hexakis-(4-cyanophenyloxy)cyclotriphosphazene | 174097-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: hexakis-(4-cyanophenyloxy)cyclotriphosphazene
• 英文别名: hexakis(4-cyanophenoxy)cyclotriphosphazene；N3P3(OC6H4CN-p)6；4-[[2,4,4,6,6-pentakis(4-cyanophenoxy)-1,3,5-triaza-2λ5,4λ5,6λ5-triphosphacyclohexa-1,3,5-trien-2-yl]oxy]benzonitrile
• CAS: 174097-79-1
• 化学式: C₄₂H₂₄N₉O₆P₃
• 分子量: 843.631
• InChiKey: OVEMIPDYOMHVSM-UHFFFAOYSA-N

物化性质

• 熔点：
  270-274 °C(Solv: N,N-dimethylformamide (68-12-2))
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  60
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  hexakis-(4-cyanophenyloxy)cyclotriphosphazene 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88.9%的产率得到hexakis-(4-tetrazolylphenyloxy)cyclotriphosphazene
  参考文献：
  名称：

  Synthesis of Hexakis-(4-tetrazolylphenyloxy)cyclotriphosphazene and Its Alkylonitrile Derivative

  摘要：

  [image omitted] Tetrazoles were introduced into cyclotriphosphazenes to obtain hexakis-(4-tetrazolylphenyloxy)cyclotriphosphazene (2) in good yield (88.9%) by reacting hexakis-(4-cyanophenyloxy)cyclotriphosphazene (1) with sodium azide in N,N-dimethylformamide (DMF) in the presence of NH4Cl as a catalyst. Its alkylonitrile derivative, hexakis-(4-cyanoethyltetrazolylphenyloxy)cyclotriphosphazene (3), was prepared by the reaction of 2 with acrylonitrile in acetonitrile, using triethylamine as a catalyst.

  DOI：

  10.1080/00397911.2010.486501
• 作为产物：
  描述：

  4-羟基苯甲腈 在 六氯环三磷腈 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以85%的产率得到hexakis-(4-cyanophenyloxy)cyclotriphosphazene
  参考文献：
  名称：

  Synthesis of Hexakis-(4-tetrazolylphenyloxy)cyclotriphosphazene and Its Alkylonitrile Derivative

  摘要：

  [image omitted] Tetrazoles were introduced into cyclotriphosphazenes to obtain hexakis-(4-tetrazolylphenyloxy)cyclotriphosphazene (2) in good yield (88.9%) by reacting hexakis-(4-cyanophenyloxy)cyclotriphosphazene (1) with sodium azide in N,N-dimethylformamide (DMF) in the presence of NH4Cl as a catalyst. Its alkylonitrile derivative, hexakis-(4-cyanoethyltetrazolylphenyloxy)cyclotriphosphazene (3), was prepared by the reaction of 2 with acrylonitrile in acetonitrile, using triethylamine as a catalyst.

  DOI：

  10.1080/00397911.2010.486501

文献信息

• Synthesis and characterization of alkyl- and acyl-substituted oxime–phosphazenes
  作者：Erol Çil、Mustafa Arslan、Ahmet Orhan Görgülü

  DOI：10.1139/v05-223

  日期：2005.12.1

  Two oxime–cyclophosphazenes were prepared from the hexakis(4-formylphenoxy)cyclotriphosphazene (2) and hexakis(4-acetylphenoxy)cyclotriphosphazene (8). The reactions of these oximes with ethyl bromide, allyl bromide, propanoyl chloride, and acriloyl chloride were studied. Hexasubstituted compounds were obtained from the reactions of hexakis4-[(hydroxyimino)methyl]phenoxy}cyclotriphosphazene (3) with ethyl bromide (4), allyl bromide (5), and propanoyl chloride (6), however, the oxime groups on 3 rearranged to nitrile (7) in the reaction of 3 with acriloyl chloride. Hexasubstituted compounds were also obtained from the reactions of hexakis4-[(1)-N-hydroxyethaneimidoyl]phenoxy}cyclotriphosphazene (9) with allyl bromide (11) and propanoyl chloride (12). Tetra- and penta-substituted products were obtained from the reactions of 9 with ethyl bromide (10) and acriloyl chloride (13), respectively. All products were generally obtained in high yields. The structures of the compounds were defined by elemental analysis, IR, ¹H, ¹³C, and ³¹P NMR spectroscopy. Key words: hexachlorocyclotriphosphazene, phosphazene, oxime, oxime derivatives, oxime–phosphazenes.

  两种羟肟基-环磷腈分别由六(4-甲醛基苯氧基)环三磷氮杂环烷(2)和六(4-乙酰基苯氧基)环三磷氮杂环烷(8)制备而成。研究了这些羟肟基与溴乙烷、烯丙基溴、丙酰氯和丙烯酰氯的反应。从六4-[(羟肟基)甲基]苯氧基}环三磷氮杂环烷(3)与溴乙烷(4)、烯丙基溴(5)和丙酰氯(6)的反应中获得了六取代化合物，然而，3上的羟肟基在与丙烯酰氯反应时重新排列成腈(7)。从六4-[(1)-N-羟基乙烷亚咪基]苯氧基}环三磷氮杂环烷(9)与烯丙基溴(11)和丙酰氯(12)的反应中也获得了六取代化合物。从9与溴乙烷(10)和丙烯酰氯(13)的反应中分别获得四取代和五取代产物。所有产物通常以高收率获得。通过元素分析、红外光谱、1H、13C和31P核磁共振光谱确定了化合物的结构。关键词：六氯环三磷氮杂环烷、磷氮杂环烷、羟肟基、羟肟基衍生物、羟肟基-磷氮杂环烷。
• PHOSPHAZENE COMPOUND COMPRISING CYANO GROUP, PREPARATION METHOD AND USES THEREOF
  申请人：Guangdong Guangshan New Materials Co., Ltd.

  公开号：US20170197998A1

  公开（公告）日：2017-07-13

  The present invention relates to a phosphazene compound comprising cyano group having a molecular structure of Formula (I); wherein, Y and Y′ are independently selected from organic groups; M 1 and M 2 are independently selected from phosphazene groups, and M 1 contains m 1 phosphorus atoms, and M 2 contains m 2 phosphorus atoms; X 1 , X 1 ′, X 2 , X 3 and X 4 are independently selected from any one of the sixth main-group elements; R and R′ are independently selected from divalent organic groups; a is an integer greater than or equal to 0; b is an integer greater than or equal to 1; and c is an integer greater than or equal to 0; and a+b=2m 1 , d+2=2m 2 . The present invention achieves a synergistic effect with P and N of phosphazene group by introducing cyano group to the phosphazene group, and thus improves thermal stability and flame retardancy of the phosphazene compound, and the compatibility thereof with other components is excellent. The resin composition comprising the phosphazene compound of the present invention has good heat resistance, water resistance, adhesive properties and mechanical properties, and thus the application thereof is widened.

  本发明涉及一种分子结构为式（I）的含氰基磷氮化合物；其中，Y和Y'分别选择有机基团；M1和M2分别选择磷氮化合物基团，M1含有m1个磷原子，M2含有m2个磷原子；X1、X1'、X2、X3和X4分别选择第六主族元素中的任意一种；R和R'分别选择二价有机基团；a为大于或等于0的整数；b为大于或等于1的整数；c为大于或等于0的整数；且a+b=2m1，d+2=2m2。本发明通过将氰基引入磷氮化合物中，与磷氮化合物的P和N产生协同作用，从而提高了磷氮化合物的热稳定性和阻燃性，并且与其他组分的相容性非常好。本发明所述的磷氮化合物树脂组成物具有良好的耐热性、耐水性、粘接性和机械性能，因此其应用范围得到了拓宽。
• Synthesis and electrochemistry of polymeric complexes with cationic manganese carbonyl fragments coordinated to polyphosphazenes through nitrile ligands
  作者：Gabino A. Carriedo、Lucía Fernández-Catuxo、Francisco J. García Alonso、Paloma Gómez-Elipe

  DOI：10.1016/0022-328x(95)05540-6

  日期：1995.11

  The cyclotriphosphazenes N3P3(O-C6H4-R-4)(5)(O-C6H4-CN-4), R = H(1a) or (t)Bu(1b), reacted with trans-[MnBr(CO)(2)(dppm) P(OPh)(3)}] and TIPF6 in dichloromethane to give the monocationic complexes [N3P3(O-C(6)H(4)R-4)(5)(O-C6H4-CN)}Mn(CO)(2)(dppm) P(OPh)(3)}][PF6], R=H(2a) or (t)Bu(2b). Similarly, the hexafunctionalized cyclotriphosphazene N3P3(O-C6H4-CN-4)(6) (4) reacted in CH2Cl2 with trans-[MnBr(CO)(2)(dppm)P(OPh)(3)}] in the presence of TIPF6, and with fac-[Mn(OClO3)(CO)(3)(PP)](PP = dppm or dppe), to give the hexacationic complexes [N3P3(O-C6H4-CN)Mn(CO)(2)(dppm)[P(OPh)(3)]}][PF6](6) (5a), [N3P3(O-C6H4-CN)Mn(CO)(3)(PP)}(6)]-(ClO4)(6) (PP = dppm, 6a, or dppe, 6b). In all cases, the changes in the P-31 P NMR chemical shifts for the phosphorus of the phosphazene ring, the molar conductivities in acetone solution and the cyclic voltammograms in CH2Cl2 of the complexes containing the trans-Mn(CO)(2)(dppm)[P(OPh)3] moiety showed a good correlation with the number of metal-carbonyl units bonded to the phosphazene in the mono- and hexa-cationic complexes. Similarly, the nitrile-containing phosphazene polymers NP(O-C6H5)(2-x)(O-C6H4-CN-4)(x)}(n) (x = 0.06, 7a; x = 0.28, 7b), reacted with the corresponding manganese carbonyls to give the complexes NP(O-C6H5)(2-x)[O-C6H4-CNMn(Co)(2)(dppm)P(OPh)(3)}(pF(6))](x)}(n) (x = 0.06, 8a; x = 0.28, 8b) and NP(O-C6H5)(1.94)[O-C6H4-CNMn(CO)(3)(dppe)(ClO4)](0.06)}(n) (9).The cyclic voltammogram of the polymers 8a and 8b in CH2Cl2 showed a very extended oxidation wave with large Delta E(p).