39735-79-0

Usage

Type of Compound

Chiral chloropropanol compound

Primary Uses

Pesticide, germicide, intermediate in chemical synthesis, pharmaceuticals

Properties

Strong antimicrobial, effective in controlling pathogens, inhibits growth of bacteria

Potential Medical Applications

Treatment of certain medical conditions

Health Risks

Yes, requires careful regulation and monitoring

Environmental Concerns

Yes, requires careful regulation and monitoring

InChI:InChI=1/C9H10Cl2O2/c10-5-8(12)6-13-9-3-1-7(11)2-4-9/h1-4,8,12H,5-6H2

Upstream product

• 104-29-0 chlorphenesin 
• 96-23-1 1,3-Dichloro-2-propanol 
• 106-48-9 4-chloro-phenol 
• 106-89-8 epichlorohydrin 
• 2212-05-7 4-chlorophenyl 2,3-epoxypropyl ether 
• 122-60-1 Phenyl glycidyl ether 

Downstream Products

• 20807-79-8 4-(4-chlorophenoxy)-3-hydroxybutanenitrile 
• 5790-34-1 1-(Isopropylamino)-3-(4-chlorophenoxy)-2-propanol 
• 57264-54-7 1-chloro-3-(p-chlorophenoxy)-2-propanone 
• 946528-30-9 1-(4-chlorophenoxy)-3-thiocyanatopropan-2-one 
• 7417-88-1 (+/-)-4-(4-chloro-phenoxy)-3-hydroxy-butyric acid 

Relevant academic research and scientific papers

Visible-light-triggered Catalytic Halohydrin Synthesis from Epoxides and Trichloroacetonitrile by Copper and Iron Salts

Preparation of vicinal halohydrins, in which copper or iron chlorides catalyze the ring-opening reaction of epoxides with visible light effectively, is described. The use of trichloroacetonitrile as a halogen source enables catalytic HCl generation under the mild conditions. This method can also be applied to the aziridine ring-opening reaction.

Protective opening of epoxide using pivaloyl halides under catalyst-free conditions

An efficient and environmentally benign protocol for protective opening of epoxide (POE) with pivaloyl halides in solvent-free conditions and in aqueous media under catalyst-free conditions has been developed. The green reaction conditions, simple work-up procedures, high yields and broad scope of the reaction illustrate the good synthetic utility of this method. The key advantages of the reaction are regioselectivity and reconvertability of products into their prior epoxides in the presence of mild reaction conditions.

Facile, high regio- And chemoselective conversion of epoxides to β-chlorohydrins using chlorodiphenylphosphine under solvent-free conditions

A new method is described for the mild and high regioselective conversion of epoxides to β-chlcrohydrins in high yields even in the presence of alcohols, carboxylic acids, oximes, amides, thiols and tetrahydropyranyl ethers using chlorodiphenylphosphine (ClPPh2) under solvent-free and neutral conditions at room temperature and in short reaction times. In addition, some other functional groups such as carbon-carbon double bonds, ester groups and also phenyl ring that are present in the epoxide molecules remain intact in this method.

Synthesis of β-chlorohydrins in water

2,4,6-Trichloro-1,3,5-triazine (TCT, cyanuric chloride) was found to mediate the regio- and stereoselective ring opening of epoxides in H 2O in the presence of morpholine at room temperature to afford the corresponding β-chlorohydrins in excellent yields (Table). The transformation is very simple, fast, efficient, and ecologically beneficial.

Regio- and stereoselective ring opening of epoxides and aziridines using zirconyl chloride: An efficient approach for the synthesis of β-chlorohydrins and β-chloroamines

Zirconyl chloride mediated regio- and stereoselective ring opening of epoxides and aziridines at room temperature affords the corresponding β-chlorohydrins and β-chloroamines, respectively in high yields. Copyright

Asymmetric reduction of α-thiocyanatoketones by Saccharomyces cerevisiae and Mortierella isabellina-a new route to optically active thiiranes

A simple method for the preparation of optically active 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-oles from racemic 1-chloro-3-aryloxy- and 1-chloro-3-arylsulphanyl-2-propanols via 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-ones has been developed. The enantiomerically enriched β-hydroxythiocyanates were obtained by a microbiological reduction of the thiocyanatoketones with Saccharomyces cerevisiae or Mortierella isabellina and subsequently converted into optically active thiiranes on treatment with a lithium hydroxide solution.

Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism

Some 3-aryloxy-1,2-epoxypropanes, interesting as potential synthons in β-adrenergic receptor antagonists preparation, were obtained in excellent yields (65-96% within 2-17 min) by microwave activation (monomode system) using solid-liquid solvent-free phase transfer catalysis (PTC). The best results for the O-alkylation of some phenols with epichlorohydrin were obtained using TBAB and NaOH/K2CO3 (1:4 mol/mol) as phase transfer catalyst and more acceptable basic system, respectively. These new procedure is compared with classical methods. Significant specific microwave effect (non-purely thermal) was evidenced in all cases. They were discussed in terms of reaction medium and mechanism, taking into account the variations in polarity of the systems.

Conversion of epoxides to β-chlorohydrins with thionyl chloride and β-cyclodextrin in water

Several epoxides are efficiently converted to the corresponding β-chlorohydrins in impressive yields with thionyl chloride in the presence of β-cyclodextrin using water as solvent at room temperature. Copyright Taylor & Francis, Inc.

Green protocol for the synthesis of vicinal-halohydrins from oxiranes using the [Bmim]PF6/LiX reagent system

Epoxides undergo rapid ring-opening with lithium halides in [bmim]PF 6 or [bmim]BF4 ionic liquids under mild and neutral conditions to afford the corresponding vic-halohydrins in high to quantitative yields. The epoxides show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly. The recovered ionic liquid can be reused in three to four subsequent runs with consistent activity.

Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin

Highly regioselective ring opening of epoxides to halohydrins has been carried out in impressive yields with hydrogen and lithium halides in presence of β-cyclodextrin using water as solvent.