37859-25-9

Basic information

• Product Name: 2-(2-Naphthyl)acetyl chloride
• Synonyms: BUTTPARK 52\15-93;2-(2-NAPHTHYL)ACETYL CHLORIDE;NAPHTHALEN-2-YL-ACETYL CHLORIDE;2-Naphth-2-ylacetyl chloride;2-(2-Naphthyl)acetyl chloride, tech;2-Naphthaleneacetylchloride;2-Naphthylacetyl chloride;(Naphth-2-yl)acetyl chloride
• CAS NO: 37859-25-9
• Molecular Formula: C₁₂H₉ClO
• Molecular Weight: 204.65
• Mol File: 37859-25-9.mol
• Article Data: 59

Chemical Properties

• Melting Point: 61-65°C
• Boiling Point: 333.7 °C at 760 mmHg
• Flash Point: 156.4 °C
• Appearance: /
• Density: 5 g/cm3
• Vapor Pressure: 0.000134mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 2-(2-Naphthyl)acetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Naphthyl)acetyl chloride(37859-25-9)
• EPA Substance Registry System: 2-(2-Naphthyl)acetyl chloride(37859-25-9)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• Hazardous Substances Data: 37859-25-9(Hazardous Substances Data)

Usage

General Description

2-(2-Naphthyl)acetyl chloride, also referred to by its IUPAC name, 2-naphthacenoyl chloride, is a chemical compound known for its role in organic synthesis. Its chemical formula is C12H9ClO, meaning it contains carbon, hydrogen, chloride, and oxygen atoms. 2-(2-Naphthyl)acetyl chloride is typically in a liquid state at room temperature and has a dark, amber color. Like other acyl chlorides, it is highly reactive, particularly with compounds containing amino or hydroxy groups. It requires specific handling due to its potential hazards, such as its reactivity and corrosiveness. However, this chemical is widely used in the synthesis of various pharmaceutical substances and other chemical intermediates.

InChI:InChI=1/C12H9ClO/c13-12(14)8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H,8H2

Upstream product

• 581-96-4 2-naphthylacetic acid 
• 114373-76-1 N-<2-(2-Naphthyl)-1-thioxoethyl>piperidine 
• 93-08-3 methyl 2-naphthyl ketone 
• 93579-03-4 tert-butyl α-(naphthalen-2-yl)acetate 

Downstream Products

• 100597-44-2 (Z)-2-(2-Naphthalen-2-yl-acetylsulfanyl)-3-p-tolyl-acrylic acid 
• 53342-32-8 2-naphthylacetic acid benzyl ester 
• 175223-64-0 2-phenyl-4-phenanthrol 
• 201802-02-0 N-[5-(2,4-Dioxo-thiazolidin-5-ylmethyl)-2-hydroxy-phenyl]-2-naphthalen-2-yl-acetamide 
• 158535-61-6 phenyl 2-(naphthalen-2-yl)acetate 
• 7498-57-9 2-naphthaleneacetonitrile 
• 676566-00-0 N-propyl-N-(2-phenylethyl)-2-(2-naphthyl)acetamide 
• 766514-66-3 (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 932378-51-3 12-(2'-naphthylacetyl)aminododecanoic acid p-nitrophenyl ester 
• 932378-50-2 1-(12'-N-[2''-naphthylacetyl]aminolauroyl)-3-(p-toluenesulfonyl)-sn-glycerol 

Relevant articles and documents

Synthesis and evaluation of benzenesulfonic acid derivatives as human neutrophil elastase (hNE) inhibitors

Herein we report our investigation concerning the development of Human neutrophil elastase (hNE) inhibitors for the treatment of Acute Respiratory Distress Syndrome (ARDS). Various benzenesulfonic acid derived compounds were synthesized and evaluated as competitive inhibitors of hNE. Biological screening revealed that compound 4f shows moderate inhibitory activity (IC50 = 35.2 μM) against hNE. Compound 4f was also superimposed onto the active center of hNE to understand the binding mode.

HIGH PURITY 2-NAPHTHYLACETONITRILE AND METHOD FOR PRODUCING SAME

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Novel Pyridine-Based Hydroxamates and 2′-Aminoanilides as Histone Deacetylase Inhibitors: Biochemical Profile and Anticancer Activity

Starting from the N-hydroxy-3-(4-(2-phenylbutanoyl)amino)phenyl)acrylamide (5 b) previously described by us as a HDAC inhibitor, we prepared four aza-analogues, 6–8, 9 b, as regioisomers containing the pyridine nucleus. Preliminary screening against mHDAC1 highlighted the N-hydroxy-5-(2-(2-phenylbutanoyl)amino)pyridyl)acrylamide (9 b) as the most potent inhibitor. Thus, we further developed both pyridylacrylic- and nicotinic-based hydroxamates (9 a, 9 c–f, and 11 a–f) and 2′-aminoanilides (10 a–f and 12 a–f), related to 9 b, to be tested against HDACs. Among them, the nicotinic hydroxamate 11 d displayed sub-nanomolar potency (IC50: 0.5 nM) and selectivity up to 34 000 times that of HDAC4 and from 100 to 1300 times that of all the other tested HDAC isoforms. The 2′-aminoanilides were class I-selective HDAC inhibitors, generally more potent against HDAC3, with the nicotinic anilide 12 d being the most effective (IC50HDAC3=0.113 μM). When tested in U937 leukemia cells, the hydroxamates 9 e, 11 c, and 11 d blocked over 80 % of cells in G2/M phase, whereas the anilides did not alter cell-cycle progress. In the same cell line, the hydroxamate 11 c and the anilide 10 b induced about 30 % apoptosis, and the anilide 12 c displayed about 40 % cytodifferentiation. Finally, the most potent compounds in leukemia cells 9 b, 11 c, 10 b, 10 e, and 12 c were also tested in K562, HCT116, and A549 cancer cells, displaying antiproliferative IC50 values at single-digit to sub-micromolar level.