619-55-6

Basic information

• Product Name: P-TOLUAMIDE
• Synonyms: p-Toluamide 99%;p-Toluamide;4-methyl-benzamid;Benzamide,4-methyl-;p-Tolylamide;Tolylsαureamid;P-TOLUAMIDE;PTAD
• CAS NO: 619-55-6
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• EINECS: 210-600-6
• Product Categories: AMIDE;Benzene derivatives;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Amides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 619-55-6.mol
• Article Data: 323

Chemical Properties

• Melting Point: 159-162 °C
• Boiling Point: 248.86°C (rough estimate)
• Flash Point: 117.3 °C
• Appearance: /
• Density: 1.1031 (rough estimate)
• Vapor Pressure: 0.00686mmHg at 25°C
• Refractive Index: 1.5635 (rough estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 16.21±0.50(Predicted)
• Sensitive: Air Sensitive
• BRN: 774353
• CAS DataBase Reference: P-TOLUAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLUAMIDE(619-55-6)
• EPA Substance Registry System: P-TOLUAMIDE(619-55-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 24/25-26
• WGK Germany: 3
• RTECS: CV5570150
• TSCA: Yes
• Hazardous Substances Data: 619-55-6(Hazardous Substances Data)

Usage

Description

p-Toluamide is an organic compound with the chemical formula C7H7NO. It is a white crystalline solid that is soluble in water and has a melting point of approximately 184°C. It is derived from toluene, a common aromatic hydrocarbon, and is used in various industrial applications.

Uses

Used in Calibration of Melting Point Instruments:
p-Toluamide is used as a calibration substance for Mettler-Toledo melting point instruments, specifically the ME 30130597 calibration substance. It helps to ensure the accuracy and reliability of the melting point measurements taken by these instruments.
Used in the Preparation of p-Tolloyl Isocyanate:
p-Toluamide is used in the synthesis of p-toloyl isocyanate, an important chemical intermediate in the production of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Preparation of High-Efficiency Nitriding Reagents:
4-Methylbenzamide, a derivative of p-toluamide, is used in the preparation of high-efficiency nitriding reagents. These reagents are essential in the surface treatment of metals, particularly in the nitriding process, which enhances the hardness, wear resistance, and corrosion resistance of metal surfaces.

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 1448, 1955 DOI: 10.1021/jo01127a025

InChI:InChI=1/C8H9NO/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H2,9,10)

Upstream product

• 99-75-2 4-methyl-benzoic acid methyl ester 
• 104-85-8 para-methylbenzonitrile 
• 119044-76-7 cyclohexylidene-carbamic acid ethyl ester 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 22693-32-9 4-methylbenzoyl azide 
• 64931-86-8 4-phenyl-1H-<1,2,4>oxadiazino<4,5-a>benzimidazole 
• 99-94-5 p-Toluic acid 
• 57-13-6 urea 
• 21443-49-2 3,4-bis(p-methylbenzoyl)-1,2,5-oxadiazole-N-oxide 
• 7664-41-7 ammonia 
• 732-93-4 4-methyl-N-(4-methylbenzoyl)-benzamide 
• 7732-18-5 water 
• 104-87-0 4-methyl-benzaldehyde 
• 59046-28-5 p-toluoyl-1H-1,2,3-benzotriazole 

Downstream Products

• 100-47-0 benzonitrile 
• 65-85-0 benzoic acid 
• 58010-65-4 N-(4-methylbenzoyl)benzamide 
• 104-85-8 para-methylbenzonitrile 
• 99-94-5 p-Toluic acid 
• 52786-38-6 4-Methyl-N-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-benzamide 
• 1153-93-1 2-p-tolyl-8H-pyrano[3,4-e][1,3]oxazine-4,5,7-trione 
• 81637-87-8 N-(dimethyl-λ⁴-sulfanylidene)-4-methylbenzamide 
• 33667-88-8 4-methyl-N-(4-nitrophenyl)-benzamide 
• 20972-43-4 trans-azoxybenzene 
• 83081-31-6 4-methyl-2-(p-tolyl)oxazole 
• 121876-97-9 (E)-N-((dimethylamino)methylene)-4-methylbenzamide 
• 143949-80-8 N-(Benzotriazol-1-ylmethyl)-4-methylbenzamide 
• 5602-96-0 methyl p-tolylcarbamate 

Relevant articles and documents

ALUMINA CATALYZED TRANSFORMATION OF O-(3-OXOBUTYL) URETHANES

The alumina-catalyzed transformations of urethane to a secundary amine and a sulfonyl urethane to a sulfonamide are described.Alumina is also shown to catalyze the conjugate addition of p-toluenesulfonamide to methyl vinyl ketone.

Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.