水合肼和10滴三乙胺。将0.23 g（1.9 mmol）水杨醛溶解于30 mL乙醇中，置于恒压漏斗中缓慢滴加至三颈烧瓶内。滴加结束后，反应回流4小时。冷却后，生成的白色固体沉淀被过滤出来，并用乙醇洗涤，最后在真空条件下干燥，得到产物水杨醛腙。

反应信息

• 作为反应物：
  描述：

  水杨醛腙 在 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 46.0h， 以85%的产率得到水杨醛
  参考文献：
  名称：

  Attanasi, Orazio; Gasperoni, Simonetta; Carletti, Claudio, Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 6, p. 1063 - 1066

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到水杨醛腙
  参考文献：
  名称：

  使用芳基和二茂铁基席夫碱衍生的配体，铑催化1-辛烯的加氢甲酰化

  摘要：

  通过Schiff碱缩合反应合成了带有螯合N，O齿状芳基和二茂铁基的Rh（I）的单金属和杂双金属配合物，并使用1 H NMR，13 C { 11 H NMR和傅立叶变换红外光谱，元素分析和质谱。新的单金属和杂双金属配合物被评估为在95°C和40 bar下1-辛烯加氢甲酰化反应中潜在的催化剂前体。二茂铁亚胺单核化合物在加氢甲酰化实验中没有活性。Rh（I）单金属和二茂铁-Rh（I）异双金属预催化剂在加氢甲酰化反应中表现出良好的活性和1-辛烯的转化率以及对醛的出色化学选择性。

  DOI：

  10.1002/aoc.3593
• 作为试剂：
  描述：

  咪唑 、 对溴三氟甲苯 在 copper(I) oxide 水杨醛腙 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以94%的产率得到1-(4-三氟甲基苯基)咪唑
  参考文献：
  名称：

  高效，温和的铜催化的芳基溴化物和碘化物的N-和C-芳基化反应。

  摘要：

  已经开发出用于氮杂环，酰胺，氨基甲酸酯的温和，有效的铜催化的N-芳基化方法，以及丙二酸衍生物的C-芳基化方法，可以提供高收率的芳基化产物，且具有出色的选择性。发现廉价的，空气稳定的催化剂体系将催化铜盐或氧化物与一组结构简单的螯合配体结合在一起，可大大促进咪唑与芳基溴化物或碘化物的N-芳基化反应。该反应显示与宽范围的芳基卤化物相容，包括空间受阻的，贫电子的和富电子的卤化物，可在特别温和的条件下（50-82摄氏度）提供芳基化产物。还研究了配体和催化剂载量的下限以及由带有那些配体的配合物相对于亲核体催化的Ullmann型缩合的范围。螯合席夫碱Chxn-Py-Al（1c）生成一种非常通用的铜催化剂，用于吡咯，吲哚，1,2,4-三唑，酰胺和氨基甲酸酯的N-芳基化；在温和的条件下（50-82摄氏度）将丙二酸二乙酯，氰基乙酸乙酯和丙二腈与芳基碘化物进行C-芳基化反应。就某些这类亲核试剂的乌尔曼型芳基化而

  DOI：

  10.1002/chem.200400582

文献信息

• Synthesis and Characterization of Hydrazone and Azine Derivatives of Bis(cyclopentadienyl)titanium(IV)
  作者：Brij Khera、Anand Kumar Sharma、Narender Kumar Kaushik

  DOI：10.1246/bcsj.58.793

  日期：1985.2

  Pentacoordinated hydrazone and azine derivatives of bis(cyclopentadienyl)titanium(IV) of the type [(OC6H4CR : NNHR′)TiCl(Cp)2] and [(OC6H4CR″ : NN : CR″C6H4O)Ti(Cp)2], where R=H or CH3, R′=H, C6H5 or C6H3(NO2)2 and R″=H or CH3, have been prepared. The products were characterized by chemical analyses, electrical conductance, IR, 1H NMR, and electronic spectral studies.

  [(OC6H4CR:NNHR')TiCl(Cp)2]和[(OC6H4CR″:NN:CR″C6H4O)Ti(Cp)2]型双(环戊二烯基)钛(IV)的五配位腙和吖嗪衍生物，其中R=H 或 CH3、R'=H、C6H5 或 C6H3(NO2)2 和 R"=H 或 CH3 已制备。通过化学分析、电导率、IR、1H NMR 和电子光谱研究对产物进行表征。
• Calix[4]arene Schiff bases—potential ligands for fluorescent studies
  作者：Mary F. Mahon、John McGinley、A. Denise Rooney、John M.D. Walsh

  DOI：10.1016/j.tet.2008.09.091

  日期：2008.12

  derivatives incorporating imine substituents were synthesised from the Schiff-base reaction of 25,27-bis[2-[(1-formyl-2-phenyl)oxy]ethyl]-p-tert-butylcalix[4]arene (1) with the appropriate amine or hydrazone. All compounds were characterised by various spectroscopic and analytical techniques, and in three cases, by X-ray crystallographic studies. In the case of compound 2, inclusion compounds were synthesised

  从25,27-双[2-[（[1-甲酰基-2-苯基）氧基]乙基] -p-的席夫碱反应合成了一系列新的掺有亚胺取代基的双臂杯[4]芳烃衍生物。叔丁基杯[4]芳烃（1）与适当的胺或。所有化合物均通过各种光谱学和分析技术进行了表征，在三种情况下，通过X射线晶体学研究对其进行了表征。在化合物的情况下2，用两个合成的包接化合物米-二甲苯和二甲基甲酰胺及其X射线结构揭示了这些包含位点-分别位于悬臂之间和上腔中。在所有情况下，悬吊臂都弯曲成彼此远离，而不是采用面对面的构造。
• Facile Method for the Conversion of Semicarbazones/Thiosemicarbazones into Azines (Under Microwave Irradiation) and Oxadiazoles (by Grinding)
  作者：Gautam Chattopadhyay、Partha Sinha Ray

  DOI：10.1080/00397911.2010.515334

  日期：2011.9.1

  Abstract In an effective transformation, semicarbazones/thiosemicarbazones are smoothly converted into azines under microwave irradition. Oxadiazoles are also obtained from semicarbazones by reaction with bromine generated in situ via a grinding reaction in the solid phase.

  摘要 在有效的转化过程中，缩氨基脲/缩氨基硫脲在微波照射下顺利转化为吖嗪。恶二唑也可通过与通过固相研磨反应原位产生的溴反应而从缩氨基脲反应获得。
• The reaction of lead tetraacetate with unsubstituted hydrazones of some aromatic ketones and aldehydes
  作者：A. Stojiljković、N. Orbović、S. Sredojević、M.Lj. Mihailović

  DOI：10.1016/s0040-4020(01)98787-3

  日期：1970.1

  N-Unsubstituted hydrazones of some aromatic ketones and aldehydes were found to react with lead tetraacetate giving the corresponding diazo compounds as primary reaction products, and the derived 1-monoacetoxy- and 1,1-diacetoxy-1-arylalkanes, as well as azines, as final products. The yields obtained depend on the stability of the diazo compound initially formed and on the experimental conditions employed

  发现某些芳族酮和醛的N-未取代与四乙酸铅反应，生成相应的重氮化合物作为主要反应产物，以及衍生的1-单乙酰氧基和1,1-二乙酰氧基-1-芳基烷烃以及嗪类，作为最终产品。所获得的产率取决于最初形成的重氮化合物的稳定性以及所采用的实验条件（四乙酸铅的量，酸或碱的存在）。讨论了产品形成的机制。
• A novel dual-channel chemosensor for CN− using asymmetric double-azine derivatives in aqueous media and its application in bitter almond
  作者：Peng-Xiang Pei、Jing-Han Hu、Ying Chen、You Sun、Jing Qi

  DOI：10.1016/j.saa.2017.03.052

  日期：2017.6

  In this paper, we have designed and synthesized a novel sensor L1 based on asymmetric double-azine derivatives, which showed both "naked eye" recognition and fluorescence responses for CN- in DMSO/H2O (v/v=4:1, pH=7.20) solution. This simple sensor L1 could distinguish CN- from coexisting anions via the way of deprotonation and sensing mechanism of intramolecular charge transfer (ICT), and the minimum

  在本文中，我们设计并合成了基于不对称双嗪衍生物的新型传感器L1，该传感器在DMSO / H2O（v / v = 4：1，pH = 7.20）解决方案。这种简单的传感器L1可以通过去质子化和分子内电荷转移（ICT）的感应机制将CN-与共存阴离子区分开，并且传感器L1对CN-的荧光响应的最小检测限降至9.47×10-7M 。此外，我们已经成功地利用传感器L1来检测苦杏仁中的CN-。还准备了含有L1的测试条，可以用作检测水性介质中CN-的实用比色工具。