2,3,4,5,6-五氟苯氧基乙酸 | 14892-14-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,3,4,5,6-五氟苯氧基乙酸
• 中文别名: 五氟苯氧基乙酸
• 英文名称: Pentafluor-phenoxy-essigsaeure
• 英文别名: pentafluorophenoxyacetic acid；(2,3,4,5,6-pentafluorophenoxy)acetic acid；2-(2,3,4,5,6-pentafluorophenoxy)acetic acid
• CAS: 14892-14-9
• 化学式: C₈H₃F₅O₃
• 分子量: 242.102
• InChiKey: SMXPFEBIAASLOR-UHFFFAOYSA-N

物化性质

• 熔点：
  108-110 °C(lit.)
• 沸点：
  267.6±35.0 °C(Predicted)
• 密度：
  1.5580 (estimate)
• 稳定性/保质期：
  常温常压下稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  常温下应密闭避光保存，并保持通风和干燥。

SDS

Name:	Pentafluorophenoxyacetic Acid 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	14892-14-9

Section 1 - Chemical Product MSDS Name:Pentafluorophenoxyacetic Acid 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14892-14-9	Pentafluorophenoxyacetic Acid	97	238-964-1

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.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. 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 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:
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# 14892-14-9: 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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 112 deg C
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: C8H3F5O3
Molecular Weight: 242.0112

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents, strong bases.
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# 14892-14-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Pentafluorophenoxyacetic Acid - 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# 14892-14-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14892-14-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14892-14-9 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：

  2,3,4,5,6-五氟苯氧基乙酸 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 以6%的产率得到(2-hydroxy-F-phenoxy)acetic acid
  参考文献：
  名称：

  邻二取代的 F-苯。三、F-苯甲酸和F-苯酚制备(F-苯并)杂环化合物，以及一些中间体F-苯甲酰基和F-苯氧基化合物的反应

  摘要：

  为了通过分子内亲核环化实现 F-苯甲酸和 F-苯酚的选择性邻位取代，研究了一些必需的前体 F-苯甲酰基和 F-苯氧基化合物的制备及其亲核环化反应。1,2-(F-Benz)isoxazol-3(2H)-one, 2-(p-tolyl)-1,2-(F-benz)isoxazol-3(2H)-one, 1,3-二甲基( F-苯并)嘧啶-2,4(1H,3H)-dione 和 1,4-(F-Benz)oxazin-3(2H)-one 从各自的前体 F-苯异羟肟酸 N-(p -甲苯基)-N-羟基-F-苯甲酰胺、N,N'-二甲基-N-(F-苯甲酰基)脲和2-(F-苯氧基)乙酰肼。2-(F-苯氧基)乙酰异羟肟酸和(F-苯氧基)乙酸的环化尝试伴随同时开环并导致形成相同的产物：(2-羟基-F-苯氧基)乙酸。

  DOI：

  10.1246/bcsj.54.3447
• 作为产物：
  描述：

  pentafluorophenolate anion 、 氯乙酸 生成 2,3,4,5,6-五氟苯氧基乙酸
  参考文献：
  名称：

  Skeletal rearrangements preceding CO loss from metastable phenoxymethylene ions derived from phenoxyacetic acid and anisole

  摘要：

  AbstractThe loss of CH2˙ from the molecular ion of phenoxyacetic acid and the expulsion of an H˙ atom from ionized anisole lead to phenoxymethylen ions, which fragment predominantly by CO loss on the microsecond time‐scale. Carbon‐13 labelling reveals that ∼90% of the CO molecules expelled from the metastable ions derived from phenoxyacetic acid incorporate the carbon atom from the 1‐position of the phenyl group of the parent compound, whereas the residual CO molecules contain one of the other carbon atoms of the aromatic ring. The 2‐fluoro‐ and 2‐methylphenoxymethylene ions derived from the appropriate aryloxyacetic acids behave similarly, i.e. the carbon atom of the methylene group of the parent compound is not incorporated in the expelled CO molecules. In contrast, ∼45% of the CO molecules eliminated from the metastable phenoxymethylene ions formed from ionized anisole contain the carbon atom of the methyl group, while the remaining part contains the carbon atom from the 1‐position of the phenyl ring of the parent compound. This result is taken as evidence for the occurrence of a skeletal rearrangement of the anisole molecular ion leading to an interchange between the carbon atom of the methyl group and the carbon atom at the 1‐position of the ring. The elimination of CO from the metastable ions generated from either phenoxyacetic acid or anisole gives rise to a composite metastable peak. Conclusive evidence as to the formation of [C7H7O]+ isomers other than the phenoxymethylene ion is not obtained, indicating that the composite metastable peak is a result of two competing reactions both leading to CO loss. Possible mechanisms of these reactions are discussed together with the mechanism of the skeletal rearrangement of the molecular ion of anisole prior to H˙ loss.

  DOI：

  10.1002/oms.1210281031

文献信息

• Synthesis and cytotoxicity of novel 20-<i>O</i>-linked homocamptothecin ester derivatives as potent topoisomerase I inhibitors
  作者：Di-Zao Li、Cun-Ying Wang、Rui-Hua Liu、Yan-Ming Wang、Teng-Fei Ji、Yu-Rong Li、Xian-Dao Pan

  DOI：10.1080/10286020.2013.855203

  日期：2013.11.1

  attempt to improve the antitumor activity of homocamptothecins (hCPTs), a series of novel 20-O-linked hCPT ester derivatives were first designed and synthesized based on a synthetic route, by which hCPTs are acylated with different substituted phenoxyacetic acid ester derivatives. Most of the derivatives were assayed for in vitro cytotoxicity against six human cancer cell lines KB, KB/VCR, A549, HCT-8, Bel7402

  为了改善高喜树碱（hCPT）的抗肿瘤活性，首先基于合成路线设计和合成了一系列新颖的20- O-连接的hCPT酯衍生物，通过该合成路线，hCPT被不同的取代的苯氧基乙酸酯衍生物酰化。对大多数衍生物进行了针对六种人类癌细胞系KB，KB / VCR，A549，HCT-8，Bel7402和A2780的体外细胞毒性测定，并且大多数测定的化合物对这些肿瘤细胞系表现出良好的抗增殖活性，尤其是对KB
• Camptothecin derivatives
  申请人：California Pacific Medical Center

  公开号：US06350756B1

  公开（公告）日：2002-02-26

  (20S) esters of camptothecin analogs are provided. The compounds are (20S) esters of an oxyalkanoic acid and camptothecin, which is optionally substituted at the 7, 9, 10, 11, and 12 positions of the camptothecin ring. The compounds are useful for treating cancer.

  紫杉醇类似物的(20S)酯类化合物已提供。这些化合物是紫杉醇和氧烷羧酸的(20S)酯类，紫杉醇在7、9、10、11和12位的环上可选择性地被取代。这些化合物可用于治疗癌症。
• An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
  作者：Da-Wei Wang、Hong-Yan Lin、Bo He、Feng-Xu Wu、Tao Chen、Qiong Chen、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1021/acs.jafc.6b04110

  日期：2016.11.30

  4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is an important target for new bleaching herbicides discovery. As a continuous work to discover novel crop selective HPPD inhibitor, a series of 2-(aryloxyacetyl)cyclohexane-1,3-diones were rationally designed and synthesized by an efficient one-pot procedure using N,N′-carbonyldiimidazole (CDI), triethylamine, and acetone cyanohydrin in CH2Cl2

  4-羟基苯基丙酮酸双加氧酶（EC 1.13.11.27，HPPD）是发现新的漂白除草剂的重要目标。为发现新型农作物选择性HPPD抑制剂而进行的持续工作，使用N，N'-羰基二咪唑（CDI），通过高效的一锅法合理设计和合成了一系列2-（芳氧基乙酰基）环己烷-1,3-二酮，三乙胺和丙酮氰醇在CH 2 Cl 2中。总共以良好至优异的产率合成了58种三酮化合物。一些三酮类化合物显示出有效的体外拟南芥HPPD（At HPPD）抑制活性。2-（2-（（（1-溴萘-2-基）氧基）乙酰基）-3-羟基环己基-2-烯-1-酮，II-13，在37.5–150 g ai / ha的剂量下表现出高，广谱和芽后除草活性，几乎与甲基磺草酮对某些杂草一样有效。此外，II-13在150 g ai / ha的速率下对玉米和低芥酸菜籽显示出良好的农作物安全性，这表明II-13可能作为除草剂用于控制玉米和低芥酸菜子田中的杂草。II
• Colorant compounds
  申请人：Banning H. Jeffrey

  公开号：US20060020141A1

  公开（公告）日：2006-01-26

  Compounds of the formula wherein M is either (1) a metal ion having a positive charge of +y wherein y is an integer which is at least 2, said metal ion being capable of forming a compound with at least two chromogen moieties, or (2) a metal-containing moiety capable of forming a compound with at least two chromogen moieties, z is an integer representing the number of chromogen moieties associated with the metal and is at least 2, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d, Y, and z are as defined herein, Q − is a COO − group or a SO 3 — group, A is an organic anion, and CA is either a hydrogen atom or a cation associated with all but one of the Q − groups.

  式中的化合物，其中M是一个带有正电荷+y的金属离子，其中y是至少为2的整数，该金属离子能够与至少两个色团基团形成化合物，或者M是一个含金属基团的基团，能够与至少两个色团基团形成化合物，z是表示与金属相关的色团基团数量的整数，至少为2，R1、R2、R3、R4、R5、R6、R7、a、b、c、d、Y和z的定义如上所述，Q-是一个COO-基团或SO3-基团，A是一个有机阴离子，CA是一个氢原子或与除一个Q-基团之外的所有Q-基团相关联的阳离子。
• COLCHICINE DERIVATIVES
  申请人：——

  公开号：US20040204370A1

  公开（公告）日：2004-10-14

  Certain N-deacetylcolchicine and N-deacetylthiocolchine derivatives are described wherein the 7-N position on the B ring is substituted with the group —C(O)—(CHR 4 ) m -AR, wherein m is an integer of 0-10, A is S, O, N or a covalent bond; R 1 is substituted phenyl or substituted benzoyl; optionally substituted cycloalkyl of 3-7 carbons; optionally substituted naphtyl; an optionally substituted imide ring; an optionally substituted 5 or 6 member heterocycle with at least one N, S, or O in the ring; or an optionally substituted fused heterocyclic or fused carboxyclic ring system; R 2 (at the 2 -position of the A ring) is methoxy, hydroxy, or methylenedioxy when taken together with R 3 ; R 3 (at the 3 -position of the A ring) is methoxy, hydroxy, a monosaccharide radical, or is methylenedioxy when taken together with R 2 ; and R 4 is H or is H or methyl when m is 1. Also dimers of such compounds are disclosed. When combined with suitable pharmaceutical excipients, these compounds are useful for treating various types of cancer.

  描述了某些N-去乙酰基秋水仙碱和N-去乙酰基硫秋水仙碱衍生物，其中B环上的7-N位置被取代为基团—C(O)—(CHR4)m-AR，其中m为0-10的整数，A为S、O、N或共价键；R1为取代苯基或取代苯甲酰基；可选择取代的含有3-7个碳原子的环烷基；可选择取代的萘基；可选择取代的亚胺环；可选择取代的含有至少一个N、S或O的5或6元杂环；或可选择取代的融合杂环或融合环戊二酸环系统；R2（在A环的2位）为甲氧基、羟基或与R3一起时为亚甲二氧基；R3（在A环的3位）为甲氧基、羟基、单糖基团，或与R2一起时为亚甲二氧基；R4为H或在m为1时为H或甲基。此外，还公开了这些化合物的二聚体。与适当的药用辅料结合时，这些化合物可用于治疗各种类型的癌症。

表征谱图