2243-83-6

Basic information

• Product Name: 2-Naphthoyl chloride
• Synonyms: BETA-NAPHTHOYL CHLORIDE;2-NAPHTHOYL CHLORIDE;2-NAPHTHOYL CHLORIDE(BETA-);2-NAPTHOYL CHLORIDE;2-NAPHTHALENECARBOXYLIC ACID CHLORIDE;2-NAPHTHALENECARBONYL CHLORIDE;2-(Chlorocarbonyl)naphthalene;2-Naphthoic chloride
• CAS NO: 2243-83-6
• Molecular Formula: C₁₁H₇ClO
• Molecular Weight: 190.63
• EINECS: 218-822-5
• Product Categories: Aromatic Halides (substituted);Absolute Configuration Determination (Exciton Chirality CD Method);Analytical Chemistry;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Method (for Hydroxyl Groups);Naphthalene series
• Mol File: 2243-83-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 50-52 °C(lit.)
• Boiling Point: 160-162 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Gray to brown/Crystalline Chunks
• Density: 1.1664 (rough estimate)
• Vapor Pressure: 0.000726mmHg at 25°C
• Refractive Index: 1.6530 (estimate)
• Storage Temp.: 2-8°C
• Solubility: soluble in Toluene
• Sensitive: Moisture Sensitive
• BRN: 907776
• CAS DataBase Reference: 2-Naphthoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthoyl chloride(2243-83-6)
• EPA Substance Registry System: 2-Naphthoyl chloride(2243-83-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2243-83-6(Hazardous Substances Data)

Usage

Chemical Properties

White low melting solid

Uses

Different sources of media describe the Uses of 2243-83-6 differently. You can refer to the following data:
1. 2-Naphthoyl Chloride can be used for anticancer and antiinflammatory agents.
2. 2-Naphthoyl chloride has been used in:preparation of amide derivatives of the amphetamine enantiomerssynthesis of 7-dimethylamino-2-methyl-3-naphthamido-phenothiazinium saltmodification of self-assembled monolayer formed on silica surface from ((((aminoethyl)amino)-methyl)phenethyl)trimethoxysilane

InChI:InChI=1/C11H7ClO/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

Upstream product

• 613-46-7 2-naphthalenecarbonitrile 
• 2459-25-8 methyl naphthalene-2-carboxylate 
• 13577-85-0 N,N-dimethyl-2-naphthylcarboxamide 
• 66-99-9 β-naphthaldehyde 
• 580-13-2 2-bromonaphthalene 
• 141-75-3 butyryl chloride 
• 3857-83-8 2-naphthyl triflate 
• 115298-62-9 2-naphthoic acid tert-butyl ester 
• 93-08-3 methyl 2-naphthyl ketone 
• 532-02-5 2-naphthalenesulfonic acid sodium salt 

Downstream Products

• 6967-92-6 2-(diazoacetyl)naphthalene 
• 109249-36-7 N-benzoyl-N'-[2]naphthoyl-hydrazine 
• 28118-49-2 S-phenyl naphthalene-2-carbothioate 
• 130956-03-5 N-(2-nitrophenyl)-2-naphthamide 
• 19044-96-3 benzenesulfonyl-[2]naphthoyl-amine 
• 3007-91-8 ethyl-2-naphthoate 
• 1590-22-3 4-(2-naphthyl)-4-oxobutyric acid 
• 132104-10-0 6-(naphthalen-2-yl)-6-oxohexanoic acid 
• 109393-21-7 (5-chloro-2-methylsulfanyl-phenyl)-[2]naphthyl ketone 
• 856207-18-6 [2]naphthoic acid-(2-hydroxy-anilide) 
• 6917-53-9 1-α-Naphthoyl-2-β-naphthoyl-hydrazin 

Relevant articles and documents

One-step Conversion of Amides and Esters to Acid Chlorides with PCl3

A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.