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
• Article Data: 190

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

Chemical Properties

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Uses

Different sources of media describe the Uses of 120-66-1 differently. You can refer to the following data:
1. o-Methylacetanilide is a substituted acetanilide that is used as precursor for various pharmaceuticals including their intermediates.
2. Acetanilide is used as an inhibitor of peroxides and?stabilizer for cellulose ester varnishes.?It is used as an intermediate for the synthesis of?rubber accelerators, dyes and dye intermediate and camphor. It is used as a precursor in penicillin synthesis and other pharmaceuticals including painkillers and intermediates.

Synthesis Reference(s)

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

General Description

Colorless crystals. Insoluble in water.

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

• 64-19-7 acetic acid 
• 95-53-4 o-toluidine 
• 16080-08-3 (2-methylphenyl)carbonimidic dichloride 
• 71-43-2 benzene 
• 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 
• 88-72-2 1-methyl-2-nitrobenzene 
• 108-24-7 acetic anhydride 
• 636-21-5 o-toluidine hydrochloride 
• 5152-76-1 N-chloro-2'-methylacetanilide 

Downstream Products

• 158979-23-8 N-(2-methylphenyl)-N-phenylacetamide 
• 85448-89-1 N-(4-methoxyphenyl)-2-methylbenzenamine 
• 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 
• 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 
• 2719-15-5 2-methyl-4-nitroacetanilide 
• 35274-15-8 N-(2-methylphenyl)ethanethioamide 
• 5202-86-8 4-chloro-2-methylacetanilide 
• 13632-46-7 2-acetylamino-toluene-4-sulfonyl chloride 
• 30273-00-8 2-methyl-4,6-dichloroaniline 

Relevant articles and documents

Selective Preparation. 38. A Convenient Preparation of 2-(Acylamino)biphenyls and N-Acetylaniline Derivatives Using the tert-Butyl Group as a Positional Protective Function

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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.

Ortho-Alkylation of Acetanilides Using Alkyl Halides and Palladium Acetate

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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.

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.

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.