1-吡啶甲酯 | 1530-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-吡啶甲酯
• 中文别名: 1-哌啶羰腈
• 英文名称: 1-piperidinonitrile
• 英文别名: 1-piperidinylcarbonnitrile；1-piperidinecarbonitrile；piperidine-1-carbonitrile
• CAS: 1530-87-6
• 化学式: C₆H₁₀N₂
• 分子量: 110.159
• InChiKey: NVPICXQHSYQKGM-UHFFFAOYSA-N

物化性质

• 沸点：
  102 °C10 mm Hg(lit.)
• 密度：
  0.951 g/mL at 25 °C(lit.)
• 闪点：
  207 °F
• 最大波长(λmax)：
  214nm(MeOH)(lit.)
• 稳定性/保质期：
  避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2933399090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• WGK Germany：
  3
• 危险品运输编号：
  UN 3276
• 储存条件：
  密封储存，存放在阴凉干燥的库房中，并远离火源。

SDS

Name:	1-Piperidinecarbonitrile 97+% Material Safety Data Sheet
Synonym:	None Known
CAS:	1530-87-6

Section 1 - Chemical Product MSDS Name:1-Piperidinecarbonitrile 97+% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1530-87-6	1-Piperidinecarbonitrile	97+	216-233-8

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin. May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May cause cardiac disturbances. May cause central nervous system depression. Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
Causes respiratory tract irritation. May cause cardiac abnormalities. Can produce delayed pulmonary edema. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration. Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. Effects may be delayed. Chronic exposure to cyanide solutions may lead to the development of a "cyanide" rash, characterized by itching, and by macular, papular, and vesicular eruptions, and may be accompanied by secondary infections.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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 breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively. 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. Vapors may form an explosive mixture with air.
During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air.
They can spread along the ground and collect in low or confined areas. Containers may explode when heated. Combustible material; may burn but does not ignite readily. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray. 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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 1530-87-6: 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 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: Clear liquid
Color: clear almost colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 102 deg C @ 10.00mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 97 deg C ( 206.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9510g/cm3
Molecular Formula:
Molecular Weight: 110.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong acids, strong bases, strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1530-87-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Piperidinecarbonitrile - 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
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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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.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 1530-87-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1530-87-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1530-87-6 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：

  1-吡啶甲酯 在 OsCl₂(η⁶-p-cymene)(PMe₂OH) 、 水 作用下， 反应 1.5h， 以91%的产率得到1-氨基甲酰基哌啶
  参考文献：
  名称：

  亚膦酸基钌（II）和（II）配合物催化水合氰胺：范围和机理的见解

  摘要：

  通过使用水合相应的氰胺R 1 R 2 NC N成功地完成了多种脲R 1 R 2 NC（O）NH 2的合成（R 1和R 2 =烷基，芳基或H； 26个实例）的三价膦酸基配合物[的MC1 2（η 6 - p -cymene）（PME 2 OH）]（M =茹（1），锇（2））作为催化剂。反应在温和的条件下（40-70°C）干净进行，没有任何添加剂，使用低金属负载量（1 mol％）和水作为唯一溶剂。在几乎所有情况下，complex配合物2的反应活性都比钌配合物1高。另外，对于两种催化剂，氰酰胺底物水合所观察到的反应速率明显快于涉及传统脂族和芳族腈的反应速率。计算研究使我们能够合理化所有这些趋势。因此，计算表明存在直接与碳原子相连的氮原子当与金属中心配位时，N键通过感应效应使腈碳电子减少，从而促进次膦酸配体的OH基团对该碳的分子内亲核攻击。另一方面，Os对Ru的较高反应性似乎与初始金属环上较低的环应

  DOI：

  10.1039/d0cy00523a
• 作为产物：
  描述：

  1-氨基甲酰基哌啶 在 sodium hydroxide 、 三乙胺 作用下， 以 氯仿 为溶剂， 以65%的产率得到1-吡啶甲酯
  参考文献：
  名称：

  Schroth, W.; Kluge, H.; Frach, R., Journal fur praktische Chemie (Leipzig 1954), 1983, vol. 325, # 5, p. 787 - 802

  摘要：

  DOI：
• 作为试剂：
  描述：

  4,5-dimethoxy-2-methylbenzonitrile 在 1-吡啶甲酯 、 N,N-二甲基丙烯基脲 、 lithium diisopropyl amide 作用下， 生成 1-amino-6,7-dimethoxy-3-piperidin-1-ylisoquinoline hydrochloride 、 1-amino-6,7-dimethoxy-3-(2-methyl-4,5-dimethoxyphenyl)isoquinoline hydrochloride
  参考文献：
  名称：

  1,3-二氨基-6,7-二甲氧基异喹啉衍生物作为潜在的α1-肾上腺素受体拮抗剂。

  摘要：

  用LDA处理2-甲基-4,5-二甲氧基苄腈（3），然后与N，N-二取代的氰胺反应，得到一系列的1,3-二氨基-6,7-二甲氧基异喹啉（2），对其进行评估α-肾上腺素受体结合亲和力和降压活性。1-氨基-3-（二甲基氨基）-6,7-二甲氧基异喹啉（4）对α1-肾上腺素受体没有明显的亲和力（Ki远大于10（-6）M），而相应的3-（2-呋喃基哌嗪- 1-yl）类似物（8; Ki = 1.6 X 10（-7）M）的效力比哌唑嗪低约1000倍。pKa数据显示，在生理pH值下会发生4的N-2质子化（34％）（pKa = 7.1），这与8.HCl的X射线晶体学分析一致。质子化4与相应的喹啉和喹唑啉阳离子质子化后的正电荷分布的比较证实，N-1质子化是这些杂环核有效结合至α1-肾上腺素受体所必需的。计算机辅助比较8和哌唑嗪的X射线结构表明，α1-肾上腺素受体结合能的4.0 kcal / mol差异主要是由于

  DOI：

  10.1021/jm00400a026

文献信息

• Oxidative cleavage of the CN bond during singlet oxygenations of amidoximates
  作者：Nüket Öcal、Ihsan Erden

  DOI：10.1016/s0040-4039(01)00887-5

  日期：2001.7

  Amidoximes are inert toward singlet oxygen (1O2), however, the photooxygenation of amidoximate anions proceeds smoothly and in high yield to give mixtures of amides and nitriles. The mechanism of these reactions appears to involve carbonyl oxide intermediates. The oxidative cleavage of amidoximates closely resembles the results obtained from nitric oxide synthase (NOS) oxidations of N-hydroxyarginine

  酰胺基肟对单线态氧（1 O 2）呈惰性，但是，酰胺基肟酸根阴离子的光氧化作用平稳且高收率，可生成酰胺和腈的混合物。这些反应的机理似乎与羰基氧化物中间体有关。mid胺肟酸的氧化裂解与N-羟基精氨酸的一氧化氮合酶（NOS）氧化获得的结果非常相似。
• Nickelocene as an Air- and Moisture-Tolerant Precatalyst in the Regioselective Synthesis of Multisubstituted Pyridines
  作者：Il Young Cho、Woo Gyum Kim、Ji Hwan Jeon、Jeong Woo Lee、Jeong Kon Seo、Jongcheol Seo、Sung You Hong

  DOI：10.1021/acs.joc.1c00577

  日期：2021.7.16

  Ni(COD)2-catalyzed cycloaddition reactions to access pyridines have been extensively studied. However, this catalyst typically requires drying procedures and inert-atmosphere techniques for the reactions. Herein, we report operationally simple nickel(0) catalysis to access substituted pyridines from various nitriles and 1,6-diynes without the aid of air-free techniques. The Ni-Xantphos-based catalytic

  镍(COD) 2已经广泛研究了用于获得吡啶的催化环加成反应。然而，这种催化剂通常需要干燥程序和惰性气氛技术来进行反应。在此，我们报告了操作简单的镍 (0) 催化，无需借助无空气技术即可从各种腈和 1,6-二炔中获得取代吡啶。基于 Ni-Xantphos 的催化歧管耐受空气、水分和热量，同时促进 [2 + 2 + 2] 环加成反应，反应产率高，底物范围广。此外，我们公开了不仅空间效应而且前沿分子轨道相互作用都可以在确定镍催化的 [2 + 2 + 2] 环加成合成取代吡啶的区域化学结果方面发挥关键作用。
• [EN] PYRIDIN- 2 -AMIDES USEFUL AS CB2 AGONISTS<br/>[FR] PYRIDIN-2-AMIDES UTILES COMME AGONISTES DE CB2
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012168350A1

  公开（公告）日：2012-12-13

  The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  本发明涉及式(I)的化合物，其中R1至R4的定义如描述和权利要求中所述。式(I)的化合物可以用作药物。
• [EN] DIMERIC PIPERIDINE DERIVATIVES<br/>[FR] DERIVES DE PIPERIDINE DIMERES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006008260A1

  公开（公告）日：2006-01-26

  The compounds of the following formula (I) : the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, useful in the treatment of neurodegenerative mediated disorders.

  以下公式（I）的化合物：N-氧化物形式，药用可接受的添加盐及其立体异构形式，在治疗神经退行性媒介紊乱中具有用途。
• Peracid oxidation of an N-hydroxyguanidine compound: a chemical model for the oxidation of N.omega.-hydroxy-L-arginine by nitric oxide synthase
  作者：Jon M. Fukuto、Dennis J. Stuehr、Paul L. Feldman、Michael P. Bova、Patrick Wong

  DOI：10.1021/jm00070a010

  日期：1993.9

  enzymes called the nitric oxide synthases (NOS) to generate citrulline and, presumably, nitric oxide (.NO). N-Hydroxylation of a guanidinium nitrogen of arginine to generate N-hydroxyarginine (NOHA) has been shown to be a step in the biosynthesis of .NO. In an effort to elucidate the mechanism by which further oxidation of NOHA occurs, the oxidation of a model N-hydroxyguanidine compound by several

  精氨酸被称为一氧化氮合酶（NOS）的一类酶氧化，从而生成瓜氨酸和一氧化氮（.NO）。精氨酸的胍氮的N-羟基化反应生成N-羟基精氨酸（NOHA）已被证明是.NO生物合成的一个步骤。为了阐明NOHA进一步氧化的机理，深入研究了模型N-羟基胍化合物被几种过酸氧化的过程。该氧化化学是酶促过程的可能模型，因为获得了相应的尿素（或瓜氨酸当量产物）以及氧化的氮物质。但是，氧化的氮产物不是NO，而是HNO。在该化学系统和酶促过程中，NO的产生将需要另一种单电子氧化。

表征谱图