85-98-3

Basic information

• Product Name: N,N'-DIETHYL-N,N'-DIPHENYLUREA
• Synonyms: BIS(N-ETHYL-N-PHENYL)UREA;1,3-DIETHYL-1,3-DIPHENYLUREA;SYM-DIETHYLDIPHENYLUREA;N,N'-DIETHYLCARBANILIDE;N,N'-DIETHYL-N,N'-DIPHENYLUREA;1,3-Diethyl-1,3-difenylmocovina;1,3-diethyl-1,3-diphenyl-ure;Bis-(N-ethyl-N-fenyl)mocovina
• CAS NO: 85-98-3
• Molecular Formula: C₁₇H₂₀N₂O
• Molecular Weight: 268.35
• EINECS: 201-645-2
• Product Categories: Industrial/Fine Chemicals;Carbonyl Compounds;Organic Building Blocks;Ureas;CENTRALIT 1;centralite I
• Mol File: 85-98-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 73-75 °C(lit.)
• Boiling Point: 411.52°C (rough estimate)
• Flash Point: 150℃
• Appearance: white crystalline powder
• Density: 1.0208 (rough estimate)
• Vapor Density: 9.3 (vs air)
• Vapor Pressure: 7.74E-06mmHg at 25°C
• Refractive Index: 1.5486 (estimate)
• Storage Temp.: 2-8°C
• Solubility: acetone: soluble(lit.)
• PKA: 0.63±0.50(Predicted)
• Water Solubility: Insoluble watery, soluble in most organic solvents.
• Stability: Shock sensitive.
• Merck: 13,3144
• CAS DataBase Reference: N,N'-DIETHYL-N,N'-DIPHENYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIETHYL-N,N'-DIPHENYLUREA(85-98-3)
• EPA Substance Registry System: N,N'-DIETHYL-N,N'-DIPHENYLUREA(85-98-3)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36-52/53-22
• Safety Statements: 22-24/25-36/37-16-61
• WGK Germany: 2
• RTECS: FE0350000
• Hazardous Substances Data: 85-98-3(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 85-98-3 differently. You can refer to the following data:
1. 1,3-Diethyl-1,3-diphenylurea is a gunshot residue and a stabilizer for smokeless powder.
2. As stabilizer of smokeless explosives.

General Description

White flakes or white crystalline solid. Peppery odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

N,N'-DIETHYL-N,N'-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). N,N'-DIETHYL-N,N'-DIPHENYLUREA is incompatible with acids and oxidizing agents. N,N'-DIETHYL-N,N'-DIPHENYLUREA reacts violently when severely shocked or exposed to extreme temperatures.

Health Hazard

ACUTE/CHRONIC HAZARDS: N,N'-DIETHYL-N,N'-DIPHENYLUREA may react violently when severely shocked or heated to extreme temperatures.

Fire Hazard

N,N'-DIETHYL-N,N'-DIPHENYLUREA is combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Combustible when exposed to heat or flame. Probably a slight explosion hazard, although it is a component of smokeless explosive mixtures. When heated o decomposition it burns and emits very toxic fumes of NOx. To fight fire, use dry chemical, CO2, spray or mist. An explosion regulator.

InChI:InChI=1/C17H20N2O/c1-3-18(4-2)17(20)19(15-11-7-5-8-12-15)16-13-9-6-10-14-16/h5-14H,3-4H2,1-2H3

Synthetic route

diethyl sulfate (64-67-5) + bis(diphenyl)urea (102-07-8) → ethyl centralite (85-98-3)

Conditions	Yield
With sodium hydroxide; potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In toluene for 3h; Alkylation; Heating;	97%

N-ethyl-N-phenyl carbamoyl chloride (33758-39-3) → ethyl centralite (85-98-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium hydrogencarbonate In 1,4-dioxane at 100℃; for 48h; Schlenk technique; Inert atmosphere;	59%

carbon monoxide (201230-82-2) + N-ethyl-N-phenylamine (103-69-5) → ethyl centralite (85-98-3)

Conditions	Yield
With oxygen; potassium iodide In neat (no solvent) at 122℃; for 6h; Green chemistry;	48%

pyridine (110-86-1) + N-ethyl-N-phenyl carbamoyl chloride (33758-39-3) + benzamide (55-21-0) → ethyl centralite (85-98-3)

Conditions	Yield
at 120℃;

N,N'-diethyl-N,N'-diphenyl-thiourea (4338-94-7) → ethyl centralite (85-98-3)

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide

N-ethyl-N-phenyl carbamoyl chloride (33758-39-3) + N-ethyl-N-phenylamine (103-69-5) → ethyl centralite (85-98-3)

Conditions	Yield
With zinc(II) oxide at 200℃;
at 130℃;

phosgene (75-44-5) + N-ethyl-N-phenylamine (103-69-5) + N,N-diethylaniline (91-66-7) → ethyl centralite (85-98-3)

Conditions	Yield
at 160 - 210℃;

phosgene (75-44-5) + N,N-diethylaniline (91-66-7) → ethyl centralite (85-98-3)

N-ethyl-N-phenyl carbamoyl chloride (33758-39-3) + N,N-diethylaniline (91-66-7) → ethyl centralite (85-98-3)

Conditions	Yield
With zinc(II) oxide at 200℃;

N-ethyl-N-phenyl carbamoyl chloride (33758-39-3) + benzamide (55-21-0) + sodium carbonate → ethyl centralite (85-98-3)

Conditions	Yield
at 120℃;

N,N'-diethyl-N,N'-diphenyl-thiourea (4338-94-7) + dihydrogen peroxide (7722-84-1) + aqueous KOH-solution → ethyl centralite (85-98-3)

N-ethyl-N-phenylamine (103-69-5) → ethyl centralite (85-98-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene 2: aqueous hydrogen peroxide; aqueous KOH-solution View Scheme

molybdenum pentachloride + ethyl centralite (85-98-3) → MoCl4((EtPhN)2CO) (1421853-53-3)

Conditions	Yield
In dichloromethane at 20℃; for 18h; Inert atmosphere;	85%

ethyl centralite (85-98-3) → 1,3-diethyl-1,3-bis(4-nitrophenyl)urea (3846-49-9)

Conditions	Yield
With ethyl centralite; nitric acid In acetic acid for 1h;	48%
With water; nitric acid; acetic acid

ethyl centralite (85-98-3) + nitric acid (7697-37-2) → 1,3-diethyl-1,3-bis(4-nitrophenyl)urea (3846-49-9)

ethyl centralite (85-98-3) + nitric acid (7697-37-2) → 1,3-bis(2,4-dinitrophenyl)-1,3-diethylurea (4596-98-9)

Conditions	Yield
unter Kuehlung;

ethyl centralite (85-98-3) + HNO3+H2SO4 → 1,3-bis(2,4-dinitrophenyl)-1,3-diethylurea (4596-98-9)

Conditions	Yield
at 60℃;

ethyl centralite (85-98-3) → 1,3-bis(2,4-dinitrophenyl)-1,3-diethylurea (4596-98-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / nitric acid, ethyl centralite / acetic acid / 1 h 2: 48 percent / sulfuric acid, nitric acid View Scheme

Upstream product

• 33758-39-3 N-ethyl-N-phenyl carbamoyl chloride 
• 103-69-5 N-ethyl-N-phenylamine 
• 75-44-5 phosgene 
• 91-66-7 N,N-diethylaniline 
• 55-21-0 benzamide 
• 201230-82-2 carbon monoxide 
• 4338-94-7 N,N'-diethyl-N,N'-diphenyl-thiourea 
• 7722-84-1 dihydrogen peroxide 
• 64-67-5 diethyl sulfate 
• 102-07-8 bis(diphenyl)urea 
• 110-86-1 pyridine 

Downstream Products

• 3846-49-9 1,3-diethyl-1,3-bis(4-nitrophenyl)urea 
• 4596-98-9 1,3-bis(2,4-dinitrophenyl)-1,3-diethylurea 
• 1421853-53-3 MoCl₄((EtPhN)₂CO) 

Relevant articles and documents

Palladium-catalyzed decarbonylative C–N coupling to convert arylcarbamoyl chlorides to urea derivatives

This paper describes the development of a palladium-catalyzed decarbonylative C–N coupling reaction that transforms arylcarbamoyl chlorides into tetrasubstituted ureas under a nitrogen atmosphere. A broad range of functional groups are compatible with this reaction, and diverse urea derivatives can be obtained with good to high yields.

PHASE-TRANSFER CATALYZED N-ALKYLATION OF sym-N,N'-DIARYLUREAS

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