Overview
Cis-Diol refers to organic compounds containing two hydroxyl groups (-OH) attached to adjacent carbon atoms in a cis configuration. This structural motif is prevalent in natural products and synthetic chemistry, where it serves as a versatile building block. The proximity of the hydroxyl groups in the cis arrangement imparts unique reactivity, enabling transformations like oxidative cleavage or protection as cyclic derivatives. The term 'Cis-Diol' is often used interchangeably with 'Vicinal Diol' when emphasizing the 1,2-relationship, though strictly it specifies the stereochemistry. These compounds play critical roles in carbohydrate chemistry (e.g., sugar derivatives) and as intermediates in asymmetric synthesis for pharmaceuticals and fine chemicals.
Physical and Chemical Properties
Cis-Diols exhibit distinct physical properties based on their molecular structure. Smaller aliphatic variants are typically water-soluble due to hydrogen bonding, while aromatic derivatives may have limited solubility. The hydroxyl groups engage in intramolecular hydrogen bonding, affecting boiling points and crystalline structures. Chemically, the adjacent hydroxyl groups make these compounds prone to periodate oxidation (cleaving the C-C bond) and enable protection strategies using aldehydes/ketones to form cyclic acetals or ketals. This reactivity is harnessed in synthetic routes where selective manipulation of one hydroxyl group is required. The stereochemistry also influences biological activity, making cis-configuration crucial for drug design.
Main Applications
In pharmaceuticals, Cis-Diols are key intermediates for antiviral and anticancer agents. Their ability to form stable cyclic derivatives aids in protecting sensitive functional groups during multi-step syntheses. For example, nucleoside analogues often incorporate this motif. Industrial applications include polymer chemistry, where Cis-Diols act as monomers for polyesters or crosslinking agents. In asymmetric catalysis, chiral diols serve as ligands for transition metal complexes. Additionally, they're used in analytical chemistry as chelating agents for metal ions and in the production of specialty chemicals like flavors and fragrances.
Safety and Storage
While generally stable, Cis-Diols require careful handling due to potential skin/eye irritation. Powdered forms may form combustible dust clouds, necessitating proper ventilation. Incompatibilities include strong oxidizers and acid chlorides, which may cause vigorous reactions. Storage recommendations include airtight containers in cool (below 30°C), dry conditions, away from direct sunlight. For moisture-sensitive derivatives, inert gas purging or desiccants are advisable. Larger quantities should be stored in corrosion-resistant secondary containment, with clear labeling of stereochemical information to prevent misuse in sensitive syntheses.
B2B Procurement Guide
When sourcing Cis-Diols, buyers should prioritize suppliers with stereochemical expertise, as impurities in enantiomeric or diastereomeric forms can critically impact downstream applications. Technical specifications should include: enantiomeric excess (if chiral), water content, and residual solvent levels. Bulk procurement (kilograms to metric tons) typically offers cost advantages, with pricing tiers based on purity (98%, 99%, or HPLC-grade). Consider suppliers providing comprehensive COA (Certificate of Analysis) and stability data. For regulated industries (pharma), ensure vendors comply with cGMP standards. Logistics planning should account for potential sensitivity to temperature fluctuations during transit.
Related Manufacturers
- 主营：叔碳酸、十八醛、溶菌酶、癸二醇、癸烷撑二醇、海藻糖、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、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：有机原料、中间体、香精香料、催化剂、有机硅、表面活性剂
- 主营：全氟三丁胺、二苄叉山梨醇、六氟丙烯二聚体、顺式丁烯二醇、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：中间体、抗氧剂、甘露糖醇、丁烯二醇、微量元素、光敏塑料、绿色农药、磷酸二氢铝、表面活性剂、组织改进剂、间苯二甲胺、工业级甲酸钙、工业级二甘醇、聚醋酸乙烯酯、紫外线吸收剂、n-辛基吡咯烷酮、活性剂耐火材料、纺织助剂增塑剂
- 主营：丁烯二醇、麦芽糖酸、苯氧基环磷腈、甲巯基四氮唑
- 主营：10ul吸头、巴氏吸管、离心管、透析袋、琼脂糖、国产试剂
- 主营：合成树脂、固化剂、不饱和树脂、环己二醇、环氧树脂、聚酯多元醇、酚醛树脂、医药中间体
- 主营：三甲基羟乙基乙二胺、五甲基二乙烯三胺、钛酸四丁酯、顺式1、三氯叔丁醇、氨基钠、碳酸胍、降龙涎香醚、甲基丙烯酸纳、四溴双酚A、正辛基三乙氧基硅烷
- 主营：ELISA试剂盒、细胞培养系列、PCR相关、透析袋系列、实验耗材系列、实验室试剂系列
- 主营：甘氨酸、阻燃剂、硫酸锰、顺式、十八酸、3188-00-9、碳酸镧、磷酸铁、丙酸铵、特戊醛、赖氨酸、增塑剂、咖啡酸、葡糖苷、蛋白粉、氨酰胺、酸性红、羟乙基、脂肪酶、7327-87-9、甲酸钙、58#石蜡、防腐剂、防水剂、聚丙烯、度米芬
- 主营：氯菊酯、转移剂、聚酯树脂、二甲氧基、驱蚊原液、食品香料、缩水甘油酯、蚊香增效剂、丙烯酸缩水、环氧稀释剂、硅烷偶联剂、超疏水材料、对甲氧基苯酚、对羟基苯甲醚、乙烯基双封头、苯基缩水甘油醚
- 主营：树脂合、木质素、分析纯、己二醇酯、二乙二醇酯、聚碳酸酯二醇、己二酸乙二醇、化学试剂、涂覆金属、油墨pu树脂、水性pu树脂、二酸二甲酯、聚酯多元醇、树脂固化剂、水性聚氨酯、聚酰胺树脂、聚氨酯树脂、聚氨酯弹性体、水性喷墨打印、面料柔软整理、改性聚酰亚胺
- 主营：甘氨酰、酸性橙、二苯胺、丁烯二醇、基嘧啶、氟甲烷、甲苯氟、脱乙基、苯丁锡、氰酸银、含苯基、咯喹酮、嘧菌酯、丁酸铝、肉桂醇、二辛基、特戊醛、茜素红、叶绿素、氟苯基、碲化钠、酸性红、噻虫啉、恶唑磷、颜料蓝、甲酰胺
- 主营：聚乳酸、三辛胺、钛酸铝、鱼溶浆、苯戊酮、7691-02-3、福美钠、卡波姆、醋酸菌、聚苯胺、3-苯丙醇、焦谷氨酸、松叶菊碱、邻苯二甲、四甲基二、四氯苯醌、假丝酵母、二甲氧基、肉桂酸苄酯、海藻糖原料、吡啶硫酮锌、苯甲酸苄酯、羟丙基甲基、聚乙烯亚胺、蓖麻油酸锌
- 主营：百里香酚、戊基黄药、矿物浮选剂