2,3,5,6-四氟苯肼 | 653-11-2

• 物质功能分类: 化学试剂 - 有机试剂 - 肼
• 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: 2,3,5,6-四氟苯肼
• 中文别名: 2,3,5,6-四氟苯基肼
• 英文名称: 2,3,5,6-tetrafluorophenylhydrazine
• 英文别名: 2,3,5,6-Tetrafluor-phenylhydrazin；(2,3,5,6-tetrafluorophenyl)hydrazine
• CAS: 653-11-2
• 化学式: C₆H₄F₄N₂
• mdl: MFCD00007575
• 分子量: 180.105
• InChiKey: TYMFVEOXNZYYTF-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C(lit.)
• 沸点：
  136.3±40.0 °C(Predicted)
• 密度：
  1.4197 (estimate)
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S23,S26,S37/39
• 危险类别码：
  R20/21
• WGK Germany：
  3
• 海关编码：
  2928000090
• 危险品运输编号：
  UN 2811
• 储存条件：
  常温常压下存储。

SDS

Name:	2 3 5 6-Tetrafluorophenylhydrazine 97+% Material Safety Data Sheet
Synonym:	None Known
CAS:	653-11-2

Section 1 - Chemical Product MSDS Name:2 3 5 6-Tetrafluorophenylhydrazine 97+% Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
653-11-2	2,3,5,6-Tetrafluorophenylhydrazine	97+%	211-494-4

Hazard Symbols: XN
Risk Phrases: 20/21

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation and in contact with skin.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.

---

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:

---

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 agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or alcohol-resistant foam.

---

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. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 653-11-2: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Flakes
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 91.00 - 93.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H4F4N2
Molecular Weight: 180.10

---

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, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen fluoride gas, nitrogen.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 653-11-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3,5,6-Tetrafluorophenylhydrazine - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21 Harmful by inhalation and in contact with
skin.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
WGK (Water Danger/Protection)
CAS# 653-11-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 653-11-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 653-11-2 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,3,5,6-四氟苯肼 在 phosphorus pentoxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 32.0h， 生成 4-(3-Hydroxypropyl)-1-(2,3,5,6-tetrafluorophenyl)-5-trifluoromethylpyrazole
  参考文献：
  名称：

  Synthesis of fluorinated pyrazole derivatives from β-alkoxyvinyl trifluoroketones

  摘要：

  1.1.1-Trifluoro-4-ethoxy-3-butane-2-one, 3-trifluoroacetyl-3, 4-dihydro-2H-pyran or furan reacted readily with pentafluorophenylhydrazine or per(poly)fluoroacectylhydrazine RtCO-NHNH2 (R-1: BrCF2, C3F7) to give N-substituted-5-hydroxy-5-trifluoromrthyl I heterocycles Y-N-N=CH-CH(R)C(OH)CF3 (Y: H, Ar-f - or RtCO), which were dehydrated by treatment with P2O5 or SOCl2 to form N-substituted 5-trifluoromethyl pyrazoles Y-N-N=CH-C(R)=C CF3 (Y: H, Ar-f - or RtCO) in good yields.[GRAPHICS](C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(00)00348-1
• 作为产物：
  描述：

  五氟苯 在 一水合肼 作用下， 以 乙醇 为溶剂， 以75 %的产率得到2,3,5,6-四氟苯肼
  参考文献：
  名称：

  多氟苯基取代的 Blatter 自由基：合成和结构-性能相关性

  摘要：

  布拉特自由基是极其稳定的有机缺电子顺磁体，具有作为多种应用中的自旋轴承构件的良好潜力。这些基团的堆积模式和分子构象适合于获得独特的磁和电子特性。在此，在系统探索氟化布拉特自由基固有的“结构-性质”相关性的框架内，1-(2,3,4-三氟苯基)-(2a)和1-(2,3,5,6-四氟苯基) )-3-苯基-1,4-二氢苯并[e][1,2,4]三嗪-4-基 (2b) 被合成并完全表征。发现基团2a和2b的晶体结构由两个不同的中心对称二聚体组成，苯并三嗪基部分的原子之间的分子间距离相对较短。 2-300 K 范围内的 SQUID 磁力测量表明，这两个自由基的晶体，就像之前合成的 1-(五氟苯基)-3-苯基-1,4-二氢苯并[e][1,2,4]三嗪的晶体一样-4-基（2c），以相当强的反铁磁相互作用为主。对于这两种二聚体类型，自旋非限制对称性破缺 DFT 计算预测相似的参数 J 相差不到 20%。随后使用理论预测的磁性基序拟合

  DOI：

  10.1021/acs.cgd.4c00537
• 作为试剂：
  描述：

  二苯并噻吩-4-硼酸 在 caesium carbonate 、 2,3,5,6-四氟苯肼 作用下， 以 水 为溶剂， 反应 12.0h， 以90%的产率得到4-H氧基二苯并噻吩
  参考文献：
  名称：

  一种催化氧化芳硼类化合物制备酚的方法

  摘要：

  本发明公开了一种催化氧化芳硼类化合物合成酚类化合物的方法，在溶剂醇或醇的水溶液中，在碱的作用下，加入水合肼或肼类化合物催化剂，催化氧化芳硼类化合物直接制备酚类化合物。本发明的制备酚类化合物的方法，催化剂是廉价的水合肼或肼类化合物，氧化剂为常压下的空气或氧气，反应无需金属催化剂且活性好，底物来源广泛且稳定，底物敏感官能团相容性好且适用范围广。在优化的反应条件之下，目标产品分离收率高达99%。

  公开号：

  CN103936538B

文献信息

• N-arylheteroaromatic products compositions containing them and use thereof
  申请人：Le-Brun Alain

  公开号：US20050130989A1

  公开（公告）日：2005-06-16

  N-Arylheteroaromatic products, compositions containing them and use thereof. The present invention relates to novel chemical compounds, particularly to novel N-arylheteroaromatic products, to compositions containing them and to their use as medicinal products, in particular in oncology.

  N-芳基杂芳产物，含有它们的组合物及其用途。本发明涉及新型化合物，特别是新型N-芳基杂芳产物，含有它们的组合物以及它们作为药用产品的用途，特别是在肿瘤学中的用途。
• On the application of the extended Fujita–Nishioka equation to polysubstituted systems. A kinetic study of the rearrangement of several poly-substituted Z-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole into 2-aryl-4-benzoylamino-5-phenyl-1,2,3-triazoles in dioxane/water
  作者：Francesca D'Anna、Fiammetta Ferroni、Vincenzo Frenna、Susanna Guernelli、Camilla Zaira Lanza、Gabriella Macaluso、Vitalba Pace、Giovanni Petrillo、Domenico Spinelli、Raffaella Spisani

  DOI：10.1016/j.tet.2004.10.054

  日期：2005.1

  or penta-substituted Z-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1a–18a) into the relevant 2-aryl-4-benzoylamino-5-phenyl-1,2,3-triazoles (1b–18b) have been determined in 1:1 (v:v) dioxane/water in a wide range of pS+ (3.80–12.50) at different temperatures. The kinetic data obtained have been correlated with those previously collected for the rearrangement of ortho-, meta- and para-substituted

  3-苯甲酰基-5-苯基-1，2，4-恶二唑（1a – 18a）的几个二，三，四或五取代的Z-芳基hydr重排成相关的2-芳基-4-的重排率苯甲酰氨基-5-苯基-1,2,3-三唑（1b – 18b）已在不同温度下在1：1 p（v：v）二恶烷/水中以较大的p S +（3.80–12.50）测定。获得的动力学数据已与先前收集的用于重排邻，间和对位取代的Z-芳基azo（19a – 38a）的数据相关。）通过藤田和西冈提出，从而在考虑空间位线性自由能关系（LFER）的延伸的装置（Ë小号）和场（˚F ø在除了正常的电子效应）邻近效应（σ邻，间， p）。良好的相关系数被计算出（- [R ≥0.999），具有易感性常数（ρ，δ和˚F）接近先前对所获得的那些19A - 38A，当仅不包括数据的2,6-双-邻-取代的ž -arylhydrazones 11a和16 –图18a显示了比可预见的高得多的反应性，证
• Antibacterial dimeric copper(II) complexes with chromone-derived compounds
  作者：Zahid H. Chohan、Mohammad S. Iqbal、Syed K. Aftab、A. Rauf

  DOI：10.3109/14756366.2011.585135

  日期：2012.4.1

  A new series of six chromone-derived compounds and their Cu(II) complexes have been synthesized and characterized by their physical, spectral and analytical data. The ligands and their Cu(II) complexes were screened for their in vitro antibacterial activity against four Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Shigella flexneri) and two Gram-positive (Bacillus subtilis

  已经合成了一系列新的六种色酮衍生化合物及其Cu（II）配合物，并通过其物理，光谱和分析数据进行了表征。通过以下方法筛选配体及其Cu（II）配合物对四种革兰氏阴性菌（大肠杆菌，铜绿假单胞菌，鼠伤寒沙门氏菌，弗氏志贺氏菌）和两种革兰氏阳性菌（枯草芽孢杆菌，金黄色葡萄球菌）的体外抗菌活性。琼脂井扩散法。发现该配体对一种或多种细菌物种不显示或不显示中度活性，而Cu（II）配合物则显示中到高活性。在络合之前没有活性的配体在与Cu（II）金属离子络合后变得有活性，而活性较低的则变得更有活性。
• Salicylic Acid Based Small Molecule Inhibitor for the Oncogenic Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (SHP2)
  作者：Xian Zhang、Yantao He、Sijiu Liu、Zhihong Yu、Zhong-Xing Jiang、Zhenyun Yang、Yuanshu Dong、Sarah C. Nabinger、Li Wu、Andrea M. Gunawan、Lina Wang、Rebecca J. Chan、Zhong-Yin Zhang

  DOI：10.1021/jm901645u

  日期：2010.3.25

  homology-2 domain containing protein tyrosine phosphatase-2 (SHP2) plays a pivotal role in growth factor and cytokine signaling. Gain-of-function SHP2 mutations are associated with Noonan syndrome, various kinds of leukemias, and solid tumors. Thus, there is considerable interest in SHP2 as a potential target for anticancer and antileukemia therapy. We report a salicylic acid based combinatorial library approach

  Src homology-2 域包含蛋白酪氨酸磷酸酶-2 (SHP2) 在生长因子和细胞因子信号传导中起关键作用。功能获得性 SHP2 突变与 Noonan 综合征、各种白血病和实体瘤有关。因此，人们对 SHP2 作为抗癌和抗白血病治疗的潜在靶点有相当大的兴趣。我们报告了一种基于水杨酸的组合文库方法，旨在结合活性位点和附近独特的亚袋，以提高亲和力和选择性。文库的筛选导致鉴定出具有高效细胞活性的 SHP2 抑制剂 II-B08（化合物9）。化合物9阻断生长因子刺激的 ERK1/2 激活和造血祖细胞增殖，提供支持证据表明 SHP2 的化学抑制可能对抗癌和抗白血病治疗有治疗作用。与9复合的 SHP2 结构的 X 射线晶体学分析揭示了可用于获得更有效和选择性 SHP2 抑制剂的分子决定因素。
• Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles
  作者：Larisa Politanskaya、Irina Bagryanskaya、Evgeny Tretyakov

  DOI：10.1016/j.jfluchem.2018.06.011

  日期：2018.10

  derivatives, while E-isomers were not active and were isolated unchanged. Molecular and crystal structures of prepared polyfluorinated (E)-arylhydrazones as well as selected 3-methyl-1-aryl-1H-indazoles were solved by the X-ray diffraction analysis. Meanwhile, the polyfluorinated acetophenone reacted with hydrazine in THF in the absence of a catalyst through a condensation–nucleophilic substitution

  在对甲苯磺酸的作用下，由1-（4-氨基-四氟苯基）乙酮和多氟芳基肼开始合成多氟芳基肼。然后在室温下在MeCN中用K 2 CO 3处理所得的E-和Z-异构体的混合物。在这些温和的反应条件下，Z-异构体经历了分子内亲核环化反应，形成了3-甲基-1-芳基-1 H-吲唑衍生物，而E-异构体则没有活性，分离状态不变。制备的多氟（E）-芳基hydr和选定的3-甲基-1-芳基-1的分子和晶体结构通过X射线衍射分析来解析H-吲唑。同时，在不存在催化剂的情况下，多氟苯乙酮与THF中的肼通过缩合-亲核取代级联过程反应，以极好的收率形成了3-甲基-1 H-吲唑衍生物。

表征谱图