2,2,2-trifluoro-1-phenylethan-1-one

• ChemBase编号: 8127
• 分子式: C8H5F3O
• 平均质量: 174.1199096
• 单一同位素质量: 174.02924944
• SMILES: C(C(=O)c1ccccc1)(F)(F)F
• Canonical SMILES: O=C(C(F)(F)F)c1ccccc1
• InChI: InChI=1S/C8H5F3O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5H
• InChIKey: KZJRKRQSDZGHEC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,2,2-trifluoro-1-phenylethan-1-one
• IUPAC传统名: trifluoroacetophenone
• 别名: α,α,α-三氟苯乙酮; 三氟苯丙酮; 2,2,2-三氟苯乙酮; 1-Phenyl-2,2,2-trifluoroethan-1-one; 2,2,2-Trifluoroacetophenone 99%; Trifluoroacetylbenzene; 2,2,2-trifluoro-1-phenylethan-1-one; (Trifluoroacetyl)benzene; 2,2,2-Trifluoro-1-phenyl-1-ethanone; 2,2,2-Trifluoro-1-phenylethanone; NSC 42752; Trifluoromethyl Phenyl Ketone; ω,ω,ω-Trifluoroacetophenone; 2,2,2-Trifluoroacetophenone; α,α,α-Trifluoroacetophenone; Phenyl trifluoromethyl ketone; 2,2,2-Trifluoroacetophenone

登记号

• CAS号: 434-45-7
• EC号: 207-103-1
• MDL号: MFCD00000420
• Beilstein号: 1866286
• PubChem SID: 160971434; 24889525; 24846784
• PubChem CID: 9905

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 2.663222
• LogD (pH = 7.4): 2.663222
• Log P: 2.663222
• 摩尔折射率: 37.471 cm^3
• 极化性: 13.466405 Å^3
• 极化表面积: 17.07 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: Clear Colourless Oil
• 熔点: -40°C
• 沸点: 165-166 °C(lit.); 165-166°C; 165-166°C; 46-48 °C/14 mmHg(lit.)
• 闪点: 105.8 °F; 41 °C; 41°C; 42°C(108°F)
• 密度: 1.24; 1.24 g/mL at 25 °C(lit.); 1.240
• 折射率: 1.4595; n20/D 1.458; n20/D 1.458(lit.)
• 疏水性(logP): 2.14

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Flammable/Lachrymatory/Irritant; LACHRYMATOR, FLAMMABLE
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1224; UN1224
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 10-36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: true; 是
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• GHS危险声明: H226-H315-H319-H335
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1224 3/PG 3

产品相关信息

• 纯度: ≥98.5% (GC); 95%; 98%; 99%
• 级别: puriss.
• 线性分子式: CF3COC6H5

详细说明

Sigma Aldrich - 107840

包装
5, 25, 100 g in glass bottle

Toronto Research Chemicals - T786450

2,2,2-Trifluoroacetophenone is a fluorinated acetophenone with inhibitory activity of acetylcholinesterase. 2,2,2-Trifluoroacetophenone was shown to have neuroprotective activity by inhibiting apoptosis in cerebellar granule neurons.

参考文献

• Brodbeck, U. et al.: Biochim. Biphys. Acta Enzymol., 567, 357 (1979)
• Kawase, M. et al.: Biol. Pharmac. Bull., 24, 1335 (1979)
• Olefination with methanesulfonyl chloride, promoted by KF in DMF, gives ɑ -(trifluoromethyl)styrene in 92% yield: J. Org. Chem., 59, 2898 (1994).
• Trifluoromethyl ketones undergo selective C-F bond cleavage with Mg in the presence of TMSCl, providing a convenient synthesis of 2,2-difluoro enol silanes: Chem. Commun., 1323 (1999).
• Reaction with Dimethyl acetylenedicarboxylate, A11437, in the presence of triphenylphosphine, gives a highly-functionalized -butyrolactone: J. Org. Chem., 61, 4516 (1996):
  
• In the presence of potassium monopersulfate (Oxone ), catalyzes the epoxidation of allylic alcohols via the in situ formed dioxirane: Tetrahedron, 56, 989 (1999).
• In the presence of KO-t-Bu, acts as a nucleophilic trifluoromethylating agent, converting carbonyl compounds to trifluoromethyl alcohols: Tetrahedron Lett., 44, 1055 (2003).