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2387-23-7

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2387-23-7 Usage

Chemical Properties

white crystalline powder

Uses

N,N''-Dicyclohexylurea,is a substituted Urea (U822500) compound, which has shown to be a potent inhibitor of juvenile hormone epoxide hydrolase (JHEH) of the tobacco hornworm M. sexta. Lomustine USP Related Compound C.

Preparation

An excess of dry ice (200 g) was added gradually to a solution of dicyclohexylcarbodiimide (2.06 g, 0.01 mol), cyclohexylamine (1.98 g, 0.02 mol), and triethylamine (2.2 g, 0.02 mol) in THF at 75 ℃ over a period of 8 h. After stirring for 8 h, the reaction mixture was concentrated under reduced pressure and the resultant precipitate was collected. Fractional recrystallization of the precipitate from acetone/methanol gave N,N'-dicyclohexylurea; yield 2.2 g (98% based on dicyclohexylcarbodiimide and cyclohexylamine).

Synthesis Reference(s)

The Journal of Organic Chemistry, 61, p. 4175, 1996 DOI: 10.1021/jo9522825

Check Digit Verification of cas no

The CAS Registry Mumber 2387-23-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,8 and 7 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2387-23:
(6*2)+(5*3)+(4*8)+(3*7)+(2*2)+(1*3)=87
87 % 10 = 7
So 2387-23-7 is a valid CAS Registry Number.

2387-23-7 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (D0441)  1,3-Dicyclohexylurea  >98.0%(GC)(T)

  • 2387-23-7

  • 25g

  • 325.00CNY

  • Detail
  • TCI America

  • (D0441)  1,3-Dicyclohexylurea  >98.0%(GC)(T)

  • 2387-23-7

  • 100g

  • 740.00CNY

  • Detail
  • TCI America

  • (D0441)  1,3-Dicyclohexylurea  >98.0%(GC)(T)

  • 2387-23-7

  • 500g

  • 2,290.00CNY

  • Detail
  • Alfa Aesar

  • (B20805)  N,N'-Dicyclohexylurea, 98%   

  • 2387-23-7

  • 25g

  • 394.0CNY

  • Detail
  • Alfa Aesar

  • (B20805)  N,N'-Dicyclohexylurea, 98%   

  • 2387-23-7

  • 100g

  • 764.0CNY

  • Detail
  • Alfa Aesar

  • (B20805)  N,N'-Dicyclohexylurea, 98%   

  • 2387-23-7

  • 500g

  • 3466.0CNY

  • Detail
  • USP

  • (1369442)  LomustineRelatedCompoundC  United States Pharmacopeia (USP) Reference Standard

  • 2387-23-7

  • 1369442-25MG

  • 13,501.80CNY

  • Detail
  • Aldrich

  • (D80800)  N,N′-Dicyclohexylurea  98%

  • 2387-23-7

  • D80800-25G

  • 452.79CNY

  • Detail

2387-23-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-dicyclohexylurea

1.2 Other means of identification

Product number -
Other names F0902-7614

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2387-23-7 SDS

2387-23-7Synthetic route

1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodo-4-methoxyphenyl)propanoic acid
622336-82-7

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodo-4-methoxyphenyl)propanoic acid

A

C19H23IN2O7
911675-87-1

C19H23IN2O7

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,2-dimethoxyethaneA 100%
B n/a
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

N3,N6-di(tert-butoxycarbonyl)-3,6-diazaoctane-1,8-diol
167407-91-2

N3,N6-di(tert-butoxycarbonyl)-3,6-diazaoctane-1,8-diol

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

N,N'-di-tert-butylcarbonyl-N,N'-bis(2-hydroxyethyl)ethylenediamine dioleate
167951-93-1

N,N'-di-tert-butylcarbonyl-N,N'-bis(2-hydroxyethyl)ethylenediamine dioleate

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
dmap In n-heptane at 20 - 40℃; Product distribution / selectivity;A n/a
B 99.6%
carbon monoxide
201230-82-2

carbon monoxide

cyclohexylamine
108-91-8

cyclohexylamine

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
Stage #1: carbon monoxide; cyclohexylamine With selenium at 20℃; under 750.075 Torr; for 2h; neat (no solvent);
Stage #2: With oxygen at 20℃; under 750.075 Torr; for 1h; neat (no solvent);
99%
With palladium; oxygen; potassium iodide In 1,4-dioxane at 130℃; under 30003 Torr; for 24h; Autoclave; Green chemistry;99%
With oxygen In tetrahydrofuran at 90℃; under 6000.6 Torr; for 72h; Catalytic behavior; Reagent/catalyst; Autoclave; Schlenk technique; Inert atmosphere;96%
Cyclohexyl isocyanate
3173-53-3

Cyclohexyl isocyanate

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With [Pr(SPh)3(THF)3] In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;99%
With Trimethylsilanol In acetonitrile at 20℃; Green chemistry;92%
With Ta(η5-C5Me5)(η3-1-phenylallyl)2 In toluene for 12h; Ambient temperature;89%
carbon dioxide
124-38-9

carbon dioxide

cyclohexylamine
108-91-8

cyclohexylamine

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
Stage #1: cyclohexylamine With titanium tetrachloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With pyridine In dichloromethane for 0.5h; Inert atmosphere;
Stage #3: carbon dioxide Further stages;
99%
With cesium hydroxide; 1-butyl-3-methylimidazolium chloride at 170℃; under 45600 Torr; for 4h;98%
Stage #1: cyclohexylamine With tetrachloromethane; triphenylphosphine In dichloromethane for 24h; Heating;
Stage #2: With triethylamine at 20℃; for 2h;
Stage #3: carbon dioxide; cyclohexylamine at 20℃; for 24h; Further stages.;
96%
chloroform
67-66-3

chloroform

cyclohexylamine
108-91-8

cyclohexylamine

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate; triethylamine In water for 1h; Irradiation;99%
With oxygen; sodium hydroxide In water at 20℃; for 3h; Reagent/catalyst; Irradiation;62%
tetradecylthioacetic Acid
2921-20-2

tetradecylthioacetic Acid

methyl 2,3-diaminopropanoate dihydrochloride
6059-44-5, 106973-48-2, 147857-43-0

methyl 2,3-diaminopropanoate dihydrochloride

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

methyl 2,3-di{[(tetradecylthio)acetyl]amino}propanoate

methyl 2,3-di{[(tetradecylthio)acetyl]amino}propanoate

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine In dichloromethane at 0 - 20℃; for 49h;A 96%
B n/a
N-cyclohexyl-2-phenylimidazo[1,2-a]pyridin-3-amine

N-cyclohexyl-2-phenylimidazo[1,2-a]pyridin-3-amine

A

N-(pyrid-2-yl)benzamide
4589-12-2

N-(pyrid-2-yl)benzamide

B

cyclohexylamine
108-91-8

cyclohexylamine

C

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With potassium tert-butylate; copper diacetate In m-xylene for 8h; Reagent/catalyst; Solvent; Schlenk technique; Heating; chemoselective reaction;A 96%
B n/a
C n/a
L-tyrosine methyl ester HCl
3417-91-2

L-tyrosine methyl ester HCl

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

A

C17H16ClNO4
254899-76-8

C17H16ClNO4

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
dmap In dichloromethane at 20℃; Inert atmosphere;A 95.3%
B n/a
4-nitro-phenol
100-02-7

4-nitro-phenol

4-[(2R,3S,5R)-5-(thymin-1-yl)-2-(trityloxymethyl)tetrahydrofuran-3-yloxy]-4-oxobutanoic acid

4-[(2R,3S,5R)-5-(thymin-1-yl)-2-(trityloxymethyl)tetrahydrofuran-3-yloxy]-4-oxobutanoic acid

A

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

B

5'-O-tritylthymidine-3'-O-succinyl-(4-nitro)phenylester

5'-O-tritylthymidine-3'-O-succinyl-(4-nitro)phenylester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane; pyridine for 12h; Ambient temperature;A n/a
B 95%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

methyl L-isoleucinate hydrochloride
18598-74-8

methyl L-isoleucinate hydrochloride

A

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

B

(tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester
102342-09-6

(tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) ice bath, 1 h, 2.) 23 deg C, 15 h;A n/a
B 95%
bis-(p-nitrophenyl) carbonate
5070-13-3

bis-(p-nitrophenyl) carbonate

cyclohexylamine
108-91-8

cyclohexylamine

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
In dichloromethane for 4h; Ambient temperature;95%
dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With acetic acid; N-hydroxybenzenecarboximidamide In chloroform for 4h; Heating;95%
With tert-butyloxycarbonyl-methionyl-leucyl-phenylalanine; benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 0℃; for 3h;
With 1,3:2,4-di-O-methylene-L-arabinitol In pyridine; dimethyl sulfoxide at 20 - 25℃; for 2h;
cyclohexylamine
108-91-8

cyclohexylamine

5-nitro-1-indazolecarboxylic acid cyclohexylamide
401638-49-1

5-nitro-1-indazolecarboxylic acid cyclohexylamide

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 155℃; for 6h;95%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

4-hydroxyphenylacetic acid N-hydroxysuccinimide ester
73158-83-5

4-hydroxyphenylacetic acid N-hydroxysuccinimide ester

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
In ethyl acetate at 0 - 4℃; for 22h;A 94.6%
B n/a
cyclohexylamine
108-91-8

cyclohexylamine

1-indazolecarboxylic acid cyclohehylamide

1-indazolecarboxylic acid cyclohehylamide

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 155℃; for 8h;94%
cyclohexane-1,3-dicarboxylic acid
3971-31-1

cyclohexane-1,3-dicarboxylic acid

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

A

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

B

3-oxabicyclo[3.3.1]nonane-2,4-dione
4355-31-1

3-oxabicyclo[3.3.1]nonane-2,4-dione

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;A n/a
B 94%
1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
With dichloromethylenedimethyliminium chloride; triethylamine In dichloromethane at 0℃;100%
With bis(trichloromethyl) carbonate In 1-methyl-pyrrolidin-2-one at 30 - 40℃; for 6h; Autoclave;99.5%
With pyridine; chloroacetyl chloride In dichloromethane at 0 - 60℃; for 10h; Solvent; Temperature; Reagent/catalyst;97.3%
1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

cyclohexylamine
108-91-8

cyclohexylamine

Conditions
ConditionsYield
With sodium hydroxide at 450℃; for 8h; Temperature; Autoclave; Large scale;99.49%
1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

ethyl N-cyclohexylcarbamate
1541-19-1

ethyl N-cyclohexylcarbamate

Conditions
ConditionsYield
96%
93%
8%
2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

N-cyclohexyl carbamic acid(2,6-dimethylphenyl)ester
201137-64-6

N-cyclohexyl carbamic acid(2,6-dimethylphenyl)ester

Conditions
ConditionsYield
Reflux; Large scale;95%

2387-23-7Relevant articles and documents

Highly efficient ionic liquid-mediated palladium complex catalyst system for the oxidative carbonylation of amines

Shi, Feng,Peng, Jiajian,Deng, Youquan

, p. 372 - 375 (2003)

A highly efficient catalyst system, palladium-ionic liquid, was developed for the carbonylation of amines to give carbamate or urea. The desired products could be precipitated by adding water into the resulting mixture and the catalyst system could be reused with slight loss of catalytic activity. BMImBF4 ionic liquid + Pd(phen)Cl2 was an effective catalytic system for the oxidative carbonylation of aniline to give corresponding carbamate and for the cyclohexyl amine to give urea. The diversity of the ionic liquids could form an optimal homogeneous catalyst system with a specific organometallic toward specific reactions. There existed strong interactions between the ionic liquid and the Pd complex, which might enhance and stabilize the Pd complex catalyst.

Preparation of 5-diaminomethylenebarbiturates by barbituric acid addition to carbodiimides

Jursic, Branko S.,Douelle, Fred,Stevens, Edwin D.

, p. 3427 - 3432 (2003)

Through NMR spectroscopic monitoring of barbituric acid addition to carbodiimide, a general synthetic procedure for the preparation of 5-diaminomethylenebarbiturates (DABA) was developed. This procedure is very simple and applicable to the preparation of large quantities of DABA derivatives. Through an X-ray structural study of one of the DABA derivatives, it was established that these compounds have an ylide-type structure with strong charge separation within the molecule.

Molecular interactions of β-cyclodextrins with monolayers containing adamantane and anthraquinone guest groups

Swiech, Olga,Chmurski, Kazimierz,Bilewicz, Renata

, p. 461 - 466 (2010)

Complexing abilities of β-cyclodextrin (β-CD) towards anthraquinone derivatives in solution and immobilised on gold surfaces were studied by voltammetry. The association constant of β-CD with 1-aminoanthraquinone in solution was found to be 1.03±0.05×103 M-1 hence, smaller than that with anthraquinone. Capping the surface-immobilised N-(1-anthraquinone) lipoamide with β-CD led to decrease in the heterogeneous electron transfer rate constant due to the change in the immediate environment around the electroactive group. To detect the interactions of β-CD with a non-electroactive guest, N-(1-adamantane) lipoamide (AD-Lip), the CD was modified by the attachment of an anthraquinone group as the electroactive marker. The appearance of the voltammetric peak corresponding to the reduction of the anthraquinone side-group indicated the binding of β-CD to the AD-Lip self-assembled in a monolayer on the gold electrode.

Total Synthesis of (+)-3-Demethoxyerythratidinone and (+)-Erysotramidine via the Oxidative Amidation of a Phenol

Paladino, Marco,Zaifman, Joshua,Ciufolini, Marco A.

, p. 3422 - 3425 (2015)

Oxidative amidation chemistry provides a unified route to aromatic Erythrina alkaloids through a sequence that illustrates new principles and improved conditions to effect a crucial eliminative Curtius-Schmidt rearrangement.

Hofer,Schloegl

, p. 443 (1968)

One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and α-bromoketones

Haung, Jia-Yun,Barve, Indrajeet J.,Sun, Chung-Ming

, p. 3040 - 3047 (2019)

A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one intermediates revealed a possible reaction mechanism. The strategy was further extended to the synthesis of 2-iminothiazolines and 2-thioxoimidazolin-4-ones.

Improvement of warfarin biopharmaceutics by conjugation with poly(ethylene glycol)

Zacchigna, Marina,Di Luca, Gabriella,Cateni, Francesca,Maurich, Venerando

, p. 379 - 384 (2004)

One of the most used and useful polymers, poly(ethylene glycol) (PEG) was used as a carrier for warfarin. The drug-polymer conjugate was freely water soluble at room temperature. The hydrolytic stability of the PEG-warfarin was investigated at physiological pH and confirmed the stability of the conjugate. In vivo release studies demonstrated a good release of parent drug, without the initial high plasma level of warfarin.

Hydrosilane-Assisted Synthesis of Urea Derivatives from CO2and Amines

Zhao, Yulei,Guo, Xuqiang,Si, Zhiyao,Hu, Yanan,Sun, Ying,Liu, Yunlin,Ji, Zhongyin,You, Jinmao

, p. 13347 - 13353 (2020/11/02)

A methodology employing CO2, amines, and phenylsilane was discussed to access aryl- or alkyl-substituted urea derivatives. This procedure was characterized by adopting hydrosilane to promote the formation of ureas directly, without the need to prepare silylamines in advance. Control reactions suggested that FeCl3 was a favorable additive for the generation of ureas, and this 1,5,7-triazabicyclo[4.4.0]dec-5-ene-catalyzed reaction might proceed through nucleophilic addition, silicon migration, and the subsequent formal substitution of silylcarbamate.

METHOD OF PREPARING UREA USING AMINE COMPOUND AND CARBON DIOXIDE

-

Paragraph 0073-0075; 0134-0138; 0164-0165; 0168; 0196, (2020/11/14)

Disclosed is a production method of urea using an amine compound and carbon dioxide. The production method of urea includes a step of producing urea by using the amine compound and a 2-pyrrolidone derivative as a solvent and reacting with the carbon dioxide, thereby producing high yield cyclic urea under mild reaction conditions and no catalyst conditions.

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