2-chloro-1,4-phenylenedioxy-bis-acetic acid | 84794-72-9

• 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: 2-chloro-1,4-phenylenedioxy-bis-acetic acid
• 英文别名: 2,2'-[(2-Chloro-1,4-phenylene)bis(oxy)]diacetic acid；2-[4-(carboxymethoxy)-3-chlorophenoxy]acetic acid
• CAS: 84794-72-9
• 化学式: C₁₀H₉ClO₆
• mdl: MFCD12966033
• 分子量: 260.631
• InChiKey: QRPNBYVVLXWRTC-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C(Solv: ethanol (64-17-5))
• 沸点：
  475.9±35.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-1,4-phenylenedioxy-bis-acetic acid 在 三氯氧磷 作用下， 反应 4.33h， 生成 3-[[3-Chloro-4-[[6-(4-nitrophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]methoxy]phenoxy]methyl]-6-(4-nitrophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
  参考文献：
  名称：

  New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents

  摘要：

  A series of bis-phenoxyacetic acids 2 were prepared starting from corresponding unsubstituted/substituted 1,4-quinols 1. The fusion of bis-phenoxyacetic acids 2 with thiocarbohydrazide gave the corresponding bis-[4-amino-5-mercapto-1,2,4-triazol-3-yl-methyleneoxy]phenylenes (3) in a one pot reaction. The reaction of bis-triazoles 3 with various reagents afforded N-bridged heterocycles 4-6 in good yields. The newly synthesised compounds were screened for their anticancer activity against a panel of 60 cell lines derived from seven cancer types namely, lung, colon, melanoma, renal, ovarian, CNS and leukemia. Some of the tested compounds showed promising anticancer properties.

  DOI：

  10.1016/s0223-5234(02)01358-2
• 作为产物：
  描述：

  氯乙酸 、 氯氢醌 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2-chloro-1,4-phenylenedioxy-bis-acetic acid
  参考文献：
  名称：

  New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents

  摘要：

  A series of bis-phenoxyacetic acids 2 were prepared starting from corresponding unsubstituted/substituted 1,4-quinols 1. The fusion of bis-phenoxyacetic acids 2 with thiocarbohydrazide gave the corresponding bis-[4-amino-5-mercapto-1,2,4-triazol-3-yl-methyleneoxy]phenylenes (3) in a one pot reaction. The reaction of bis-triazoles 3 with various reagents afforded N-bridged heterocycles 4-6 in good yields. The newly synthesised compounds were screened for their anticancer activity against a panel of 60 cell lines derived from seven cancer types namely, lung, colon, melanoma, renal, ovarian, CNS and leukemia. Some of the tested compounds showed promising anticancer properties.

  DOI：

  10.1016/s0223-5234(02)01358-2

文献信息

• Process for making phenylene dioxydiacetic acid and use thereof
  申请人：Durairaj B. Raj

  公开号：US20070004898A1

  公开（公告）日：2007-01-04

  A process for making phenylene dioxydiacetic acid comprises (a) contacting a dihydroxybenzene under reaction conditions with a salt of haloacetic acid in a solution without adding a haloacetic acid to produce a salt of phenylene dioxydiacetic acid; and (b) optionally converting the salt of phenylene dioxydiacetic acid to free phenylene dioxydiacetic acid. In some embodiments, 1,3-phenylene dioxydiacetic acid (RDOA) is made by reacting resorcinol with sodium chloroacetic acid in a reaction mixture with a pH in the range of about 7 to about 11 and at a temperature from about 70° C. to 105° C. By adjusting the reactions conditions, a relatively high yield of 1,3-phenylene dioxydiacetic acid (i.e., greater than 80%) is obtained. The purified acid can be used in the synthesis of polyester, such as polyethylene terephthalate.
• US7276571B2
  申请人：——

  公开号：US7276571B2

  公开（公告）日：2007-10-02
• [EN] PROCESS FOR MAKING PHENYLENE DIOXYDIACETIC ACID AND USE THEREOF<br/>[FR] PROCÉDÉ DE FABRICATION D'ACIDE DIOXYDIACÉTIQUE DE PHÉNYLÈNE ET SON UTILISATION
  申请人：INDSPEC CHEMICAL CORP

  公开号：WO2007005086A1

  公开（公告）日：2007-01-11

  [EN] A process for making phenylene dioxydiacetic acid comprises (a) contacting a dihydroxybenzene under reaction conditions with a salt of haloacetic acid in a solution without adding a haloacetic acid to produce a salt of phenylene dioxydiacetic acid; and (b) optionally converting the salt of phenylene dioxydiacetic acid to free phenylene dioxydiacetic acid. In some embodiments, 1,3-phenylene dioxydiacetic acid (RDOA) is made by reacting resorcinol with sodium chloroacetic acid in a reaction mixture with a pH in the range of about 7 to about 11 and at a temperature from about 70 °C to 105 °C. By adjusting the reactions conditions, a relatively high yield of 1,3-phenylene dioxydiacetic acid (i.e., greater than 80%) is obtained. The purified acid can be used in the synthesis of polyester, such as polyethylene terephthalate.
  [FR] L'invention présente a trait à un procédé de fabrication d'acide dioxydiacétique de phénylène consistant à (a) mettre en contact un dihydroxybenzène dans des conditions de réaction avec un sel d'acide halogénoacétique dans une solution sans ajouter d'acide halogénoacétique afin de produire un sel d'acide dioxydiacétique de phénylène ; et (b) convertir éventuellement le sel d'acide dioxydiacétique de phénylène pour libérer l'acide dioxydiacétique de phénylène. Dans divers modes de réalisation, l'acide dioxydiacétique de 1,3-phénylène (RDOA) est fabriqué par réaction de résorcinol avec de l'acide chloracétique de sodium dans un mélange de réaction dont le pH est compris entre environ 7 et environ 11 et dont la température est comprise entre environ 70 °C et 105 °C. En ajustant les conditions de réactions, un rendement relativement élevé d'acide dioxydiacétique de 1,3-phénylène (c'est-à-dire supérieur à 80%) est obtenu. L'acide purifié peut être utilisé pour la synthèse du polyester, comme le polyéthylène téréphthalate.
• New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents
  作者：B Shivarama Holla、K Narayana Poojary、B Sooryanarayana Rao、M.K Shivananda

  DOI：10.1016/s0223-5234(02)01358-2

  日期：2002.6

  A series of bis-phenoxyacetic acids 2 were prepared starting from corresponding unsubstituted/substituted 1,4-quinols 1. The fusion of bis-phenoxyacetic acids 2 with thiocarbohydrazide gave the corresponding bis-[4-amino-5-mercapto-1,2,4-triazol-3-yl-methyleneoxy]phenylenes (3) in a one pot reaction. The reaction of bis-triazoles 3 with various reagents afforded N-bridged heterocycles 4-6 in good yields. The newly synthesised compounds were screened for their anticancer activity against a panel of 60 cell lines derived from seven cancer types namely, lung, colon, melanoma, renal, ovarian, CNS and leukemia. Some of the tested compounds showed promising anticancer properties.
• Holla, B. Shivarama; Poojary, K. Narayana; Bhat, K. Subrahmanya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 8, p. 1669 - 1673
  作者：Holla, B. Shivarama、Poojary, K. Narayana、Bhat, K. Subrahmanya、Ashok, Mithun、Poojary, Boja

  DOI：——

  日期：——