2007-13-8

Basic information

• Product Name: 2-(1-naphthyloxy)propanoyl chloride
• Synonyms: 2-(1-naphthyloxy)propanoyl chloride;propanoyl chloride, 2-(1-naphthalenyloxy)-
• CAS NO: 2007-13-8
• Molecular Formula: C13H11ClO2
• Molecular Weight: 234.67824
• Mol File: 2007-13-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(1-naphthyloxy)propanoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-naphthyloxy)propanoyl chloride(2007-13-8)
• EPA Substance Registry System: 2-(1-naphthyloxy)propanoyl chloride(2007-13-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2007-13-8(Hazardous Substances Data)

Usage

Derivative

Naphthalene

Usage

Reagent in organic synthesis

Primary application

Manufacturing of pharmaceuticals (e.g. nalfurafine for treating itching in patients with liver disease)

Secondary applications

Production of agrochemicals and fragrance compounds

Handling precautions

Reactive and potentially hazardous; should be handled with care and in accordance with proper safety procedures.

Upstream product

• 13949-67-2 2-Methyl-2-α-naphthylacetic acid 
• 33798-78-6 2-(naphthalene-1-yloxy)propionic acid ethyl ester 
• 90-15-3 α-naphthol 

Downstream Products

• 57128-29-7 (R)-2-Methyl-2-α-naphthylacetic acid 
• 57128-28-6 (S)-2-(1-naphthoxy)propanoic acid 

Relevant articles and documents

Stereoinversion in the diastereoselective acylation of benzoxazine derivatives with 2-aryloxypropionyl chlorides

A comparative study of the kinetic resolution of racemic derivatives of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using racemic 2-aryloxypropionyl chlorides was performed. It was found that the acylation of racemic amines with racemic 2-(1-naphthyloxy)propionyl chloride leads to amides enriched with (3R*,2′R*)-diastereomers, while the acylation with 2-phenoxypropionyl chloride gives predominantly (3R*,2′S*)-amides. Quantum chemical modeling of the process of kinetic resolution at the COSMO-CH2Cl2-B3LYP-D3-gCP/def2-TZVP//B3LYP-D3-gCP/def2-SVP level of theory was performed. The computational results are in a good agreement with the experimental data.

Presynaptic cholinergic modulators as potent cognition enhancers and analgesic drugs. 2. 2-Phenoxy-, 2-(phenylthio)-, and 2-(phenylamino)alkanoic acid esters

Further modifications of the leads ((R)-(+)-hyoscyamine and (p- chlorophenyl)propionic acid α-tropanyl ester), which show analgesic and nootropic activities as a consequence of increased central presynaptic ACh release, are reported. 2-Phenoxy- and 2-(phenylthio)alkanoic acid esters showed the best results. Several members of these classes possess analgesic properties which are comparable to that of morphine and at the same time are able to reverse dicyclomine-induced amnesia. Confirmation was found that the mechanism of action is due to an increase in ACh release at central muscarinic synapses and that both auto- and heteroreceptors controlling ACh release are very likely involved. According to the results obtained with (R)- (+)-hyoscyamine, analgesic activity is stereochemistry dependent, since the R-(+)-enantiomers are always more efficacious than the corresponding S-(-)- ones. On the basis of their potency and acute toxicity, compounds (±)-28 (SM21) and (±)-42 (SM32) were selected for further study.