(3-氨基苯基)膦酸 | 5427-30-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (3-氨基苯基)膦酸
• 英文名称: m-aminophenylphosphonic acid
• 英文别名: (3-aminophenyl)phosphonic acid；m-aminobenzenephosphonic acid
• CAS: 5427-30-5
• 化学式: C₆H₈NO₃P
• mdl: MFCD01706347
• 分子量: 173.108
• InChiKey: MZZQBSHNCYWSTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 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：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  (3-氨基苯基)膦酸 在 盐酸 、 亚硝酸乙酯 作用下， 生成 3-羟基苯基膦酸
  参考文献：
  名称：

  Synthesis of Phosphanilic Acid and Related Compounds¹

  摘要：

  DOI：

  10.1021/ja01123a049
• 作为产物：
  描述：

  1-碘-3-硝基苯 在 四(三苯基膦)钯 、 三甲基溴硅烷 、 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 (3-氨基苯基)膦酸
  参考文献：
  名称：

  EP2551262

  摘要：

  公开号：
• 作为试剂：
  描述：

  (3-氨基苯基)膦酸 、 sodium hydroxide 、 羟基甲酸酯 、 1-氨基-4-溴蒽醌 在 无水氯化铜 resultant mixture 、 (3-氨基苯基)膦酸 、 氯化钠 、 alcohol 作用下， 以 水 为溶剂， 以to obtain a blue anthraquinone compound (20 g)的产率得到蒽醌
  参考文献：
  名称：

  Organic solvent based ink composition

  摘要：

  本发明揭示了一种有机溶剂基墨水组合物，其中包含一种特定的染料和一种有机溶剂，特别是一种醇或一种甘醇，并且具有良好的时间稳定性和书写性能。该有机溶剂基墨水组合物包括一种染料和一种有机溶剂，其中该染料由##STR1##所表示，其中D表示没有磺酸基和羧基的偶氮或蒽醌染料的残基，X表示氧原子或亚甲基基团，Y表示C.sub.2-C.sub.12烷基，C.sub.2-C.sub.4羟基烷基，C.sub.2-C.sub.12烷氧基烷基，聚丁醇残基，聚乙烯醇残基，酚醛树脂残基或纤维素残基，m表示0或1。

  公开号：

  US05069719A1

文献信息

• The assembly of rotaxane-like dye/cyclodextrin/surface complexes on aluminium trihydroxide or goethite
  作者：Rachel J. Cooper、Philip J. Camp、Ross J. Gordon、David K. Henderson、Dorothy C. R. Henry、Hamish McNab、Sonali S. De Silva、Daniel Tackley、Peter A. Tasker、Paul Wight

  DOI：10.1039/b518260c

  日期：——

  Simple azo-dyes carrying phosphonic acid and arsonic acid substituents such as 4-(4-hydroxyphenyl azo)phenylphosphonic acid (5) and 4-(4-hydroxyphenylazo)phenylarsonic acid (6) bind more strongly to high surface area oxides such as aluminium trihydroxide and goethite than their carboxylic and sulfonic acid analogues and the phosphonate-functionalized dyes have been shown to have greater humidity fastness

  带有膦酸和砷酸取代基的简单偶氮染料，例如4-（4-羟基苯基偶氮）苯基膦酸（5）和4-（4-羟基苯基偶氮）苯基ar磺酸（6）与高表面积氧化物（如铝）结合更牢固三羧酸盐和针铁矿要比它们的羧酸和磺酸类似物和膦酸酯官能化的染料具有更高的耐湿坚牢度。吸附等温线测量为三元染料/环糊精/表面复合物的形成提供了证据。当以包含α-环糊精的油墨配方印刷到氧化铝涂层纸上时，形成这种三元络合物的染料显示出更高的耐光牢度。
• [EN] DIAMINOPTERIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE DIAMINOPTÉRIDINE
  申请人：BIORELIX INC

  公开号：WO2010110907A1

  公开（公告）日：2010-09-30

  The present invention relates novel diaminopteridine derivatives, their compositions and method of treatment comprising the same for use as anti-infectives.

  本发明涉及新型二氨基喹噁啉衍生物，其组成和治疗方法，包括将其用作抗感染剂。
• Process for preparing m-aminobenzenephosphonic acid
  申请人：Burlington Industries, Inc.

  公开号：US04028403A1

  公开（公告）日：1977-06-07

  M-Aminobenzenephosphonic acid is prepared from the relatively inexpensive starting material benzenephosphonous acid by nitrating the acid starting material under controlled conditions followed by oxidation and reduction procedures to produce the desired product in high yields.

  M-氨基苯基膦酸是通过对相对便宜的起始材料苯基膦酸进行受控条件下的硝化，然后进行氧化和还原程序，以高产率生产所需产品制备的。
• Ink composition and ink jet recording method using the same
  申请人：Seiko Epson Corporation

  公开号：US05616174A1

  公开（公告）日：1997-04-01

  An ink composition is provided which enables high-quality recording on plain paper and can record an image having excellent water resistance. The ink composition comprises a dye represented by the following formula (I): ##STR1## wherein M represents an unsubstituted or substituted ammonium, R.sup.1 represents COOM, R.sup.2 represents --P(=O)n--(OM).sub.2, where n is 0 or 1, R.sup.3 represents SO.sub.3 M, R.sup.4 and R.sup.5 independently represent H, an alkyl group, or an alkoxyl group, R.sup.6 represents H, a phenyl group which may be substituted, an alkylcarbonyl group, or an alkyl group which may be substituted with a hydroxyl or alkoxyl group, and m is 0 or 1.

  提供了一种墨水组合物，可以在普通纸上进行高质量的记录，并且可以记录具有优异耐水性的图像。该墨水组合物包括由以下式子（I）表示的染料：##STR1## 其中M代表未取代或取代的铵，R.sup.1代表COOM，R.sup.2代表--P（=O）n--（OM）.sub.2，其中n为0或1，R.sup.3代表SO.sub.3M，R.sup.4和R.sup.5独立地代表H，烷基或烷氧基，R.sup.6代表H，苯基（可以取代），烷基羰基或烷基（可以取代羟基或烷氧基），m为0或1。
• Phosphonophenylaminonaphthalene compounds
  申请人：Imperial Chemical Industries Limited

  公开号：US04051175A1

  公开（公告）日：1977-09-27

  Naphthalene compounds of the formula: ##STR1## WHEREIN M IS 0, 1 OR 2 n is 0 or can be 1 if m is 1 or 2, in which case X.sub.1 is NH.sub.2 or OH in m position to a SO.sub.3 H group X is a divalent alkylene, aralkylene or arylene radical, which may be substituted and p is 1 or 2. The new compounds are useful dyestuff intermediates, especially as coupling components for the manufacture of azo dyestuffs. This invention relates to new naphthalene compounds and more particularly to new naphthalene compounds valuable for use in the synthesis of dyestuffs. According to the invention, there are provided compounds of the formula: ##STR2## WHEREIN M IS 0, 1 OR 2 n is 0 or can be 1 if m is 1 or 2, in which case X.sub.1 is NH.sub.2 or OH in m position to a SO.sub.3 H group X is a divalent alkylene, aralkylene or arylene radical, which may be substituted, and p is 1 or 2. An alkylene group represented by X in formula (1) may be straight chain or branched, and may contain OH. It preferably contains less than 6 carbon atoms, e.g. methylene, trimethylene, tetramethylene, propylene, hexamethylene or hydroxypropylene, but the preferred alkylene radical is ethylene. An aralkylene radical represented by X is preferably m- or p-benzylene, having the NH group preferably attached to the benzene nucleus and the phosphorus atom preferably attached to the methylene group. An arylene radical represented by X is preferably a phenylene or naphthylene radical, and in the first case is preferably m- or p-phenylene, optionally substituted by CH.sub.3, F, Cl, Br or NO.sub.2 ; in the case of naphthylene is preferably a 1,3-, 1,6-, 1,7- or 2,7-naphthylene radical, optionally substituted by SO.sub.3 H. The invention also provides a process for manufacture of the new naphthalene compounds which comprises heating together a naphthalene compound of the formula: ##STR3## WHEREIN X.sub.1, m, n and p have the meanings stated above and X.sub.2 is OH, NH.sub.2 or NHR, where R is an alkyl group of 1 to 4 carbon atoms, which is not in meta position to SO.sub.3 H, and an amine of the formula: NH.sub.2 -- X -- PO(OH).sub.2 ( 3) wherein X has the meaning stated above, in the presence of an aqueous solution of an alkali metal bisulphite. The process can be carried out under a variety of conditions according to the ease with which the group X.sub.2 is replaced by the group NH -- X -- PO(OH).sub.2. As a general rule, compounds in which X.sub.2 is NH.sub.2 react more readily than the corresponding OH or NHR compound; also the presence of SO.sub.3 H in ortho position to X.sub.2 lowers the reactivity of the latter so that higher reaction temperatures are desirable. As a general rule also, the compounds of formula (3) in which X is alkylene or aralkylene are more reactive than those in which X is arylene. Within these broad limitations it is sometimes possible to effect the reaction at from 90.degree. C upwards, but it is usually more practical to operate within the range of 100.degree.-200.degree. C in order to achieve a satisfactory rate of reaction. It is usually preferable to use a small excess of the compound of formula (3) over the theoretical amount required for reaction. The new compounds can be isolated by acidification and boiling to decompose sulphites followed by filtration. In some cases salting or spray drying may be necessary. The following table gives examples of naphthalene compounds which can be used in the above process, together with an indication of the kinds of product obtained therefrom; as can be seen from the table, there is frequently a choice of starting material for preparing a class of the new naphthalene compounds. __________________________________________________________________________ Starting material __________________________________________________________________________ 1-naphthol 1-naphthylamine ##STR4## (4) 2-naphthol 2-naphthylamine ##STR5## (5) 1,2-dihydroxynaphthalene 1-amino-2-naphthol ##STR6## (6) 1,4-dihydroxynaphthalene 1-amino-4-naphthol ##STR7## (7) and ##STR8## (8) 1,5-dihydroxynaphthalene 1-amino-5-hydroxynaphthalene ##STR9## (9) and ##STR10## (10) 1-amino-8-naphthol ##STR11## (11) 2,7-dihydroxynaphthalene ##STR12## (12) and ##STR13## (13) 1-naphthol-4-sulphonic acid 1-aminonaphthalene-4-sulphonic acid 1-methylaminonaphthalene-4- sulphonic acid ##STR14## (14) 2-naphthol-1-sulphonic acid Tobias acid N-methyl Tobias ##STR15## (15) 2-naphthol-6-sulphonic acid 2-aminonaphthalene-6- sulphonic acid 2-methylaminonaphthalene- 6-sulphonic acid ##STR16## (16) 2-naphthol-7-sulphonic acid 2-aminonaphthalene-7- sulphonic ##STR17## (17) 2-naphthol-8-sulphonic acid 2-aminonaphthalene-8- sulphonic ##STR18## (18) 2-naphthol-5,7-disulphonic acid ##STR19## (19) 2-naphthol-6,8-disulphonic acid 2-aminonaphthalene-6,8- disulphonic ##STR20## (20) 1-aminonaphthalene-6- sulphonic acid ##STR21## (21) 1-aminonaphthalene-7- sulphonic acid ##STR22## (22) 1,5-dihydroxynaphthalene-4- sulphonic acid 1-amino-5-naphthol-4- sulphonic acid ##STR23## (23) and ##STR24## (24) 1,5-diaminonaphthalene-4- Formula (24) sulphonic acid 1,5-dihydroxynaphthalene-7- sulphonic acid 1-amino-5-naphthol-7- sulphonic acid ##STR25## (25) 1-amino-5-naphthol-2- sulphonic acid ##STR26## (26) and ##STR27## (27) 1,7-dihydroxynaphthalene- 4-sulphonic acid 1-amino-7-naphthol-4- sulphonic acid 1-methylamino-7-naphthol- 4-sulphonic acid ##STR28## (28) and ##STR29## (29) 1-amino-5-naphthol-8- sulphonic acid ##STR30## (30) 2,5-dihydroxynaphthalene-7- sulphonic acid 2-amino-5-naphthol-7- sulphonic acid 2-methylamino-5-naphthol-7- sulphonic acid ##STR31## (31) 2-amino-5-naphthol-1- sulphonic acid ##STR32## (32) and ##STR33## (33) 2,5-diaminonaphthalene-1- sulphonic acid Formula (33) 2,8-dihydroxynaphthalene-6- sulphonic acid 2-amino-8-naphthol-6- sulphonic acid 2-methylamino-8-naphthol-6- sulphonic acid ##STR34## (34) 1-amino-8-naphthol-5- sulphonic acid ##STR35## (35) __________________________________________________________________________ as examples of compounds of formula (3) which can be used, there may be mentioned: 1-aminomethylphosphonic acid 2-aminoethylphosphonic acid 3-aminopropylphosphonic 4-aminobutylphosphonic acid 5-aminopentylphosphonic acid 6-aminohexylphosphonic acid -amino-1-methylethylphosphonic acid 2-amino-1-methylethylphosphonic acid 1-amino-3-methylbutylphosphonic acid 2-amino-1-hydroxypropylphosphonic acid 3-amino-2-hydroxypropylphosphonic acid .alpha.-aminobenzylphosphonic acid .alpha.-aminophenylethylphosphonic acid 3- or 4-aminobenzylphosphonic acid 2, 3- or 4-aminophenylphosphonic acid 3-amino-4-methylphenylphosphonic acid 4-amino-2-fluorophenylphosphonic acid 2-amino-5-chlorophenylphosphonic acid 3-amino-4-chlorophenylphosphonic acid 4-amino-2-bromophenylphosphonic acid 4-amino-3-nitrophenylphosphonic acid 4-n-butylamino-3-nitrophenylphosphonic acid 1-naphthylamine-6-phosphonc acid 1-naphthylamine-7-phosphonic acid 7-phosphono-2-naphthylamine-5-sulphonic acid 2-naphthylamine-7-phosphonic acid 8-sulpho-2-naphthylamine-3-phosphonic acid 6,8-disulpho-1-naphthylamino-3-phosphonic acid. As alkali-metal bisulphite, there may be used potassium bisulphite, but it is preferred to use sodium bisulphite. As a general rule, the amount of alkali metal bisulphite used is greater than 1 mole per mole of naphthalene compound. The naphthalene compounds of formula (1) in which n is 0 and p is 1, can alternatively be obtained by heating together a compound of the formula: ##STR36## in which m has the meaning stated above preferably 0 or 1, and one X.sub.3 is H and the other is CO.sub.2 H, and an amine of formula (3) wherein X has the meaning stated above, in the presence of an aqueous solution of an alkali metal bisulphite. This alternative process can be carried out in a similar manner to the process described above, with the proviso that it is usually possible to effect the reaction at slightly lower temperatures, e.g. from 80.degree. C upwards, than is the case when using compounds of formula (2) as a reactant. The preferred range of reaction temperature is 80.degree.-150.degree. C. As examples of compounds of formulae (36) and (37), there may be mentioned: 2-hydroxy-1 and 3-naphthoic acids 1-hydroxy-4-naphthoic acid 6- and 8-sulpho-2-hydroxy-3-naphthoic acids 4- and 7-sulpho-2-hydroxy-1-naphthoic acids. The new naphthalene compounds can be used as dyestuff intermediates, e.g. in most cases as coupling components for the manufacture of azo dyes by coupling with aromatic diazonium salts in similar manner to other N-substituted naphthylamines. The new compounds having a 1-amino-4-anilino- or 1,4-dianilinonaphthalene structure, the benzene ring containing a phosphonic acid group, are useful as intermediates for the synthesis of sulphur dyes. Those having a 2,6- or 2,7-dianilinonaphthalene structure are useful for the synthesis of azine dyes.

  本发明涉及新的萘化合物，特别是用于合成染料的有用偶联组分的新的萘化合物。根据本发明，提供了下式化合物： 其中M为0、1或2，n为0或者如果m为1或2，则可以为1，此时X1为NH2或者OH，位于SO3H基团的m位置，X为二价的烷基、芳基烷基或芳基烃基，可以被取代，p为1或2。在公式（1）中所表示的烷基由直链或支链组成，可以含有OH。它通常含有少于6个碳原子，例如亚甲基、三亚甲基、四亚甲基、丙烯基、己亚甲基或羟基丙烷基，但是首选的烷基是乙烯基。在公式X中表示的芳基烷基首选为m-或p-苯基，其中NH基团首选连接到苯环上，磷原子首选连接到亚甲基上。在公式X中表示的芳基烃基首选为苯基或萘基，其中在第一种情况下，首选的是m-或p-苯基，可以选择由CH3、F、Cl、Br或NO2取代；在萘基的情况下，首选的是1,3-、1,6-、1,7-或2,7-萘基，可以选择由SO3H取代。本发明还提供了一种用于制造新的萘化合物的方法，该方法包括在碱性亚硫酸盐水溶液存在下，加热下式化合物： 其中X1、m、n和p具有上述含义，X2为OH、NH2或NHR，其中R为1至4个碳原子的烷基，不位于SO3H的间位，以及下式胺： 其中X具有上述含义，以制造新的萘化合物。新化合物可以通过酸化和沸腾以分解亚硫酸盐，然后过滤来分离。在某些情况下，可能需要盐析或喷雾干燥。本发明提供的新萘化合物可用作染料中间体，例如大多数情况下可用作合成偶氮染料的偶联组分，类似于其他N-取代萘胺。具有1-氨基-4-苯胺基或1,4-二苯胺萘基结构的新化合物，苯环含有磷酸基团，可用作合成硫染料的中间体。具有2,6-或2,7-二苯胺萘基结构的化合物可用于合成偶氮染料。