57277-25-5

Basic information

• Product Name: Diethyl (2-naphtylmethyl)phosphonate
• Synonyms: Diethyl (2-naphtylmethyl)phosphonate;Diethyl (naphthalen-2-ylMethyl)phosphonate
• CAS NO: 57277-25-5
• Molecular Formula: C₁₅H₁₉O₃P
• Molecular Weight: 278.283321
• Mol File: 57277-25-5.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Diethyl (2-naphtylmethyl)phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl (2-naphtylmethyl)phosphonate(57277-25-5)
• EPA Substance Registry System: Diethyl (2-naphtylmethyl)phosphonate(57277-25-5)

Safety Data

• Hazardous Substances Data: 57277-25-5(Hazardous Substances Data)

Usage

General Description

Diethyl (2-naphtylmethyl)phosphonate is a chemical compound that belongs to the group of phosphonates, which are organic compounds containing a carbon-phosphorus bond. This particular compound is composed of two ethyl groups, a 2-naphthylmethyl group, and a phosphonate group. It is commonly used as a reagent in organic synthesis, particularly in the formation of carbon-phosphorus bonds. Diethyl (2-naphtylmethyl)phosphonate has also been studied for its potential biological and pharmaceutical applications, including as a precursor for the synthesis of medicinal drugs and as an inhibitor for certain enzymes. Additionally, it has been investigated for its potential use as a flame retardant and pesticide.

Upstream product

• 939-26-4 2-bromomethylnaphthyl bromide 
• 122-52-1 triethyl phosphite 
• 3167-63-3 diethyl chloromethylphosphonate 
• 580-13-2 2-bromonaphthalene 
• 762-04-9 phosphonic acid diethyl ester 
• 1592-38-7 2-Naphthalenemethanol 
• 78-40-0 triethyl phosphate 
• 66-99-9 β-naphthaldehyde 
• 19350-74-4 2-naphthaldehyde tosylhydrazone 

Downstream Products

• 1372151-85-3 C₂₂H₂₄FO₃P 
• 126479-93-4 9-benzenesulfonyl-3-(2-naphthylethenyl)carbazole 
• 16672-84-7 2-Naphthylmethylphosphonic acid 

Relevant articles and documents

The development of HEC-866 and its analogues for the treatment of idiopathic pulmonary fibrosis

Idiopathic pulmonary fibrosis (IPF) is a chronic progressive lung disease with a typical survival time between three to five years. Two drugs, pirfenidone and nintedanib have been approved for the treatment of IPF, but they have limited efficacy. Thus, th

Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes

Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.

Benzyl Mono-P-Fluorophosphonate and Benzyl Penta-P-Fluorophosphate Anions Are Physiologically Stable Phosphotyrosine Mimetics and Inhibitors of Protein Tyrosine Phosphatases

α,α-Difluoro-benzyl phosphonates are currently the most popular class of phosphotyrosine mimetics. Structurally derived from the natural substrate phosphotyrosine, they constitute classical bioisosteres and have enabled the development of potent inhibitors of protein tyrosine phosphatases (PTP) and phosphotyrosine recognition sites such as SH2 domains. Being dianions bearing two negative charges, phosphonates, however, do not permeate membranes and thus are often inactive in cells and have not been a successful starting point toward therapeutics, yet. In this work, benzyl phosphonates were modified by replacing phosphorus-bound oxygen atoms with phosphorus-bound fluorine atoms. Surprisingly, mono-P-fluorophosphonates were fully stable under physiological conditions, thus enabling the investigation of their mode of action toward PTP. Three alternative scenarios were tested and mono-P-fluorophosphonates were identified as stable reversible PTP1B inhibitors, despite of the loss of one negative charge and the replacement of one oxygen atom as an H-bond donor by fluorine. In extending this replacement strategy, α,α-difluorobenzyl penta-P-fluorophosphates were synthesized and found to be novel phosphotyrosine mimetics with improved affinity to the phosphotyrosine binding site of PTP1B.