22978-49-0

Basic information

• Product Name: 2,2''-DIMETHYLBENZANILIDE,99%
• Synonyms: 2,2''-DIMETHYLBENZANILIDE,99%;2-Methyl-N-o-tolylbenzaMide;2,2'-DIMETHYLBENZANILIDE;BenzaMide, 2-Methyl-N-(2-Methylphenyl)-;2-methyl-N-(2-methylphenyl)benzamide
• CAS NO: 22978-49-0
• Molecular Formula: C₁₅H₁₅NO
• Molecular Weight: 225.29
• Mol File: 22978-49-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 145 °C
• Boiling Point: 289.244 °C at 760 mmHg
• Flash Point: 172.098 °C
• Appearance: /
• Density: 1.122 g/cm³
• Vapor Pressure: 0.00223mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.54±0.70(Predicted)
• CAS DataBase Reference: 2,2''-DIMETHYLBENZANILIDE,99%(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2''-DIMETHYLBENZANILIDE,99%(22978-49-0)
• EPA Substance Registry System: 2,2''-DIMETHYLBENZANILIDE,99%(22978-49-0)

Safety Data

• Hazardous Substances Data: 22978-49-0(Hazardous Substances Data)

Usage

General Description

2,2''-Dimethylbenzanilide, 99% is a chemical compound belonging to the group of anilides which are organic compounds derived from aniline. It is often used in the production of pigments, medicines, and pesticides. It is characterized by its purity of 99%, indicating a highly concentrated chemical substance. Its molecular formula is C15H17NO and the CAS Number is 1149-59-3. The chemical, which is generally available in solid form, must be handled with caution, as ingestion, inhalation, or absorption through the skin might lead to harmful effects.

InChI:InChI=1/C15H15NO/c1-11-7-3-5-9-13(11)15(17)16-14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H,16,17)

Synthetic route

ortho-toluoyl chloride (933-88-0) + o-toluidine (95-53-4) → 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	87%
With triethylamine In toluene 1) reflux, 3 h, 2) room temperature, 16 h;	70%
With pyridine

ortho-methylphenyl iodide (615-37-2) + carbon monoxide (201230-82-2) → 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0)

Conditions	Yield
With sodium azide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium dichloride In 1,4-dioxane at 130℃; for 12h;	78%

bis(2-methylphenyl)methanimine (22627-01-6) → 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0)

Conditions	Yield
Stage #1: bis(2-methylphenyl)methanimine With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 0.0833333h; Stage #2: With triethylamine In acetonitrile at 20℃;	71%

carbon monoxide (201230-82-2) + 2-methylphenyl bromide (95-46-5) → 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0)

Conditions	Yield
With sodium azide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium dichloride In 1,4-dioxane at 130℃; for 12h;	69%

ortho-methylbenzoic acid (118-90-1) + o-toluidine (95-53-4) → 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0)

Conditions	Yield
With phosphorus trichloride at 120℃;

bis-o-tolyl N-hydroxyoxime (108714-78-9) → 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0)

Conditions	Yield
With phosphoric acid; dicyclohexyl-carbodiimide In dimethyl sulfoxide; benzene for 16h;

ortho-methylbenzoic acid (118-90-1) + potassium hydroxide → 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: Py View Scheme

2-methyl-N-(2-methylphenyl)benzamide (22978-49-0) → 2-(o-methylphenyl)phthalimidine (17372-63-3)

Conditions	Yield
Stage #1: 2-methyl-N-(2-methylphenyl)benzamide With iodine; potassium carbonate In acetonitrile at 20℃; for 0.166667h; Sealed tube; Stage #2: With di-tert-butyl peroxide In acetonitrile at 140℃; Sealed tube;	80%

2-methyl-N-(2-methylphenyl)benzamide (22978-49-0) → 2-methyl-benzoic acid-(4-chloro-2-methyl-anilide) (123862-46-4)

Conditions	Yield
With sulfuryl dichloride; benzene

carbon dioxide (124-38-9) + 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0) → 2-(2-methylphenyl)-4-phenylisoquinoline-1,3(2H,4H)-dione (78987-19-6)

Conditions	Yield
With n-butyllithium 1) THF, -25 deg C, then room temperature, 3 h; Yield given. Multistep reaction;

carbon dioxide (124-38-9) + 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0) → 2-<<(2-carboxymethyl)benzoyl>amino>benzeneacetic acid (78987-18-5)

Conditions	Yield
With n-butyllithium 1) THF, -25 deg C, then room temperature, 3 h; Yield given. Multistep reaction;

2-methyl-N-(2-methylphenyl)benzamide (22978-49-0) → 2-Methyl-thiobenzoyl-(2-methylanilid) (34743-36-7)

Conditions	Yield
With pyridine; phosphorus pentoxide Heating;

sulfuryl dichloride (7791-25-5) + 2-methyl-N-(2-methylphenyl)benzamide (22978-49-0) + benzene (71-43-2) → 2-methyl-benzoic acid-(4-chloro-2-methyl-anilide) (123862-46-4)

2-methyl-N-(2-methylphenyl)benzamide (22978-49-0) → C15H15NOS (34751-81-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: P2O5, Py / Heating 2: aq. H2O2 / CH2Cl2; methanol View Scheme

Upstream product

• 118-90-1 ortho-methylbenzoic acid 
• 95-53-4 o-toluidine 
• 615-37-2 ortho-methylphenyl iodide 
• 144-62-7 oxalic acid 
• 201230-82-2 carbon monoxide 
• 95-46-5 2-methylphenyl bromide 
• 22627-01-6 bis(2-methylphenyl)methanimine 
• 933-88-0 ortho-toluoyl chloride 
• 108714-78-9 bis-o-tolyl N-hydroxyoxime 

Downstream Products

• 78987-19-6 2-(2-methylphenyl)-4-phenylisoquinoline-1,3(2H,4H)-dione 
• 78987-18-5 2-<<(2-carboxymethyl)benzoyl>amino>benzeneacetic acid 
• 537684-22-3 2-o-tolyl-1H-indole 
• 17372-63-3 2-(o-methylphenyl)phthalimidine 
• 34751-81-0 C₁₅H₁₅NOS 
• 34743-36-7 2-Methyl-thiobenzoyl-(2-methylanilid) 
• 123862-46-4 2-methyl-benzoic acid-(4-chloro-2-methyl-anilide) 

Relevant articles and documents

Palladium Catalyzed Cascade Azidation/Carbonylation of Aryl Halides with Sodium Azide for the Synthesis of Amides

Amide synthesis is one of the most important transformations in organic chemistry due to their ubiquitous presence in our daily life. In this communication, a palladium catalyzed cascade azidation/carbonylation of aryl halides for the synthesis of amides was developed. Both iodo- and bromobenzene derivatives were transformed to the corresponding amides using PdCl2/xantphos as the catalyst system and sodium azide as the nitrogen-source. The reaction proceeds via a cascade azidation/carbonylation process. A range of alkyl and halogen substituted amides were prepared in moderate to good yields.

Supported-Pd catalyzed tandem approach for N-arylbenzamides synthesis

Aryl iodides as dual arylating agent for C-terminal from oxalic acid [(CO2H)2] and N-terminal from sodium azide (NaN3) for N-aryl benzamides (Ar-CO-NH-Ar) synthesis is a rare invention which has been attempted successfully under this study. A single step tandem approach for the synthesis of N-aryl benzamides has been developed through bifunctional transformation of aryl iodides with in-situ CO from (CO2H)2 and NaN3 following two different pathways of carbonylation and azidation. The polystyrene supported palladium (Pd@PS) catalyst was found to be well compatible to perform the domino-reaction in a double layer vial (DLV) system under base, ligand and additive-free conditions. Moreover, the same approach was further extended with aryl azides for unsymmetric N-aryl benzamides (Ar-CO-NH-Ar') synthesis. Furthermore, the DFT studies were also performed to support the proposed mechanism.

Transition metal free intramolecular selective oxidative C(sp3)-N coupling: Synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp3)-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 °C.