120-66-1

Basic information

• Product Name: 2-METHYLACETANILIDE
• Synonyms: Acetamide,N-(2-methylphenyl)-;Acet-o-toluidide;n-(2-methylphenyl)-acetamid;N-(2-Methylphenyl)acetamide;N-(2-Methyl-phenyl)acetamide;O-TOLYLACETAMIDE;O-METHYLACETANILIDE;N-ACETYL-O-TOLUIDINE
• CAS NO: 120-66-1
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• EINECS: 204-414-4
• Product Categories: Anilines, Amides & Amines
• Mol File: 120-66-1.mol

Chemical Properties

• Melting Point: 109-112 °C
• Boiling Point: 296 °C
• Flash Point: 296°C
• Appearance: off white to brown flake
• Density: 1.16
• Refractive Index: 1.5279 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: It is slightly soluble in acetone, chloroform, toluene, benzene.
• PKA: 15.13±0.70(Predicted)
• Merck: 14,74
• BRN: 2207054
• CAS DataBase Reference: 2-METHYLACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLACETANILIDE(120-66-1)
• EPA Substance Registry System: 2-METHYLACETANILIDE(120-66-1)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36-36/37
• RTECS: AN2900000
• TSCA: Yes
• Hazardous Substances Data: 120-66-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYLACETANILIDE is used as a precursor for the synthesis of various pharmaceuticals, including painkillers and their intermediates. It plays a crucial role in the production of penicillin and other medications.
Used in Chemical Industry:
2-METHYLACETANILIDE serves as an intermediate for the synthesis of rubber accelerators, dyes, and dye intermediates. It is also used in the production of camphor.
Used as a Peroxide Inhibitor and Stabilizer:
In the chemical industry, 2-METHYLACETANILIDE is utilized as an inhibitor of peroxides and a stabilizer for cellulose ester varnishes, ensuring the stability and longevity of these products.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 5759, 1984 DOI: 10.1021/ja00331a073Organic Syntheses, Coll. Vol. 5, p. 650, 1973

Air & Water Reactions

Water insoluble.

Reactivity Profile

2-METHYLACETANILIDE is an amide. Amides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

ACUTE/CHRONIC HAZARDS: Toxic. Hazardous decomposition products.

Safety Profile

Moderately toxic by ingestion.Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise the toluidide from hot H2O (solubility 1g/210mL), EtOH or aqueous EtOH. UV: max 230 and 280nm (EtOH). [Beilstein 12 H 792, 12 I 376, 12 II 439, 12 III 1853, 12 IV 1755.]

Upstream product

• 108-24-7 acetic anhydride 
• 95-53-4 o-toluidine 
• 71-43-2 benzene 
• 614-63-1 1,3-di-o-tolyltriazene 
• 137-97-3 N,N'-di(o-tolyl)thiourea 
• 64-19-7 acetic acid 
• 16080-08-3 (2-methylphenyl)carbonimidic dichloride 
• 75-36-5 acetyl chloride 
• 60-35-5 acetamide 
• 507-09-5 thioacetic acid 
• 625-77-4 N-acetylacetamide 
• 201230-82-2 carbon monoxide 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 
• 85336-18-1 N-acetyl-5-tert-butyl-2-methylaniline 

Downstream Products

• 16209-14-6 4-oxo-4-(4-acetylamino-3-methyl-phenyl)-trans-crotonic acid 
• 158979-23-8 N-(2-methylphenyl)-N-phenylacetamide 
• 85448-89-1 N-(4-methoxyphenyl)-2-methylbenzenamine 
• 121791-90-0 acetic acid-(2-methyl-4-trityl-anilide) 
• 5202-86-8 4-chloro-2-methylacetanilide 
• 5152-76-1 N-chloro-2'-methylacetanilide 
• 109042-02-6 acetic acid-[5-(2,2-dichloro-ethyl)-2-methyl-anilide] 
• 103503-67-9 1,1-bis-(3-acetylamino-4-methyl-phenyl)-ethane 
• 570-24-1 2-Methyl-6-nitroaniline 
• 617-00-5 2,2'-dimethyldiphenylamine 
• 95-20-5 2-methyl-1H-indole 
• 91-22-5 quinoline 
• 90557-56-5 acetic acid-(N-nitroso-o-toluidide) 
• 615-59-8 1,4-dibromo-2-methylbenzene 

Relevant articles and documents

Synthesis of 2-methylbenzoxazoles directly from: N -phenylacetamides catalyzed by palladium acetate

A method to synthesize 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by Pd(OAc)2 in the presence of K2S2O8 and TfOH has been developed. The desired products were obtained in moderate to excellent yields. This approach provides a facile procedure to prepare benzoxazoles with available substrates. It is found that TfOH is the key factor for this cyclization reaction. A plausible mechanism of the reaction is proposed according to the control reactions and the literature.

Late-Stage Diversification of Biarylphosphines through Rhodium(I)-Catalyzed C-H Bond Alkenylation with Internal Alkynes

We report herein P(III)-directed C-H bond alkenylation of (dialkyl)- and (diaryl)biarylphosphines using internal alkynes. Chloride-free [Rh(OAc)(COD)]2 acts as a better catalyst than commercially available [RhCl(COD)]2. Conditions were developed to control the mono- and difunctionalization depending on the alkyne stoichiometry. One of these novel bisalkenylated (dialkyl)biarylphosphines was employed for the preparation of a palladium(II) complex, and some of these functionalized ligands outperformed their corresponding unfunctionalized phosphines in Pd-catalyzed amidation with sterically hindered aryl chlorides.

Syntheses and resolutions of new chiral biphenyl backbones: 2-Amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and 2-amino-2′-hydroxy-4,4′,6,6′-tetramethyl-1,1′- biphenyl

The new chiral backbones (R)-(+)- and S-(-)-2-amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and (R)-(+)- and (S)-(-)-2-amino-2′-hydroxy-4,4′,6,6′- tetramethyl-1,1′-biphenyl were synthesized from o-methylaniline and 2,4-dimethyl-aniline respectively in seven steps. A new resolution method was developed to provide homochiral enantiomers (from diastereomeric salts) in reasonably high yields. The absolute configuration of the new biphenyls was confirmed by X-ray structural analysis.

Sunlight-assisted decomposition of cephalexin by novel synthesized NiS-PPY-Fe3O4 nanophotocatalyst

In this research, the catalytic performance of NiS and NiS immobilized into the matrix of magnetite polypyrrole core/shell (Fe3O4@PPY) for degradation of cephalexin was investigated. After characterization, by FTIR, TG, XRD, VSM, DRS, PL, Brunauer–Emmett–Teller (BET), TEM and SEM techniques, the photocatalysts were used for degradation of a pharmaceutical pollutant; cephalexin under UV and sunlight irradiations. The results indicated that application of PPY-Fe3O4 as the catalyst supports significantly enhanced the photocatalytic activity of NiS. The degradation efficiency obtained by NiS-PPY-Fe3O4 was higher than the value obtained by NiS alone. Moreover, by use of the support, a significant red shift was occurred on the band gap energy of NiS resulting higher degradation of the pollutant under sunlight irradiation. Paramagnetic nature of the NiS-PPY-Fe3O4 photocatlyst enabled effective separation of the used catalysts from the reaction solution with the aid of an external magnetic field and avoiding the tedious filtration or centrifugation. Upon regeneration, the photocatalyst retained most of its initial efficiency. Addition of H2O2 to the photocatalyst mixture had an enhancing effect on the cephalexin degradation. The photodegradation products were identified by GC–MS technique.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

Visible-light induced one-pot hydrogenation and amidation of nitroaromatics with carboxylic acids over 2D MXene-derived Pt/N-TiO2/Ti3C2

Pt nanoparticles supported on N doped titanium dioxide/titanium carbide (MXene) heterojunctions were employed as photocatalysts for the tandem reactions between aromatic nitro compounds and carboxylic acids to produce amide products. The 3%Pt/N-TiO2/Ti3C2 heterojunction was prepared by in situ grew TiO2 on Ti3C2 nanosheets and then N doped TiO2 with melamine, Pt nanoparticles with 3.3 nm mean diameter well dispersed on N-TiO2/Ti3C2. 3%Pt/N-TiO2/Ti3C2 had excellent amidation activity and chemoselectivity under visible-light irradiation. The elevated catalytic performance of 3%Pt/N-TiO2/Ti3C2 was owing to the improvement in photogenerated electron and hole separation efficiency through charge short-range directional transmission caused by the intimate contact between the TiO2 and the conductive Ti3C2. This direct hydrogenation along with amidation between nitroaromatics and carboxylic acids own actual merits in the amides produce with no harmful byproducts. In situ DRIFTS spectra verified that the amidation activation with visible light irradiation at 25 °C was much faster than heating.

Method for catalyzing one-pot hydrogenation and amidation of nitroaromatic hydrocarbon and carboxylic acid by visible light

The invention discloses a method for catalyzing one-pot hydrogenation and amidation reaction of nitroaromatic hydrocarbon and carboxylic acid by visible light. The method comprises the following steps: preparing Pt nanoparticles uniformly dispersed on an N-doped titanium dioxide/titanium carbide (MXene) heterojunction as a photocatalyst (3% Pt/N-TiO2/Ti3C2), and applying the catalyst to a cascade reaction of an aromatic nitro compound and carboxylic acid to prepare an amide product. The 3% Pt/N-TiO2/Ti3C2 has excellent tandem hydrogenation and amidation activity and chemical selectivity of an aromatic nitro compound and carboxylic acid under the irradiation of visible light. The excellent catalytic performance of 3% Pt/N-TiO2/Ti3C2 is attributed to the close contact of TiO2 and conductive Ti3C2, and the separation efficiency of photo-induced electrons and holes is improved through charge short-range directional transmission. The preparation method of the catalyst is simple and easy to operate, the catalyst can be used for photocatalytic efficient one-pot hydrogenation and amidation reactions, the reaction conditions are mild, and the catalyst is easy to recycle.

Highly Efficient and Practical Synthesis of the Key Intermediate of Telmisartan

We reported herein an efficient and practical method to access 1,7′-dimethyl-2′-propyl-2,5′-bi(1H-benzimidazole) 1, a key intermediate for the synthesis of telmisartan. The synthetic route was based on readily available o-methylaniline as the starting material, and the target product 1 was prepared through a six-step process, including amidation, formylation, cyclization, hydrolysis, amidine, and oxidation. The overall yield for the preparation of 1 was 51.5% on the 100 g scale, with a purity of 99.91%. The salient features of this method include economic and easily available starting materials, operational simplicity, and environmentally friendly, which is suitable for the industrial production.

Method for synthesizing P-chloroO-toluidine

The invention discloses a method for synthesizing p-chloroo-toluidine, which comprises the following steps: synthesizing o-toluidine and a protective agent in an organic solvent to obtain an amino-protected intermediate. The amino protected intermediate is added into hydrochloric acid, an oxidant is added for chlorination reaction, and a chlorination product is obtained. The chlorinated product is removed and the amino protecting group is removed to give p-chloroo-toluidine. The method for synthesizing p-chloroo-toluidine provided by the invention is high in yield, simple to operate, less in three wastes, high in product content and good in quality, and can be suitable for industrial mass production.

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines

Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.