6950-84-1

Usage

Uses

Used in Chemical Synthesis:
1-Naphthylurea is used as a starting material for the production of various chemicals. Its unique chemical structure allows it to be a versatile building block in the creation of different compounds, which can be utilized in a wide range of applications across different industries.
Used in Pharmaceutical Industry:
1-Naphthylurea is used as an intermediate in the synthesis of pharmaceutical compounds. Its chemical properties make it a valuable component in the development of new drugs, particularly those targeting specific medical conditions.
Used in Dye Industry:
In the dye industry, 1-Naphthylurea is used as a precursor for the production of various dyes and pigments. Its chemical structure contributes to the color and stability of the final product, making it an essential component in the manufacturing process.
Used in Agricultural Industry:
1-Naphthylurea is also utilized in the agricultural industry as a starting material for the synthesis of certain agrochemicals, such as herbicides and pesticides. Its role in the production of these chemicals helps to improve crop yields and protect plants from pests and diseases.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1-NAPHTHYLUREA 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

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Purification Methods

Crystallise the urea from EtOH (m 213-214o also 215o). [Beilstein 12 H 1238, 12 IV 3076.]

InChI:InChI=1/C11H10N2O/c12-11(14)13-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H3,12,13,14)

Upstream product

• 134-32-7 1-amino-naphthalene 
• 57-13-6 urea 
• 13256-79-6 1-benzyl-3-(naphthalen-1-yl)urea 
• 90-11-9 1-Bromonaphthalene 
• 90-14-2 1-Iodonaphthalene 
• 86-88-4 naphthalen-1-yl-thiourea 
• 41279-57-6 1-naphthylcyanamide 
• 116120-22-0 N-(naphthalen-2-yl)cyanamide 
• 917-61-3 sodium isocyanate 
• 590-28-3 potassium cyanate 

Downstream Products

• 607-56-7 1,3-dinaphthalen-1-ylurea 
• 57-13-6 urea 
• 575-36-0 1-acetamidonaphthalene 
• 91955-31-6 N-acetyl-N'-[1]naphthyl-urea 
• 95872-87-0 N--N'-<2-(cyclohexen-(1)-yl)-cyclohexen-(1)-yl>-harnstoff 
• 13256-79-6 1-benzyl-3-(naphthalen-1-yl)urea 
• 143028-47-1 3-Naphthalen-1-yl-10-p-tolyl-10H-pyrimido[4,5-b]quinoline-2,4-dione 
• 143028-62-0 3-Naphthalen-1-yl-6-p-tolylamino-1H-pyrimidine-2,4-dione 
• 100381-97-3 2-α-Naphthylamino-oxazol 
• 634-42-4 N-1-naphthalenyl-benzamide 

Relevant academic research and scientific papers

A green and facile approach for the synthesis of N-monosubstituted ureas in water: Pd catalyzed reaction of arylcyanamides (an unexpected behavior of electron withdrawing groups)

The Fe3O4 magnetic nano-particles were prepared, coated with tetraethyl orthosilicate (TEOS), functionalized with 3-chloropropyltrimethoxysilane (CPTMS), further functionalized with 2,2′-(piperazine-1,4-diylbis(methylene) dianiline (PDMD) and the corresponding Pd complex synthesized as a novel nano-magnetic heterogeneous catalyst (Fe3O4@SiO2@CPTMS@PDMD@Pd) to be used for the synthesis of various N-monosubstituted ureas in water. Also, in another attempt to see the effect of HCOOH, the hydration reaction of arylcyanamide was carried out in the presence of HCOOH (water + 98% HCOOH) which had two effects: it decreased the amount of the Pd catalyst from 40 to 30 mg, and the reaction condition was changed from the reflux condition to room temperature. Interestingly, the arylcyanamides with electron withdrawing groups influence the course of the reaction and need more reaction times for completion which is an unexpected behavior, probably due to the high electron density around the central carbon atom of the nitrile group.

Selective and facile oxidative desulfurization of thioureas and thiobarbituric acids with singlet molecular oxygen generated from trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane

An efficient and facile procedure using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane has been developed for oxidative desulfurization of thioureas and thiobarbituric acids. The reactions proceeded smoothly very fast under mild conditions in basic media at room temperature to afford the respective ureas in excellent yields. Simple procedure and work up, mild conditions, high yields, short reaction times, use of highly potent and non-toxic oxidant are the main merits of the present method.

Hybrid Pd/Fe3O4 nanowires: Fabrication, characterization, optical properties and application as magnetically reusable catalyst for the synthesis of N-monosubstituted ureas under ligand-free conditions

This paper reports the synthesis and use of Pd/Fe3O4 nanowires, as magnetically separable catalysts for ligand-free amidation coupling reactions of aryl halides with benzylurea under microwave irradiation. Then, the in situ hydrogenolysis of the products was performed to afford the N-monosubstituted ureas from good to excellent yields. This method has the advantages of high yields, simple methodology and easy work up. The catalyst can be recovered by using a magnet and reused several times without significant loss of its catalytic activity. The catalyst was characterized using the powder XRD, SEM, EDS and UV-vis spectroscopy. Experimental absorbance spectra was compared with results from the Gans theory.

Green synthesis, optical properties and catalytic activity of silver nanoparticles in the synthesis of N-monosubstituted ureas in water

We report the green synthesis of silver nanoparticles by using Euphorbia condylocarpa M. bieb root extract for the synthesis of N-monosubstituted ureas in water. UV-visible studies show the absorption band at 420 nm due to surface plasmon resonance (SPR) of the silver nanoparticles. This reveals the reduction of silver ions (Ag+) to silver (Ago) which indicates the formation of silver nanoparticles (Ag NPs). This method has the advantages of high yields, simple methodology and easy work up.

Synthesis of N-arylureas in water and their N-arylation with aryl halides using copper nanoparticles loaded on natural Natrolite zeolite under ligand-free conditions

A new method for the synthesis of N-arylureas and their N-arylation with aryl halides has been developed using copper nanoparticles supported on natural Natrolite zeolite as a reusable heterogeneous catalyst under ligand-free conditions.

Nano cerium oxide as a recyclable catalyst for the synthesis of N-monosubstituted ureas with the aid of acetaldoxime as an effective water surrogate

A new method for the synthesis of N-monosubstituted ureas has been developed by the reaction of cyanamides with acetaldoxime in the presence of nano cerium oxide as an efficient and recyclable catalyst.

Combating oxidative stress in epilepsy: Design, synthesis, quantum chemical studies and anticonvulsant evaluation of 1-(substituted benzylidene/ethylidene) -4-(naphthalen-1-yl)semicarbazides

A series of 1-(substituted benzylidene/ethylidene)-4-(naphthalen-1-yl) semicarbazides (3a-19a; 3b-6b) were synthesized in good yield and evaluated for their anticonvulsant and antioxidant activities. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. All of the compounds were found to be active in MES and scPTZ tests. Quantum chemical studies were carried out on these compounds to understand the structural features essential for activity. Electronic properties were found to be the principal modulator of both anticonvulsant and antioxidant activities. A computational study was carried out for prediction of pharmacokinetic properties and none of the compounds violated Lipinski's rule of 5, making them potentially promising agents for the treatment of epilepsy.