1-硝基-4-(1,2,2-三氟乙烯基)苯 | 85019-86-9

• 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: 1-硝基-4-(1,2,2-三氟乙烯基)苯
• 英文名称: Benzene, 1-nitro-4-(trifluoroethenyl)-
• 英文别名: 1-nitro-4-(1,2,2-trifluoroethenyl)benzene
• CAS: 85019-86-9
• 化学式: C₈H₄F₃NO₂
• 分子量: 203.12
• InChiKey: OBGFKVKIPOGPDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  209.4±40.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-硝基-4-(1,2,2-三氟乙烯基)苯 在 sodium tetrahydroborate 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 29.5h， 生成 1,2-bis(para-aminophenyl)tetrafluorocyclobutene
  参考文献：
  名称：

  Synthesis of new fluorinated polyimides

  摘要：

  Two monomers 1,2-bis(meta-aminophenyl)hexafluorocyclobutane (1), and 1,2-bis(para-aminophenyl)hexafluorocyclobutene (2), were prepared from meta- or para-nitroiodobenzenes. Palladium-catalyzed coupling reaction of trifluorovinylzine reagents with nitroiodo-benzenes gave the corresponding nitrotrifluorovinylbenzenes, which dimerized at 130-150 degreesC to give hexafluorocyclobutane derivatives. Reduction of 1,2-di(Tizeta-nitrophenyl)hexafluorocyclobutane with NaBH4 and SnCl2 afforded the diamine I in high yield. Upon treatment of 1,2-di(para-nitrophenyl)hexafluorocyclobutane with NaBH4 and SnCl2, reduction-defluorination occurred to give 2. Diamines, I or 2, polymerized with pyromellitic anhydride (A), 3,3,4,4-biphenyltetracarboxylic dianhydride (B), and 4,4'-(hexafluoroisopropylidene)-diphthalic anhydride (C), to give the corresponding poly(amic acids), which were imidized at above 250 degreesC to give thermally stable and amorphous polyimide films. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00462-6
• 作为产物：
  描述：

  4-硝基碘苯 、 1,1,1,2-四氟乙烷 在 四(三苯基膦)钯 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以37%的产率得到1-硝基-4-(1,2,2-三氟乙烯基)苯
  参考文献：
  名称：

  Room Temperature Preparation of Trifluoroethenylzinc Reagent by Metalation of the Readily Available Halocarbon HFC-134a and an Efficient, Economically Viable Synthesis of 1,2,2-Trifluorostyrenes

  摘要：

  Trifluoroethenylzinc reagent [CF2=CFZnX] was generated from the readily available halocarbon HFC-134a by an in situ metalation-transmetalation procedure at temperatures near to room temperature (15-20 degreesC). By systematic standardization of the metalation experiments by manipulation of solvent, cosolvent, temperature, zinc salt, and the base, the trifluoroethenylzinc reagent was produced in 73% yield at 20 degreesC in THF medium. The palladium-catalyzed cross-coupling reaction of the trifluoroethenylzinc reagent with various aryl iodides was carried out under mild reaction conditions to produce 1,2,2-trifluorostyrenes in 59-86% isolated yields. The stability of the intermediate trifluoroethenyllithium reagent was compared at different temperatures and solvent systems. Experimental evidence for the mono-anion from HFC-134a (CF3CHF-) was obtained by the trapping of the mono-anion with zinc halide in THF/TMEDA medium. The structure and complexation of both the mono- and bis-trifluoroethenylzinc reagents with TMEDA and other ligands are discussed.

  DOI：

  10.1021/jo049179c

文献信息

• Site directed synthesis of mono and disubstituted SF5-polyfluoroalkyl benzenes
  作者：R.W. Winter、R. Dodean、J.A. Smith、Anilkumar R.、D.J. Burton、G.L. Gard

  DOI：10.1016/j.jfluchem.2005.05.009

  日期：2005.8

  method for the preparation of o-, m-, p-SF5CF2CFYC6H4X (Y = Br, F and X = m-Br, p-Br, Cl, CH3, CF3, NO2, o-NO2, F, CF3, CH(CH3)2) derivatives was devised by a two-step reaction: SF5Br-addition to o-, m-, p-CF2CFC6H4X followed by reaction of AgBF4 with the o-, m-, p-SF5CF2CFBrC6H4X adducts. Additional studies have been carried out with several derivatives and includes the preparation of SF5CF2C(O)C6H5

  一种制备o-，m-，p -SF 5 CF 2 CFYC 6 H 4 X（Y = Br，F和X =  m -Br，p -Br，Cl，CH 3，CF 3，NO的新方法2，通过两步反应设计了o -NO 2，F，CF 3，CH（CH 3）2）衍生物：SF 5 Br加成到o-，m-，p -CF 2 CFC 6 H 4X随后的AgBF的反应4与ø - ，米- ，p -SF 5 CF 2 CFBrC 6 ħ 4 X加合物。已对几种衍生物进行了进一步的研究，包括制备SF 5 CF 2 C（O）C 6 H 5，对-CF 3 CFBrC 6 H 4 NO 2，SF 5 CF 2 CF 2 CF 2 C 6 H 3（NO 2）2，SF 5 CF 2 CF 2 C 6 H 3（NH 2）2以及含SF 5 CF 2 CF 2的聚酰亚胺和染料。给出了这些化合物的完整表征（IR，NMR和MS）。
• The application of novel methodology for the synthesis of o-, m-, and p-(SF5-perfluoroethyl) benzene derivatives
  作者：R.W. Winter、R. Dodean、J.A. Smith、R. Anilkumar、D.J. Burton、G.L. Gard

  DOI：10.1016/s0022-1139(03)00086-1

  日期：2003.8

  The reaction of o-, m-, and p-F2CCFC6H4X with SF5Br produces an intermediate adduct, F5SCF2CFBrC6H4X, which, on treatment with AgBF4, affords the first useful, high yield preparation of o-, m-, and p-F5SCF2CF2C6H4X.

  的反应ø - ，米- ，和p -F 2 CCFC 6 ħ 4 X具有SF 5溴产生一个中间加合物，F 5 SCF 2 CFBrC 6 ħ 4 X，其中，与治疗的AgBF 4，，得到的第一有用，高产率制备ø - ，米- ，和p -F 5 SCF 2 CF 2 C ^ 6 ħ 4 X.
• Sorokina, R. S.; Rybakova, L. F.; Kalinovskii, I. O., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 11, p. 2180
  作者：Sorokina, R. S.、Rybakova, L. F.、Kalinovskii, I. O.、Chernoplekova, V. A.、Beletskaya, I. P.

  DOI：——

  日期：——
• SOROKINA, R. S.;RYBAKOVA, L. F.;KALINOVSKIJ, I. O.;CHERNOPLEKOVA, V. A.;B+, ZH. ORGAN. XIMII, 1982, 18, N 11, 2458-2459
  作者：SOROKINA, R. S.、RYBAKOVA, L. F.、KALINOVSKIJ, I. O.、CHERNOPLEKOVA, V. A.、B+

  DOI：——

  日期：——
• HEINZE, PAMELA L.;BURTON, DONALD J., J. ORG. CHEM., 53,(1988) N 12, 2714-2720
  作者：HEINZE, PAMELA L.、BURTON, DONALD J.

  DOI：——

  日期：——