1-甲基-1,2,3,6-四氢吡啶 | 694-55-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1-甲基-1,2,3,6-四氢吡啶
• 英文名称: N-methyl-3,4-didehydropiperidine
• 英文别名: N-methyl-1,2,3,6-tetrahydropyridine；1-methyl-1,2,5,6-tetrahydropyridine；1-methyl-1,2,3,6-tetrahydropyridine；1-methyl-3,6-dihydro-2H-pyridine
• CAS: 694-55-3
• 化学式: C₆H₁₁N
• 分子量: 97.16
• InChiKey: AUFIRGPROMANKW-UHFFFAOYSA-N

物化性质

• 熔点：
  198-202 °C
• 沸点：
  112.5 °C
• 密度：
  0.876±0.06 g/cm3(Predicted)
• 保留指数：
  1030
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090
• 储存条件：
  密封储存，应存放在阴凉、干燥的库房中。

SDS

Name:	1-Methyl-1 2 3 6-tetrahydropyridine hydro- chloride 98% Material Safety Data Sheet
Synonym:
CAS:	694-55-3

Section 1 - Chemical Product MSDS Name:1-Methyl-1 2 3 6-tetrahydropyridine hydro- chloride 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
694-55-3	1-methyl-1,2,3,6-tetrahydropyridine hy	98	211-773-0

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:
Dust may cause mechanical irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause digestive tract disturbances. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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.
Extinguishing Media:
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 or absorb material, then place into a suitable clean, dry, closed 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. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation. Use with adequate ventilation.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 694-55-3: 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:
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: Powder
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 198.00 - 200.00 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: C6H11N.HCl
Molecular Weight: 133.62

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 694-55-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-methyl-1,2,3,6-tetrahydropyridine hydro- chloride, 98% - 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.
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# 694-55-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 694-55-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 694-55-3 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-甲基-1,2,3,6-四氢吡啶 在 盐酸 、 乙醚 作用下， 生成 1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Lukes; Pliml, Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 502

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基-2H-吡啶 在 高氯酸 作用下， 以 甲醇 为溶剂， 生成 1-甲基-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Exploratory and mechanistic aspects of the electron-transfer photochemistry of olefin-N-heteroaromatic cation systems

  摘要：

  DOI：

  10.1021/ja00343a022

文献信息

• Some reactions of 1-methyl-1,2,3,4-tetrahydropyridine with organic azides. Synthesis of 1-methylpiperidylidene-2-sulfon(cyan)amides
  作者：B. K. Warren、E. E. Knaus

  DOI：10.1002/jhet.5570190562

  日期：1982.9

  The 1,3-dipolarcycloaddition reaction of 1-methyl-1,2,3,4-tetrahydropyridine (1) with organic azides 2 affords 1-methylpiperidylidene-2-sulfon(cyan)amides 4 in high yield. The reaction proceeds via a 2,3,4,9-tetrazabicyclo[4.3.0]non-3-ene intermediate. Acid hydrolysis of 4d gives rise to 1-methyl-2-piperidone.

  1-甲基-1，2，3，4-四氢吡啶（1）与有机叠氮化物2的1，3-偶极环加成反应以高收率提供1-甲基哌啶基-2-磺（氰）酰胺4。反应通过2,3,4,9-四氮杂双环[4.3.0]非-3-烯中间体进行。4d的酸水解产生1-甲基-2-哌啶酮。
• [EN] PYRROLOTRIAZINE COMPOUNDS AS KINASE INHIBITORS<br/>[FR] COMPOSES DE PYRROLOTRIAZINE SERVANT D'INHIBITEURS DE KINASES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005066176A1

  公开（公告）日：2005-07-21

  The present invention provides compounds of formula (I); and pharmaceutically acceptable salts thereof. The formula (I) compounds inhibit tyrosine kinase activity of growth factor receptors such as HER1, HER2 and HER4 thereby making them useful as antiproliferative agents. The formula (I) compounds are also useful for the treatment of other diseases associated with signal transduction pathways operating through growth factor receptors.

  本发明提供了式（I）的化合物；以及其药学上可接受的盐。式（I）的化合物抑制生长因子受体如HER1、HER2和HER4的酪氨酸激酶活性，从而使它们作为抗增殖剂有用。式（I）的化合物还可用于治疗与通过生长因子受体进行的信号转导途径相关的其他疾病。
• Base catalysed rearrangements involving ylide intermediates. Part 7. The rearrangements of allyl(pentadienyl)- and propynyl(pentadienyl)ammonium cations. The [5,4] sigmatropic rearrangement
  作者：Trevor Laird、W. David Ollis、Ian O. Sutherland

  DOI：10.1039/p19800002033

  日期：——

  The base catalysed rearrangements of the cations (7), (17), (22), and (27) gave the enamines (9), (18), (23), and (28), which on hydrolysis yielded the aldehydes (10), (19), (24), and (29) respectively. The reactions are shown to be concerted [5,4] sigmatropic rearrangements proceeding via a nine-membered transition state involving 10π electrons. The base catalysed rearrangements of the 3-phenylprop-2-ynyl

  阳离子（7），（17），（22）和（27）的碱催化重排产生烯胺（9），（18），（23）和（28），水解后产生醛（ 10），（19），（24）和（29）。该反应显示为通过包含10π电子的九元过渡态进行的[5,4]σ重排。3-苯基丙-2-炔基（戊二烯基）铵阳离子的碱催化重排（51），（52），（60）和（61），但仅产生[1,2]，[3， 2]和[5,2]σ重排。
• Catalytic Asymmetric Hydrogen Migration of Allylamines
  作者：Sei Otsuka、Kazuhide Tani

  DOI：10.1055/s-1991-26541

  日期：——

  This review describes some preparative aspects and practical applications of BINAP-Rh(I) catalyzed enantioselective isomerization of prochiral allylamines recently developed through the joint effort of several groups in Japan. In addition, the novel, sophisticated reaction mechanisms are discussed. 1. Introduction 2. Catalyst Development 2.1. Cobalt Catalysts 2.2. Rhodium Catalysts 2.3. The Ligand BINAP 3. Preparative Aspects 3.1. Isomerization on a Laboratory Scale 3.2. The Industrial Process 4. Substrates and the Scope 4.1. Allylamine 4.2. Allyl Alcohol 5. Reaction Mechanisms 5.1. Catalytic Pathways 5.2. Mechanism of Chiral Recognition 5.3. Conclusion 6. Applications 6.1. (-)-Menthol 6.2. Citronellol 6.3. Citronellal Derivatives 6.4. α-Tocopherol Side Chain 6.5. Methoprene

  本篇综述介绍了日本多个研究小组共同努力下近期开发的BINAP-Rh(I)催化不对称异构化前手性烯丙胺的一些制备方面和实际应用。此外，还讨论了新颖而复杂的反应机理。 1. 引言 2. 催化剂开发 2.1. 钴催化剂 2.2. 铑催化剂 2.3. 配体BINAP 3. 制备方面 3.1. 实验室规模的异构化 3.2. 工业过程 4. 底物与范围 4.1. 烯丙胺 4.2. 烯丙醇 5. 反应机理 5.1. 催化途径 5.2. 手性识别机制 5.3. 结论 6. 应用 6.1. 薄荷醇 6.2. 香茅醇 6.3. 香茅醛衍生物 6.4. 生育酚侧链 6.5. 灭虫脲
• A convenient racemic synthesis of two isomeric tetrahydropyridyl alkaloids: Isoanatabine and anatabine
  作者：Anne Rouchaud、William R. Kem

  DOI：10.1002/jhet.359

  日期：——

  contributed to the knowledge of the mechanism of this oxidative rearrangement. On the other hand, the reduction of 1‐methylpyridinium iodide with sodium borohydride and with potassium cyanide present since the start of the reaction in a two layer ether‐water system, gave 2‐cyano‐1‐methyl‐4‐piperideine. This was transformed into (±)‐anatabine by the same sequence of reactions used for the synthesis of (±)‐isoanatabine

  Anatabine是烟草的主要生物碱，其异构体isoanatabine最近在海洋蠕虫中被发现。用硼氢化钠还原1-甲基碘化碘，得到1-甲基-3-哌啶，然后用过氧化氢转化成N-氧化物。N氧化物先后与三氟乙酸酐和氰化钾反应，生成2氰基1甲基3哌啶。它与3-吡啶基氯化镁反应生成（±）-N-甲基-异他他滨。这与转化的米氯过苯甲酸入Ñ氧化物这是Ñ用硫酸铁（II）脱甲基，得到（±）-异anatabatin。通过N氧化物分解进行N脱甲基化的文献方法的连续应用，有助于人们了解这种氧化重排的机理。另一方面，自两层醚-水系统中反应开始以来，用硼氢化钠和氰化钾还原1-甲基吡啶碘化物，得到2-氰基-1-甲基-4-哌啶。通过合成（±）-异anatabine的相同反应顺序，将其转化为（±）-anatabine。J.杂环化​​学。（2010）。

表征谱图