5121-00-6

Basic information

• Product Name: 2-(1-NAPHTHYL)ETHANOYL CHLORIDE
• Synonyms: NAPHTH-1-YLACETYL CHLORIDE;BUTTPARK 97\57-54;2-(1-NAPHTHYL)ETHANOYL CHLORIDE;AKOS BBS-00004087;1-NAPHTHYLACETYLCHLORIDE;2-(Naphth-1-yl)ethanoyl chloride;1-Naphthaleneacetylchloride
• CAS NO: 5121-00-6
• Molecular Formula: C₁₂H₉ClO
• Molecular Weight: 204.65
• Product Categories: Carbonyl Chlorides;Carbonyl Chlorides;Fused Ring Systems
• Mol File: 5121-00-6.mol
• Article Data: 95

Chemical Properties

• Melting Point: 137-139 °C(Solv: ligroine (8032-32-4); dichloromethane (75-09-2))
• Boiling Point: 130℃/0.6mm
• Flash Point: 156.4 °C
• Appearance: /
• Density: 1.23
• Vapor Pressure: 0.000134mmHg at 25°C
• Refractive Index: 1.6210
• CAS DataBase Reference: 2-(1-NAPHTHYL)ETHANOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-NAPHTHYL)ETHANOYL CHLORIDE(5121-00-6)
• EPA Substance Registry System: 2-(1-NAPHTHYL)ETHANOYL CHLORIDE(5121-00-6)

Safety Data

• Hazard Codes: C
• Statements: 34-36
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5121-00-6(Hazardous Substances Data)

Usage

General Description

2-(1-Naphthyl)ethanoyl chloride, also known as 2-(1-Naphthyl)acetyl chloride, is a chemical compound with the formula C12H9ClO. It is an acetyl chloride derivative of 1-naphthyl and is commonly used in organic synthesis as a reagent for the introduction of the acyl group into organic compounds. 2-(1-NAPHTHYL)ETHANOYL CHLORIDE is a colorless to pale yellow liquid and is sensitive to moisture, air, and light, making it important to handle and store in a controlled environment. It is primarily utilized in the pharmaceutical and agrochemical industries for the synthesis of various pharmaceutical and agricultural compounds.

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

Upstream product

• 61-31-4 sodium salt of 1-naphthylacetic acid 
• 86-87-3 naphth-1-yl acetic acid 
• 4732-69-8 Chloro-oxo-acetic acid 
• 91-20-3 naphthalene 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 101895-37-8 N-[1]naphthylacetyl-anthranilic acid 
• 2235-15-6 1(2H)-acenaphthylenone 
• 31283-78-0 1-phenyl-3-(1-naphthyl)-2-propanone 
• 548772-87-8 (1S,2S)-2-(1-naphthylacetylamino)-1-phenyl-propane-1,3-diol 
• 676565-99-4 N-propyl-N-(2-phenylethyl)-2-(1-naphthyl)acetamide 
• 1094501-60-6 C₄₇H₆₂N₄O₂₁ 
• 1114985-52-2 C₂₈H₂₈N₂O₂ 
• 694506-58-6 2-(naphthalen-1-yl)-N-(pyridin-3-yl)acetamide 
• 2122-70-5 ethyl 2-(1-naphthyl)acetate 
• 189057-82-7 ethyl 4-(1-naphthyl)-3-oxobutanoate 
• 1353649-55-4 C₂₀H₂₁ClO 
• 1380402-63-0 (3R,4R)-3-(naphthalen-1-yl)-4,6-diphenyl-1-tosyl-3,4-dihydropyridin-2(1H)-one 
• 1372996-86-5 (3S,4S)-3-(naphthalen-1-yl)-4,6-diphenyl-1-tosyl-3,4-dihydropyridin-2(1H)-one 
• 143100-22-5 N-(p-nitro-benzoylthiourea)-α-naphthalen-acetylhydrazine 

Relevant articles and documents

IDENTIFICATION OF NAA-L-ASPARTATE AMIDE AS THE MAJOR METABOLITE SYNTHESIZED BY TOBACCO MESOPHYLL PROTOPLASTS INCUBATED IN THE PRESENCE OF THE AUXIN ANALOGUE NAA

A major metabolite of naphthalene 1-acetic acid (NAA) is rapidly accumulated by tobacco mesophyll protoplasts induced to divide by this growth regulator.A comparison of the natural product with various chemically synthesized NAA-amino acid conjugates was performed.Themetabolite was identified as NAA-aspartate amide by negative CIMS.The biological activity of NAA-aspartate on protoplasts was further studied.The significance of the accumulation of this metabolite in dividing protoplasts is descussed.Key words: Nicotiana tabacum; Solanaceae; protoplast; NAA; auxin-amino acid; conjugates; isolation; identification.

L-Amino acid derived pyridinium-based chiral compounds and their efficacy in chiral recognition of lactate

A series of pyridinium-based chiral compounds 1-6 have been designed and synthesized. l-Amino acids have been used as the chiral source in the molecules. Among the chiral compounds, an l-valine derived compound 1 was found to exhibit enantioselective recognition of d-lactate in fluorescence. Structural tuning of this derivative, either by replacing l-valine with l-alanine or l-phenylglycine or by reducing the number of chiral centres around the binding site, does not result in any significant change in enantioselectivity in the recognition process. Change of the urea site to amide introduces compound 6 that displays good enantiodiscrimination for lactate (enantiomeric fluorescence difference ratio ef = 28.33 for d-lactate), even better than that of the l-valine derived compound 1 and of other reported structures in the literature.

Synthesis, characterization and slow release properties of O-naphthylacetyl chitosan

O-naphthylacetyl chitosan (NA-chitosan) was first prepared via protecting the amino groups with phthalic anhydride, followed by reaction with 1-naphthylacetyl chloride. The intermediates were hydrolyzed with anhydrous hydrazine to obtain final product. The derivatives of each step were characterized with Fourier transform infrared spectroscopy (FT-IR) and 13C solid state nuclear magnetic resonance (NMR). Results showed NA-chitosan had both naphthylacetyl and amino groups in the main chain of the polysaccharide. Elemental analysis showed that the substitution degree of hydroxyl was 0.4. Thermogravimetric analysis (TGA, DTG) of NA-chitosan was observed with much lower decomposition peak at 283°C than that of chitosan at 300°C. The release of 1-naphthylacetic acid was dependent on both pH values and the medium temperature, and at pH 12.0, 60°C the release period could last for 55 days.

Synthesis and characterization of 3-O-esters of N-acetyl-D-glucosamine derivatives as organogelators

Carbohydrate derived low molecular weight organogelators are interesting compounds with many potential applications. Selective functionalization of the different hydroxyl substituents on d-glucose and d-glucosamine resulted in small molecular gelators. Previously we have found that the C-2 acylated derivatives including esters and carbamates of 4,6-O-benzylidene protected glucose and glucosamine derivatives have shown remarkable applications as molecular gelators. In this research, in order to probe the structural influence of sugar derivatives on molecular self-assembly, we introduced acylation functional groups to the 3-hydroxyl group of 4,6-O-benzylidene acetal protected N-acetyl glucosamine derivatives. A library of fourteen ester derivatives was synthesized and characterized. The ester derivatives typically formed gels in pump oil and aqueous mixtures of dimethyl sulfoxide or ethanol. The resulting gels were characterized using optical microscopy, and rheology, etc. All alkyl ester derivatives were gelators for pump oil. A short chain ester derivative was able to form gels in a few different oils and the corresponding oil water mixtures phase selectively. The compound was also used to trap naproxen sodium and formed a stable co-gel. The controlled release of the drug from the gel to the aqueous phase was analyzed using UV-vis spectroscopy. These results show that the functionalization at the 3-OH position of the N-acetyl glucosamine derivative is a feasible strategy in designing new classes of organogelators.

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.

Benzoic acid derivative as well as preparation method and medicinal application thereof

The invention discloses a benzoic acid derivative as well as a preparation method and a pharmaceutical application thereof, and belongs to the technical field of medicines. The invention specifically discloses a benzoic acid derivative represented by a co