114012-41-8

Basic information

• Product Name: 3-OXETANECARBOXYLIC ACID
• Synonyms: 3-OXETANECARBOXYLIC ACID
• CAS NO: 114012-41-8
• Molecular Formula: C4H6O3
• Molecular Weight: 102.08864
• Mol File: 114012-41-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 244℃
• Flash Point: 115°(239°F)
• Appearance: /
• Density: 1.374
• Vapor Pressure: 0.0101mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: ?20°C
• PKA: 3.88±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: 3-OXETANECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXETANECARBOXYLIC ACID(114012-41-8)
• EPA Substance Registry System: 3-OXETANECARBOXYLIC ACID(114012-41-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 114012-41-8(Hazardous Substances Data)

Usage

Uses

Oxetane-3-carboxylic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

InChI:InChI=1/C4H6O3/c5-4(6)3-1-7-2-3/h3H,1-2H2,(H,5,6)

Upstream product

• 1638760-80-1 3-oxetanecarboxylic acid methyl ester 

Downstream Products

• 1449276-91-8 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide 

Relevant articles and documents

Chagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series

Acylaminobenzothiazole hits were identified as potential inhibitors of Trypanosoma cruzi replication, a parasite responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure-activity relationship, allowing optimization of antiparasite activity, physicochemical parameters, and ADME properties. We identified compound 50 as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079 μM) and an enhanced metabolic stability (human clearance = 0.41 mL/min/g) and opportunity for the oral route of administration. After tolerability assessment, 50 demonstrated a promising in vivo efficacy.

Preparation method of 3-oxetanecarboxylic acid

The invention provides a preparation method of 3-oxetanecarboxylic acid. According to the preparation method, 2-hydroxymethyl-2-nitro-1,3-propylene glycol is taken as a raw material, hydroxyl in 2-hydroxymethyl-2-nitro-1,3-propylene glycol is subjected to a group protection reaction, nitryl in 2-hydroxymethyl-2-nitro-1,3-propylene glycol is subjected to a reductive elimination reaction and hydrolysis reaction, and 2-hydroxymethyl-1,3-propylene glycol is obtained; 2-hydroxymethyl-1,3-propylene glycol is continuously subjected to a cyclization reaction and an oxidation reaction, and 3-oxetanecarboxylic acid is obtained. The provided preparation method can be completed only through five-step reactions; compared with existing preparation methods through ten-step reactions, the preparation method has the advantages that the reaction steps are greatly reduced, the reaction routes are greatly shortened, the overall yield is increased, and the final yield can be up to 50% or above on the basisof the raw material, namely, 2-hydroxymethyl-2-nitro-1,3-propylene glycol; the related reactions are simple, and the method is easy to operate and favorable for industrial production.

Process for the preparation of 2,2-bis-chloro-methylalkanecarboxylic acid chlorides

A process for the preparation of a 2,2-bis-chloro-methyl-alkanecarboxylic acid of the formula STR1 in which R is hydrogen, alkyl, cycloalkyl or optionally substituted phenyl, which comprises reacting an oxetane-3-carboxylic acid of the formula STR2 or a salt thereof, with an inorganic acid chloride at a temperature between 20° C. and the boiling point of the reaction mixture. The products are known intermediates for fungicides and herbicides.