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

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

Used in Propellant Industry:
3-METHYL-1,1-DIPHENYLUREA is used as a stabilizing agent for thermal propellants to enhance their performance and safety. Its application reason is to improve the stability and reliability of propellants under various temperature conditions, thereby reducing the risk of accidental ignition or degradation.
Used in Pharmaceutical Industry:
3-METHYL-1,1-DIPHENYLUREA is used as a reference compound in the development and analysis of temozolomide USP. Its application reason is to assist in the identification, quality control, and standardization of temozolomide, a chemotherapeutic drug used in the treatment of certain types of cancer.

Synthesis Reference(s)

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

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.

Contra-thermodynamic trans-esteripication of carbamates by counter-attack strategy: A viable non-phosgene, non-mic route to carbamate pesticides

Treatment of methyl N-methylcarbaaate (1, R= Me) with phosphorus oxychloride and 1-naphthol results in the formation of the transesterified product, 1-naphthyl N-methylcarbamate (2, Ar=1-naphthy 1) in good yield. Similarly, ethyl N-methylthiocarbamate (5) is converted to 1-naphthyl N-methylcarbamate (2, Ar= 1-naphthyl) on treatment with phosphorus oxychloride and 1-naphthol. The mechanism of these interesting and industrially important transformations is discussed.

Method of treating the symptoms of senile cognitive decline employing di- or trisubstituted urea cholinergic agents

Certain trisubstituted alkyl, aryl, pyridinyl, piperidinyl, and piperazinyl urea compounds stimulate the release of acetylcholine and are thus useful agents for the treatment of senile cognitive decline characterized by decreased cerebral acetylcholine production or release. A method for treating the symptoms of senile cognitive decline is disclosed.

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.