874-89-5 4-(羟甲基)苯腈

中文名称: 4-(羟甲基)苯腈
英文名称: 4-(Hydroxymethyl)benzonitrile
CAS号

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名称和标识

中文名: 4-(羟甲基)苯腈
英文名: 4-(Hydroxymethyl)benzonitrile
CAS号: 874-89-5
分子式: C8H7NO
分子量: 133.15
中文别名: 4-(羟基甲基)苯腈; 4-氰基苄醇; 4-(羟甲基)苯甲腈; 4-氰基苯甲醇; 4-(羟甲基)苯腈
英文别名: 4-CYANOBENZYL ALCOHOL; 4-Cyanobenzenemethanol; Tranexamic Acid Impurity 13; 4-(hydroxymethyl)benzenecarbonitrile; 4-methylolbenzonitrile; 4-cyanobeznyl alcohol

物化属性

LogP: 0.47
MLOGP: 0.85
PSA: 44.02 Å²
SILICOS-IT LogP: 1.65
WLOGP: 0.9
XLogP3

安全信息

安全说明

运输信息：常温运输。危险描述：危险品运输编号3439（UN 3439），WGK Germany:3，F:10，危险等级6.1，海关编码29269090，存储类别11 - 可燃固体，危险性类别急性毒性类别4（经皮、吸入、经口）、眼部刺激类别2、经皮刺激类别2、特异性靶器官毒性-一次接触类别3。

生产及用途

用途与制备

化学合成。

化学合成

路线1（4-氰基苯甲酸还原）

步骤: 将三氟化硼二乙基醚合物（0.85 mL，6.8 mmol）加入4-氰基苯甲酸（1.0 g，6.8 mmol）和四氢呋喃（10 mL）的溶液中，室温下逐滴加入硼烷-四氢呋喃络合物（1.0 M，13.6 mL），搅拌2小时后真空浓缩，残余物经乙酸乙酯溶解、饱和碳酸氢钠和盐水洗涤、无水硫酸钠干燥、过滤、真空浓缩得目标产物。
条件: 室温，2小时。
收率: 95%。
参考文献: [1] Patent: US2007/270438, 2007, A1. Location in patent: Page/Page column 39; [2] Tetrahedron Letters, 2003, vol. 44, #16, p. 3427-3428; [3] Advanced Synthesis and Catalysis, 2014, vol. 356, #2-3, p. 308-312; [4] Dalton Transactions, 2016, vol. 45, #19, p. 8265-8271。

路线2（4-氯甲基苄腈水解）

步骤: 向3000mL四颈烧瓶中加入138g碳酸钾、151.5g 4-氯甲基苄腈和2300g水，加热至80℃反应10小时，HPLC检测完成后，二氯甲烷萃取（每次800mL，室温萃取3次），蒸馏萃取物得目标产物。
条件: 80℃，10小时。
收率: 96.2%。
参考文献: [1] Patent: CN107556214, 2018, A. Location in patent: Paragraph 0031; 0032; 0035; 0038; 0041; 0044; 0047; [2] Journal of the Chemical Society, 1942, p. 103,107; [3] Journal of Organic Chemistry, 2015, vol. 80, #4, p. 2310-2318。

路线3（醛转移氢化）

步骤: 在双相体系中，将醛（2.5 mmol）、HCOONH4（10 mmol，0.63 g）和络合物（如1.25 μmol，1 mg；S/C=2000）转移至50 mL Schlenk管，依次加入甲苯（1.2 mL）和水（5 mL），经四次真空-氩气循环后，90℃油浴反应3.5小时，通过GC或H-NMR分析，分离有机相，干燥、过滤、减压除溶剂得目标产物。

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