糠醛肟 | 1121-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 糠醛肟
• 中文别名: Β-呋喃酰一肟
• 英文名称: 2-furaldehyde oxime
• 英文别名: furfural oxime；furan-2-carbaldehyde oxime；furan-2-aldoxime；2-furfuraldoxime；2-furancarboxaldehyde oxime；2-furancarbaldehyde oxime；2-furylaldehyde oxime；furfuraldehyde oxime；2-furyl aldoxime；2-furaldoxime；furfuryl oxime；N-(furan-2-ylmethylidene)hydroxylamine
• CAS: 1121-47-7
• 化学式: C₅H₅NO₂
• mdl: MFCD08445568
• 分子量: 111.1
• InChiKey: UYTMLDBQFLIQJA-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C
• 沸点：
  208.19°C (rough estimate)
• 密度：
  1.3113 (rough estimate)
• 保留指数：
  1048

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 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：
  45.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22
• 海关编码：
  2932190090
• 储存条件：
  存储条件：室温、密封保存，并置于干燥处。

SDS

Name:	2-Furaldehyde oxime 97% Material Safety Data Sheet
Synonym:
CAS:	1121-47-7

Section 1 - Chemical Product MSDS Name:2-Furaldehyde oxime 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1121-47-7	2-Furaldehyde oxime	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1121-47-7: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 78 - 80 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: C5H5NO2
Molecular Weight: 111.1

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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.
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# 1121-47-7: LT7900000 LD50/LC50:
Not available.
Carcinogenicity:
2-Furaldehyde oxime - 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
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.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 1121-47-7: No information available.
Canada
CAS# 1121-47-7 is listed on Canada's NDSL List.
CAS# 1121-47-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1121-47-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：用于合成呋喃类药物。

反应信息

• 作为反应物：
  描述：

  糠醛肟 在 phosphotungstic acid 双氧水 作用下， 以 various solvent(s) 为溶剂， 反应 4.0h， 以84%的产率得到糠醛
  参考文献：
  名称：

  金属卟啉和杂多酸催化离子液体中CNOH键的氧化：一氧化氮合酶的仿生模型

  摘要：

  离子液体中的水溶性铁（III）卟啉和磷钨酸是有效的催化剂，可用于H 2 O 2介导的N-羟基精氨酸和其他肟中CNOH键的氧化。可以容易地从反应介质中分离出作为氧化产物而生成的羰基化合物。这些系统可作为一氧化氮合酶（NOS）的仿生模型，固定在离子液体中的催化剂可以轻松回收和再利用。

  DOI：

  10.1016/j.tetlet.2005.02.088
• 作为产物：
  描述：

  糠醛 在 盐酸羟胺 、 sodium carbonate 作用下， 以 正己烷 、 水 为溶剂， 反应 2.0h， 生成 糠醛肟
  参考文献：
  名称：

  通过串联化学-酶级联对醛类到腈类的无氰转化和酰胺的一锅法合成进行编程

  摘要：

  腈由于其多功能转化而被广泛应用于合成药物、农用化学品和材料。尽管已经开发了多种将腈基引入有机分子的方法，但其中大多数都需要使用剧毒化学品、过渡金属或苛刻的条件。在这项工作中，我们报道了一种更环保的化学酶级联反应，可以从容易获得的醛中合成烷基腈和芳基腈，并通过人工酶级联进一步转化为相应的酰胺。设计了一个双相反应系统，通过简单的相分离来桥接化学合成和酶催化。双相系统主要完美避免了羟胺对恶臭假单胞菌醛肟脱水酶的失活(OxdF1) 和来自Aurantimonas manganoxydans ATCC BAA-1229 (NHase1229) 的腈水合酶。对于各种腈的合成，通过化学-酶级联获得了大约 60% 的中等分离产率。有趣的是，在大肠杆菌细胞中，通过 OxdF1 和 NHase1229 的协同催化，脱水和水合这两个看似矛盾的反应依次进行合成酰胺。在一升规模下，苯甲酰胺的分离产率约为 62%。此

  DOI：

  10.1039/d2ra03256b

文献信息

• Convenient One-Pot Synthesis of 2,5-Disubstituted Oxazoles via a Catalytic Oxidative Dehydrogenation of F₃CSO₃H·SiO₂-DDQ/CuCl₂/LiCl
  作者：Shizhen Yuan、Zhen Li、Ling Xu

  DOI：10.1002/jhet.1637

  日期：2013.11

  A facile one‐pot synthesis of 2,5‐disubstituted oxazoles was developed via cyclization of aldoximes and phenylacetylene then dehydrogenation oxidation. 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone was studied for the selective oxidation of oxazolines using Cu2+/Li+ as catalyst and O2 as indirect oxidant. The reaction results showed that this catalyst system can effectively catalyze the oxidation of oxazolines

  通过醛肟和苯乙炔的环化然后脱氢氧化制得了一种简便的一锅合成2,5-二取代的恶唑。以Cu 2+ / Li +为催化剂，O 2为间接氧化剂，研究了2,3-二氯-5,6-二氰基-1,4-苯醌对氧化唑啉的选择性氧化。反应结果表明，该催化剂体系可有效催化恶唑啉氧化为相应的恶唑。因此，通过2,3-二氯-5,6-二氰基-1,4-苯醌/ CuCl 2 / LiCl / O 2的催化氧化，很容易以高收率合成各种多取代的恶唑。
• TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes
  作者：Jalil Noei、Ahmad R. Khosropour

  DOI：10.1016/j.tetlet.2008.09.084

  日期：2008.12

  The combination of TiCl3OTf with 1-butyl-3-methylimidazolium bromide is found to be an efficient and novel catalytic system for chemoselective one-pot transformation of arylaldoximes to their corresponding thioamides in high to excellent yields.

  发现TiCl 3 OTf与1-丁基-3-甲基咪唑鎓溴化物的组合是一种高效新颖的催化系统，用于以高产率至优异产率将芳基醛肟化学选择性地一锅转化为相应的硫代酰胺。
• Copper-Catalyzed Regioselective Synthesis of<i>N</i>-Aryl Amides from Aldoximes and Aryl Halides
  作者：Niranjan Panda、Raghavender Mothkuri、Dinesh Kumar Nayak

  DOI：10.1002/ejoc.201301868

  日期：2014.3

  Ligand-assisted copper-catalyzed reaction of aldoximes with aryl halides is described for the regioselective synthesis of N-aryl amides. This protocol is simple and compatible with a wide range of functional groups attached to the aryl ring of the halides as well as aldoximes.

  配体辅助铜催化醛肟与芳基卤化物的反应被描述为 N-芳基酰胺的区域选择性合成。该协议简单且与连接到卤化物和醛肟的芳环上的各种官能团兼容。
• One-Pot Copper(I)-Catalyzed Synthesis of 3,5-Disubstituted Isoxazoles
  作者：Trond V. Hansen、Peng Wu、Valery V. Fokin

  DOI：10.1021/jo050163b

  日期：2005.9.1

  3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used

  通过便利的一锅三步程序，利用原位生成的腈氧化物和末端乙炔之间的区域选择性铜（I）催化的环加成反应，以方便的一锅三步程序以高收率获得了3,5-二取代的异恶唑。大多数官能团不干扰反应，该反应可以在水性溶剂中进行而无需氧气的保护。由于所有试剂都以化学计量的形式使用，因此副产物的形成得以最小化。
• Copper(<scp>ii</scp>)-promoted direct conversion of methylarenes into aromatic oximes
  作者：Jiatao Yu、Ming Lu

  DOI：10.1039/c5ob00923e

  日期：——

  A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)₂ as catalyst, NHPI (N-hydroxyphthalimide) as additive, tert-butyl nitrite (TBN) as both the nitrogen source and the oxidant. The process proceeds under mild conditions, tolerates a wide range of substrates, affording the corresponding aromatic oximes in 63–86% yields.

  一个简单高效的催化体系已经开发出来，可以直接将甲基芳烃转化为芳香肟，使用Cu(OAc)2作为催化剂，NHPI（N-羟基邻苯二甲酰亚胺）作为添加剂，叔丁基硝rite（TBN）既作为氮源也作为氧化剂。该过程在温和条件下进行，能够容忍广泛的底物范围，以63-86%的产率得到相应的芳香肟。