叔丁基乙烯基醚 | 926-02-3

• 物质功能分类: 有机原料 - 醚类化合物及其衍生物 - 醚、醚醇
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 叔丁基乙烯基醚
• 中文别名: 叔丁基乙烯醚；乙烯基叔丁醚
• 英文名称: tert-butyl vinyl ether
• 英文别名: 2-methyl-2-(vinyloxy)propane；t-butyl vinyl ether；vinyl 2-methyl-2-propyl ether；2-ethenoxy-2-methylpropane
• CAS: 926-02-3
• 化学式: C₆H₁₂O
• mdl: MFCD00048246
• 分子量: 100.161
• InChiKey: PGYJSURPYAAOMM-UHFFFAOYSA-N

物化性质

• 熔点：
  -112°C
• 沸点：
  75-76 °C(lit.)
• 密度：
  0.762 g/mL at 25 °C(lit.)
• 闪点：
  1 °F
• LogP：
  1.805 (est)
• 保留指数：
  559
• 稳定性/保质期：

  避免与不相容的材料、火源或热源接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  3.1
• 危险品标志：
  F,Xi
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R11
• WGK Germany：
  3
• 海关编码：
  2909199090
• 包装等级：
  II
• 危险类别：
  3.1
• 危险品运输编号：
  UN 3271 3/PG 2
• 危险标志：
  GHS02,GHS07
• 危险性描述：
  H225,H315
• 危险性防范说明：
  P210
• 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，并需冷藏。避免阳光直射。

SDS

Name:	tert-Butyl vinyl ether stabilized 98% Material Safety Data Sheet
Synonym:
CAS:	926-02-3

Section 1 - Chemical Product MSDS Name:tert-Butyl vinyl ether stabilized 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
926-02-3	tert-Butyl vinyl ether	98%	unlisted

Hazard Symbols: F
Risk Phrases: 11 52/53

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

---

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 can travel to a source of ignition and flash back. Will burn if involved in a fire. Flammable liquid and vapor.
Containers may explode if exposed to fire.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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. Remove all sources of ignition.
Use a spark-proof tool.

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Section 7 - HANDLING and STORAGE
Handling:
Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Take precautionary measures against static discharges.
Storage:
Keep away from sources of ignition. Do not store in direct sunlight.
Store in a tightly closed container. Refrigerator/flammables.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 926-02-3: Personal Protective Equipment Eyes: Not available.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless to yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: 105mbar @20 deg C
Viscosity: 0.41 mPa.s @20 deg C
Boiling Point: 78 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: 275 deg C ( 527.00 deg F)
Flash Point: -17 deg C ( 1.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Slightly soluble.
Specific Gravity/Density: 0.762
Molecular Formula: C6H12O
Molecular Weight: 100.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, ignition sources, heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: May occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 926-02-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
tert-Butyl vinyl ether - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Daphnia: Daphnia: TLm = 15 ppm; 48h; .

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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: ETHERS, N.O.S.*
Hazard Class: 3
UN Number: 3271
Packing Group: II
IMO
Shipping Name: ETHERS, N.O.S.
Hazard Class: 3
UN Number: 3271
Packing Group: II
RID/ADR
Shipping Name: ETHERS, N.O.S.
Hazard Class: 3
UN Number: 3271
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F
Risk Phrases:
R 11 Highly flammable.
R 52/53 Harmful to aquatic organisms, may cause
long-term adverse effects in the aquatic environment.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 61 Avoid release to the environment. Refer to
special instructions/safety data sheets.
WGK (Water Danger/Protection)
CAS# 926-02-3: No information available.
Canada
CAS# 926-02-3 is listed on Canada's NDSL List.
CAS# 926-02-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 926-02-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

叔丁基乙烯基醚具有高反应活性、强稀释性以及低收缩性，在光固化体系中能够显著提高固化速度，并改善固化膜层的附着力和柔韧性。因此，它被广泛应用于制造乙烯树脂、涂料、粘合剂和印刷油墨。此外，这种化合物还可用作聚合物单体或医药及农药中间体。

反应信息

• 作为反应物：
  描述：

  叔丁基乙烯基醚 在 [TripCH2N2(NMe)C2Ph]RuHCl(p-cymene) 、 氢气 作用下， 以 二氯甲烷-D2 为溶剂， 50.0 ℃ 、405.33 kPa 条件下， 反应 24.0h， 以41%的产率得到叔丁基乙醚
  参考文献：
  名称：

  半夹心氢化钌（ii）：末端，内部，环状和官能化烯烃的氢化†

  摘要：

  使双（1,2,3-三唑基亚烷基）银（I）配合物1a与[RuCl 2（p- Cymene）] 2反应，得到钌配合物[PhCH 2 N 2（NMe）C 2（C 6 H 4 CF 3）] RuCl 2（p- Cymene）（2a）作为次要的C（sp 2）–H活化副产物[PhCH 2 N 2（NMe）C 2（C 6 H 3 CF 3）] RuCl （p -cymene）（2a'）。类似的钌配合物2b，2c，2d和2e，通式为RuCl 2（对-cymene）（NHC）（NHC = MesCH 2 N 2（NMe）C 2 Ph 2b，PhCH 2 N 2（NMe）C 2 Ph 2c，还合成了TripCH 2 N 2（NMe）C 2 Ph 2d，IMes 2e。Me 3 SiOSO 2 CF 3与2a的后续反应和2b产生阳离子钌物种[[PhCH 2 N 2（NMe）C 2（C 6 H 4 CF 3））RuCl（p

  DOI：

  10.1039/c4dt02407a
• 作为产物：
  描述：

  acetaldehyde-(tert-butyl-phenyl-acetal) 生成 叔丁基乙烯基醚
  参考文献：
  名称：

  Schostakowskii et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 1099,1102; engl. Ausg. S. 959, 960

  摘要：

  DOI：
• 作为试剂：
  描述：

  4-乙炔苯酚 、 丙二醇甲醚醋酸酯 在 4-甲基苯磺酸吡啶 、 2-环己基乙醇 、 叔丁基乙烯基醚 、 三乙胺 、 乙酸乙酯 、 水 、 丙酮 作用下， 反应 5.0h， 以to obtain 54 g of the desired compound的产率得到p-(1-(Cyclohexylethoxy)ethoxy)styrene p-Hydroxystyrene
  参考文献：
  名称：

  Positive photoresist composition

  摘要：

  一种正向光阻组合物，包括（A）一种树脂，其具有通过酸作用分解的基团，以增加在碱性显影液中的溶解度，和（B）一种化合物，其在受到光辐射后生成至少一个含氟基团的脂肪族或芳香族羧酸。本发明的正向光阻组合物在使用具有可进行超细加工的短波长光源和化学放大型正向光阻的光刻技术中，具有分辨率和工艺允许度的改进，例如曝光余量和焦点深度。此外，当电子束用作曝光光源时，它表现出优异的性能。

  公开号：

  US20010041300A1

文献信息

• Intramolecular homolytic substitution at the sulfur atom: an alternative way to generate phosphorus- and sulfur-centered radicals
  作者：Paola Carta、Nicolas Puljic、Carine Robert、Anne-Lise Dhimane、Cyril Ollivier、Louis Fensterbank、Emmanuel Lacôte、Max Malacria

  DOI：10.1016/j.tet.2008.08.108

  日期：2008.12

  Two efficient procedures involving tin hydride or thiophenol-mediated intramolecular homolytic substitution at the sulfur atom are reported. They lead to the generation of varied P(V)-centered radicals from the corresponding aryl or alkyne thiophosphorus substrates. The radical formed can be trapped by an olefin via an intermolecular addition, leading to the construction of C–P bonds. Thiophosphination

  报道了在硫原子上涉及氢化锡或硫酚介导的分子内均溶取代的两种有效方法。它们导致从相应的芳基或炔基硫代磷底物生成各种以P（V）为中心的基团。形成的自由基可以通过分子间加成被烯烃捕获，从而导致C-P键的构建。还使用自由基环异构化方法实现了三键的硫代磷酸化。检验了该方法对含硫物质的扩展。
• A Heteroleptic Dirhodium Catalyst for Asymmetric Cyclopropanation with α‐Stannyl α‐Diazoacetate. “Stereoretentive” Stille Coupling with Formation of Chiral Quarternary Carbon Centers
  作者：Fabio P. Caló、Alois Fürstner

  DOI：10.1002/anie.202004377

  日期：2020.8.10

  The heteroleptic dirhodium paddlewheel catalyst 7 with a chiral carboxylate/acetamidate ligand sphere is uniquely effective in asymmetric [2+1] cycloadditions with α‐diazo‐α‐trimethylstannyl (silyl, germyl) acetate. Originally discovered as a trace impurity in a sample of the homoleptic parent complex [Rh2((R )‐TPCP)4] (5 ), it is shown that the protic acetamidate ligand is quintessential for rendering

  具有手性羧酸盐/乙酰氨基甲酸酯配体球的杂多丙二酸桨轮催化剂7在乙酸α-重氮-α-三甲基锡烷基（甲硅烷基，胚芽基）的不对称[2 + 1]环加成中具有独特的作用。最初在同质母体复合物[Rh 2（（R）-TPCP）4 ]（5）的样品中作为痕量杂质发现，表明质子对乙酰氨基酸盐配体对于精制7具有典型意义高对映选择性。‐NH基团被认为通过配体氢键将随后的金属卡宾锁定在适当的位置。生成的甲锡烷基化环丙烷经历“立体固位”交叉偶联，这首次表明，斯蒂勒-米吉塔反应甚至可以形成手性季碳中心。
• Radical-Mediated Synthesis of Racemic Deoxypodophyllotoxin and Related Lignans
  作者：Philippe Renaud、Tanja Kolly-Kovač

  DOI：10.1055/s-2005-865358

  日期：——

  An approach for the synthesis of lignans related to the podophyllotoxin family is reported. The key reaction is a highly diastereoselective iodoacetal cyclization under iodine atom transfer conditions followed by a homolytic aromatic substitution. The second aromatic ring is introduced at a later stage via addition of aryllithium to an aryl ketone. A novel and very mild method for the deoxygenation

  报告了一种合成与鬼臼毒素家族相关的木脂素的方法。关键反应是在碘原子转移条件下的高度非对映选择性碘缩醛环化，然后是均裂芳族取代。第二个芳环在稍后阶段通过将芳基锂添加到芳基酮中引入。描述了一种新颖且非常温和的中间体叔苄醇脱氧方法。
• Radical Transfer Hydroamination with Aminated Cyclohexadienes Using Polarity Reversal Catalysis:  Scope and Limitations
  作者：Joyram Guin、Christian Mück-Lichtenfeld、Stefan Grimme、Armido Studer

  DOI：10.1021/ja0692581

  日期：2007.4.1

  The synthesis of various new 1-aminated-2,5-cyclohexadienes is described. These reagents can be used in radical transfer hydroaminations of unactivated and electron-rich double bonds. With thiols as polarity reversal catalysts good yields are obtained. The radical hydroamination occurs with good to excellent anti-Markovnikov selectivity. Many functional groups such as alcohols, silyl ethers, phosphonates

  描述了各种新的 1-胺化-2,5-环己二烯的合成。这些试剂可用于未活化和富电子双键的自由基转移加氢胺化。使用硫醇作为极性反转催化剂可获得良好的产率。自由基加氢胺化以良好至极好的抗马尔可夫尼科夫选择性发生。许多官能团如醇、甲硅烷基醚、膦酸酯、芳基溴化物、酰亚胺、酰胺以及酸性质子在反应条件下是可以耐受的。DFT 计算提供了对甲硅烷基、烷基和氨基取代的环己二烯基的芳构化以生成相应的 C-、Si-和 N-中心自由基的见解。
• Mild and Efficient Nickel-Catalyzed Heck Reactions with Electron-Rich Olefins
  作者：Thomas M. Gøgsig、Jonatan Kleimark、Sten O. Nilsson Lill、Signe Korsager、Anders T. Lindhardt、Per-Ola Norrby、Troels Skrydstrup

  DOI：10.1021/ja2084509

  日期：2012.1.11

  A new efficient protocol for the nickel-catalyzed Heck reaction of aryl triflates with vinyl ethers is presented. Mild reaction conditions that equal those of the corresponding palladium-catalyzed Heck reaction are applied, representing a practical and more sustainable alternative to the conventional regioselective arylation of vinyl ethers. A catalytic system comprised of Ni(COD)(2) and 1,1'-bis(

  提出了一种新的有效协议，用于镍催化芳基三氟甲磺酸酯与乙烯基醚的 Heck 反应。应用了与相应钯催化的 Heck 反应相同的温和反应条件，代表了乙烯基醚传统区域选择性芳基化的实用且更可持续的替代方案。由 Ni(COD)(2) 和 1,1'-双（二苯基膦基）二茂铁 (DPPF) 与叔胺 Cy(2)NMe 组成的催化系统在广泛的芳基三氟甲磺酸酯的烯化中证明是有效的。缺电子芳烃和富电子芳烃都被证明是相容的，并且相应的芳基甲基酮可以在水解后以接近定量的产率获得。观察到良好的官能团耐受性，与类似 Pd 催化的 Heck 反应的特征相匹配。高水平的催化活性可以通过阳离子镍 (II) 配合物的中介作用来解释，该配合物可能负责连续的 β-氢化物消除和碱促进催化剂再生。尽管这些基本反应通常被认为具有挑战性，但 DFT 计算表明该途径在所应用的反应条件下是有利的。