622-51-5

Basic information

• Product Name: P-TOLYLUREA
• Synonyms: P-TOLYLUREA;4-METHYLPHENYLUREA;AKOS B028828;nci-c02153;p-tolycarbamide;p-tolyl-ure;p-Tolylurea,98+%;Urea, p-tolyl.
• CAS NO: 622-51-5
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.18
• EINECS: 210-739-2
• Mol File: 622-51-5.mol
• Article Data: 45

Chemical Properties

• Melting Point: 178-181 °C
• Boiling Point: 255℃
• Flash Point: 108℃
• Appearance: /
• Density: 1.192
• Vapor Pressure: 0.0166mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• Storage Temp.: 2-8°C
• PKA: 14.61±0.50(Predicted)
• Water Solubility: 3.07g/L(45 oC)
• BRN: 2208088
• CAS DataBase Reference: P-TOLYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLYLUREA(622-51-5)
• EPA Substance Registry System: P-TOLYLUREA(622-51-5)

Safety Data

• Statements: 33
• Safety Statements: 24/25
• RTECS: YU4200000
• HazardClass: IRRITANT
• Hazardous Substances Data: 622-51-5(Hazardous Substances Data)

Usage

Chemical Properties

beige crystalline powder

General Description

Colorless crystals.

Reactivity Profile

P-TOLYLUREA is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides 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: Slightly toxic. Hazardous decomposition products.

Purification Methods

Crystallise the urea from H2O (m 186o), EtOH/water (1:1) or aqueous AcOH (m 184o). [Beilstein 12 H 941, 12 I 425, 12 II 512, 12 III 2084, 12 IV 1923.]

InChI:InChI=1/C8H10N2O/c1-6-2-4-7(5-3-6)10-8(9)11/h2-5H,1H3,(H3,9,10,11)

Upstream product

• 420-05-3 cyanic acid 
• 370-88-7 p-tolyl-carbamoyl fluoride 
• 540-23-8 p-toluidine hydrochloride 
• 4747-87-9 isopropenyl isocyanate 
• 106-49-0 p-toluidine 
• 684-93-5 1-methyl-1-nitrosourea 
• 556-89-8 nitrourea 
• 590-28-3 potassium cyanate 
• 92114-96-0 mercury fulminate 
• 57-13-6 urea 
• 621-00-1 1,3-di-p-tolylurea 
• 94398-06-8 N-(p-tolylcarbamoyl)benzamide 
• 124-41-4 sodium methylate 
• 85754-40-1 N-nitroso-N-p-tolyl-urea 

Downstream Products

• 2314-79-6 N-(p-tolyl)succinimide 
• 153261-68-8 N-(toluene-4-sulfinyl)-N'-p-tolyl-urea 
• 150-69-6 N-(p-ethoxyphenyl)urea 
• 25157-30-6 N',N'''-di-p-tolyl-N,N''-methanediyl-di-urea 
• 75457-02-2 N-p-tolyl-N'-(2,2,2-trichloro-1-hydroxy-ethyl)-urea 
• 62774-57-6 N-(4-methylphenyl)hydrazinecarboxamide 
• 621-00-1 1,3-di-p-tolylurea 
• 861519-01-9 4-ureido-toluene-3-sulfonic acid 
• 85754-40-1 N-nitroso-N-p-tolyl-urea 
• 622-58-2 p-Tolylisocyanate 
• 57-13-6 urea 

Relevant articles and documents

Reaction of N-arylcarbamoyl-1,4-benzoquinone imines with sodium arenesulfinates

N-Arylcarbamoyl-1,4-benzoquinone imines possessing at least one free ortho position with respect to the carbonyl carbon atom in the quinoid ring react with sodium arenesulfinates according to the nucleophilic 1,4-addition pattern with complete regioselect

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.