2-(1-乙氧基亚乙基)丙二腈 | 5417-82-3

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(1-乙氧基亚乙基)丙二腈
• 中文别名: 1-氧基马来腈；乙氧基乙缩醛马来腈；1-(乙氧基乙烯基)丙二腈
• 英文名称: (1-ethoxyethylidene)malononitrile
• 英文别名: 3,3-dicyano-2-ethoxyprop-2-ene；2-(1-ethoxyethylidene)malononitrile；2-(1-ethoxyethylidene)propanedinitrile
• CAS: 5417-82-3
• 化学式: C₇H₈N₂O
• mdl: MFCD00001852
• 分子量: 136.153
• InChiKey: BOSVWXDDFBSSIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C(lit.)
• 沸点：
  250.42°C (rough estimate)
• 密度：
  1.1778 (rough estimate)
• 溶解度：
  可溶于氯仿、二氯甲烷
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与不相容材料及强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xi
• 安全说明：
  S26,S28,S36/37/39,S45
• 危险类别码：
  R20/21/22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险品运输编号：
  UN 3439 6.1/PG 3
• 危险类别：
  6.1(b)
• RTECS号：
  TY1510000
• 包装等级：
  III
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352+P312,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P403+P233,P405,P501
• 危险性描述：
  H301,H311,H331,H315,H319,H335
• 储存条件：
  密封储存，宜存放在阴凉、干燥的仓库中。

SDS

Name:	(1-Ethoxyethylidene)-Malononitrile 99+% Material Safety Data Sheet
Synonym:	(1-Ethoxyethylidene)propanedinitrile
CAS:	5417-82-3

Section 1 - Chemical Product MSDS Name:(1-Ethoxyethylidene)-Malononitrile 99+% Material Safety Data Sheet
Synonym:(1-Ethoxyethylidene)propanedinitrile

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5417-82-3	(1-Ethoxyethylidene)malononitrile	99+	226-521-5

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.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.
Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration.

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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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
May be partially metabolized to cyanide in the body.
Antidote: Always have a cyanide antidote kit on hand when working with cyanide compounds. Get medical advice to use.

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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.
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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. 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 ingestion and inhalation.
Storage:
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# 5417-82-3: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: beige
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 90.00 - 92.00 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:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5417-82-3: TY1510000 LD50/LC50:
Not available.
Carcinogenicity:
(1-Ethoxyethylidene)malononitrile - 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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 5417-82-3: No information available.
Canada
CAS# 5417-82-3 is listed on Canada's NDSL List.
CAS# 5417-82-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5417-82-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

介绍

1-氧基马来腈的沸点为312.6°C（760mmHg），熔点为90-92°C，是一种典型的丙二腈类衍生物。它被广泛用作除草剂和生长调节剂。

用途

在农药领域，1-氧基马来腈表现出优异的活性，在除草剂、杀虫剂及杀菌剂等方面都有深入的研究。

制备过程

以4-戊烷基苯甲酸甲酯作为起始物料，经过碱性水解制得4-戊烷基苯甲酸。随后通过芳香环的氢化反应，并进行结晶分离，最终获得高纯度的反式-4-戊基环己烷甲酸。

在上述氢化过程中，含钌催化剂的性能优于铂或钯碳催化系统。近年来，我们开发并应用了高效的钌镍-碳催化剂（RNC-5，5% Ru - Ni/C，Ru:Ni=9:1），该催化体系能高效合成多种不同的立体异构体，并获得含量较高的反式4-烷基环己基羧酸衍生物。图1展示了反式-4-戊基环己烷甲酸的合成路线。


反应信息

• 作为反应物：
  描述：

  2-(1-乙氧基亚乙基)丙二腈 在 碘代三甲硅烷 、 氨 作用下， 以 甲醇 、 乙二醇乙醚 、 水 、 乙腈 为溶剂， 反应 43.0h， 生成 4-氨基-5-氧代-8h-吡啶并[2,3-d]嘧啶
  参考文献：
  名称：

  [DE] SULFONAMIDE
  [EN] SULFONAMIDES
  [FR] SULFONAMIDES

  摘要：

  公式（I）中R6、R7、R8、R9和X具有权利要求1中指定的含义，是酪氨酸激酶抑制剂，特别是TIE-2和Raf激酶，可用于治疗肿瘤。

  公开号：

  WO2005105797A1
• 作为产物：
  描述：

  原乙酸三乙酯 、 丙二腈 反应 0.75h， 以99%的产率得到2-(1-乙氧基亚乙基)丙二腈
  参考文献：
  名称：

  作为具有新型结合模式的 PDHc-E1 抑制剂的 2,6-二甲基-4-氨基嘧啶腙的设计、合成和抗真菌活性

  摘要：

  一系列新型 2,6-二甲基-4-氨基嘧啶腙5被合理设计和合成为丙酮酸脱氢酶复合物 E1 (PDHc-E1) 抑制剂。化合物5强烈抑制大肠杆菌（E.coli）PDHc-E1（IC 50值为 0.94–15.80 μM）。分子对接、定点诱变、酶促和抑制动力学分析表明，化合物5竞争性抑制 PDHc-E1 并以“直线”模式结合在大肠杆菌PDHc-E1 活性位点，这是一种新的结合模式. 在体外抗真菌试验中，大多数化合物5在50μg/ mL的显示针对六个测试植物病原性真菌，包括菌丝生长超过80％的抑制灰霉病，念珠菌fructigena，炭疽病菌，和葡萄座腔dothidea侵染。值得注意的是，5f和5i对M. fructigena 的效力是商业杀菌剂克菌丹和百菌清的1.8-380 倍。在体内，与商业杀菌剂戊唑醇相比，5f和5i控制M. fructigena的生长。因此，5f和5i对防治果蝇桃褐腐病具有潜在的商业价值。

  DOI：

  10.1021/acs.jafc.0c07701

文献信息

• Synthesis of New Pyrazolopyrimidinedithiones and Pyrazolopyrimidinephosphines from Aminocyanopyrazoles
  作者：Fatma Allouche、Fahker Chabchoub、Mansour Salem、Gilbert Kirsch

  DOI：10.1080/00397911.2010.486516

  日期：2011.4.19

  Abstract A general, high-yielding synthetic protocol for the expedited synthesis of functionalized pyrazolopyrimidine dithione 2 and pyrazolodiazaphosphininethione 3 from amino-cyano pyrazole 1 precursors is presented.

  摘要 提出了一种从氨基-氰基吡唑 1 前体快速合成官能化吡唑并嘧啶二硫酮 2 和吡唑二氮杂膦硫酮 3 的通用、高产合成方案。
• Synthesis and properties of sildenafil isostere
  作者：Ziqi Su、Qi Zhang、Qieqiang Zhao、Wenyi Liu、Tao Zhao、Huiping Wang、Jiarong Li、Juan Xu

  DOI：10.1002/ardp.202100145

  日期：2021.10

  series of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized and evaluated for their anti-phosphodiesterase-5 (PDE-5) activity. A total of 28 compounds, containing alkyl and aryl groups at the 1-N and 3-C positions on the pyrazole ring, and also bearing different alkyl substituents on the piperazine ring were synthesized. Four compounds (4d, 5d, 6d, and 5o) were found to have better

  合成了一系列新型吡唑并[3,4- d ]嘧啶-4-酮衍生物，并评估了它们的抗磷酸二酯酶5 (PDE-5) 活性。共合成了 28 种化合物，它们在吡唑环的 1-N 和 3-C 位含有烷基和芳基，在哌嗪环上也带有不同的烷基取代基。发现四种化合物（4d、5d、6d和5o）对 PDE-5 具有更好的抑制活性（IC 50  < 10 nM）。所有四种最活跃的化合物都在 N1 位包含一个苯环。含有 3,5-二甲基哌嗪基的化合物比其他化合物表现出更好的活性。这些结果表明化合物5o可用作开发新的 PDE-5 抑制剂的先导结构。
• Pyrazolo [1,5-A] pyrimidine adenosine A2a receptor antagonists
  申请人：Clasby C. Martin

  公开号：US20060135526A1

  公开（公告）日：2006-06-22

  Compounds having the structural formula I are disclosed, wherein A is alkylene, or optionally substituted arylene, cycloalkylene or heteroaryldiyl; X is —C(O)— or —S(O) 2 —; R 1 is alkyl or cycloalkyl; R 2 is hydrogen, halo or —CN; R 3 is hydrogen or alkyl; R 4 is hydrogen, alkyl, alkoxy, hydroxyalkyl, aminoalkyl-, cycloalkyl, heterocycloalkyl, heterocycloalkyl substituted by alkyl, optionally substituted arylalkyl or optionally substituted heteroarylalkyl; or R 3 and R 4 , form an optionally substituted 5-7 membered ring, said ring optionally comprising an additional heteroatom ring member; R 7 is alkyl, optionally substituted phenyl, optionally substituted heteroaryl, cycloalkyl, halo, morpholinyl, optionally substituted piperazinyl, or optionally substituted azacycloalkyl. Also disclosed is the use of the compounds in the treatment of Parkinson's disease, alone or in combination with other agents for treating Parkinson's disease, pharmaceutical compositions comprising them and kits comprising the components of the combinations.

  揭示了具有结构式I的化合物，其中A是烷基，或者可选择地取代的芳基，环烷基或杂芳基二基；X是—C(O)—或—S(O)2—；R1是烷基或环烷基；R2是氢，卤素或—CN；R3是氢或烷基；R4是氢，烷基，烷氧基，羟基烷基，氨基烷基，环烷基，杂环烷基，被烷基取代的杂环烷基，可选择地取代的芳基烷基或可选择地取代的杂芳基烷基；或者R3和R4形成一个可选择地取代的5-7成员环，所述环可选择地包含一个额外的杂原子环成员；R7是烷基，可选择地取代的苯基，可选择地取代的杂芳基，环烷基，卤素，吗啉基，可选择地取代的哌嗪基，或可选择地取代的氮杂环烷基。还揭示了这些化合物在帕金森病治疗中的用途，单独或与其他治疗帕金森病的药剂组合使用，包含它们的药物组合物和包含组合物组分的工具包。
• [EN] THIOPHENE AND FURAN COMPOUNDS<br/>[FR] COMPOSES DE THIOPHENE ET DE FURANE
  申请人：LILLY CO ELI

  公开号：WO2005070916A1

  公开（公告）日：2005-08-04

  The present invention relates to thiophene and furan compounds and their pharmaceutically acceptable salts, and further relates to their use in treating schizophrenia, cognitive deficits associated with schizophrenia, Alzheimer's disease, dementia of the Alzheimer's type, mild cognitive impairment, or depression.

  本发明涉及噻吩和呋喃化合物及其药用可接受的盐，以及它们在治疗精神分裂症、与精神分裂症相关的认知缺陷、阿尔茨海默病、阿尔茨海默型痴呆、轻度认知障碍或抑郁症方面的用途。
• [EN] DIHYDROPYRAZOLOPYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS DIHYDROPYRAZOLOPYRIMIDINONE UTILISÉS EN TANT QU'EN TANT QU'INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2016192083A1

  公开（公告）日：2016-12-08

  The present invention is directed to dihydropyrazolopyrimidinonecompounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及式(I)的二氢吡唑并嘧啶酮化合物，该化合物作为治疗与磷酸二酯酶2 (PDE2)相关的中枢神经系统障碍的治疗剂是有用的。本发明还涉及使用这些化合物来治疗神经和精神障碍，如精神分裂症、精神病、帕金森病、帕金森病痴呆（PDD）或亨廷顿病，以及与纹状体功能减退或基底神经节功能障碍相关的疾病。

表征谱图