Overview
(S,S)-Cyclohexanediamine ((1S,2S)-1,2-diaminocyclohexane) is a chiral organic compound belonging to the diamine class. It is a valuable building block in asymmetric synthesis due to its rigid cyclohexane backbone and two stereogenic centers. The compound is commonly abbreviated as (S,S)-DACH in industrial contexts. As a bidentate ligand, it forms stable complexes with transition metals, making it indispensable in enantioselective catalysis. Its commercial availability in high optical purity (typically >99%) has expanded its use in pharmaceuticals, agrochemicals, and fine chemical production.
Physical and Chemical Properties
(S,S)-Cyclohexanediamine exhibits typical diamine characteristics with moderate hygroscopicity. The crystalline solid melts at 45-50°C and boils at 220-225°C under standard pressure. Its solubility profile favors polar solvents, including water, methanol, and dichloromethane. The compound's chirality enables diastereomeric differentiation in reactions, while its cyclohexane ring provides conformational rigidity. Technical-grade material may contain traces of the (R,R)-enantiomer, which must be controlled for critical applications. Stability concerns include sensitivity to air oxidation, requiring inert atmosphere storage.
Main Applications
In pharmaceuticals, (S,S)-cyclohexanediamine serves as a chiral auxiliary in β-lactam antibiotic synthesis and oncology drug intermediates. Its metal complexes (particularly with ruthenium and rhodium) are workhorse catalysts for asymmetric hydrogenation reactions. The chemical industry employs it in producing chiral ligands like TsDPEN for Noyori-type transfers. Emerging applications include MOF (Metal-Organic Framework) construction and corrosion inhibitors. Japanese patents highlight its use in electronic material precursors, demonstrating cross-industry versatility.
Safety and Storage
As a corrosive substance, (S,S)-cyclohexanediamine requires handling with nitrile gloves, goggles, and chemical-resistant clothing. Spills should be neutralized with dilute acetic acid before cleanup. The compound's hygroscopic nature demands moisture-proof packaging with nitrogen purging. Long-term storage recommendations include amber glass bottles or lined steel drums at <25°C. Shelf life typically exceeds 2 years when properly sealed. Transport regulations classify it as UN3259 (amine solids, corrosive, n.o.s.), requiring Class 8 hazard labeling.
B2B Procurement Guide
Industrial buyers should verify certificates of analysis for enantiomeric purity (HPLC/chiral GC), heavy metal content (<10ppm), and residual solvent levels. Bulk orders (100kg+) often attract 15-20% price discounts from specialty chemical distributors. Just-in-time procurement is advisable due to limited shelf life. Top suppliers include TCI Chemicals, Alfa Aesar, and chiral specialty producers in China (e.g., Jiangsu Aikon Biopharmaceutical). Consider vendor audits for GMP-grade material intended for pharmaceutical applications.
Related Manufacturers
- 主营：氯化氢乙醇、二苯基硅二醇、甲基磺酸铋、环己二胺、阻燃剂DDP、萃取剂、HTPB、防老剂
- 主营：防老剂、香精香料、乳化剂、环己二胺、壳聚糖
- 主营：羟基磷灰石头、二醋酸纤维素、甲基丙烯酸镁、DL-苹果酸、间苯二甲酸二甲酯、苯代三聚氰胺、苄索氯铵、柏木脑、乳酸铵、咪唑、明胶、靛红酸酐、异噻唑啉酮、抗氧化剂1135、海藻酸
- 主营：医药中间体、香精香料、选矿药剂、环己二胺、化工原料、助剂、偶联剂、扩链剂、化妆品原料
- 主营：涂料助剂、工业清洗剂、表面活性剂、环己二胺、合成材料助剂、合成香料、溶剂、香精和香料中间、合成材料中间体、选矿药剂、萃取剂
- 主营：氧化石蜡皂、水杨羟肟酸、烷基羟肟酸、环己二胺、苯甲羟肟酸、幸基羟肟酸、苄基胂酸、乙硫氨酯、氧化铜活化剂T41、二羟吲哚、磷钼酸、四乙酰核糖、吲哚丙酸
- 主营：甘氨酸、溴化物、戊酸鈉、蒽甲酸、联吡啶、紫苏葶、锂电池、牛磺酸、褪黑素、磷酸铟、新癸酸、赖氨酸、溴化鏻、乙氧基、藏花醛、豆甾醇、羟乙基、维素酶、庚二酸、呋虫胺、丹参素、萘甲醛、槐豆胶、黄柏酮、元明粉
- 主营：异硫氰酸胍、β巯基乙醇、蛋白酶k、三(羟甲基)氨基甲烷tris、二硫苏糖醇(DTT)、焦碳酸二乙酯DEPC、EDTA二钠、十二烷基苯磺酸钠
- 主营：单磷酸、白果酸、银杏酸、澳洲茄胺、红四氮唑、白当归脑、曲氟胸苷、安石榴苷、二磷酸葡、白术内酯、四氮唑蓝、澳洲茄碱、巴卡亭iii、白藜芦醇、脱氧尿苷、澳洲茄边、白当归素、脱氧腺苷、腺苷一水合、二磷酸钠盐、白花前胡丙、羟甲香豆素、尿苷三磷酸、菝葜皂苷元、磷酸二钠盐
- 主营：酸性橙、钒酸铯、吩恶噻、7675-65-2、脱乙基、嘧菌酯、丙酸铵、碳酸镍、丙酸铯、新癸酸、混杀威、赖氨酸、乙氧基、乙酸铯、戊唑醇、吡唑胺、乙醇铜、叶绿素、氟苯基、乙醇铌、酸性红、羟乙基、分散橙、异恶唑、丹酰肼
- 主营：乙酸镥、二缩物、甘氨酰、dl-半胱、alnusdiol、去铁酮、硫酸锑、基嘧啶、硫酸锆、硫酸锂、钒酸铋、硫酸锰、氰基苯、硫酸锡、二苯胍、紫苏葶、普利醇、平平加、含苯基、苄乙铵、磷酸银、磷酸铵、二辛基、肉桂醛、异丁酯