13114-72-2

Basic information

• Product Name: 3-METHYL-1,1-DIPHENYLUREA
• Synonyms: N,N-Diphenyl-N’-methylurea;N,N-Diphenyl-N'-methylurea;n’-methyl-n,n-diphenyl-ure;Urea, N'-methyl-N,N-diphenyl-;Urea,N’-methyl-N,N-diphenyl-;Urea,N’-methylN,N-diphenyl-;METHYL CARBANILIDE;ACARDITE-II
• CAS NO: 13114-72-2
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.27
• EINECS: 236-039-7
• Product Categories: Carbonyl Compounds;Organic Building Blocks;Ureas;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 13114-72-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 172-174 °C(lit.)
• Boiling Point: 367.89°C (rough estimate)
• Flash Point: 203.5 °C
• Appearance: Needles or grayish-white powder
• Density: 1.0852 (rough estimate)
• Vapor Pressure: 5E-07mmHg at 25°C
• Refractive Index: 1.6419 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.83±0.46(Predicted)
• Water Solubility: 234.8mg/L at 20℃
• CAS DataBase Reference: 3-METHYL-1,1-DIPHENYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-1,1-DIPHENYLUREA(13114-72-2)
• EPA Substance Registry System: 3-METHYL-1,1-DIPHENYLUREA(13114-72-2)

Safety Data

• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 13114-72-2(Hazardous Substances Data)

Usage

Uses

N''-Methyl-N,N-diphenylurea is used in the stabilization of thermal propellants. Temozolomide USP Related Compound B.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 651, 1988 DOI: 10.1016/S0040-4039(00)80173-2

General Description

Needles or grayish-white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-METHYL-1,1-DIPHENYLUREA 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).

Fire Hazard

Flash point data for 3-METHYL-1,1-DIPHENYLUREA are not available. 3-METHYL-1,1-DIPHENYLUREA is probably combustible.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C14H14N2O/c1-15-14(17)16(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3,(H,15,17)

Synthetic route

Ethyl N-methylcarbamate (105-40-8) + diphenylamine (122-39-4) → N-methyl-N',N'-diphenylurea (13114-72-2)

Conditions	Yield
With trichlorophosphate at 80 - 90℃; 10-12 h;	83%

diphenylcarbamic chloride (83-01-2) + methylamine (74-89-5) → N-methyl-N',N'-diphenylurea (13114-72-2)

Conditions	Yield
With diethyl ether
In water at 76.2℃; for 1.08333h;

methyl isocyanate (624-83-9) + dibutyl phosphate (107-66-4) → N-methyl-N',N'-diphenylurea (13114-72-2)

Conditions	Yield
With diphenylamine In toluene

phosgene (75-44-5) + N-methyl-N',N'-diphenylurea (13114-72-2) → C15H13ClN2O2

Conditions	Yield
In tetrahydrofuran; toluene at 20 - 60℃; for 384h;

N-methyl-N',N'-diphenylurea (13114-72-2) → N'-(2,6-bis(1-methylethyl)phenyl)-2-methyl-N,N-diphenyliminodicarbonic diamide

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene; tetrahydrofuran / 384 h / 20 - 60 °C 2: tetrahydrofuran / Ambient temperature View Scheme

N-methyl-N',N'-diphenylurea (13114-72-2) → methyl isocyanate (624-83-9)

Conditions	Yield
In dimethyl sulfoxide at 260℃; for 2h;
Heating;
at 260 - 280℃;

1,4-dioxane (123-91-1) + N-methyl-N',N'-diphenylurea (13114-72-2) → methyl isocyanate (624-83-9)

Upstream product

• 624-83-9 methyl isocyanate 
• 107-66-4 dibutyl phosphate 
• 105-40-8 Ethyl N-methylcarbamate 
• 122-39-4 diphenylamine 
• 83-01-2 diphenylcarbamic chloride 
• 74-89-5 methylamine 

Downstream Products

• 624-83-9 methyl isocyanate 

Relevant articles and documents

PROCESS FOR PREPARING TEMOZOLOMIDE

The present invention relates to a process for preparing temozolomide.

Process for the preparation of N,N-diaryl-ureas

N,N-Diaryl-ureas of the formula wherein R1 and R2 denote aryl and R3 denotes alkyl, aralkyl or aryl, can be prepared by a process in which a diarylamine of the formula is reacted with an isocyanate of the formula wherein R1, R2 and R34 have the above meaning, in the presence of acid compounds and in the presence or absence of an inert solvent and/or diluent at elevated temperature.