3,6-二氯苯-1,2,4-三羧酸 | 137071-78-4

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 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: 3,6-二氯苯-1,2,4-三羧酸
• 中文别名: 2,5-二氯-1,3,4-苯三甲酸
• 英文名称: 2,5-dicholoro-1,3,4-trimellitic acid
• 英文别名: 3,6-Dichlorobenzene-1,2,4-tricarboxylic acid
• CAS: 137071-78-4
• 化学式: C₉H₄Cl₂O₆
• 分子量: 279.033
• InChiKey: WFLALXNBVTWGKP-UHFFFAOYSA-N

物化性质

• 沸点：
  487.7±45.0 °C(Predicted)
• 密度：
  1.848
• 溶解度：
  可溶于甲醇；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2917399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性化合物3,6-二氯三甲基戊二酸是制备多种二氯化荧光素（如TET和HEX）及罗丹明的关键前体试剂，这些氯化荧光素和罗丹明广泛用于标记寡核苷酸和DNA测序。

反应信息

• 作为反应物：
  描述：

  3,6-二氯苯-1,2,4-三羧酸 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 2.33h， 生成 6-carboxy-4,7,2',7'-tetrachlorofluorescein
  参考文献：
  名称：

  Improved Synthetic Procedures for 4,7,2‘,7‘-Tetrachloro- and 4‘,5‘-Dichloro-2‘,7‘-dimethoxy-5(and 6)-carboxyfluoresceins

  摘要：

  Literature syntheses of 4,7,2',7'-tetrachloro-5(and 6)-carboxyfluorescein ("5 and 6 TET") 1 and 4',5' dichloro-2',7'-dimethoxy-5(and 6) carboxyfluorescein ("5 and 6 JOE") 2 are reviewed, and new, preparatively useful methods are presented. A three-step synthesis of 1 was developed, which proved to be more efficient than the published seven step synthesis of this compound. The published synthesis of 2 also proved difficult to reproduce, and a better workup of the key intermediate 2-chloro-4-methoxy resorcinol was devised. Isolation of purified single isomers of both dyes is described.

  DOI：

  10.1021/op000292o
• 作为产物：
  描述：

  2,5-二氯对二甲苯 在 aluminum (III) chloride 、 potassium permanganate 、 potassium carbonate 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 5.5h， 生成 3,6-二氯苯-1,2,4-三羧酸
  参考文献：
  名称：

  Improved Synthetic Procedures for 4,7,2‘,7‘-Tetrachloro- and 4‘,5‘-Dichloro-2‘,7‘-dimethoxy-5(and 6)-carboxyfluoresceins

  摘要：

  Literature syntheses of 4,7,2',7'-tetrachloro-5(and 6)-carboxyfluorescein ("5 and 6 TET") 1 and 4',5' dichloro-2',7'-dimethoxy-5(and 6) carboxyfluorescein ("5 and 6 JOE") 2 are reviewed, and new, preparatively useful methods are presented. A three-step synthesis of 1 was developed, which proved to be more efficient than the published seven step synthesis of this compound. The published synthesis of 2 also proved difficult to reproduce, and a better workup of the key intermediate 2-chloro-4-methoxy resorcinol was devised. Isolation of purified single isomers of both dyes is described.

  DOI：

  10.1021/op000292o

文献信息

• 4,7-dichlorofluorescein dyes as molecular probes
  申请人：The Perkin-Elmer Corporation

  公开号：US20020081616A1

  公开（公告）日：2002-06-27

  Long wavelength, narrow emission bandwidth fluorecein dyes are provided for detecting spacially overlapping target substances. The dyes comprise 4,7-dichlorofluoresceins, and particularly 2′,4′,5′,7′-tetrachloro-4,7-dichloro-5- (and 6-) carboxyfluoresceins. Methods and kits for using the dyes in DNA analysis are provided.

  长波长、窄发射带宽荧光素染料可用于检测空间重叠的目标物质。这些染料包括 4,7-二氯荧光素，特别是 2′,4′,5′,7′-四氯-4,7-二氯-5-（和 6-）羧基荧光素。提供了在 DNA 分析中使用这些染料的方法和试剂盒。
• Asymmetric benzoxanthene dye labelling reagents
  申请人：The Perkin-Elmer Corporation

  公开号：US20020115067A1

  公开（公告）日：2002-08-22

  A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure 1 wherein Y 1 and Y 2 are individually hydroxyl amino, imminium, or oxygen, R 1 -r 8 are hydrogen, fluorine, chlorine, alkyl, alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof and R 9 is acetylene, alkane, alkene, cyano, substituted phenyl, and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure 2 where substituents R 3 -R 7 correspond to like-referenced substituents in the structure of described above, and Y 2 is hydroxyl or amine. In another aspect the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect the present invention includes reagents labeled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.

  公开了一类可用作荧光染料的不对称单苯并氧蒽化合物，其结构为 1 其中 Y 1 和 Y 2 分别为羟基氨基、铱或氧，R 1 -r 8 是氢、氟、氯、烷基、烯基、炔基、磺酸基、氨基、酰胺基、腈基、烷氧基、连接基团及其组合，以及 R 9 是乙炔、烷烃、烯烃、氰基、取代苯基及其组合。本发明还包括用于合成具有一般结构的不对称苯并氧杂蒽化合物的新型中间体化合物 2 其中取代基 R 3 -R 7 对应于上述结构中的同类取代基，而 Y 2 是羟基或胺。在另一方面，本发明包括合成上述染料化合物和中间体的方法。在另一个方面，本发明包括用不对称苯并氧杂蒽染料化合物标记的试剂，包括脱氧核苷酸、双脱氧核苷酸、磷酰胺和多核苷酸。在另一方面，本发明还包括利用此类染料化合物和试剂的方法，包括双脱氧多核苷酸测序和片段分析方法。
• Asymmetric benzoxanthene dyes
  申请人：Applera Corporation

  公开号：US20040225119A1

  公开（公告）日：2004-11-11

  A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure 1 wherein Y 1 and Y 2 are individually hydroxyl, amino, imminium or oxygen, R 1 -R 8 are hydrogen, fluorine, chlorine, alkyl alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof and R 9 is acetylene, alkane, alkene, cyano, substituted phenyl and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure 2 where substituents R 3 -R 7 correspond to like-referenced substituents in the structure of described above, and Y 2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labeled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.

  公开了一类可用作荧光染料的不对称单苯并氧蒽化合物，其结构为 1 其中 Y 1 和 Y 2 分别为羟基、氨基、铵或氧，R 1 -R 8 是氢、氟、氯、烷基烯烃、炔烃、磺酸盐、氨基、酰胺、腈、烷氧基、连接基团及其组合，以及 R 9 是乙炔、烷烃、烯烃、氰基、取代苯基及其组合。本发明还包括用于合成具有一般结构的不对称苯并氧杂蒽化合物的新型中间体化合物 2 其中取代基 R 3 -R 7 对应于上述结构中的同类取代基，而 Y 2 是羟基或胺。另一方面，本发明包括合成上述染料化合物和中间体的方法。再一方面，本发明包括用不对称苯并氧杂蒽染料化合物标记的试剂，包括脱氧核苷酸、双脱氧核苷酸、磷酰胺和多核苷酸。在另一方面，本发明还包括利用此类染料化合物和试剂的方法，包括双脱氧多核苷酸测序和片段分析方法。
• [EN] IMPROVED NUCLEIC ACID SEQUENCE ANALYSIS WITH NUCLEOSIDE-5'-0-(1-THIOTRIPHOSPHATES)
  申请人：APPLIED BIOSYSTEMS, INC.

  公开号：WO1992006219A1

  公开（公告）日：1992-04-16

  (EN) A chain-termination method of nucleic acid sequence determination is provided wherein nucleoside triphosphate precursors are replaced with their 1-thiotriphosphate analogs in the polymerization step. This substitution results in more uniform bands of electrophoretically separated DNA fragments which, in turn, results in more accurate base determination.(FR) L'invention se rapporte à un procédé de détermination en fin de chaîne de la séquence d'acides nucléiques, dans lequel les précurseurs des triphosphates de nucléoside sont remplacés par leurs analogues de 1-thiotriphosphates dans l'étape de polymérisation. Cette substitution permet d'obtenir des bandes plus uniformes de fragments d'ADN séparés par électrophorèse, qui, a leur tour, permettent d'obtenir une détermination plus précise de la séquence des bases.

  一种用于核苷酸序列测定的连锁终止法，通过在聚合步中将核苷酸三磷酸核苷的前驱体替换为其1-硫三磷酸核苷的同分异构体。此替换导致电泳分离的DNA片段产生更均匀的带宽，从而带来更精确的碱基测定结果。
• 4,7-DICHLOROFLUORESCEIN DYES AS MOLECULAR PROBES
  申请人：APPLIED BIOSYSTEMS, INC.

  公开号：EP0500779A1

  公开（公告）日：1992-09-02