RB 4 | 13324-20-4

• 物质功能分类: 染料及颜料 - 染料 - 活性染料(反应染料)
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: RB 4
• 英文别名: disodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate；reactive brilliant blue；active bright blue KKh；C.I. reactive blue 4；reactive blue 4；CI 61502；Sodium;1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate
• CAS: 13324-20-4
• 化学式: C₂₃H₁₂Cl₂N₆O₈S₂*2Na
• 分子量: 681.401
• InChiKey: DOMKJRBNQVWUKS-UHFFFAOYSA-L

物化性质

• 沸点：
  291°C (rough estimate)
• 密度：
  1.5315 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  254
• 氢给体数：
  3
• 氢受体数：
  14

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36
• WGK Germany：
  3
• RTECS号：
  CB1030000

制备方法与用途

化学性质

活性艳蓝X-ARL（活性蓝4）是一种深蓝色粉末，在水中溶解度 (20℃) 为 80g/L，(50℃) 为 90g/L。在强硫酸中呈红棕色，稀释后转为蓝色；在硝酸中显橙色，稀释后无变化。水溶液是蓝色的，加入1mol/L 氢氧化钠仍保持蓝色；继续加入保险粉并温热后变为暗红色；再加过硼酸钠转为红色，稀释后颜色不发生变化。化学性质较为活泼，稳定性较差，在碱性条件下容易发生水解，但在酸性条件下则不易水解。

用途

活性艳蓝X-ARL（活性蓝4）又称活性艳蓝X-BR，是一种用于棉布直接印花的少数品种之一，主要用于染色和印花。它适用于棉、丝、粘胶等织物，并且与活性红紫S-2R（用量5%）拼染玫瑰红色；与活性嫩黄X-6G拼染绿色，比例为10：1。此外，在针棉织品漂白时，可作为上蓝剂增加白度。

生物活性

Reactive Blue 4 是一种蒽醌类染料，能在水介质中连续测定具有不同光学响应的多种分析物，并作为一种单一的比色化学传感器使用。它还表现出植物毒性、细胞毒性和基因毒性。

生产方法

活性艳蓝X-BR 的生产主要以溴氨酸、2,4-二氨基苯磺酸和三聚氯氰为原料，首先将 2,4-二氨基苯磺酸与溴氨酸缩合，然后进一步与三聚氯氰进行第二次缩合。具体步骤如下：

1. 往第一次缩合锅中加入500L清水，在搅拌下升温至85℃。
2. 加入191kg 溴氨酸（100%），搅拌形成均匀悬浮液（总体积约 1000L）。
3. 接着，加入112.8kg 2,4-二氨基苯磺酸（100%）、200kg 碳酸氢钠（100%），升温至85℃并保温30分钟。随后加入10kg 氯化亚铜（不含游离亚硫酸钠）溶液，控制温度在83-85℃，pH=9 反应3小时。
4. 在90℃继续保温2小时后加水稀释至4500L，搅拌15分钟后加入轻质碳酸钙150kg，在75-80℃下搅拌30分钟，趁热过滤除去紫色副品染料。
5. 将滤液倒入中和锅内，用盐酸调节pH=2，并添加溶液体积的10%-15%食盐。充分搅拌后取样测终点（以滤纸上无蓝色渗圈为终点），过滤得精制滤饼。
6. 在溶解锅内加水1000L，在搅拌下加入30kg碳酸钠和精制滤饼，打浆并调整体积至3000L，pH=7.5，获得精制液。
7. 将上述精制液倒入第二次缩合锅中。先在0℃以下打浆45分钟，再加入81.1kg（约0.44kmol）三聚氯氰，在15℃下调整体积至4500L并搅拌1小时。加入磷酸三钠使pH值约为6.5；继续搅拌3小时，并保持pH在6.3-6.5之间，温度不超过18℃后过滤，去除三聚氯氰杂质。
8. 最终将滤液收集于盐析锅中，加入尿素26.4kg（约0.44kmol），升温至43℃。加入总体积20%的食盐，在40-42℃下搅拌2小时后取样，过滤得染料约410kg。

反应信息

• 作为反应物：
  描述：

  RB 4 在 水 、 sodium carbonate 作用下， 反应 1.0h， 以97%的产率得到disodium 1-amino-4-[3-(4,6-dihydroxy-[1,3,5]triazine-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
  参考文献：
  名称：

  Discovery of Potent Competitive Antagonists and Positive Modulators of the P2X2 Receptor

  摘要：

  Evaluation and optimization of anthraquinone derivatives related to Reactive Blue 2 at P2X2 receptors yielded the first potent and selective P2X2 receptor antagonists. The compounds were tested for inhibition of ATP (10 mu M) mediated currents in Xenopus oocytes expressing the rat P2X2 receptor. The most potent antagonists were sodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (63, PSB-10211, IC50 86 nM) and disodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (57, PSB-1011, IC50 79 nM). Compound 57 exhibited a competitive mechanism of action (pA(2) 7.49). It was > 100-fold selective versus P2X4, P2X7, and several investigated P2Y receptor sub-types (P2Y(2,4,6,12)); selectivity versus P2X1 and P2X3 receptors was moderate ( > 5-fold). Compound 57 was > 13-fold more potent at the homomeric P2X2 than at the heteromeric P2X2/3 receptor. Several anthraquinone derivatives were found to act as positive modulators of ATP effects at P2X2 receptors, for example, sodium 1-amino-4-(3-phenoxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (51, PSB-10129, EC50 489 nM), which led to about a 3-fold increase in the ATP-elicited current.

  DOI：

  10.1021/jm1012193
• 作为产物：
  描述：

  sodium 1-amino-4-bromoanthraquinone-2-sulfonate 在 铜 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 RB 4
  参考文献：
  名称：

  Discovery of Potent Competitive Antagonists and Positive Modulators of the P2X2 Receptor

  摘要：

  Evaluation and optimization of anthraquinone derivatives related to Reactive Blue 2 at P2X2 receptors yielded the first potent and selective P2X2 receptor antagonists. The compounds were tested for inhibition of ATP (10 mu M) mediated currents in Xenopus oocytes expressing the rat P2X2 receptor. The most potent antagonists were sodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (63, PSB-10211, IC50 86 nM) and disodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (57, PSB-1011, IC50 79 nM). Compound 57 exhibited a competitive mechanism of action (pA(2) 7.49). It was > 100-fold selective versus P2X4, P2X7, and several investigated P2Y receptor sub-types (P2Y(2,4,6,12)); selectivity versus P2X1 and P2X3 receptors was moderate ( > 5-fold). Compound 57 was > 13-fold more potent at the homomeric P2X2 than at the heteromeric P2X2/3 receptor. Several anthraquinone derivatives were found to act as positive modulators of ATP effects at P2X2 receptors, for example, sodium 1-amino-4-(3-phenoxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (51, PSB-10129, EC50 489 nM), which led to about a 3-fold increase in the ATP-elicited current.

  DOI：

  10.1021/jm1012193

文献信息

• Vorozheva; Romanova; Solodova, Journal of applied chemistry of the USSR, 1985, vol. 58, # 5 pt 2, p. 1108 - 1110
  作者：Vorozheva、Romanova、Solodova、Stepanenko

  DOI：——

  日期：——
• Discovery of Potent Competitive Antagonists and Positive Modulators of the P2X2 Receptor
  作者：Younis Baqi、Ralf Hausmann、Christiane Rosefort、Jürgen Rettinger、Günther Schmalzing、Christa E. Müller

  DOI：10.1021/jm1012193

  日期：2011.2.10

  Evaluation and optimization of anthraquinone derivatives related to Reactive Blue 2 at P2X2 receptors yielded the first potent and selective P2X2 receptor antagonists. The compounds were tested for inhibition of ATP (10 mu M) mediated currents in Xenopus oocytes expressing the rat P2X2 receptor. The most potent antagonists were sodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (63, PSB-10211, IC50 86 nM) and disodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (57, PSB-1011, IC50 79 nM). Compound 57 exhibited a competitive mechanism of action (pA(2) 7.49). It was > 100-fold selective versus P2X4, P2X7, and several investigated P2Y receptor sub-types (P2Y(2,4,6,12)); selectivity versus P2X1 and P2X3 receptors was moderate ( > 5-fold). Compound 57 was > 13-fold more potent at the homomeric P2X2 than at the heteromeric P2X2/3 receptor. Several anthraquinone derivatives were found to act as positive modulators of ATP effects at P2X2 receptors, for example, sodium 1-amino-4-(3-phenoxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (51, PSB-10129, EC50 489 nM), which led to about a 3-fold increase in the ATP-elicited current.