2',4',5'-三氟苯乙酮 | 129322-83-4

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酮
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2',4',5'-三氟苯乙酮
• 中文别名: 1-乙酰基-2,4,5-三氟苯；2’,4’,5’-三氟苯乙酮
• 英文名称: 2',4',5'-trifluoroacetophenone
• 英文别名: 1-(2,4,5-trifluorophenyl)ethanone
• CAS: 129322-83-4
• 化学式: C₈H₅F₃O
• mdl: MFCD00061193
• 分子量: 174.122
• InChiKey: GVTLJUZWNNFHMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  -7
• 沸点：
  76 °C
• 密度：
  1.331 g/mL at 25 °C(lit.)
• 闪点：
  160 °F
• 稳定性/保质期：
  如果按照规定使用和储存，则不会分解，没有已知的危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2914700090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H227,H315,H319,H335
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥处。确保工作环境有良好的通风或排气设施。

SDS

Name:	2 4 5 -Trifluoroacetophenone 98% Material Safety Data Sheet
Synonym:	1-(2,4,5-Trifluorphenyl)-ethanon
CAS:	129322-83-4

Section 1 - Chemical Product MSDS Name:2 4 5 -Trifluoroacetophenone 98% Material Safety Data Sheet
Synonym:1-(2,4,5-Trifluorphenyl)-ethanon

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
129322-83-4	2,4,5-Trifluoroacetophenone	98%	unlisted

Hazard Symbols: XN
Risk Phrases: 22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed.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.
Inhalation:
May cause respiratory tract irritation.
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.
Ingestion:
Get medical aid. 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.
Notes to Physician:

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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.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 129322-83-4: 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 minimize contact with skin.
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: Aromatic odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 76 - 79 deg C @ 760.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 100 deg C (> 212.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 0.5 G/L WATER(20C)
Specific Gravity/Density: 1.3800g/cm3
Molecular Formula: C8H5F3O
Molecular Weight: 174.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 129322-83-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,4,5-Trifluoroacetophenone - 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: XN
Risk Phrases:
R 22 Harmful if swallowed.
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 129322-83-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 129322-83-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 129322-83-4 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',4',5'-三氟苯乙酮 在 吡啶 、 盐酸 、 乙醇 、 乙酸酐 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 替马沙星盐酸盐
  参考文献：
  名称：

  An alternative synthesis of temafloxacin, a potent antibacterial agent

  摘要：

  开发了一种合成（±）-7-（3-甲基哌嗪-1-基）-6-氟-1-（2,4-二氟苯基）-1,4-二氢-4-氧喹啉-3-羧酸盐酸盐4的替代方法，这是一种有效的抗菌剂。该方法的特点是通过2-甲基哌嗪对2,4,5-三氟乙酮的4-氟基进行区域特异性置换，产生关键中间体2,5-二氟-4-（3-甲基哌嗪-1-基）乙酮12，随后通过分子内亲核置换环化反应将其转化为4。

  DOI：

  10.1139/v92-170
• 作为产物：
  描述：

  2',3',4',5',6'-五氟苯乙酮 在 水 、 三乙基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以72%的产率得到2,3,5,6-tetrafluorophenylethanone
  参考文献：
  名称：

  三乙基膦对功能化氟代芳烃的加氢脱氟化氢：理论和实验研究†

  摘要：

  最近，我们报道了使用三乙基膦作为唯一的脱氟剂对选定的氟代芳族化合物进行无金属的加氢脱氟。这促使我们评估机械方案，并且根据这些结果以及新的实验证据，我们现在对初始方案进行了修改。新的机理避免了在393.15 K时六氟苯和五氟吡啶大约71 kcal mol -1的高能β消除步骤，从而引起水的参与。使用D 2O证实了水作为氢源的作用，产生了相应的氘代脱氟产物；DFT计算与此新提出的机制相吻合。我们在此还报告了这种一锅加氢脱氟方法在更广泛的氟代芳香族衍生物上的应用。其中一些允许收集关键的机械证据。

  DOI：

  10.1039/c9nj00721k

文献信息

• α-Palladation of Imines as Entry to Dehydrogenative Heck Reaction: Aerobic Oxidative Cyclization of <i>N</i>-Allylimines to Pyrroles
  作者：Zhiyuan Chen、Beili Lu、Zhenhua Ding、Ke Gao、Naohiko Yoshikai

  DOI：10.1021/ol400638q

  日期：2013.4.19

  here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization

  我们在这里报告钯（II）催化的N-烯丙胺衍生自甲基酮（通常为苯乙酮）的氧化环化反应，在室温下在氧气气氛下提供吡咯衍生物。该反应可能通过亚胺的α-palletation继之以烯烃迁移插入和β-氢化物消除而进行，因此代表了好氧脱氢Heck环化的新实例。
• N,O- vs N,C-Chelation in Half-Sandwich Iridium Complexes: A Dramatic Effect on Enantioselectivity in Asymmetric Transfer Hydrogenation of Ketones
  作者：Gang Zhou、Ahmed H. Aboo、Craig M. Robertson、Ruixia Liu、Zhenhua Li、Konstantin Luzyanin、Neil G. Berry、Weiping Chen、Jianliang Xiao

  DOI：10.1021/acscatal.8b02068

  日期：2018.9.7

  to a N,C- or N,O-chelated Cp*Ir(III) complex, depending on whether or not water was present in the reaction. While derived from the same precursor, these two complexes behaved in a dramatically different manner in asymmetric transfer hydrogenation (ATH) of ketones by formic acid, with the N,O-chelated complex being much more selective and active. The sense of asymmetric induction is also different, with

  [Cp * IrCl 2 ] 2的环金属化在NaOAc存在下与（S）-2-苯基-4,5-二氢恶唑-4-羧酸甲酯一起选择性地导致N，C-或N，O螯合的Cp * Ir（III）络合物，具体取决于反应中没有水。尽管这两种配合物均来自相同的前体，但在甲酸的酮的不对称转移氢化（ATH）中表现出明显不同的方式，其中N，O螯合的配合物具有更高的选择性和活性。不对称感应的感觉也不同，N，O-络合物提供S，而N，C-类似物R醇。进一步的研究表明，基础添加剂的性质极大地影响对映选择性和有效的HCOOH /胺比。这些观察结果表明配体配位模式和为ATH反应使用正确的碱基的重要性。
• Rhodium-Catalyzed Oxidative Perfluoroalkenylation by Carbonyl Group Directed C-H Bond Activation
  作者：Subban Kathiravan、Ian A. Nicholls

  DOI：10.1002/ejoc.201402904

  日期：2014.11

  The selective activation of C-H bonds under mild Rh-III catalytic conditions has been developed for the perfluoroalkenylation of various cyclic and acyclic aromatic ketones. This protocol uses versatile reagents and mild conditions. It requires a very low catalyst loading and has exceptional functional group tolerance as well as provides products in good to excellent yields. An application of this

  在温和的 Rh-III 催化条件下，CH 键的选择性活化已被开发用于各种环状和非环状芳族酮的全氟烯基化。该协议使用通用试剂和温和的条件。它需要非常低的催化剂负载量，并具有出色的官能团耐受性，并提供具有良好至优异产率的产品。描述了这种方法用于制备生物活性物质的全氟乙基丙烯酸酯衍生物的应用。
• 2-Alkynyl-and 2-alkenyl-pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2a receptor antagonists
  申请人：Schering Corporation

  公开号：US20040220194A1

  公开（公告）日：2004-11-04

  Compounds having the structural formula I 1 or a pharmaceutically acceptable salt thereof, wherein R is 2 R 1 , R 2 , R 3 , R 4 and R 5 are H, alkyl or alkoxyalkyl; R 6 is H, alkyl, hydroxyalkyl or —CH 2 F; R 7 , R 8 and R 9 are H, alkyl, alkoxy, alkylthio, alkoxyalkyl, halo or —CF 3 ; and Z is optionally substituted aryl, heteroaryl or heteroaryl-alkyl are disclosed. Also disclosed is the use of compounds of formula I in the treatment of central nervous system diseases, in particular Parkinson's disease, alone or in combination with other agents for treating Parkinson's disease, and pharmaceutical compositions comprising them.

  具有结构式I或其药用可接受盐的化合物，其中R是R1，R2，R3，R4和R5为H，烷基或烷氧基烷基；R6为H，烷基，羟基烷基或—CH2F；R7，R8和R9为H，烷基，烷氧基，烷硫基，烷氧基烷基，卤素或—CF3；以及Z是可选择地取代的芳基，杂环芳基或杂环芳基烷基。还公开了化合物I的应用于治疗中枢神经系统疾病，特别是帕金森病，单独或与其他治疗帕金森病的药剂联合使用，以及包含它们的药物组合物。
• Cobalt(ii)-catalyzed asymmetric hydrosilylation of simple ketones using dipyridylphosphine ligands in air
  作者：Feng Yu、Xi-Chang Zhang、Fei-Fei Wu、Ji-Ning Zhou、Wenjun Fang、Jing Wu、Albert S. C. Chan

  DOI：10.1039/c1ob05494e

  日期：——

  In the presence of PhSiH3 as the hydride donor, catalytic amounts of non-racemic dipyridylphosphine and an easy-to-handle cobalt salt Co(OAc)2·4H2O formed in situ an effective catalyst system for the asymmetric reduction of a diverse range of aryl alkyl ketones with moderate-to-excellent enantioselectivities (up to 96% ee). This approach tolerated the handling of both catalyst and reactants under air without special precautions.

  在存在作为氢供体的PhSiH3的情况下，非消旋的二吡啶膦和易于操作的钴盐Co(OAc)2·4H2O现场形成有效的催化系统，用于多种芳基烷基酮的对映选择性还原，其对映选择性从中等到优秀（最高可达96% ee）。这种方法在空气中处理催化剂和反应物时不需要特别预防措施。