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1-Naphthoic anhydride is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 64985-86-0 Structure
  • Basic information

    1. Product Name: 1-Naphthoic anhydride
    2. Synonyms: 1-Naphthoic anhydride;naphthalene-1-carbonyl naphthalene-1-carboxylate
    3. CAS NO:64985-86-0
    4. Molecular Formula: C22H14O3
    5. Molecular Weight: 326.34
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 64985-86-0.mol
  • Chemical Properties

    1. Melting Point: 138-142 °C
    2. Boiling Point: 538.6°C at 760 mmHg
    3. Flash Point: 269.2°C
    4. Appearance: /
    5. Density: 1.279g/cm3
    6. Vapor Pressure: 1.14E-11mmHg at 25°C
    7. Refractive Index: 1.701
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 1-Naphthoic anhydride(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-Naphthoic anhydride(64985-86-0)
    12. EPA Substance Registry System: 1-Naphthoic anhydride(64985-86-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 64985-86-0(Hazardous Substances Data)

64985-86-0 Usage

Appearance

White solid 1-Naphthoic anhydride has a white solid appearance.

Melting point

215-217°C The compound has a melting point ranging between 215 and 217 degrees Celsius.

Solubility

Insoluble in water, soluble in organic solvents 1-Naphthoic anhydride does not dissolve in water but can dissolve in certain organic solvents.

Primary uses

Production of dyes and pigments, synthesis of pharmaceuticals and agrochemicals The main applications of 1-Naphthoic anhydride include the manufacturing of dyes and pigments, as well as the synthesis of pharmaceutical and agrochemical products.

Reagent in organic synthesis

Preparation of naphthalene dicarboxylic anhydride 1-Naphthoic anhydride is used as a reagent in organic synthesis reactions, particularly for the preparation of naphthalene dicarboxylic anhydride.

Potential properties

Anti-inflammatory and antioxidant 1-Naphthoic anhydride has been studied for its possible anti-inflammatory and antioxidant properties, making it a subject of interest in pharmaceutical research.

Health and environmental risks

Handle and dispose with care 1-Naphthoic anhydride may pose health and environmental risks, so it is important to handle and dispose of the compound carefully to minimize potential hazards.

Check Digit Verification of cas no

The CAS Registry Mumber 64985-86-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,9,8 and 5 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 64985-86:
(7*6)+(6*4)+(5*9)+(4*8)+(3*5)+(2*8)+(1*6)=180
180 % 10 = 0
So 64985-86-0 is a valid CAS Registry Number.
InChI:InChI=1/C22H14O3/c23-21(19-13-5-9-15-7-1-3-11-17(15)19)25-22(24)20-14-6-10-16-8-2-4-12-18(16)20/h1-14H

64985-86-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Naphthoic anhydride

1.2 Other means of identification

Product number -
Other names 1-Naphthalenecarboxylic acid, anhydride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:64985-86-0 SDS

64985-86-0Relevant articles and documents

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

Mayr, Stefanie,Marin-Luna, Marta,Zipse, Hendrik

, p. 3456 - 3489 (2021/03/01)

Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.

Size-Induced Inversion of Selectivity in the Acylation of 1,2-Diols

Mayr, Stefanie,Zipse, Hendrik

supporting information, p. 18084 - 18092 (2021/12/02)

Relative rates for the Lewis base-catalyzed acylation of aryl-substituted 1,2-diols with anhydrides differing in size have been determined by turnover-limited competition experiments and absolute kinetics measurements. Depending on the structure of the anhydride reagent, the secondary hydroxyl group of the 1,2-diol reacts faster than the primary one. This preference towards the secondary hydroxyl group is boosted in the second acylation step from the monoesters to the diester through size and additional steric effects. In absolute terms the first acylation step is found to be up to 35 times faster than the second one for the primary alcohols due to neighboring group effects.

TBHP/ n -Bu 4 PBr-Promoted Oxidative Cross-Dehydrogenative Coupling of Aryl Methanols: A Facile Synthesis of Symmetrical Carboxylic Anhydride Derivatives

Adib, Mehdi,Pashazadeh, Rahim

supporting information, p. 136 - 140 (2017/12/27)

A transition-metal-free oxidative cross-dehydrogenative coupling reaction has been developed for the preparation of symmetrical carboxylic anhydrides through self-coupling dual C-O bond formations of aryl methanols. In the presence of a catalytic amount of tetrabutylphosphonium bromide (TBPB) as transfer agent and aqueous tert -butyl hydroperoxide (TBHP) as oxidant and reactant, methylene groups of aryl methanols were efficiently oxidized to C=O and coupled with the peroxide oxygen from TBHP to form a diverse array of symmetrical carboxylic anhydride derivatives.

An investigation on practical synthesis of carboxylic acid derivatives using p-toluenesulfonyl chloride

Eskandari, Parvin,Kazemi, Foad

, p. 431 - 439 (2017/07/24)

Carboxylic acid derivatives are well recognized as important class of reagents frequently used in the preparation of a variety of fine or special chemicals such as amides, esters, peptides, drugs, and dyes. Although several methods were developed for the preparation of these compounds, many of them present difficulties, including low yield, high reaction temperature, harsh reaction conditions, tedious work-up, and incompatibility with scale-up. Methods: The synthesis of carboxylic anhydrides is developed through the reaction of carboxylic acids with TsCl in the presence of K2CO3 and acetonitrile as a solvent under ultrasound irradiation and conventional conditions. In addition, one-pot synthesis of acyl azides was carried out in the presence of produced carboxylic anhydrides and the addition of sodium azide under identical condition. Results: A series of carboxylic anhydrides and acyl azides were synthesized using TsCl under ultrasound irradiation and conventional stirring with simple procedure, mild reaction conditions, high yields, and scale-up ability without any restriction. In most cases, the reaction under ultrasound irradiation was better in both yields and the reaction times compared to the conventional method. Conclusion: A convenient method has been developed for the preparation of carboxylic anhydrides and acyl azides under ultrasound irradiation and conventional stirring. The present method is practical and a highly effective alternative for previous reports. The major advantages of this method are: (i) simplicity of the procedure (ii) high yields and high purity of product (iii) scale-up capacity without considerable limitation in conventional system. Under ultrasound irradiation short reaction times as compared to conventional method are observed; yields are comparable to or better than conventional method.

Acid anhydrides and the unexpected N,N-diethylamides derived from the reaction of carboxylic acids with Ph3P/I2/Et3N

Phakhodee, Wong,Duangkamol, Chuthamat,Wangngae, Sirilak,Pattarawarapan, Mookda

supporting information, p. 325 - 328 (2016/01/12)

The formation of acid anhydrides from the phosphorous-mediated activation of carboxylic acids was investigated. Under various systems, activation of benzoic acid in the presence of base led to the formation of benzoic anhydride at different rates depending on the reactivity of the reagents. Using the Ph3P-I2/Et3N combination, most aryl acids were converted into the corresponding anhydrides in high yields within 5-10 min. However, for nitro-substituted derivatives, unexpectedly, N,N-diethylamides were isolated without anhydride formation. These results indicated the pronounced effect of substituents in governing these potential side reactions which can significantly affect the yields of acylation reactions promoted by phosphonium species.

Metal-free cross-dehydrogenative coupling of aryl aldehydes to give symmetrical carboxylic anhydrides promoted by the TBHP/nBu4PBr system

Adib, Mehdi,Pashazadeh, Rahim,Rajai-Daryasarei, Saideh,Mirzaei, Peiman,Jamal Addin Gohari, Seyed

supporting information, p. 3071 - 3074 (2016/07/06)

A novel, efficient, and metal-free dual C–O bond formation reaction for the synthesis of carboxylic anhydrides from aryl aldehydes via cross-dehydrogenative coupling is described. Heating a mixture of aromatic aldehydes and an aqueous solution of tert-butyl hydroperoxide as oxidant in the presence of catalytic nBu4PBr in chlorobenzene at 80?°C for 3?h afforded the corresponding carboxylic anhydrides in good to excellent yields.

Carboxylic acid anhydrides via Pd-catalyzed carbonylation of aryl halides at atmospheric CO pressure

Li, Yang,Xue, Dong,Wang, Chao,Liu, Zhao-Tie,Xiao, Jianliang

supporting information; experimental part, p. 1320 - 1322 (2012/02/04)

A convenient method has been developed, which allows for the direct transformation of aryl iodides into the corresponding carboxylic acid anhydrides via Pd-catalyzed carbonylation under atmospheric CO pressure. The Royal Society of Chemistry 2012.

Reducing the cost, smell, and toxicity of the Barton reductive decarboxylation: Chloroform as the hydrogen atom source

Ko, Eun Jung,Williams, Craig M.,Savage, G. Paul,Tsanaktsidis, John

, p. 1944 - 1947 (2015/02/18)

When used as solvent, chloroform was found to act as a hydrogen atom donor in Barton reductive decarboxylation reactions. Chloroform offers a substantial practical advantage over pre-existing hydrogen atom donors.

Substrate activity screening: A fragment-based method for the rapid identification of nonpeptidic protease inhibitors

Wood, Warren J. L.,Patterson, Andrew W.,Tsuruoka, Hiroyuki,Jain, Rishi K.,Ellman, Jonathan A.

, p. 15521 - 15527 (2007/10/03)

A new fragment-based method for the rapid development of novel and distinct classes of nonpeptidic protease inhibitors, Substrate Activity Screening (SAS), is described. This method consists of three steps: (1) a library of N-acyl aminocoumarins with diverse, low molecular weight N-acyl groups is screened to identify protease substrates using a simple fluorescence-based assay, (2) the identified N-acyl aminocoumarin substrates are optimized by rapid analogue synthesis and evaluation, and (3) the optimized substrates are converted to inhibitors by direct replacement of the aminocoumarin with known mechanism-based pharmacophores. The SAS method was successfully applied to the cysteine protease cathepsin S, which is implicated in autoimmune diseases. Multiple distinct classes of nonpeptidic substrates were identified upon screening an N-acyl aminocoumarin library. Two of the nonpeptidic substrate classes were optimized to substrates with >8000-fold improvements in cleavage efficiency for each class. Select nonpeptidic substrates were then directly converted to low molecular weight, novel aldehyde inhibitors with nanomolar affinity to cathepsin S. This study demonstrates the unique characteristics and merits of this first substrate-based method for the rapid identification and optimization of weak fragments and provides the framework for the development of completely nonpeptidic inhibitors to many different proteases.

A Cheap, Simple and Efficient Method for the Preparation of Symmetrical Carboxylic Acid Anhydrides

Kazemi, Foad,Sharghi, Hashem,Nasseri, Mohammad Ali

, p. 205 - 207 (2007/10/03)

A manipulatively simple and facile one-pot procedure for the synthesis of symmetrical anhydride is reported. Treatment of carboxylic acids with tosyl chloride in K2CO3 media under solvent free conditions gives the corresponding anhydrides in good to excellent yields in a short reaction time via carboxylic sulfonic anhydride as the key intermediate.

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