61397-56-6

Usage

Uses

Used in Pharmaceutical Industry:
cis-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-ylmethyl benzoate is used as a key intermediate in the preparation of antifungal agents for the treatment of various fungal infections. Its application is primarily due to its ability to be incorporated into the molecular structure of antifungal drugs, enhancing their efficacy and potency.
Specifically, cis-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-ylmethyl benzoate is used in the synthesis of the following antifungal agents:
1. Ketoconazole (K186000): This antifungal medication is used to treat a wide range of fungal infections, including those affecting the skin, nails, and internal organs. cis-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-ylmethyl benzoate's presence in Ketoconazole contributes to its antifungal properties.
2. Itraconazole (I937500): Another potent antifungal agent, Itraconazole is used to treat various fungal infections, such as aspergillosis, candidiasis, and cryptococcal meningitis. cis-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-ylmethyl benzoate's role in Itraconazole aids in its effectiveness against these infections.
3. Terconazole: This antifungal drug is commonly used to treat vaginal yeast infections caused by Candida species. The inclusion of cis-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-ylmethyl benzoate in its molecular structure enhances its antifungal activity.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C18H15BrCl2O4/c19-11-18(15-7-6-13(20)8-16(15)21)24-10-14(25-18)9-23-17(22)12-4-2-1-3-5-12/h1-8,14H,9-11H2

Upstream product

• 68751-57-5 2-(2,4-dichlorophenyl)-2-bromomethyl-4-hydroxymethyl-1,3-dioxolane 
• 98-88-4 benzoyl chloride 
• 532-32-1 sodium benzoate 
• 497250-93-8 (+/-)-2-(bromomethyl)-4-(chloromethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 2631-72-3 2,4-dichlorophenacyl bromide 
• 172032-21-2 (2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methanol 

Downstream Products

• 70894-66-5 Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 
• 84499-45-6 cis-2-(2,4-dichlorophenyl)-2-(4H-1,2,4-triazol-4-ylmethyl)-1,3-dioxolane-4-methanol 
• 67914-85-6 cis-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol 
• 67914-84-5 Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 
• 61397-58-8 cis-2-(2,4-Dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane-4-methanol 
• 67914-86-7 cis-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate 
• 67915-31-5 (+/-)-Terconazole 
• 89614-29-9 cis-2-(2,4-dichlorophenyl)-2-(1,2,3,5-tetrazol-1-ylmethyl)-1,3-dioxolan-4-ylmethanol 
• 89614-30-2 cis-2-(2,4-dichlorophenyl)-4-methanesulfonyloxymethyl-2-(1,2,3,5-tetrazol-1-ylmethyl)-1,3-dioxolane 
• 113770-65-3 Toluene-4-sulfonic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 
• 85650-50-6 cis-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate 

Relevant academic research and scientific papers

Synthesis, antifungal activity and structure-activity relationships of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)- 1,3-dioxolanes

A series of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)-1,3-dioxolanes Ia-u was synthesized and tested in vitro against pathogenic fungi in man, animals and plants: Candida albicans, Aspergillus flavus and Fusarium solani. Compounds Iq-t with two polyazol groups have an in vitro activity against these fungi with MIC (minimum inhibitory concentration) value of 5 μg mL-1.

Stereoselective Syntheses of Both Enantiomers of Ketoconazole from (R)- and (S)-Epichlorohydrin

Stereoselective syntheses of both enantiomers of ketoconazole (1) from commercially available (R)- or (S)-epichlorohydrin has been developed.The key-step of syntheses involves the selective substitution of the methylene chlorine atom by benzoate on a mixture of (2S,4R)-14a and (2R,4R)-15a or of their enentiomers, followed by crystalization of the corresponding cis-benzoates, (2R,4R)-18 or (2S,4S)-18, from which (+)- or (-)-1 were obtained as described for (+/-)-1.The ee's of (+)- and (-)-ketocanazole were determined by HPLC on the CSP Chiracel OD-H.

Synthesis and 13C NMR Spectra of cis- and trans-methyl>>-1,3-dioxolane-4-methanols

Syntheses and 13C nmr spectra of a number of cis and trans 2-(haloaryl)-2--4-(hydroxymethyl)-1,3-dioxolanes are described.The haloaryl groups are 2,4-dichloro, 2,4-difluoro-, 4-chloro- and 4-bromophenyl.In these series, some of the cis compounds become available through crystalline bromo benzoates 5.Separations of some trans isomers are achieved through fractional crystallizations of imidazolyl benzoate nitrates 6.Stereochemical assignments are based primarily on one major 13C chemical shift difference, namely that of C-4 of the 1,3-dioxolane ring, the chemical shift of the trans isomers being 1.0-2.5 ppm downfield from that of the cis isomers.