4-甲基-2-戊醇 | 5362-56-1

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 无环醇
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲基-2-戊醇
• 中文别名: 4-甲基-2-戊烯醛
• 英文名称: 4-methylpent-2-enal
• 英文别名: 4-methyl-2-pentenal；2-Pentenal, 4-methyl-
• CAS: 5362-56-1
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: RIWPMNBTULNXOH-UHFFFAOYSA-N

物化性质

• 熔点：
  -78°C (estimate)
• 沸点：
  70 °C (75 mmHg)
• 密度：
  0.844
• 闪点：
  32 °C
• LogP：
  1.39
• 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接触，并远离高温环境。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S16
• 危险类别码：
  R10
• 海关编码：
  2912190090
• 储存条件：
  密封储存于阴凉、干燥的库房中，远离火源和易燃易爆区域，并常使用氮气进行保护。需冷藏保存。

SDS

Name:	4-Methyl-2-Pentenal 95% Material Safety Data Sheet
Synonym:	None
CAS:	5362-56-1

Section 1 - Chemical Product MSDS Name:4-Methyl-2-Pentenal 95% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5362-56-1	4-Methyl-2-Pentenal	95	226-348-5

Hazard Symbols: None Listed.
Risk Phrases: 10

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable.
Potential Health Effects
Eye:
May cause eye irritation. May cause chemical conjunctivitis and corneal damage.
Skin:
May cause irritation and dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. Ingestion of large amounts may cause CNS depression.
Inhalation:
The toxicological properties of this substance have not been fully investigated. Aspiration may lead to pulmonary edema. Vapors may cause dizziness or suffocation. May cause burning sensation in the chest.
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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Water may be ineffective. Material is lighter than water and a fire may be spread by the use of water. Containers may explode in the heat of a fire.
Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water.

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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. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. A vapor suppressing foam may be used to reduce vapors.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Refrigerator/flammables.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 5362-56-1: 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: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 70 deg C @ 75.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 32 deg C ( 89.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density: .8440g/cm3
Molecular Formula: C6H10O
Molecular Weight: 98.14

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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, ignition sources, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
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# 5362-56-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Methyl-2-Pentenal - 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: FLAMMABLE LIQUID, N.O.S.*
Hazard Class: 3
UN Number: 1993
Packing Group: III
IMO
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3.3
UN Number: 1993
Packing Group: III
RID/ADR
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3
UN Number: 1993
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
R 10 Flammable.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 28A After contact with skin, wash immediately with
plenty of water.
S 33 Take precautionary measures against static
discharges.
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# 5362-56-1: No information available.
Canada
CAS# 5362-56-1 is listed on Canada's DSL List.
CAS# 5362-56-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5362-56-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

先由丙酮在碱性催化剂（如氢氧化钙或氢氧化钡）存在下，在压缩机中加压反应，转化为二丙酮醇（见11360）。为确保液相接触反应接近均相反应，需使用表面积较大的催化剂。此过程会放出热量，因此原料丙酮应预冷，并在低温（0-10℃）条件下操作。生成的二丙酮醇进一步脱水生成异丙叉丙酮。通过常压蒸馏浓缩二丙酮醇至80%，同时分离和回收未转化的丙酮。

在酸性催化剂（如硝酸、硼酸或苯磺酸）存在下，加热到100-200℃，二丙酮醇会脱水生成异丙叉丙酮。由于二丙酮醇能受热分解成丙酮，因此脱水产物需回收其中的丙酮。

最后一步是异丙叉丙酮加氢反应生成4-甲基-2-戊醇。以镍或铜为催化剂，在温和条件下可获得较多的部分加氢产物甲基异丁基甲酮；而温度控制在170-210℃，氢与异丙叉丙酮的摩尔比增加时，则会得到更多的完全加氢产物甲基异丁基甲醇。通常情况下，两者混合物是主要产物，精馏分离时采用减压蒸馏系统。

此外，甲基-异丁基（甲）酮也可以经镍催化加氢制成，再通过精馏塔分馏得成品。

用途简介

4-甲基-2-戊醇是一种优良的中沸点溶剂。主要用于染料、石油、橡胶、树脂、石蜡、硝化纤维素和乙基纤维素等的溶剂，并用作硝化纤维素漆的惰性溶剂，能增加涂料的光泽和平整性，改善泛红性能；在润滑油添加剂制造中作为溶剂等。

4-甲基-2-戊醇还用于有机合成原料、矿物浮选洗涤剂（如萃取硅和硫酸铜矿）以及刹车液。此外，它还可作为发泡剂、分散剂、洗涤剂、增塑剂、表面活性剂、润滑剂及化妆品、照相工业用药品的制造材料。

反应信息

• 作为反应物：
  描述：

  4-甲基-2-戊醇 在 硫酸 、 palladium 10% on activated carbon 、 磷酸吡哆醛 、 氢气 、 异丙基氨盐酸盐 、 potassium carbonate 、 异丙胺 、 potassium hydroxide 作用下， 以 正庚烷 、 水 为溶剂， 55.0 ℃ 、500.01 kPa 条件下， 反应 25.58h， 生成 普瑞巴林
  参考文献：
  名称：

  [EN] PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PREGABALIN
  [FR] PROCESSUS ET INTERMÉDIAIRES POUR LA PRÉPARATION DE PRÉGABALINE

  摘要：

  该发明提供了制备化合物（IA）的工艺。该发明还提供了将化合物（IA）转化为普拉帕林的改进方法。

  公开号：

  WO2014155291A1
• 作为产物：
  描述：

  4-methyl-2-pentenol 在 2,2,6,6-四甲基哌啶氧化物 、 氧气 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 4-甲基-2-戊醇
  参考文献：
  名称：

  用TEMPO合并染料敏化的TiO 2的可见光光催化：醇的选择性好氧氧化

  摘要：

  当氧化剂是分子氧（O 2）并且反应在环境条件下进行时，很难将醇选择性氧化为醛或酮。为了应对这些挑战，开发了可见光光催化技术，以使O 2可以在室温下用于醇的选择性氧化。在该方案中，将曙红Y（一种有机染料）与TiO 2连接捕获可见光，从而导致相应的光催化过程。更重要的是，这些光催化过程可以与TEMPO的氧化还原催化循环巧妙地合并，从而在可见光照射下诱导醇的氧化。这项工作表明可见光光催化和TEMPO催化的合并具有巨大的潜力执行具有挑战性的氧化转化。

  DOI：

  10.1039/c7cy01510k

文献信息

• Traceless Rhodium-Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of β-Aryl Ketones
  作者：Anaïs Bouisseau、Ming Gao、Michael C. Willis

  DOI：10.1002/chem.201604035

  日期：2016.10.24

  A one‐pot three‐step sequence involving Rh‐catalyzed alkene hydroacylation, sulfide elimination and Rh‐catalyzed aryl boronic acid conjugate addition gave products of traceless chelation‐controlled hydroacylation employing alkyl aldehydes. The stereodefined β‐aryl ketones were obtained in good yields with excellent control of enantioselectivity. Good variation of all three reaction components is possible

  一锅三步序列涉及 Rh 催化的烯烃加氢酰化、硫化物消除和 Rh 催化的芳基硼酸缀合物加成，得到使用烷基醛的无痕螯合控制的加氢酰化产物。立体定义的β-芳基酮以良好的产率获得，并且对映选择性具有出色的控制。所有三种反应组分的良好变化是可能的。
• Re-visiting the diastereoselectivity of organocatalytic conjugate addition of 2-trimethylsiloxyfuran to trans-crotonaldehyde
  作者：Liubo Li、Anton El Khoury、Brennan O. Clement、Patrick G. Harran

  DOI：10.1016/j.tetlet.2021.153056

  日期：2021.5

  We describe the re-assignment of configuration previously ascribed to product diastereomers resultant from imidazolidinone-catalyzed conjugate addition of 2-trimethylsiloxyfuran to trans-crotonaldehyde. A modified procedure that uses a diphenylprolinol catalyst was subsequently developed to selectively provide the ‘syn’ diastereomeric product in high enantiomeric excess on decagram scales.

  我们描述了先前归因于由咪唑烷酮催化的将2-三甲基甲硅烷氧基呋喃加成反式巴豆醛的共轭加成物所产生的产物非对映异构体的构型的重新分配。随后开发了使用二苯基脯氨醇催化剂的改进方法，以十毫克级的对映体过量，选择性地提供“ syn ”非对映体产物。
• Stereocontrolled construction of the dihydrothiopyrano[2,3-b]indole skeleton via an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction
  作者：Lulu Wu、Youming Wang、Zhenghong Zhou

  DOI：10.1016/j.tetasy.2014.09.005

  日期：2014.10

  We have developed an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction between 2-mercaptoindole-3-carbaldehydes and enals, which provides efficient access to the stereocontrolled construction of dihydrothiopyrano[2,3-b]indole skeletons. Under the catalysis of chiral diphenylprolinol TMS ether, the reactions ran smoothly to give the corresponding synthetically useful and pharmaceutically

  我们已经开发了2-巯基吲哚-3-甲醛和烯醛之间的有机催化的不对称级联磺胺-迈克尔-醛醇反应，它提供了对二氢硫代吡喃并[2,3- b ]吲哚骨架的立体控制结构的有效访问。在手性二苯基脯氨醇TMS醚的催化下，反应进行得很顺利，以高收率和ee的64-96％得到了相应的合成有用的和药学上有价值的二氢硫吡喃并[2,3- b ]吲哚。
• A Chiral 6-Membered <i>N</i>-Heterocyclic Carbene Copper(I) Complex That Induces High Stereoselectivity
  作者：Jin Kyoon Park、Hershel H. Lackey、Matthew D. Rexford、Kirill Kovnir、Michael Shatruk、D. Tyler McQuade

  DOI：10.1021/ol1021756

  日期：2010.11.5

  A chiral 6-membered annulated N-heterocyclic (6-NHC) copper complex that catalyzes β-borylations with high yield and enantioselectivity was developed. The chiral 6-NHC copper complex is easy to prepare on the gram scale and is very active, showing 10 000 turnovers at 0.01 mol % of catalyst without significant decrease of enantioselectivity and with useful reaction rates.

  开发了一种手性的六元环状N-杂环（6-NHC）铜络合物，它以高收率和对映选择性催化β-硼化。手性6-NHC铜络合物易于按克规模制备，并且非常活泼，在0.01 mol％的催化剂下显示出1万的周转率，而对映选择性没有显着降低，并且具有有用的反应速率。
• Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes
  作者：John C. K. Chu、Derek M. Dalton、Tomislav Rovis

  DOI：10.1021/jacs.5b00033

  日期：2015.4.8

  We report a catalytic asymmetric synthesis of piperidines through [4 + 2] cycloaddition of 1-azadienes and nitro-alkenes. The reaction uses earth abundant Zn as catalyst and is highly diastereo- and regioselective. A novel BOPA ligand (F-BOPA) confers high reactivity and enantioselectivity in the process. The presence of ortho substitution on the arenes adjacent to the bis(oxazolines) was found to

  我们报告了通过 1-氮杂二烯和硝基烯烃的 [4 + 2] 环加成反应催化不对称合成哌啶。该反应使用地球上丰富的锌作为催化剂，并且具有高度的非对映选择性和区域选择性。一种新型 BOPA 配体 (F-BOPA) 在该过程中具有高反应性和对映选择性。发现与双（恶唑啉）相邻的芳烃上存在邻位取代特别有影响，因为限制了 1-氮杂二烯与路易斯酸的不希望的配位，从而允许反应在较低温度下进行。使用一系列配体进行的一系列次级动力学同位素效应研究暗示了转化的逐步机制，包括亚胺与硝基烯烃的初始迈克尔型加成，然后是环化事件。