1,3-Dimethyl-1,3-diphenylurea Property

Melting point:

120-122 °C(lit.)

Boiling point:

383.02°C (rough estimate)

Density 

1.0611 (rough estimate)

vapor pressure 

0.001Pa at 25℃

refractive index 

1.6390 (estimate)

storage temp. 

2-8°C

solubility 

Dichloromethane (Slightly), DMSO (Slightly), Methanol (Very Slightly)

form 

Solid

pka

0.68±0.50(Predicted)

color 

White to Pale Green

Water Solubility 

76.42mg/L at 20℃

InChI

InChI=1S/C15H16N2O/c1-16(13-9-5-3-6-10-13)15(18)17(2)14-11-7-4-8-12-14/h3-12H,1-2H3

InChIKey

ADCBKYIHQQCFHE-UHFFFAOYSA-N

SMILES

N(C)(C1=CC=CC=C1)C(N(C)C1=CC=CC=C1)=O

LogP

2.82 at 25℃

CAS DataBase Reference

611-92-7(CAS DataBase Reference)

EPA Substance Registry System

Urea, N,N'-dimethyl-N,N'-diphenyl- (611-92-7)

Safety

Safety Statements 

22-24/25

WGK Germany 

2

RTECS 

FE0600000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1,3-Dimethyl-1,3-diphenylurea Chemical Properties,Usage,Production

Chemical Properties

Centralite II, also known as 1,3-Dimethyl-1,3-diphenylurea, is a white to grey crystalline powder that is soluble in water, alcohol, acetone, and chloroform. This substance is commonly used as a burning rate moderator and stabilizer for smokeless powder, as well as a plasticizer for celluloid.

Uses

Detection of Methyl Centralite (MC) as gunshot residues (GSR) has been developed.

Description

1,3-Dimethyl-1,3-diphenylurea for Stabilizer and propellant, and production of intermediates of organic chemicals.

Application

Centralite II can be used as a stabilizer for smokeless powder, explosives, nitrates and smokeless fuels, as well as intermediates for fine chemicals.

Uses

1,3-Dimethyl-1,3-diphenylurea (methyl centralite) is a stabilizer in different types of ammunition. This compound is organic gunshot residue. It is the characteristic compound for which forensic analysts test determining if a person has discharged a firearm[1-2].

Flammability and Explosibility

Not classified

Synthesis

To a 10 mL Schlenk tube equipped with a magnetic stirring bar was charged with arylcarbamoyl chlorides (0.2 mmol, 1.0 equiv), and KHCO3 (40 mg, 0.4 mmol), and then Pd(PPh3)4 (0.01 mmol, 11.56 mg) were added. Finally, 1,4-dioxane (1.0 mL) was added to the mixture via syringe at room temperature under N2. The tube was sealed and put into a preheated oil bath a 100 °C for 48 h. The mixture was cooled to room temperature, quenched with water (5 mL), and diluted with ethyl acetate (5 mL). The layers were separated, and the aqueous layer was extracted with 2 × 5 mL of ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product of 1,3-dimethyl-1,3-diphenylurea was purified by flash chromatography on silica gel (H), using 30-35% ethyl acetate/petroleum ether as the eluent.

References

[1] Ricardo J. González. “Detection of organic gunshot residues from human hands using direct sample analysis-time of flight-mass spectrometry.” Journal of Mass Spectrometry 57 5 (2022).
[2] Patrick W. Fedick , Ryan M. Bain. “Swab touch spray mass spectrometry for rapid analysis of organic gunshot residue from human hand and various surfaces using commercial and fieldable mass spectrometry systems.” Forensic Chemistry 5 (2017): Pages 53-57.