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

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

Uses

Used in Pharmaceutical Industry:
2-Naphthoyl chloride is used as a key intermediate in the synthesis of various pharmaceutical compounds, including anticancer and anti-inflammatory agents. Its unique chemical structure allows for the development of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
2-Naphthoyl chloride is used as a reagent in the preparation of amide derivatives of the amphetamine enantiomers. This application is crucial for the development of chiral compounds with specific biological activities and potential use in the pharmaceutical industry.
Used in Dye Synthesis:
2-Naphthoyl chloride is used in the synthesis of 7-dimethylamino-2-methyl-3-naphthamido-phenothiazinium salt, a type of phenothiazinium dye. These dyes have various applications, including as pigments, sensors, and in the development of new materials with unique optical properties.
Used in Surface Modification:
2-Naphthoyl chloride is used for the modification of self-assembled monolayers formed on silica surfaces from ((((aminoethyl)amino)-methyl)phenethyl)trimethoxysilane. This application is important in the field of nanotechnology and materials science, as it allows for the creation of functionalized surfaces with tailored properties for various applications, such as sensors, catalysts, and drug delivery systems.

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

Downstream Products

• 6967-92-6 2-(diazoacetyl)naphthalene 
• 101451-38-1 (2,5-dimethyl-[3]furyl)-[2]naphthyl ketone 
• 106714-93-6 O-(Naphthoyl-⁽²⁾)-all-trans-retinol 
• 67363-82-0 N-(4-methylphenyl)-2-naphthamide 
• 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 
• 70021-83-9 N-phenyl-2-naphthamide 
• 856207-18-6 [2]naphthoic acid-(2-hydroxy-anilide) 
• 69826-63-7 (naphthalene-2-carbonyl)glycine 
• 80192-95-6 N-methyl-N-phenyl-2-naphthylamide 
• 137339-74-3 N-methyl-[1]naphthanilide 
• 149358-58-7 N-benzylnaphthalene-2-carboxamide 
• 110876-52-3 (2-methyl-[1]naphthyl)-[2]naphthyl ketone 

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.

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

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.

METHOD FOR PREPARATION OF CARBOXYLIC ACID CHLORIDES FROM METHYL KETONES WITH TWO REAGENTS

The invention discloses a method for the preparation of carboxylic acid chlorides starting from methyl ketones with a sulfur chloride and a chlorinating reagent.

METHOD FOR PREPARATION OF CARBOXYLIC ACID CHLORIDES FROM METHYL KETONES

The invention discloses a method for the preparation of carboxylic acid chlorides starting from methyl ketones with a sulfur chloride.

One-Step Conversion of Methyl Ketones to Acyl Chlorides

Treatment of aromatic and heteroaromatic methyl ketones with sulfur monochloride and catalytic amounts of pyridine in refluxing chlorobenzene leads to the formation of acyl chlorides. Both electron-rich and electron-poor aryl methyl ketones can be used as starting materials. The resulting C1-byproduct depends on the precise reaction conditions chosen.

BIPHENYLOXY-ACIDS

The present invention relates generally to substituted biphenyloxy acids (such as 4'-aryl-amido-biphenyl--4(3)-yloxy-acids and 4’-aryl-amidomethyl-biphenyl-4(3)-yloxy-acids) and methods of using them.

Orally effective ion chelators related to deferoxamine

Compounds are described of the general formula: STR1 wherein: R1 is acyl of the formula --C(=O)--R5 ; R2, R3, R4, R6, R7 and R8 are each selected from the group consisting of hydrogen and acyl of the formula: wherein R5 is selected from the group consisting of alkyls, substituted alkyls, alkenyls, substituted alkenyls, cycloalkyls, substituted cycloalkyls, arylalkylenes, substituted arylalkylenes, alkylenecycloalkyls, alkylene substituted cycloalkyls, alkynyls, substituted alkynyls, aryls and substituted aryls, wherein R2, R3 and R4 are selected such that at least one of R2, R3 and R4 is an acyl. When R2, R3 and R4 include one or more acyls that are not identical to the acyl of R1, these compounds of formula I are novel compounds. The invention also includes processes to produce the compounds of formula I. Compounds of formula I complex and/or chelate tissue tri-valent ions, especially iron and aluminum (Fe+++, Al+++), when administered to a human being, and are therefore useful in therapy in the treatment of diseases in which tissue ion levels in the body have increased or toxic levels. These iron-related diseases include, for example, thalassemia major, sideroachrestic anemic, Blackfan-Diamond anemia, aplastic anemia, sickle cell anemia, hemolytic anemias and hemosiderosis brought about by multiple blood transfusions including treatment for the anemia accompanying conditions requiring kidney dialysis. Aluminum-related diseases or conditions include Alzheimer's disease, senile dementia and dialysis encephalopathy.