全氟正戊烷 | 678-26-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 中文名称: 全氟正戊烷
• 中文别名: C5-18-全氟烷；全氟五烷；十二氟戊烷；全氟戊烷
• 英文名称: perfluoropentane
• 英文别名: dodecafluoropentane；perfluoro-n-pentane；NVX-108；1,1,1,2,2,3,3,4,4,5,5,5-dodecafluoropentane
• CAS: 678-26-2
• 化学式: C₅F₁₂
• 分子量: 288.036
• InChiKey: NJCBUSHGCBERSK-UHFFFAOYSA-N

物化性质

• 熔点：
  -120°C
• 沸点：
  29°C
• 密度：
  1,664 g/cm3
• 闪点：
  29°C
• 溶解度：
  苯（可溶）、乙酸乙酯（可溶）、甲醇（可溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  12

ADMET

毒理性

• 毒性数据

大鼠 LC50 = 120,000 毫克/立方米

LC50 (rat) = 120,000 mg/m3

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  F,Xi
• 安全说明：
  S23,S9
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN 2810
• RTECS号：
  RZ9890000
• 包装等级：
  III
• 危险类别：
  6.1(b)

SDS

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Section 1: Product Identification
Chemical Name: Perfluoro-n-pentane, min. 98%
CAS Registry Number: 678-26-2
Formula: C5F12
EINECS Number: 211-647-5
Chemical Family: organofluorine compounds
Synonym: duodecafluoropentane, perfluoropentane

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 678-26-2 100% 2.5mg/m3 (as F) 2.5mg/m3 (as F)

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation, eyes and skin
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin. May cause redness, itching and pain.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
No specific information is available on the physiological effects of ingestion. May cause gastrointestinal
Ingestion:
irritation, nausea, and vomiting.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Product contains fluorine which under certain conditions of use, decomposition, or metabolism, may generate
Chronic Health Affects: fluoride ion, causing, nausea, vomiting, labored breathing, hypocalcaemia, deterioration of bone and tooth
structure, kidney and liver damage.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: not applicable
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: none required
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire, this material may emit toxic organic fumes, and corrosive hydrogen and carbonyl fluorides.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non combustible adsorbent and
Spill and Leak Procedures:
swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container in a cool well ventilated area.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: If possible, handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: If possible, handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: colorless liq.
Molecular Weight: 288.03
Melting Point: -120°
Boiling Point: 29°C
Vapor Pressure: no data
Specific Gravity: 1.63+/-0.06@25°C
Odor: none
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: (store cold)
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: None
Incompatibility: active metals, strong oxidizing agents.
Decomposition Products: carbon monoxide, organic fumes, hydrogen fluoride, and carbonyl fluoride

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SECTION 11: Toxicological Information
RTECS Data: Inhalation (rat); LC: 120 gm/m3.
Carcinogenic Effects: No data available
Mutagenic Effects: No data available
Tetratogenic Effects: No data available

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Listed in the TSCA inventory.
SARA (Title 313): Title compound not listed.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

全氟正戊烷的应用

全氟正戊烷主要用于超声波诊断中的造影剂。此外，它与C6F14及其它氢氟烃组成的液体还可用于清洁脱脂、气溶胶成分以及调色粉的调配。

制备过程

制备全氟正戊烷的过程如下：将六氟丙烯和氟氯化铝催化剂（摩尔比为7～8:1）加入镍质高压釜中，并通入四氟乙烯（摩尔比为1.02:1），同时控制反应温度在-20～20℃之间，反应压力最高不超过0.5MPa。此步骤得到的产物顺式和反式的比例约为7。

接下来，将上述产物与溶剂一同加入到镍质高压釜中，并开启搅拌。随后连续通入一定量的氟气（摩尔数至少为产物的2倍），同时控制反应温度在-20～25℃之间及反应压力在常压0.5MPa下进行，直至完成反应。

反应信息

• 作为反应物：
  描述：

  全氟正戊烷 生成 dodecafluoroheptanol
  参考文献：
  名称：

  Method for preparing storage stable colloids

  摘要：

  用于增强诊断超声波程序中对比度的药剂包括液体-液体类型的胶体分散体，即乳液或微乳液，其中分散的液相是高蒸汽压化学物质，经过从分散液相到高度回声分散气泡或库格尔沫的相变后，向生物体内施用。分散相的液态使得可以制造颗粒尺寸通常低于1000纳米的极其稳定、药学上可接受的乳液。在体温下的气态产生高度回声的微泡，直径通常低于10,000纳米，这些微泡可作为超声造影剂。描述了静脉、动脉内、口服、腹腔内和子宫内剂型、给药方法和成像技术。

  公开号：

  US05595723A1
• 作为产物：
  描述：

  decafluoro-1,2-epoxycyclohexane 在 三氟化钴 作用下， 生成 全氟正戊烷
  参考文献：
  名称：

  多氟1,2-环氧烷烃和-环烷烃。第二部分。十氟1,2-环氧环己烷的反应

  摘要：

  通过使用氢化铝锂，甲醇钠，甲基锂，叠氮化钠和氰化钾的亲核攻击，打开了标题化合物的环氧环。初级产物结合了亲核试剂（N）和烷氧基官能团，当N = CN时，烷氧基官能团通过甲基化而固定。然而，在大多数情况下，醇盐基团分解为羰基，并且当N为OMe时，酮被分离。可以在该羰基上添加更多的亲核试剂，分离得到的取代的醇盐为叔醇（N = Me）或甲基醚（N = N 3）。用氢化铝锂（N ＝ H），得到仲醇，在带有烷氧基的环碳上的氟被H取代。该途径可能不涉及游离的羰基，因为所得的醇是纯的立体异构体。这通过NMR显示，并且还因为由其制备的纯甲氧基甲基醚仅被脱氟化氢为2H-八氟环己烯基甲氧基甲基醚。

  DOI：

  10.1016/s0022-1139(00)82291-5
• 作为试剂：
  描述：

  1,2,3,4,5,6-六(三氟甲基)苯 在 全氟正戊烷 作用下， 生成 Hexakis-(trifluormethyl)-benzvalen
  参考文献：
  名称：

  六（三氟甲基）-苯和六（五氟乙基）-苯的价键异构体

  摘要：

  DOI：

  10.1039/c29690000202

文献信息

• The electrochemical fluorination of N-containing carboxylic acids (Part 4). Fluorination of methyl 3-dialkylamino-isobutyrates and methyl 3-dialkylamino-n-butyrates
  作者：Takashi Abe、Haruhiko Fukaya、Eiji Hayashi、Yoshio Hayakawa、Masakazu Nishida、Hajime Baba

  DOI：10.1016/0022-1139(93)03019-i

  日期：1994.2

  Several methyl esters of 3-dialkylamino-substituted n- and isobutyric acids have been subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides. Dimethyl, diethyl, pyrrolidino, morpholino, piperidino and N-methylpiperazino groups were investigated as dialkylamino substituents. The structure/yield relationship was evaluated both in terms of the structure of the acid and

  3-二烷基氨基取代的正丁酸和异丁酸的几种甲酯已经进行了电化学氟化反应，得到了相应的全氟代氟化物。研究了作为二烷基氨基取代基的二甲基，二乙基，吡咯烷基，吗啉代，哌啶子基和N-甲基哌嗪子基团。分别根据酸的结构和氨基的种类评价了结构/产率关系。由具有异丁酸骨架的甲酯比具有正丁酸基团的甲酯得到的全氟氟化物的收率更高，并且由具有环状氨基的酸得到的无氟氟化物的收率更高。
• Phase shift colloids as ultrasound contrast agents
  申请人：Sonus Pharmaceuticals

  公开号：US05558853A1

  公开（公告）日：1996-09-24

  Agents for enhancing the contrast in a diagnostic ultrasound procedure comprise colloidal dispersions of the liquid-in-liquid type, i.e., emulsions or microemulsions, in which the dispersed liquid phase is a liquid having a boiling point below the temperature of the animal to be imaged and which therefore undergoes a phase change from a dispersed liquid to a highly echogenic dispersed gaseous foam or kugelschaum following administration to the animal. The liquid state of the dispersed phase allows one to manufacture extremely stable, pharmaceutically acceptable emulsions with particle sizes typically below 1000 nm. The gaseous state at body temperature yields highly echogenic microbubbles, typically below 10,000 nm in diameter, which are effective as ultrasound contrast agents. Intravenous, intraarterial, oral, intraperitoneal, and intrauterine dosage forms, methods of administration, and imaging techniques are described.

  用于增强诊断超声波程序中的对比度的药剂包括液体-液体类型的胶体分散体，即乳状液或微乳液，其中分散的液相是一种具有沸点低于待成像动物温度的液体，因此在给动物注射后会发生从分散的液体到高度回声散射的气泡或"球形泡沫"的相变。分散相的液态允许制造颗粒大小通常低于1000纳米的极其稳定、药学可接受的乳剂。在体温下的气态产生高度回声散射的微泡，直径通常低于10,000纳米，这些微泡作为超声波对比剂非常有效。描述了静脉、动脉内、口服、腹腔内和子宫内给药形式、给药方法和成像技术。
• The electrochemical fluorination of nitrogen-containing carboxylic acids. Fluorination of methyl esters of 3-dialkylamino propionic acids
  作者：Takashi Abe、Eiji Hayashi、Haruhiko Fukaya、Yoshio Hayakawa、Hajime Baba、Shigeki Ishikawa、Kinya Asahino

  DOI：10.1016/s0022-1139(00)82821-3

  日期：1992.4

  Six methyl esters of 3-dialkylamino-substituted propionic acids were subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides. The following dialkylamino substituents were investigated: diethylamino, di-n-propyl-amino, di-n-butylamino, pyrrolidino, morpholino and piperidino groups. These perfluoroacid fluorides, which were obtained in fair yields, are considered to

  将3-二烷基氨基取代的丙酸的六种甲酯进行电化学氟化，得到相应的全氟代氟化物。研究了以下二烷基氨基取代基：二乙基氨基，二正丙基氨基，二正丁基氨基，吡咯烷基，吗啉代和哌啶子基。这些以合理收率获得的全氟酸氟化物被认为是制备软质（可降解）含氟化合物的潜在关键前体。这些盐在水溶液中显示出明显降低的表面张力。报告了所获得的所有全氟酸氟化物的物理性质，以及它们的光谱数据（19 F NMR，质谱和IR光谱）。
• Free radical chemistry. Part 5. [1] A new approach to the synthesis of perfluorinated ethers
  作者：Richard D. Chambers、Brian Grievson、Frederick G. Drakesmith、Richard L. Powell

  DOI：10.1016/s0022-1139(00)82331-3

  日期：1985.9

  Fluorinations of the free-radical adducts of fluorinated alkenes, to ethers, over cobalt trifluoride are described and perfluorinated ethers are obtained at temperatures in excess of 400°C. The effect of structure on the formation of perfluoroethers is outlined.

  描述了在三氟化钴上氟化烯烃的自由基加合物向醚的氟化，并且在超过400°C的温度下获得了全氟化醚。概述了结构对全氟醚形成的影响。
• The electrochemical fluorination of nitrogen-containing carboxylic acids. Fluorination of methyl esters of cyclic amino-group substituted carboxylic acids
  作者：Takashi Abe、Eiji Hayashi、Haruhiko Fukaya、Hajime Baba

  DOI：10.1016/s0022-1139(00)80494-7

  日期：1990.11

  Nine methyl esters of cyclic amino-group substituted carboxylic acids related to glycine, alanine or β-alanine were subjected to electrochemical fluorination. This afforded the corresponding perfluoroacid fluorides together with cleavage products in fair yields. As cyclic amino-substituents, pyrrolidino-, morpholino-, piperidino-, hexamethyleneimino- and N′-methyl-piperazinyl-groups were investigated

  对与甘氨酸，丙氨酸或β-丙氨酸有关的环状氨基取代的羧酸的九种甲酯进行电化学氟化。这样以合理的产率得到了相应的全氟氟化物和裂解产物。作为环状氨基取代基，研究了吡咯烷基，吗啉代，哌啶子基，六亚甲基亚氨基和N'-甲基哌嗪基。未观察到环化副产物的形成，这与脂族二烷基氨基取代的羧酸的氟化形成对比。从这样的2-环氨基丙酸甲酯[环氨基：吡咯烷基，吗啉代或哌啶子基]，与全氟酸氟化物一起得到全氟甲基酯，产率为1-2％和14-29。 ％ 分别。前一种化合物的形成归因于庞大的环状氨基的阻断作用。报告了所获得的新化合物的物理性质及其光谱（19 F NMR，质量和IR）数据。

表征谱图