5-(异丁烯酰氧基)甲基-1,3-氧硫杂环戊烷-2-硫酮 | 161196-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 中文名称: 5-(异丁烯酰氧基)甲基-1,3-氧硫杂环戊烷-2-硫酮
• 中文别名: 5-(甲基丙烯酰氧基)甲基-1,3-氧硫杂环戊烷-2-硫酮；5-(异丁烯酰基氧)甲基-1,3-氧硫杂环戊烷-2-硫酮
• 英文名称: 5-(methacryloyloxy)methyl-1,3-oxathiolane-2-thione
• 英文别名: (2-thioxo-1,3-oxathiolan-5-yl)methyl methacrylate；DTCOMA；(2-sulfanylidene-1,3-oxathiolan-5-yl)methyl 2-methylprop-2-enoate
• CAS: 161196-23-2
• 化学式: C₈H₁₀O₃S₂
• mdl: MFCD06797122
• 分子量: 218.298
• InChiKey: CHGDTKXIBWRKIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险类别码：
  R20/21/22,R
• 海关编码：
  2934999090
• 安全说明：
  S36/37/39
• 储存条件：
  保存方法：冰箱内

SDS

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Section I.Chemical Product and Company Identification
Chemical Name 5-(Methacryloyloxy)methyl-1,3-oxathiolane-2-thione
Portland OR
2-Propenoic acid, 2-methyl-, (2-thioxo-1,3-
Synonym
oxathiolan-5-yl)methyl ester (9CI)
C8H10O3S2
Chemical Formula
CAS Number 161196-23-2

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
5-(Methacryloyloxy)methyl-1,3-oxathiolane-2-thione 161196-23-2 Min. 97.0 Not available. Not available.
(GC)

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Section III. Hazards Identification
Harmful if ingested or inhaled. Minimize exposure to this material. Severe overexposure can result in injury or death.
Acute Health Effects
This material produces an irritating stench. Do not inhale and always use under a fume hood. Inhalation can result in
inflammation of the respiratory system, headaches, nausea, and vomiting. Always cover all exposed skin with an
impermeable layer and use proper eye protection. A OSHA/MSHA approved dust and vapor respirator is required when
working with this material.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
Inhalation If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the
toxic material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Auto-Ignition Not available.
Flammability May be combustible at high temperature.
Flash Points Flammable Limits Not available.
Not available.
Combustion Products These products are toxic carbon oxides (CO, CO2), sulfur oxides (SO2, SO3...).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
5-(Methacryloyloxy)methyl-1,3-oxathiolane-2-thione

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Section VI. Accidental Release Measures
Spill Cleanup Stench material. Harmful material.
Use a shovel to put the material into a convenient waste disposal container. Consult federal, state, and/or local
Instructions
authorities for assistance on disposal.

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Section VII. Handling and Storage
STENCH. HARMFUL. REFRIGERATE. Keep away from heat. Mechanical exhaust required. When not in use, tightly
Handling and Storage
seal the container and store in a dry, cool place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Splash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult
a specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solid. (Yellow Crystalline Powder.) Solubility
Physical state @ 20°C Not available.
Not available.
Specific Gravity
Molecular Weight 218.29 Partition Coefficient Not available.
Boiling Point
Not available. Vapor Pressure Not applicable.
Melting Point Not available. Vapor Density Not available.
Refractive Index Not available. Volatility Not available.
Critical Temperature Not available. Odor Stench.
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities Reactive with oxidizing agents.

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Section XI. Toxicological Information
Not available.
RTECS Number
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Toxicity Data Not available.
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects Harmful if ingested or inhaled. Minimize exposure to this material. Severe overexposure can result in injury or death.
This material produces an irritating stench. Do not inhale and always use under a fume hood. Inhalation can result in
inflammation of the respiratory system, headaches, nausea, and vomiting. Always cover all exposed skin with an
impermeable layer and use proper eye protection. A OSHA/MSHA approved dust and vapor respirator is required when
working with this material.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Continued on Next Page
5-(Methacryloyloxy)methyl-1,3-oxathiolane-2-thione

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Section XII. Ecological Information
Ecotoxicity Not available.
Not available.
Environmental Fate

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
DOT Classification DOT Class 9: Miscellaneous hazardous material.
PIN Number
Proper Shipping Name
Aviation regulated solid, n.o.s.
Packing Group (PG) Not available.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not available.
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements R20/21/22- Harmful by inhalation, in contact with skin and if swallowed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为产物：
  描述：

  二硫化碳 、 甲基丙烯酸缩水甘油酯 在 lithium tert-butoxide 作用下， 以 neat (no solvent) 为溶剂， 反应 5.0h， 以89%的产率得到5-(异丁烯酰氧基)甲基-1,3-氧硫杂环戊烷-2-硫酮
  参考文献：
  名称：

  在无溶剂和环境条件下的区域和立体选择性合成二硫代碳酸酯

  摘要：

  在此，我们报告了在环境条件下，利用现成的叔丁醇锂作为一种有效的催化剂，将二硫化碳添加到末端和内部环氧化物中的方法。值得注意的是，该反应在区域和立体选择性上进行。通过应用优化的条件，转化了14个末端和内部环氧化物。在二氧化硅上简单过滤后，分离所需的环状二硫代碳酸酯，收率高达95％。进行了核磁共振波谱实验以确定活化方式，结果表明催化剂活化了二硫化碳。顺式-2,3-环氧丁烷的反应仅生成反式-二硫代碳酸酯，而（R的转化率）-环氧丙烷以一种对映异构体（> 99％ee）的形式选择性地立体定向生成相应的硫代碳酸酯， 收率为87％

  DOI：

  10.1002/cctc.201600242

文献信息

• Atom economical synthesis of di- and trithiocarbonates by the lithium tert-butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes
  作者：J. Diebler、A. Spannenberg、T. Werner

  DOI：10.1039/c6ob01081d

  日期：——

  selective catalyst for this reaction. The influence of different reaction parameters as well as the substrate scope under optimized reaction conditions has been studied. Terminal and highly substituted epoxides as well as thiiranes were converted. In total 28 products were prepared and isolated in yields up to 95%. Notably, the reactions were performed under mild conditions without additional solvents

  研究了碱金属醇盐作为将CS 2加到环氧化物中的催化剂。几种市售醇盐的筛选显示叔丁醇锂是该反应的活性和选择性催化剂。研究了在最佳反应条件下不同反应参数以及底物范围的影响。末端和高度取代的环氧化物以及硫烷被转化。总共制备并分离了28种产品，收率高达95％。值得注意的是，该反应在温和的条件下进行，无需额外的溶剂。已经研究了反应的区域和立体选择性，例如，通过转化（R）-苯乙烯和（R）-环氧丙烷。此外，通过13 C NMR监测测试反应，并给出了末端和内部环氧化物转化的合理机理。该提议与观察到的反应的区域选择性和立体选择性一致。
• RESIST COMPOSITION, PATTERNING PROCESS, AND BARIUM, CESIUM AND CERIUM SALTS
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20170115566A1

  公开（公告）日：2017-04-27

  A resist composition comprising a base resin comprising acid labile group-containing recurring units and preferably acid generator-containing recurring units, and a sodium, magnesium, potassium, calcium, rubidium, strontium, yttrium, cesium, barium or cerium salt of α-fluorinated sulfonic acid bonded to an alkyl, alkenyl, alkynyl or aryl group exhibits a high resolution and sensitivity and forms a pattern of satisfactory profile with minimal LWR after exposure and development.

  一种抗蚀组合物包括基树脂，其中包含含酸敏感基团的重复单元，最好包含含酸发生剂的重复单元，以及与烷基、烯基、炔基或芳基结合的α-氟磺酸的钠、镁、钾、钙、铷、锶、钇、铯、钡或铈盐，表现出高分辨率和灵敏度，并在曝光和显影后形成具有最小LWR的满意轮廓图案。
• Organocatalytic one-pot synthesis of functionalized 1,3-oxathiolanes and 1,3-thiazolidines
  作者：Majid Ghazanfarpour-Darjani、Alieh Khodakarami

  DOI：10.1007/s00706-015-1543-3

  日期：2016.4

  AbstractAn efficient organocatalytic approach for the synthesis of 1,3-oxathiolanes and 1,3-thiazolidines is reported. In this methodology, conjugated base of nitromethane was employed as a potential organocatalyst to promote cyclization reaction between strained heterocyclic compounds and heterocumulenes at ambient conditions. Graphical abstract

  摘要报道了一种用于合成1，3-氧杂硫杂环戊烷和1，3-噻唑烷的有效有机催化方法。在这种方法中，硝基甲烷的共轭碱被用作潜在的有机催化剂，以促进环境条件下应变杂环化合物与杂多烯之间的环化反应。 图形概要
• Six-Membered Cyclic Amidines as Efficient Catalysts for the Synthesis of Cyclic Dithiocarbonates from Carbon Disulfide and Epoxides under Mild Conditions
  作者：Naoto Aoyagi、Takeshi Endo

  DOI：10.1055/s-0039-1690266

  日期：2020.1

  Six-membered cyclic amidines effectively catalyzed the reaction of carbon disulfide with epoxides under mild conditions, such as atmospheric pressure and ambient temperature, to give the corresponding cyclic dithiocarbonates (1,3-oxathiolane-2-thiones) in high yields.

  六元环脒在温和条件下（如常压和室温）有效催化二硫化碳与环氧化物的反应，以高产率得到相应的环状二硫代碳酸酯（1,3-oxathiolane-2-thiones）。
• RADICALLY POLYMERIZABLE COMPOUND HAVING A CYCLIC DITHIOCARBONATE GROUP
  申请人：Ohta Keisuke

  公开号：US20090270574A1

  公开（公告）日：2009-10-29

  A radically polymerizable compound having a group represented by formula (1) (In the formula, R 1 to R 3 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, X represents an alkylene group having 1 to 4 carbon atoms.) and a radically polymerizable double bond and a composition for an optical material comprising the same have a high refractive index and excellent transparency and are hard to be oxidized in thermal curing and useful as an optical material with little tinting.

  具有由式（1）表示的基团的可根本聚合化合物（在该式中，R1至R3各自独立地表示氢原子或具有1至4个碳原子的烷基基团，X表示具有1至4个碳原子的烷基基团）和具有高折射率和优异透明度的光学材料组成物，难以在热固化过程中被氧化，并且作为具有少量着色的光学材料非常有用。