6587-25-3

Basic information

• Product Name: 1,3,2-Dioxaphospholan-2-amine, N-phenyl-, 2-oxide
• CAS NO: 6587-25-3
• Molecular Formula: C8H10NO3P
• Molecular Weight: 199.146
• Mol File: 6587-25-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaphospholan-2-amine, N-phenyl-, 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaphospholan-2-amine, N-phenyl-, 2-oxide(6587-25-3)
• EPA Substance Registry System: 1,3,2-Dioxaphospholan-2-amine, N-phenyl-, 2-oxide(6587-25-3)

Safety Data

• Hazardous Substances Data: 6587-25-3(Hazardous Substances Data)

Usage

Type of compound

Organic compound

Contains

a. Phosphorus atom
b. Amine group
c. Oxide group

Usage

a. Reagent in organic synthesis
b. Preparation of phosphorus-containing compounds
c. Production of pharmaceuticals and agricultural chemicals

Safety concerns

Potential hazards and risks associated with its use

Importance

Plays a significant role in various chemical processes and applications

Upstream product

• 62-53-3 aniline 
• 6609-64-9 2-Chloro-2-oxo-1,3,2-dioxaphospholane 

Downstream Products

• 62-53-3 aniline 
• 1445-36-9 N-phenylamidophosphoric acid 

Relevant articles and documents

Phosphate-based self-immolative linkers for the delivery of amine-containing drugs

Amine-containing drugs often show poor pharmacological properties, but these disadvan-tages can be overcome by using a prodrug approach involving self-immolative linkers. Accordingly, we designed L-lactate linkers as ideal candidates for amine delivery. Furthermore, we designed linkers bearing two different cargos (aniline and phenol) for preferential amine cargo release within 15 min. Since the linkers carrying secondary amine cargo showed high stability at physiological pH, we used our strategy to prepare phosphate-based prodrugs of the antibiotic Ciprofloxacin. Therefore, our study will facilitate the rational design of new and more effective drug delivery systems for amine-containing drugs.

Kinetics and mechanism of the pyridinolysis of (2R,4R,5S)-(+)-2-chloro-3,4- dimethyl-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide in acetonitrile

The nucleophilic substitution reactions of (2R,4R,5S)-(+)-2-chloro-3,4- dimethyl-5-phenyl-1,3,2-oxa-zaphospholidine 2-sulfide with X-pyridines are investigated kinetically in acetonitrile at 5.0 °C. The free energy relationships for substituent X variations in the nucleophiles exhibit biphasic concave upwards with a break point at X = 3-Ac. Unusual positive ρX (= +4.73) and negative βX (= -0.75) values are obtained with the weakly basic pyridines, and rationalized by the isokinetic relationship with isokinetic temperature at tISOKINETIC = 39.3 °C. A concerted mechanism involving a change of nucleophilic attacking direction from a frontside attack with the strongly basic pyridines to a backside attack with the weakly basic pyridines is proposed on the basis of greater magnitudes of selectivity parameters (ρX = -6.15 and βX = 1.11) with the strongly basic pyridines compared to those (ρX = 4.73 and βX = -0.75) with the weakly basic pyridines.

ACID-CATALYZED HYDROLYSIS OF N-PHENYL PHOSPHORIC AMIDES. KINETIC IMPLICATION OF THE REACTION VIA THE O-PROTONATED INTERMEDIATE

Rates of the acid-catalyzed hydrolysis of N-phenyl dimethylphosphoramidate, 2-(phenylamino)-2-oxo-1,3,2-dioxaphospholan and 2-ethoxy-2-oxo-3-phenyl-1,3,2-oxazaphospholan, as well as of the corresponding non-cyclic monoester amidates were determined.In cyc