4,4,5,5,6,6-七氟-1-(2-噻吩基)-1,3-己二酮 | 559-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4,4,5,5,6,6-七氟-1-(2-噻吩基)-1,3-己二酮
• 中文别名: 4,4,5,5,6,6,6-六氟-1-(2-噻吩)-1,3-己基二酮；七氟-1-(2-噻吩基)-1,3-己二酮
• 英文名称: 4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)hexane-1,2-dione
• 英文别名: 4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)hexane-1,3-dione；4,4,5,5,6,6,6-Heptafluor-1-(2'-thienyl)-1,3-hexandion；heptafluorovaleroylthenoylmethane；2H,2H-heptafluoro-1-[2]thienyl-hexane-1,3-dione；2H,2H-Heptafluor-1-[2]thienyl-hexan-1,3-dion；1,3-Hexanedione, 4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)-；4,4,5,5,6,6,6-heptafluoro-1-thiophen-2-ylhexane-1,3-dione
• CAS: 559-94-4
• 化学式: C₁₀H₅F₇O₂S
• mdl: MFCD00047091
• 分子量: 322.203
• InChiKey: QHOQGOZSTQAYRH-UHFFFAOYSA-N

物化性质

• 熔点：
  214.5°C
• 沸点：
  112 °C (8 mmHg)
• 密度：
  1.53
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  10

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 储存条件：
  密封保存，宜存放在阴凉、干燥的仓库中。

SDS

Name:	4 4 5 5 6 6 6-Heptafluoro-1-(2-thienyl)- 1 3-hexanedione Material Safety Data Sheet
Synonym:	Heptafluoro-(2-thienyl)-1,3-hexanedione; Perfuorobutyryl-(2-thenoyl)methane; 2-Thenoylperfluorobutyrylmethane
CAS:	559-94-4

Section 1 - Chemical Product MSDS Name:4 4 5 5 6 6 6-Heptafluoro-1-(2-thienyl)- 1 3-hexanedione Material Safety Data Sheet
Synonym:Heptafluoro-(2-thienyl)-1,3-hexanedione; Perfuorobutyryl-(2-thenoyl)methane; 2-Thenoylperfluorobutyrylmethane

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
559-94-4	1,3-hexanedione,4,4,5,5,6,6,6-heptaflu	100.0	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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 water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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.
Notes to Physician:
Antidote: None reported.

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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 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 559-94-4: 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: clear yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 112 deg C @ 8.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.5350g/cm3
Molecular Formula: C10H5F7O2S
Molecular Weight: 322.20

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 559-94-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,3-hexanedione,4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)- - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 559-94-4: No information available.
Canada
CAS# 559-94-4 is listed on Canada's NDSL List.
CAS# 559-94-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 559-94-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4,4,5,5,6,6-七氟-1-(2-噻吩基)-1,3-己二酮 生成 (Z)-4,4,5,5,6,6,6-heptafluoro-3-oxo-1-thiophen-2-ylhex-1-en-1-olate;(E)-4,4,5,5,6,6,6-heptafluoro-3-oxo-1-thiophen-2-ylhex-1-en-1-olate;neodymium(3+)
  参考文献：
  名称：

  TOPILOVA, Z. M.;RUSAKOVA, I. V.;MESHKOVA, S. B.;LOZINSKIJ, M. O.;KUDRYAVT+, ZH. ANAL. XIMII, 46,(1991) N, S. 863-869

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基噻吩 、 七氟丁酸甲酯 在 乙醇 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以93%的产率得到4,4,5,5,6,6-七氟-1-(2-噻吩基)-1,3-己二酮
  参考文献：
  名称：

  带有线性全氟烷基和2-噻吩基部分的β-二酮的方便实用合成。

  摘要：

  开发了一种通用且稳健的合成方案，用于制备带有2-噻吩基和不同长度或甲基的全氟化烷基的β-二酮。该方案适用于制备数克量的二酮，而无需繁琐的纯化程序。此外，通过铜螯合物纯化二酮的已知方法得到了很大的改进。

  DOI：

  10.3762/bjoc.14.290

文献信息

• Synthesis of dihydrofurans containing trifluoromethyl ketone and heterocycles by radical cyclization of fluorinated 1,3-dicarbonyl compounds with 2-thienyl and 2-furyl substituted alkenes
  作者：Mehmet Yılmaz

  DOI：10.1016/j.tet.2011.08.098

  日期：2011.10

  3-trifluoroacetyl and 2-trifluoromethyl-dihydrofurans in good yields. The radical cyclizations of 2-methyl-5-[(E)-2-phenylvinyl]furan 2b and 2-[(E)-2-phenylvinyl]thiophene 2c led to the formations of 5-(5-methyl-2-furyl)-4,5-dihydrofuran and 5-(2-thienyl)-4,5-dihydrofuran, respectively. In the reactions of 1,3-dicarbonyls with alkenes, 2-thienyl substituted alkenes formed 4,5-dihydrofurans in higher

  基于乙酸锰（III）的各种氟化的1,3-二羰基化合物与2-噻吩基和2-呋喃基取代的烯烃的自由基环化反应以良好的收率产生了3-三氟乙酰基和2-三氟甲基-二氢呋喃。2-甲基-5-[（E）-2-苯基乙烯基]呋喃2b和2-[（E）-2-苯基乙烯基]噻吩2c的自由基环化导致5-（5-甲基-2-呋喃基）的形成）-4，5-二氢呋喃和5-（2-噻吩基）-4，5-二氢呋喃。在1，3-二羰基与烯烃的反应中，2-噻吩基取代的烯烃以比2-呋喃基取代的烯烃更高的产率形成4，5-二氢呋喃。
• Tuning the luminescence efficiency by perfluorination of side chains in Eu³⁺ complexes with β-diketones of the thiophene series
  作者：Evgeniya A. Varaksina、Mikhail A. Kiskin、Konstantin A. Lyssenko、Lada N. Puntus、Vladislav M. Korshunov、Gustavo S. Silva、Ricardo O. Freire、Ilya V. Taydakov

  DOI：10.1039/d1cp02951g

  日期：——

  The effect of fluorinated chain length of Htta analogs in [Eu(L)₃phen] complexes on energy transfer was investigated and the complicated influence of substituents on the photophysical properties of the compounds was thoroughly discussed.

  在[Eu(L)₃phen]配合物中，Htta类似物的氟化链长度对能量转移的影响进行了研究，并深入讨论了取代基对化合物光物理性质的复杂影响。
• Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans
  作者：Mehmet Yılmaz、E. Vildan Burgaz Yılmaz、A. Tarık Pekel

  DOI：10.1002/hlca.201100105

  日期：2011.11

  Radical cyclizations of fluorinated 1,3‐dicarbonyl compounds with dienes mediated by Mn(OAc)3 afforded 4,5‐dihydrofurans containing difluoroacetyl, trifluoroacetyl, or heptafluorobutanoyl groups in good‐to‐excellent yields. Additionally, 2‐(difluoromethyl)‐4,5‐dihydrofurans and a 4,7‐dihydrooxepin derivative were obtained as unexpected products in the reaction of 4,4‐difluoro‐1‐phenylbutane‐1,3‐dione

  Mn（OAc）3介导的含二烯的氟化1,3-二羰基化合物的自由基环化以优异的产率得到了含有二氟乙酰基，三氟乙酰基或七氟丁酰基的4,5-二氢呋喃。此外，在4,4-二氟-1-苯基丁烷-1,3-二酮与1,3-二烯的反应中，以意外产物形式获得了2-（二氟甲基）-4,5-二氢呋喃和4,7-二氢氧杂庚烯衍生物。二苯基丁1,3-二烯。对称二烯（例如2,3-二甲基丁1,3-二烯和1,4-二苯基丁-1,3-二烯与1,3-二酮）的自由基环化提供了相应的低收率产品。但是，用1,3-二羰基化合物处理1-苯基丁-1,3-二烯可得到含氟酰基的4,5-二氢呋喃。用3-甲基-1-苯基丁a-1,3-二烯和1,3-二苯基丁-1,3-二烯进行的自由基环化反应产生了4,5-二氢呋喃，收率很高，
• Tumorhemmende wirkstoffe, XIII [1] aromatisch carbocyclisch und heterocyclisch substituierte 2-perfluoralkylpyrimido[1,2-a]benzimidazole
  作者：Alfred Kreutzberger、Manfred Leger

  DOI：10.1016/s0022-1139(00)81446-3

  日期：1982.8

  appropriate β-diketones carrying fluoroalkyl groupings has led to the 2-perfluoroalkylpyrimido[1,2-a]benzimidazoles as follows: 4-phenyl-, 4-(2'-naphthyl)-, 4-(3'-pyridyl)-, 4-(2'-furyl)-, and 4-(2,-thienyl)-2-trifluoromethylpyrimido[1,2-a]benzimidazole, and 4-(2'-thienyl)-2-(heptafluoropropylpyrimido [1,2-a]benzimidazole.

  2-氨基苯并咪唑与带有氟烷基的适当β-二酮的相互作用已导致2-全氟烷基嘧啶基[1,2-a]苯并咪唑的结构如下：4-苯基-，4-（2'-萘基）-，4- （3'-吡啶基）-，4-（2'-呋喃基）-和4-（2，-噻吩基）-2-三氟甲基嘧啶[1,2-a]苯并咪唑和4-（2'-噻吩基）- 2-（七氟丙基嘧啶基[1,2-a]苯并咪唑。
• Synthesis of fluoroacylated 4,5-dihydrofurans and fluoroalkylated tetrahydrofurans by the radical cyclization using manganese(III) acetate. Part II
  作者：Mehmet Yılmaz、A. Tarık Pekel

  DOI：10.1016/j.jfluchem.2011.06.023

  日期：2011.9

  Manganese(III) acetate-based radical cyclizations of various fluorinated 1,3-dicarbonyl compounds with alkenes produced 3-fluoroacylated 4,5-dihydrofurans and 2-acetyloxy-2-fluoroalkylated tetrahydrofurans in good yields. Mechanism was proposed for the formation of all compounds. The radical cyclization of fluorinated 1,3-dicarbonyls showed to form different cyclized products depending on the structure

  各种含氟的1,3-二羰基化合物与烯烃的乙酸锰（III）基自由基环化反应可制得3-氟酰化的4,5-二氢呋喃和2-乙酰氧基-2-氟烷基化的四氢呋喃。提出了形成所有化合物的机理。氟化的1,3-二羰基的自由基环化显示形成不同的环化产物，具体取决于烯烃的结构和1,3-二羰基的烯醇形式。

表征谱图