3-异丙氧基丙腈 | 110-47-4

• 物质功能分类: 有机原料 - 腈类化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-异丙氧基丙腈
• 英文名称: 3-(propan-2-yloxy)propanonitrile
• 英文别名: 3-isopropoxypropanenitrile；3-propan-2-yloxypropanenitrile
• CAS: 110-47-4
• 化学式: C₆H₁₁NO
• mdl: MFCD00019866
• 分子量: 113.159
• InChiKey: BMSYXLRQGIFLFO-UHFFFAOYSA-N

物化性质

• 沸点：
  179℃
• 密度：
  0.8969 g/cm3
• 保留指数：
  879

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

SDS

Name:	Isopropoxypropionitrile 99+% Material Safety Data Sheet
Synonym:
CAS:	110-47-4

Section 1 - Chemical Product MSDS Name:Isopropoxypropionitrile 99+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
110-47-4	3-isopropoxypropionitrile	99+	203-771-3

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Appearance: clear, colorless.
Not available.
Target Organs: None.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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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 soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat symptomatically and supportively.

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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.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits +--------------------+-------------------+-------------------+-----------------+ | Chemical Name | ACGIH | NIOSH |OSHA - Final PELs| |--------------------|-------------------|-------------------|-----------------| | 3-isopropoxypropion|none listed |none listed |none listed | | itrile | | | | +--------------------+-------------------+-------------------+-----------------+ OSHA Vacated PELs: 3-isopropoxypropionitrile: No OSHA Vacated PELs are listed for this chemical.
Personal Protective Equipment Eyes: Wear chemical goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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 a respirator's use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Appearance: clear, colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
NFPA Rating: health-1; flammability-2; reactivity-1
Explosion Limits, Lower: Not available.
Upper: Not available.
Decomposition Temperature:
Solubility:
Specific Gravity/Density:
Molecular Formula: C6H11NO
Molecular Weight: 113.15

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 110-47-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-isopropoxypropionitrile - Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Chemical waste generators must determine whether a discarded chemical is classif as a hazardous waste.
US EPA guidelines for the classification determination are listed in 40 CFR Part Additionally, waste generators must consult state and local hazardous waste regu ensure complete and accurate classification.
RCRA P-Series: None listed.
RCRA U-Series: None listed.

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Section 14 - TRANSPORT INFORMATION

CDG/CPL
Not classified as hazardous for supply.
Canadian TDG
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 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 110-47-4: 2
United Kingdom Occupational Exposure Limits
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
WHMIS: Not available.
CAS# 110-47-4 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
US FEDERAL
TSCA
CAS# 110-47-4 is listed on the TSCA inventory.
Health & Safety Reporting List
None of the chemicals are on the Health & Safety Reporting List.
Chemical Test Rules
None of the chemicals in this product are under a Chemical Test Rule.
Section 12b
None of the chemicals are listed under TSCA Section 12b.
TSCA Significant New Use Rule
None of the chemicals in this material have a SNUR under TSCA.
SARA
Section 302 (RQ)
None of the chemicals in this material have an RQ.
Section 302 (TPQ)
None of the chemicals in this product have a TPQ.
Section 313
No chemicals are reportable under Section 313.
Clean Air Act:
This material does not contain any hazardous air pollutants.
This material does not contain any Class 1 Ozone depletors.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-异丙氧基丙腈 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 3-异丙氧基丙胺
  参考文献：
  名称：

  The Cleavage of β-Oxypropionitriles with Lithium Aluminum Hydride¹

  摘要：

  DOI：

  10.1021/ja01642a067
• 作为产物：
  描述：

  3-异丙氧基丙胺 在 copper(l) iodide 、 氧气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以88%的产率得到3-异丙氧基丙腈
  参考文献：
  名称：

  胺的需氧氧化的简单铜催化剂：抗衡离子的选择性控制

  摘要：

  我们描述了在将胺选择性好氧氧化为腈或亚胺时，使用简单的铜盐催化剂的方法。这些催化剂以其出色的效率而著称，可在环境温度和压力下运行，并且无需昂贵的配体或添加剂即可氧化胺。这项研究强调了抗衡离子在控制好氧氧化中的选择性方面可以发挥重要作用。

  DOI：

  10.1002/anie.201609255

文献信息

• KO <i>t</i> Bu‐Catalyzed Michael Addition Reactions Under Mild and Solvent‐Free Conditions
  作者：Subramanian Thiyagarajan、Varadhan Krishnakumar、Chidambaram Gunanathan

  DOI：10.1002/asia.201901647

  日期：2020.2.17

  predominantly catalyze Michael addition reactions. Inorganic and organic base‐catalyzed Michael addition reactions have been reported. However, known base‐catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side‐reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu‐catalyzed Michael addition reactions. This simple

  设计的过渡金属络合物主要催化迈克尔加成反应。无机和有机碱催化的迈克尔加成反应已有报道。但是，已知的碱催化反应需要溶剂，添加剂，高压以及副反应。在此，我们展示了一种易于使用的KO t的温和且环保的策略Bu催化Michael加成反应。这种简单的无机碱可有效催化未开发的丙烯腈，酯和酰胺与（氧杂，氮杂和硫杂）杂原子亲核试剂的迈克尔加成反应。该催化过程在无溶剂条件和室温下进行。值得注意的是，该协议提供了一种简便的操作程序，宽泛的底物范围，出色的选择性，反应可扩展性和出色的TON（> 9900）。初步的机理研究表明，该反应遵循离子机理。使用该催化方案证明了丙嗪的正式合成。
• Novel amine-catalysed hydroalkoxylation reactions of activated alkenes and alkynes
  作者：Julie E. Murtagh、S�amus H. McCooey、Stephen J. Connon

  DOI：10.1039/b414895a

  日期：——

  Substoichiometric loadings of DBU catalyse the efficient 1,4-addition of alcohols and non-nucleophilic amines such as pyrrole to activated alkenes; the application of this methodology in a one-pot synthesis of a natural product, and as a novel strategy for the synthesis of mono-protected 1,3-carbonyl compounds is reported.

  DBU的亚化学计量负载可催化将醇和非亲核胺（例如吡咯）有效地进行1,4-加成反应；报道了这种方法在天然产物的一锅法合成中的应用，并且作为合成单保护的1，3-羰基化合物的新策略。
• Formation of a New, Strongly Basic Nitrogen Anion by Metal Oxide Modification
  作者：Masazumi Tamura、Ryota Kishi、Akira Nakayama、Yoshinao Nakagawa、Jun-ya Hasegawa、Keiichi Tomishige

  DOI：10.1021/jacs.7b05227

  日期：2017.8.30

  viewpoints. Here, a principle for creating a new strong base by hybridization of homogeneous and heterogeneous components is presented. It is based on the modification of organic compounds with metal oxides by using the acid-base property of metal oxides. Based on kinetic and DFT studies, combination of CeO2 and 2-cyanopyridine drastically enhanced the basicity of 2-cyanopyridine by a factor of about 109

  开发具有独特且前所未有的催化性能的新型杂化材料对化学家来说是一个挑战，而多相-均相杂化催化剂由于期望由组分组合产生的优选和特殊性能而备受关注。碱催化剂作为关键材料广泛应用于有机合成中，一类新的碱催化剂在学术和工业上都产生了很大的影响。在这里，提出了通过同质和异质成分的杂交来创建新的强碱的原理。它是利用金属氧化物的酸碱性质，用金属氧化物对有机化合物进行改性。基于动力学和 DFT 研究，CeO2 和 2-氰基吡啶的组合使 2-氰基吡啶的碱性显着提高了约 109 倍（pKa（在 CH3CN 中）约为 9），估计 pKa 为 21，这将其置于超强碱类别中。2-氰基吡啶和CeO2通过两种相互作用模式形成独特的吸附复合物：（i）CeO2的Ce原子与2-氰基吡啶中吡啶环的N原子之间的配位相互作用，以及（ii）表面O原子之间的共价相互作用通过将 CeO2 的晶格氧加成到 2-氰基吡啶的 CN 基团上，CeO2
• Effect of pressure on sterically congested cyanoalkylation reactions of alcohols
  作者：G. Jenner

  DOI：10.1016/s0040-4020(02)00347-2

  日期：2002.5

  The pressure effect on the phosphine-catalyzed nucleophilic addition of alcohols to unsaturated nitriles is examined. As a general result, pressure promotes these reactions. Their sensitivity to pressure increases with increasing steric congestion of either the alcohol or the nitrile. Activation volumes are found to be very negative pointing not only to a late transition state, but essentially to a

  考察了对膦向不饱和腈的膦催化的亲核加成反应的压力影响。通常，压力会促进这些反应。它们对压力的敏感性随着酒精或腈的空间拥塞的增加而增加。发现活化体积是非常负的，不仅指向晚期转变状态，而且还取决于取决于电离的空间位阻，基本上指向相当大的电致伸缩贡献。这意味着压力有利于碳负离子的形成和腈的侵蚀。该结果突出了高压的合成效用，以消除空间抑制作用。
• Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions
  作者：Susanne M Fischer、Simon Renner、A Daniel Boese、Christian Slugovc

  DOI：10.3762/bjoc.17.117

  日期：——

  and intermediate Michael acceptors such as acrylamide and acrylonitrile and for converting less acidic alcohols like isopropanol. With stronger Michael acceptors and more acidic alcohols, the impact of the more electron-rich catalysts is less pronounced. The experimental activity trend was rationalized by calculating the Michael acceptor affinities of all phosphine–Michael acceptor combinations. Besides

  富电子三芳基膦，即 4-(甲氧基苯基)二苯基膦 (MMTPP) 和三(4-三甲氧基苯基)膦 (TMTPP) 在催化 oxa-Michael 加成方面优于常用的三苯基膦 (TPP)。使用由三种不同强度的迈克尔受体和四种不同酸度的醇组成的基质来评估三种催化剂的活性。所有测试反应均在无溶剂条件下和室温下以 1 mol% 催化剂负载量进行。结果表明，TMTPP 在转化丙烯酰胺和丙烯腈等弱迈克尔受体和中间迈克尔受体以及转化异丙醇等弱酸性醇方面具有决定性的优势。随着迈克尔受体的增强和酸性醇的增多，富电子催化剂的影响就不那么明显了。通过计算所有膦-迈克尔受体组合的迈克尔受体亲和力，使实验活性趋势合理化。除了这个参数之外，醇的酸度对反应速度也有很大影响。还评估了膦的氧化稳定性，发现最富电子的 TMTPP 对氧化的敏感性仅比 TPP 稍高。最后，将该催化剂用于丙烯酸2-羟乙酯的氧杂-迈克尔聚合反应。使用TM

表征谱图