2122-70-5

Basic information

• Product Name: Ethyl 1-naphthaleneacetate
• Synonyms: ETHYL-1-NAPHTHALENE ACETATE;ETHYL 1-NAPHTHYLACETATE;Ethyl 1-Naphthylactetate;1-NAPHTHYLACETIC ACID ETHYL ESTER 95+%;(1-Naphtyl)acetic acid ethyl ester;2-(1-Naphtyl)acetic acid ethyl ester;2-(1-naphthyl)acetic acid ethyl ester;ethyl 2-naphthalen-1-ylacetate
• CAS NO: 2122-70-5
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.26
• EINECS: 218-332-1
• Mol File: 2122-70-5.mol
• Article Data: 51

Chemical Properties

• Melting Point: 88.5°C
• Boiling Point: 231 °C / 32mmHg
• Flash Point: 145 °C
• Appearance: Light yellow liquid
• Density: 1,11 g/cm3
• Vapor Pressure: 0.000147mmHg at 25°C
• Refractive Index: 1.5780-1.5820
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: Ethyl 1-naphthaleneacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 1-naphthaleneacetate(2122-70-5)
• EPA Substance Registry System: Ethyl 1-naphthaleneacetate(2122-70-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: QJ0948000
• Hazardous Substances Data: 2122-70-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 2122-70-5 differently. You can refer to the following data:
1. Ethyl 1-naphthaleneacetate is an ester derivative of naphthaleneacetic acid (NAA) used as a growth regulator of trees and shrubs.
2. 1-Naphthaleneacetic Acid Ethyl Ester is an ester derivative of naphthaleneacetic acid (NAA) used as a growth regulator of trees and shrubs.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 6, p. 613, 1988The Journal of Organic Chemistry, 33, p. 1675, 1968 DOI: 10.1021/jo01268a091

InChI:InChI=1/C14H14O2/c1-2-16-14(15)10-12-8-5-7-11-6-3-4-9-13(11)12/h3-9H,2,10H2,1H3

Upstream product

• 64-17-5 ethanol 
• 82985-71-5 α-trimethylsilyl-1-naphthyl-diazoketone 
• 96155-82-7 ethyl 2-bromo-2-(naphth-1-yl)acetate 
• 90-11-9 1-Bromonaphthalene 
• 6148-64-7 ethyl potassium malonate 
• 623-73-4 diazoacetic acid ethyl ester 
• 91-20-3 naphthalene 
• 13922-41-3 1-Naphthylboronic acid 
• 616-27-3 1-chlorobutan-2-one 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 90-13-1 1-Chloronaphthalene 
• 105-39-5 chloroacetic acid ethyl ester 
• 3007-97-4 ethyl 1-naphthoate 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 86-87-3 naphth-1-yl acetic acid 
• 33656-65-4 ethyl 2-(1-naphthyl)-2-oxoacetate 
• 10335-80-5 2-(naphthalen-1-yl)hydroxamic acid 
• 6341-60-2 diethyl 2-(1-naphthyl)malonate 
• 70592-03-9 trans-1,2-di(4-methoxyphenyl)-1,2-diphenylethylene 
• 773-99-9 2-naphthaleneethanol 
• 205443-29-4 Naphthalen-1-yl-phenylsulfanyl-acetic acid ethyl ester 
• 57050-62-1 Di-p-tolylimino-oxalsaeurediethylester 
• 18410-58-7 1-<(trimethylsilyl)methyl>naphthalene 
• 158833-27-3 N-benzyl-2-(naphthalen-1-yl)acetamide 

Relevant articles and documents

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Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids

A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.

One-pot borylation/Suzuki-Miyaura sp2-sp3 cross-coupling

We describe the first one-pot borylation/Suzuki-Miyaura sp2-sp3 cross-coupling between readily available aryl (pseudo)halides and activated alkyl chlorides. This method streamlines the synthesis of diaryl methanes, α-aryl carbonyls and allyl aryl compounds, substructures that are commonly found in life changing drug molecules.