Overview
1,2-Cyclohexanediamine (CHD) is an organic diamine featuring a cyclohexane backbone with two amino groups at adjacent positions. Its chiral structure makes it valuable in asymmetric synthesis, particularly as a ligand for transition-metal catalysts. Industrially, it is produced via hydrogenation of aromatic precursors like 1,2-diaminobenzene. CHD exists as cis- and trans-isomers, each with distinct stereochemical properties. The trans-isomer is more commonly used due to its superior stability and selectivity in catalytic applications. Commercial grades typically specify enantiomeric purity (e.g., 99% ee) for specialized uses.
Physical and Chemical Properties
CHD is a hygroscopic liquid at room temperature with a faint amine odor. Its solubility in polar solvents like water and ethanol facilitates its use in homogeneous catalysis. The compound’s bidentate ligand capability stems from the chelating effect of its two amino groups, which coordinate with metals such as ruthenium and rhodium. Key reactivity includes participation in Schiff base formation and epoxy ring-opening reactions. Its pKa values (≈10–11) indicate moderate alkalinity, requiring pH control in aqueous systems. Thermal stability is adequate for most synthetic applications, with decomposition above 200°C.
Main Applications
In asymmetric hydrogenation, CHD-derived ligands (e.g., TsDPEN) enable enantioselective production of pharmaceuticals like levodopa. The agrochemical industry employs CHD intermediates for herbicides and fungicides. Its epoxy-curing properties enhance adhesion and mechanical strength in coatings and composites. CHD also serves as a building block for corrosion inhibitors and chelating agents in water treatment. Recent research explores its role in metal-organic frameworks (MOFs) for gas storage. The choice of isomer (cis/trans) and purity depends on the target application’s stereochemical requirements.
Safety and Storage
CHD is corrosive and can cause severe skin burns or eye damage. Always use nitrile gloves and chemical goggles when handling. Ensure adequate ventilation to avoid inhalation of vapors, which may irritate the respiratory tract. Storage recommendations include airtight containers under nitrogen to prevent oxidation and moisture absorption. Incompatible with strong acids, oxidizers, and copper alloys. Spills should be neutralized with dilute acetic acid and absorbed with inert materials like vermiculite.
B2B Procurement Guide
Procure CHD from reputable suppliers with ISO 9001 certification. Key specifications to verify include isomer ratio (trans- preferred for catalysis), enantiomeric purity (≥98% ee for chiral applications), and residual solvent levels. Bulk shipments (200kg drums) often offer cost savings but require proper handling infrastructure. Request SDS and CoA documents to confirm compliance with REACH or TSCA regulations. For niche applications (e.g., MOFs), custom synthesis may be necessary. Lead times vary; secure samples for pilot testing before large orders.
Related Manufacturers
- 主营：磷酸三甲苯酯、氨基甲酸乙酯、磷酸甲苯二苯酯、甲乙酮肟、四乙基溴化铵、碳酸二丁酯、环烷酸铅、亚硫酸铵、二苯甲酮腙、石油磺酸钠、三乙醇胺、甲醇、乙醇、二甲苯、二氯甲烷、环烷酸铜、氨基甲酸甲酯、单过硫酸氢钾、氯化石蜡、三异丙醇胺、苄基三甲基氯化铵、苄基三乙基氯化铵、四乙基氯化铵、四甲基氯化铵、新癸酸铋
- 主营：聚苯胺、脯氨酸甲酯盐酸盐、苄基三甲基氯化铵
- 主营：叔碳酸、十八醛、溶菌酶、甲基环己二胺、海藻糖、癸二醇、氨基丙基、氢路噻嗪、邻苯二甲、乙基碳二、羟基癸酸、正十七烷、谷胱甘肽、烷二甲醇、松果体素、vc磷酸酯镁、2-甲基丁醛、朱栾倍半萜、丁烷四乙酸、表面活性剂、癸烷撑二醇、缩水甘油邻、10-羟基羊蜡酸、氢氯噻嗪杂质、盐酸邻菲罗啉、壳聚糖季铵盐
- 主营：抗氧剂、乳化剂、苯扎氯铵、环己烷二胺、烷基二甲基、氢化蓖麻油、表面活性剂、双链季胺盐、聚氧乙烯醚、二丁基羟基甲苯、甘油聚氧丙烯醚、十二烷基硫酸钠、树脂、助剂
- 主营：防酶剂、表面活性剂、次氯酸钙、福美钠、蛋白胨、氟化氢钾、氟化钠、氟化钾、浮选油
- 主营：架桥剂、YW100 锂萃取剂、端羧基液体丁腈橡胶、甲基环己二胺、10-羟基癸酸、苯乙烯磷酸、肉豆蔻酸镁、硬脂酸钴、全氟三丁胺、乙烯基磷酸二乙酯、磷酸锰铁锂、β-磷酸三钙、十一烯酸、钨酸铝、1-乙炔基环已醇、间二异丙苯、锂硅合金、溴甲酚绿、生物活性玻璃、溴代海因树脂颗粒、红铝、龙涎酮、原丁酸三甲酯
- 主营：全氟三丁胺、二苄叉山梨醇、六氟丙烯二聚体、环己二胺四乙酸、六氟环氧丙烷二聚体、异丙醇铝、纳米勃姆石、二异戊基硫醚、隐色结晶紫、邻菲罗啉
- 主营：异丙醇、冰醋酸、化工原料、甲基环己烷、正庚烷、乙二醇、苯酚、江苏异丙醇、江苏化工原料、工业吡啶、工业苯酚、正丁醇、MIBK、无水乙醇、正己烷
- 主营：有机原料、中间体、香精香料、催化剂、有机硅、表面活性剂
- 主营：化学品、香精香料、试剂、甲基环己二胺、中间体、有机硅、橡胶树脂、催化剂、纳米材料
- 主营：杜仲素、对位酯、丙烯酸酯、甲基环己二胺、二氧化硫脲、乙基麦芽酚、饲料添加剂、油酸基硬脂酸、二苯基硅二醇
- 主营：防冻液、冰醋酸、乙二醇、环己二胺四乙酸、冰乙酸、纯吡啶、丙二醇、羟基苯、14丁二醇、3-丙三醇、四氢呋喃、环保乙腈、化工苯酚、1.4丁二醇、医用苯酚、工业苯酚、精制苯酚、价位四氢、乙腈工业、乙酸乙酯、吡啶化工、甲酸乙酯、吡啶工业、求购苯酚、高纯三氯、实验乙腈
- 主营：离子液体、5-二甲基吡唑、咪唑、环己二胺四乙酸、催化剂、阻燃剂、正丁醇锆、四氟硼酸锂、香兰基丁醚、氟化物、全氟辛基三甲氧基硅烷、丙酮肟、双酚E型氰酸酯、叔丁基乙烯基醚、钯碳催化剂、钛硅分子筛、硫酸烟酰苯胺、丙酮缩氨基硫脲
- 主营：环己二胺、全氟三丁胺、木质素、吉氏色素
- 主营：福美钠、五氧化二钒、氨基磺酸、环己二胺催化反应、氨基化锂、焦性没食子酸、次氯酸钙、漂粉精、酪蛋白胨、甘油、九水硫化钠、牛油脂肪酸、酵母膏、氟硅酸钠、单乙醇胺、氢氧化钾、氟化钠、氟化钙、氧化铅、油酸钠、偏钒酸铵、氢氧化钡、EVA乳液、二硫化钼、氟化氢钾