2-丁烯酸乙酯 | 10544-63-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-丁烯酸乙酯
• 中文别名: 2-丁烯酸乙(醇)酯；巴豆酸乙酯
• 英文名称: ethyl crotonate
• 英文别名: ethyl 2-butenoate；ethyl but-2-enoate；2-Butenoic acid, ethyl ester
• CAS: 10544-63-5
• 化学式: C₆H₁₀O₂
• mdl: MFCD00009289
• 分子量: 114.144
• InChiKey: ZFDIRQKJPRINOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  37.22°C (estimate)
• 沸点：
  142-143 °C(lit.)
• 密度：
  0.918 g/mL at 25 °C(lit.)
• 蒸气密度：
  3.9 (vs air)
• 闪点：
  36 °F
• LogP：
  1.806 (est)
• 物理描述：
  Ethyl crotonate appears as a clear colorless liquid with a pungent odor. Less dense than water and insoluble in water. Vapors heavier than air.
• 溶解度：
  Insoluble in water; soluble in oils
• 折光率：
  1.422-1.428
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

毒理性

• 副作用

神经毒素 - 急性溶剂综合征

Neurotoxin - Acute solvent syndrome

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险品标志：
  F,C
• 安全说明：
  S16,S26,S36/37/39,S45
• 危险类别码：
  R11
• WGK Germany：
  2
• 海关编码：
  29161900
• 危险品运输编号：
  UN 1862 3/PG 2
• RTECS号：
  GQ3500000
• 储存条件：
  存于阴凉干燥处。

SDS

Name:	Ethyl crotonate 98% Material Safety Data Sheet
Synonym:	2-Butenoic acid, ethyl ester; But-2-enoate, ethyl; Crotonic acid, ethyl este
CAS:	10544-63-5

Section 1 - Chemical Product MSDS Name:Ethyl crotonate 98% Material Safety Data Sheet
Synonym:2-Butenoic acid, ethyl ester; But-2-enoate, ethyl; Crotonic acid, ethyl este

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10544-63-5	Ethyl crotonate	98	234-125-9

Hazard Symbols: XI F
Risk Phrases: 11 36

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Irritating to eyes.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
Produces irritation, characterized by a burning sensation, redness, tearing, inflammation, and possible corneal injury. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin irritation. May cause dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Ingestion of large amounts may cause CNS depression.
Inhalation:
Causes respiratory tract irritation. Aspiration may lead to pulmonary edema. Vapors may cause dizziness or suffocation. May cause burning sensation in the chest.
Chronic:
Effects may be delayed.

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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. Do NOT allow victim to rub eyes or keep eyes closed.
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 immediately. 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:
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. 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. 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:
Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water. 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. 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:
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 away from heat, sparks and flame. Avoid ingestion and inhalation. Use with adequate ventilation. 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. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.

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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# 10544-63-5: 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: clear, colorless
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 142.0 - 143.0 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 2 deg C ( 35.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: .9200g/cm3
Molecular Formula: C6H10O2
Molecular Weight: 114.14

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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, strong oxidants.
Incompatibilities with Other Materials:
Strong 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# 10544-63-5: GQ3470000 LD50/LC50:
CAS# 10544-63-5: Dermal, guinea pig: LD50 = >10 mL/kg; Draize test, rabbit, eye: 20 mg/24H Moderate; Oral, rat: LD50 = 3 gm/kg.
Carcinogenicity:
Ethyl crotonate - 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
Shipping Name: ETHYL CROTONATE
Hazard Class: 3
UN Number: 1862
Packing Group: II
IMO
Shipping Name: ETHYL CROTONATE
Hazard Class: 3.2
UN Number: 1862
Packing Group: II
RID/ADR
Shipping Name: ETHYL CROTONATE
Hazard Class: 3
UN Number: 1862
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI F
Risk Phrases:
R 11 Highly flammable.
R 36 Irritating to eyes.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 33 Take precautionary measures against static
discharges.
WGK (Water Danger/Protection)
CAS# 10544-63-5: No information available.
Canada
CAS# 10544-63-5 is listed on Canada's DSL List.
CAS# 10544-63-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10544-63-5 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

• 用于有机合成，也用作溶剂、油漆软化剂
• 用于有机合成。溶剂。软化剂

类别
易燃液体

毒性分级
中毒

急性毒性
口服 - 大鼠 LD50：3000 毫克/公斤

刺激数据
眼睛 - 兔子 20 毫克/24 小时

可燃性危险特性
遇明火、高温、氧化剂易燃；燃烧产生刺激烟雾

储运特性
库房应通风、低温干燥；与氧化剂、酸类分开存放

灭火剂
干粉、干砂、二氧化碳、泡沫

反应信息

• 作为反应物：
  描述：

  2-丁烯酸乙酯 在 亚硝酰氯 作用下， 以 苯 为溶剂， 生成 Ethyl α,β-dichlorobutyrate
  参考文献：
  名称：

  硝基羧酸的研究。二、α,β-不饱和β-硝基羧酸酯的合成

  摘要：

  描述了通过两种途径对 α,β-不饱和 β-硝基羧酸乙酯 (IV) 进行的合成研究。α-羟基-β-硝基羧酸乙酯（II）由α,β-不饱和羧酸乙酯与发烟硝酸反应或硝基烷烃与乙醛酸乙酯反应得到，用乙酸酐处理，得到α,-乙酰氧基-β乙酯-硝基羧酸盐 (III)，随后通过用作催化剂的碱处理将其转化为 IV。另一方面，IV 也可从α-氯-β-硝基羧酸乙酯中获得，α-氯-β-硝基羧酸乙酯来源于α,β-不饱和羧酸乙酯与硝基或亚硝酰氯的反应。IV的结构分配是基于元素分析、红外光谱及其转化为相应的α-甲氧基衍生物。

  DOI：

  10.1246/bcsj.45.3595
• 作为产物：
  描述：

  2-丁炔酸乙酯 在 氢气 作用下， 生成 2-丁烯酸乙酯
  参考文献：
  名称：

  EP3939979

  摘要：

  公开号：
• 作为试剂：
  描述：

  苯基硼酸1,3-丙二醇酯 、 环戊酮 在 2-氨基-3-甲基吡啶 、 chlorobis(ethylene)rhodium(I) dimer 、 2-丁烯酸乙酯 、 1,3-dimesityl-4,5-dimethyl-1H-imidazol-2-ylidene 、 水 、 对甲苯磺酸 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 120.0h， 以65%的产率得到苯戊酮
  参考文献：
  名称：

  通过活化无应变碳-碳键进行简单酮的铃木-宫浦偶联

  摘要：

  在这里，我们描述了通过催化激活无张力的 CC 键，简单的酮可以在 Suzuki-Miyaura 偶联反应中有效地用作亲电子试剂。一系列常见的酮，如环戊酮、苯乙酮、丙酮和1-茚满酮，可以直接与各种芳基硼酸酯以高位点选择性偶联，这为获得更多功能化的芳香酮提供了独特的途径。初步机理研究表明酮 α-CC 键通过氧化加成断裂。

  DOI：

  10.1021/jacs.8b02462

文献信息

• Studies on Application of Amino Acid as Medicinal Agent. I. Syntheses of Amino-tert-alcohol Derivatives
  作者：SEIGORO HAYASHI、MITSURU FURUKAWA、YOKO FUJINO、NAOTO MATSUISHI、TADASHI OHKAWARA

  DOI：10.1248/cpb.17.145

  日期：——

  In order to find non-narcotic analgesics, 54 compounds of amino-tert-alcohol, in which a variety of substituent groups were involved at the carbon atom in 1-position and at the amino group, were synthesized by reacting various α-and β-amino acid esters with Grignard reagents. These amino acid esters were readily reacted with alkyl Grignard reagents to give the expected compounds. However, when bulky aromatic Grignard reagents were submitted to react, the reactions were found to stop at the stage of intermediate formation of the corresponding ketones.

  为了寻找非麻醉性镇痛药，通过将各种α-和β-氨基酸酯与格氏试剂反应，合成了54种氨基叔醇化合物，这些化合物在1-位碳原子和氨基上涉及多种取代基团。这些氨基酸酯容易与烷基格氏试剂反应，得到预期的化合物。然而，当使用庞大的芳香族格氏试剂进行反应时，发现反应停止在相应的酮中间体形成阶段。
• Oxidation of alcohols by transition metal complexes—iv
  作者：Ronald Grigg、Thomas R.B. Mitchell、Somyote Sutthivaiyakit

  DOI：10.1016/0040-4020(81)85027-2

  日期：1981.1

  range of aldehydes with simple primary alcohols to give esters together with alcohols formed by reduction of the aldehydes. The proportion of ester can be increased by adding an efficient hydrogen acceptor. The reaction can also be used to produce 5- and 7-membered lactones from aromatic dialdehydes. Propan-2-ol and the in situ catalyst reduce some aromatic aldehydes to the corresponding alcohols without

  RhH（CO）PPh 3）3和由RhCl 3 ·3H 2 O，PPh 3和Na 2 CO 3原位制得的催化剂均催化多种醛与简单的伯醇反应生成酯以及由醛的还原。可以通过添加有效的氢受体来增加酯的比例。该反应也可用于由芳族二醛生产5元和7元内酯。丙-2-醇和原位催化剂可将一些芳香醛还原为相应的醇，而不会形成酯。
• Alkyl-Substituted Allylic Lithium Compounds:  Structure and Dynamic Behavior
  作者：Gideon Fraenkel、Fayang Qiu

  DOI：10.1021/ja002248u

  日期：2000.12.1

  methyl-substituted allylic lithium compounds have been prepared by CH3Li cleavage of their corresponding bis(methyl)bis(allylic)stannanes. Low-temperature 13C and proton NMR studies of 1:1 complexes of these allylic lithium compounds with TMEDA establish their structures. NMR line shape changes with temperature provide barriers to rotation. Results are listed in order as follows (allyl substituents, compound number

  几种甲基取代的烯丙基锂化合物已通过其相应的双（甲基）双（烯丙基）锡烷的 CH3Li 裂解制备。这些烯丙基锂化合物与 TMEDA 的 1:1 配合物的低温 13C 和质子 NMR 研究确定了它们的结构。NMR 谱线形状随温度的变化提供了旋转障碍。结果按如下顺序列出（烯丙基取代基、化合物编号、kcal·mol-1 中的旋转障碍和发生旋转的键）：1,1-二甲基、26、18、2-3；内-1-甲基, 27, 19, 2-3; 内-1-外-3-二甲基、28、21、1-2 和 2-3。这些观察结果与烯丙基 13C NMR 化学位移一起表明，在末端不对称烷基取代的情况下，烯丙基 C-C 键与更多取代的末端相比具有更高的键序。与对称取代的烯丙基锂化合物相比，提出了不对称取代以降低离域程度。一种机制...
• Ligand-accelerated non-directed C–H functionalization of arenes
  作者：Peng Wang、Pritha Verma、Guoqin Xia、Jun Shi、Jennifer X. Qiao、Shiwei Tao、Peter T. W. Cheng、Michael A. Poss、Marcus E. Farmer、Kap-Sun Yeung、Jin-Quan Yu

  DOI：10.1038/nature24632

  日期：2017.11

  challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C–H functionalization with arene as the limiting reagent. This protocol is compatible with

  碳氢键 (C-H) 的定向活化在合成有用反应的发展中很重要，因为通过配位官能团实现了邻近诱导的反应性和选择性。钯催化的非定向 C-H 活化有可能实现进一步有用的反应，因为它可以到达更远的位置并应用于不含适当定向基团的底物；然而，由于缺乏足够活性的钯催化剂，它的发展面临着巨大的挑战。目前使用的钯催化剂仅与富电子芳烃反应，除非使用过量的芳烃，这限制了合成应用。在这里，我们报告了一种 2-吡啶酮配体，它与钯结合并以芳烃为限制剂加速非定向 C-H 功能化。该协议与广泛的芳香底物兼容，我们展示了不能过量使用的高级合成中间体、药物分子和天然产物的直接功能化。我们还开发了 C-H 烯化和羧化方案，证明了我们的方法对其他转化的适用性。这些转化中的位点选择性受空间和电子效应的组合控制，吡啶酮配体增强了空间对选择性的影响，从而为定向 C-H 功能化提供了互补的选择性。该协议与广泛的芳香底物兼容，我们展示了不能
• First iron-catalyzed synthesis of oximes from styrenes
  作者：Saisuree Prateeptongkum、Irina Jovel、Ralf Jackstell、Nadine Vogl、Christoph Weckbecker、Matthias Beller

  DOI：10.1039/b900326f

  日期：——

  Aryl-substituted olefins react with t-butyl nitrite and sodium borohydride in the presence of iron(II)phthalocyanine to give oximes in moderate to high yields.

  芳基取代的烯烃与叔丁基亚硝酸酯和四硼酸钠在二氯铁酞菁的存在下反应，以中等至高产率生成肟。