全氟(2-甲基-2-戊烯) | 1584-03-8

• 物质功能分类: 表面活性剂 - 工业表面活性剂
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 全氟(2-甲基-2-戊烯)
• 中文别名: 全氟-2-甲基-2-戊烯；十二氟-2-甲基-2-戊烯；全氟(4-甲基-2-戊烯)；六氟丙烯二聚体；二聚六氟丙烯；全氟(4-甲基戊-2-烯)
• 英文名称: perfluoro-2-methylpent-2-ene
• 英文别名: perfluoro-2-methyl-2-pentene；hexafluoropropylene dimer；1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)pent-2-ene；1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-2-pentene
• CAS: 1584-03-8
• 化学式: C₆F₁₂
• mdl: MFCD00015724
• 分子量: 300.047
• InChiKey: FAEGGADNHFKDQX-UHFFFAOYSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  53-61 °C(lit.)
• 密度：
  1.622 g/mL at 25 °C(lit.)
• 闪点：
  10 °F
• 稳定性/保质期：
  在常温常压下稳定，避免与强氧化剂和热源直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  12

安全信息

• 危险等级：
  3
• 危险品标志：
  F
• 安全说明：
  S16
• 危险类别码：
  R11
• WGK Germany：
  3
• 海关编码：
  2903399090
• 包装等级：
  II
• 危险品运输编号：
  UN 1993
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	Perfluoro-2-methyl-2-pentene 90% Material Safety Data Sheet
Synonym:	Dodecafluoro-2-methyl-2-pentene; 1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)
CAS:	1584-03-8

Section 1 - Chemical Product MSDS Name:Perfluoro-2-methyl-2-pentene 90% Material Safety Data Sheet
Synonym:Dodecafluoro-2-methyl-2-pentene; 1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1584-03-8	Perfluoro-2-methyl-2-pentene	98.0	216-436-1

Hazard Symbols: None Listed.
Risk Phrases: 11

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable.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. Vapors may cause dizziness or suffocation.
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.
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.
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. 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. Extremely flammable liquid and vapor. Containers may explode in the heat of a fire.
Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water.

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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. 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. 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:
Wash thoroughly after handling. Use with adequate ventilation.
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 container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. 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. Keep away from sources of ignition. 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1584-03-8: 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: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: 4.31 PSI @20C
Viscosity: Not available.
Boiling Point: 53 - 61 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: -12 deg C ( 10.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density: 1.6220g/cm3
Molecular Formula: C6F12
Molecular Weight: 300.04

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1584-03-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Perfluoro-2-methyl-2-pentene - 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
Shipping Name: FLAMMABLE LIQUID, N.O.S.*
Hazard Class: 3
UN Number: 1993
Packing Group: II
IMO
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3.2
UN Number: 1993
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3
UN Number: 1993
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
R 11 Highly flammable.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 28A After contact with skin, wash immediately with
plenty of water.
S 33 Take precautionary measures against static
discharges.
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# 1584-03-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1584-03-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1584-03-8 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

制备方法与用途

物理性质

全氟-2-甲基-2-戊烯是一种全氟烯烃类化合物，沸点为50.5℃，常温常压下为无色液体。

用途

全氟-2-甲基-2-戊烯具有两个反应活性位点：碳碳双键直接相连的氟原子和碳碳双键。这使得它易于作为中间体用于合成表面活性剂、织物处理剂或纸张处理剂等。由于不含氯，不会破坏大气臭氧层；且因其双键具有一定活性，在大气中的寿命比饱和全氟烷烃短，因此它在许多方面可以替代氟氯烷烃（CFCs）。此外，它可以应用于电子元件的冷冻剂、灭火剂、泡沫材料的发泡剂和热转移剂等。

反应信息

• 作为反应物：
  描述：

  全氟(2-甲基-2-戊烯) 在 sodium hydroxide 、 (C2H5)3N*BF3 、 三乙胺 、 烯丙醇 作用下， 以 乙醚 为溶剂， 反应 28.0h， 生成 2-Trifluormethyl-3-ethoxy-1,1,1,4,4,5,5,5-octafluor-2-penten
  参考文献：
  名称：

  Reaction of perfluoro-2-methylpent-2-ene with oxygen nucleophiles

  摘要：

  DOI：

  10.1007/bf00952853
• 作为产物：
  描述：

  六氟丙烯 在 四(二甲氨基)乙烯 作用下， 反应 24.0h， 以82%的产率得到全氟(2-甲基-2-戊烯)
  参考文献：
  名称：

  反应涉及氟离子。第40部分1。胺作为氟离子催化反应的引发剂

  摘要：

  四（二甲基氨基）乙烯（TDAE）和三甲胺与无水不饱和碳氟化合物反应生成“原位”强大的氟离子源。这些用于引发碳-碳键形成反应，例如。低聚和多氟烷基化，并且其中许多反应在没有溶剂的情况下有效地进行。

  DOI：

  10.1016/0040-4020(95)00787-9

文献信息

• Chemical modification of usnic acid 1. Reaction of (+)-usnic acid with perfluoroolefins
  作者：G. G. Furin、O. A. Luzina、R. I. Sokuev、M. P. Polovinka、N. F. Salakhutdinov、G. A. Tolstikov

  DOI：10.1007/s11172-007-0188-8

  日期：2007.6

  The reactions of the natural lichen metabolite, (+)-usnic acid, with a series of commercially available polyfluoroolefins (tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropene, perfluoro-2-methylpent-2-ene, and 1,2-dichlorooctafluorocyclohex-1-ene) afford its 7-O-polyfluoroalkyl and perfluorovinyl ethers.

  天然地衣代谢物 (+)-usnic 酸与一系列市售多氟烯烃（四氟乙烯、三氟氯乙烯、六氟丙烯、全氟-2-甲基戊-2-烯和1,2-二氯八氟环己-1-烯）的反应得到其 7-O-多氟烷基和全氟乙烯基醚。
• Synthesis and chemistry of perfluoro-2-iodo-2-methyl-alkanes
  作者：A. Probst、K. Raab、K. Ulm、K. von Werner

  DOI：10.1016/s0022-1139(00)82019-9

  日期：1987.11

  perfluoro-tert-alkyl iodides CF3(CF2)C(CF3)2I have been obtained from F-alkenes CF3(CF2)nCFC(CF3)2 (n = 0 and 1) by formal additions of iodine fluoride; these required substantial alterations of known procedure. The F-tert-alkyl iodides are the most reactive alkyl halides known so far, and they are also very toxic. The following types of reactions have been studied: (a) Nucleophilic attack of anions at the iodine

  两种新型全氟叔烷基碘化物CF 3（CF 2）C（CF 3）2我已经从获得F-烯烃CF 3（CF 2）Ñ CFC（CF 3）2（n = 0和1）正式加入氟化碘；这些都需要对已知程序进行实质性更改。F-叔烷基碘化物是迄今为止已知的最具反应性的烷基卤化物，并且它们也具有很高的毒性。研究了以下类型的反应：（a）阴离子对碘的亲核攻击，导致F-烯烃，（b）消除由金属或金属络合物引起的氟化碘，（c）热解，以非常选择性地产生F-异丁烯和正全氟烷基碘，（d）光解，和（e）热诱导插入到碳-碘键中。还报道了有关碘化物和某些其他氟化合物的吸入毒性的筛选结果。
• Stable perfluoroalkyl carbanion salts
  作者：Bruce E. Smart、William J. Middleton、William B. Farnham

  DOI：10.1021/ja00276a033

  日期：1986.8

  On decrit la synthese et les proprietes de carbanions perfluoroalkyles tertiaires de tris(dimethylamino) sulfonium

  关于三（二甲氨基）锍全氟烷基三重碳负离子的合成和所有权
• Intramolecular cyclization with participation of the cyano group in reactions of fluoro-olefins with hexafluoroacetone cyanohydrin
  作者：Yu.V. Zeifman、S.A. Postovoi、A.F. Aerov、E.I. Mysov

  DOI：10.1016/s0022-1139(00)80853-2

  日期：1993.12

  The reaction of fluoro-olefins (I) with hexafluoroacetone cyanohydrin (II) catalyzed by Et3N gives fluorinated 3-iminotetrahydrofurans (III), whose structures have been confirmed by spectral methods and various chemical transformations. A mechanism for the formation of products III is suggested including nucleophilic addition of an O-anion to a CC bond followed by intramolecular cyclization in the

  Et 3 N催化的氟代烯烃（I）与六氟丙酮氰醇（II）的反应生成了氟化的3-亚氨基四氢呋喃（III），其结构已通过光谱法和各种化学转化得到了证实。提出了产物Ⅲ的形成机理，包括向C additionC键亲核加成O-阴离子，然后在中间的C-阴离子中通过CN基团进行分子内环化。
• Design and synthesis of the novel branched fluorinated surfactant intermediates with CF3CF2CF2C(CF3)2 group
  作者：Ding Zhang、Min Sha、Renming Pan、Xiangyang Lin、Ping Xing、Biao Jiang

  DOI：10.1016/j.cclet.2018.11.014

  日期：2019.3

  chemical, etc. However, these surfactants have recently been identified as toxic and undegradability in the environment. Developing an efficient approach to environment-friendly fluorosurfactants is essential. A fluorocarbon branched chain strategy was adopted to develop /PFOS substitutes. A series of intermediates of novel branched fluorinated surfactants with CF3CF2CF2C(CF3)2 group were synthesized from

  摘要全氟辛酸（PFOA）或全氟辛烷磺酸盐（PFOS）是最主要的氟表面活性剂之一，广泛用于消防和日用化工等领域。然而，这些表面活性剂最近被确认为有毒且在环境中不可降解。开发一种环保的含氟表面活性剂的有效方法至关重要。碳氟化合物支链策略被采用来开发/ PFOS替代品。由全氟-2-甲基-2-戊烯合成了一系列具有CF3CF2CF2C（CF3）2基团的新型支链氟化表面活性剂中间体。所有步骤均温和，易于操作且价格便宜。预计这将是开发非生物累积性PFOA或PFOS替代品的非常重要的方向。

表征谱图