Alpha-三氟代甲烷-beta-丁酸内酯 | 174744-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: Alpha-三氟代甲烷-beta-丁酸内酯
• 中文别名: ALPHA-三氟代甲烷-BETA-丁酸内酯；α-三氟甲基-β-丁内酯
• 英文名称: α-trifluoromethyl-γ-butyrolactone
• 英文别名: 4,5-dihydro-3-(trifluoromethyl)furan-2(3H)-one；3-(trifluoromethyl)-3,4,5-trihydrofuran-2-one；2-(Trifluoromethyl)butyrolactone；2-trifluoromethylbutyrolactone；3-(Trifluoromethyl)dihydrofuran-2(3H)-one；3-(trifluoromethyl)oxolan-2-one
• CAS: 174744-18-4
• 化学式: C₅H₅F₃O₂
• mdl: MFCD00798462
• 分子量: 154.089
• InChiKey: QNGJRLKMHRKJJL-UHFFFAOYSA-N

物化性质

• 沸点：
  50 °C (0.2 mmHg)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2932209090

SDS

Name:	alpha-Trifluoromethyl-gamma-butyrolactone Material Safety Data Sheet
Synonym:	None Known
CAS:	174744-18-4

Section 1 - Chemical Product MSDS Name:alpha-Trifluoromethyl-gamma-butyrolactone Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
174744-18-4	alpha-Trifluoromethyl-gamma-butyrolact	95.0	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
No information found.

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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.
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. Wash mouth out with 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 174744-18-4: 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:
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.

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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: 50 deg C @ 0.2 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H9F3O2
Molecular Weight: 182.057

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Excess heat.
Incompatibilities with Other Materials:
Strong bases, strong acids, strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 174744-18-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
alpha-Trifluoromethyl-gamma-butyrolactone - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 174744-18-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 174744-18-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 174744-18-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  Alpha-三氟代甲烷-beta-丁酸内酯 在 三甲基铝 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 99.5h， 生成 N-(4-Benzoylphenyl)-3-difluoromethylene-pyrrolidin-2-one
  参考文献：
  名称：

  N-Arylated pyrrolidin-2-ones and morpholin-3-ones as potassium channel openers

  摘要：

  Based on the most stable conformation of ZD6169, a series of N-arylated derivatives of oxazolidindione (2), morpholin-3-one (3-5), piperidin-2-one (6), and pyrrolidin-2-one (7-13) was synthesized and evaluated for potassium channel opening activity. In the in-vitro assays, N-(4-benzoylphenyl)-piperidin-2-one (6) and N-(4-benzoylphenyl)-3,3-dimethyl-pyrrolidin-2-one (9) demonstrated potent and selective relaxant activity at the bladder detrusor muscle [IC50, bladder = 7.4 and 6.7 muM, respectively; IC50 ratio (portal vein/bladder) = 41 and 51, respectively]. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00171-2
• 作为产物：
  描述：

  2-bromo-2-trifluoromethylbutyrolactone 在 Ra-Ni 作用下， 生成 Alpha-三氟代甲烷-beta-丁酸内酯
  参考文献：
  名称：

  The first general method for α-trifluoromethylation of carboxylic acids using BrF₃

  摘要：

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes 很容易由羧酸、CS2 和 MeI 制成，用 BrF3 处理后，最终会以良好的收率生成所需的δ-三氟甲基羧酸衍生物 RCH(CF3)COORâ² 。

  DOI：

  10.1039/b315705a

文献信息

• Synthesis of Perfluoroalkyl-Substituted<i>γ</i>-Lactones and 4,5-Dihydropyridazin-3(2<i>H</i>)-ones<i>via</i>DonorAcceptor Cyclopropanes
  作者：Daniel Gladow、Hans-Ulrich Reissig

  DOI：10.1002/hlca.201200413

  日期：2012.10

  presence of perfluoroalkyl‐ or perfluoroaryl‐substituted silyl enol ethers smoothly provided the corresponding alkyl 2‐siloxycyclopropanecarboxylates in very good yields. The generated donoracceptor cyclopropanes are equivalents of γ‐oxo esters, which we demonstrated by their one‐pot transformations to yield fluorine‐containing heterocycles. A reductive procedure selectively afforded perfluoroalkyl‐substituted

  在全氟烷基或全氟芳基取代的甲硅烷基烯醇醚存在下，Rh 2（OAc）4催化重氮酯的分解可提供非常高的收率，从而平稳地提供了相应的烷基2-甲硅烷氧基环丙烷羧酸酯。生成的供体受体环丙烷与γ-氧代酯等效，我们通过一锅转化证明了它产生含氟杂环。还原程序选择性地提供了全氟烷基取代的γ-羟基酯或γ-内酯。捐助者的待遇带有丙烷或苯肼的受体环丙烷提供了一系列全氟烷基和全氟芳基取代的4,5-二氢哒嗪-3（2 H）-酮。
• Efficient Synthesis of New Fluorinated Building Blocks by means of Hydroformylation
  作者：Lidia Fanfoni、Lisa Diab、Tomas Smejkal、Bernhard Breit

  DOI：10.2533/chimia.2014.371

  日期：——

  Hydroformylation of fluorinated alkenes is an efficient method for the preparation of fluorinated functionalized building blocks for the synthesis of biologically active target structures. In this article we summarize known hydroformylation reactions of fluorinated olefins and we add new results from our research groups. Particular attention is paid to the remarkable influence of organofluorine substituents

  氟化烯烃的加氢甲酰化是制备用于合成生物活性靶结构的氟化官能化结构单元的有效方法。在本文中，我们总结了氟化烯烃的已知加氢甲酰化反应，并增加了我们研究组的新结果。特别注意有机氟取代基对加氢甲酰化反应的催化剂活性，区域选择性和立体选择性的显着影响。
• A one-step photocatalytic synthesis of 2-(trifluoromethyl)butyrolactones
  作者：Ninja Reineke、Naveed A. Zaidi、Manju Mitra、David O'Hagan、Andrei S. Batsanov、Judith A. K. Howard、Dmitri Y. Naumov

  DOI：10.1039/p19960000147

  日期：——

  An efficient one-step procedure is described for the synthesis of 2-(trifluoromethyl)butyrolactone 1 and 4-substituted 2-(trifluoromethyl)butyrolactones by the photocatalytic conjugate addition of primary and secondary alcohols to 2-(trifluoromethyl)acrylic acid 6. With the exception of methanol, the reactions are conducted without a photosensitiser. The diastereoisomers of compounds 8 and 10 were separable by chromatography and their relative configurations were established unambiguously by X-ray analyses of suitable crystals.

  描述了一种有效的一步法，通过将伯醇和仲醇光催化共轭加成到 2-(三氟甲基)丙烯酸 6 来合成 2-(三氟甲基)丁内酯 1 和 4-取代的 2-(三氟甲基)丁内酯。除甲醇外，反应均在没有光敏剂的情况下进行。化合物8和10的非对映异构体可通过色谱法分离，并且通过合适晶体的X射线分析明确地确定它们的相对构型。
• N-Arylated pyrrolidin-2-ones and morpholin-3-ones as potassium channel openers
  作者：P Liang

  DOI：10.1016/s0968-0896(02)00171-2

  日期：2002.10

  Based on the most stable conformation of ZD6169, a series of N-arylated derivatives of oxazolidindione (2), morpholin-3-one (3-5), piperidin-2-one (6), and pyrrolidin-2-one (7-13) was synthesized and evaluated for potassium channel opening activity. In the in-vitro assays, N-(4-benzoylphenyl)-piperidin-2-one (6) and N-(4-benzoylphenyl)-3,3-dimethyl-pyrrolidin-2-one (9) demonstrated potent and selective relaxant activity at the bladder detrusor muscle [IC50, bladder = 7.4 and 6.7 muM, respectively; IC50 ratio (portal vein/bladder) = 41 and 51, respectively]. (C) 2002 Elsevier Science Ltd. All rights reserved.
• The first general method for α-trifluoromethylation of carboxylic acids using BrF₃
  作者：Aviv Hagooly、Shlomo Rozen

  DOI：10.1039/b315705a

  日期：——

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes, easily made from carboxylic acids, CS2 and MeI, were treated with BrF3 producing eventually the desired α-trifluoromethyl carboxylate derivatives – RCH(CF3)COOR′ – in good yields.

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes 很容易由羧酸、CS2 和 MeI 制成，用 BrF3 处理后，最终会以良好的收率生成所需的δ-三氟甲基羧酸衍生物 RCH(CF3)COORâ² 。