6090-79-5

Usage

Uses

Used in Pharmaceutical Industry:
2-[(Chloroacetyl)oxy]benzoic acid is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of various medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 2-[(Chloroacetyl)oxy]benzoic acid is utilized as an intermediate, playing a role in the creation of substances that contribute to agricultural and pest control solutions.
Used in Organic Chemistry:
2-[(Chloroacetyl)oxy]benzoic acid is employed as a building block for the production of other organic compounds, highlighting its versatility in organic synthesis processes.

InChI:InChI=1/C9H7ClO4/c10-5-8(11)14-7-4-2-1-3-6(7)9(12)13/h1-4H,5H2,(H,12,13)

Upstream product

• 54-21-7 sodium salicylate 
• 79-04-9 chloroacetyl chloride 
• 69-72-7 salicylic acid 

Downstream Products

• 180468-18-2 2-Hydroxy-benzoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 180266-82-4 2-{Bis-[(2S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-benzoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 101974-24-7 (2-cloroacetilsaliciloil)-4-nitrofenolo 
• 101974-27-0 O-(2-cloroacetilsaliciloil)-N-(2-acetilsaliciloil)-4-amminofenolo 
• 101974-28-1 O-(2-acetilsaliciloil)-N-(2-cloroacetilsaliciloil)-4-amminofenolo 

Relevant academic research and scientific papers

Chloroethyl acyloxy salicylic acid derivatives use in medicine

The invention relates to a salicylic acid derivative preparation and its new use of development, in particular to chloroethyl acyloxy salicylic acid derivatives (synthetic route thereof and structure are as follows expressed) in the treatment of cancer an

Neighboring group catalysis in the design of nucleotide prodrugs

An approach is described for potential application to the delivery of polar nucleosides and nucleotides across lipophilic membranes, namely, nucleotide prodrugs based on salicyl phosphate. 3'-Azido-3'-deoxythymidine (AZT) and 3'-deoxythymidine (ddT) were chosen as models. For the synthesis of prototype compounds 1 and 2, the approach was first to react either methyl salicylate (for 1) or phenyl salicylate (for 2) with phosphorus oxychloride in dry methylene chloride at 0 °C with the addition of triethylamine as acid scavenger. The resulting intermediate phosphorodichloridate was reacted immediately with excess nucleoside under the same conditions. The control model compound 3 was prepared by reaction of phenyl phosphorodichloridate and excess nucleoside in pyridine/methylene chloride at 0 °C to give 3 in 82% yield. The synthesis of triester 7 involved reaction of α- (chloroacetyl)salicyl chloride with 2,3,4,6-tetra-O-benzyl-D-glucopyranose to give [[(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-oxy]carbonyl]-2-(1- chloroacetoxy)benzene (4) which was dechloroacetylated to 5, 2,3,4,6-tetra- O-benzyl-D-glucopyranosyl salicylate. Phosphorylation of 5 with phosphorus oxychloride provided the phosphorodichloridate which was directly converted to 6 by reaction with dideoxythymidine. Removal of benzyl groups by catalytic hydrogenation gave compound 7, bis(2',3'-dideoxythymidin-5'-yl) D- glucopyranosyl phosphate. The AZT prodrug triesters, 1 and 2, underwent much more rapid hydrolysis than the triester 3, most probably due to the formation of an acyl phosphate complex from the attack on phosphorus of the salicylate carboxylate. The hydrolysis of the less lipophilic 7 was significantly slower than that of 1 or 2. Both pig liver esterase and rat brain cytosol were able to effect the cleavage to dinucleotide or mononucleotide of prodrug forms 2 and 7, much more rapidly than either 3 or 1, suggesting that the esterase- like enzymatic activity of rat brain was similar to that of pig liver esterase. This study suggests the possibility of use of salicylic acid-based prodrugs for nucleotides, subject to specific refinements in the choice of carboxylate- and phosphoric acid ester-protecting groups.