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120-93-4

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  • Ethyleneurea CAS 120-93-4 2-Imidazolidone CAS no 120-93-4 Ethylene urea 2-Imidazolidinone

    Cas No: 120-93-4

  • USD $ 3.5-5.0 / Kiloliter

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120-93-4 Usage

Chemical Properties

White to off-white solid

Uses

Different sources of media describe the Uses of 120-93-4 differently. You can refer to the following data:
1. 2-Imidazolidinone is a metabolite of ethylenethiourea (ETU), a decomposition product of the ethylenebis(dithiocarbamate) (EBDC) fungicides.
2. thiadiazole pharmaceutical intermediate
3. 2-Imidazolidone can be used as reactant for synthesis of Chiral microporous materials from achiral precursors.

General Description

Find more information here: Neonicotinoids

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise it from MeOH (charcoal). [Beilstein 24 III/IV 6.]

Check Digit Verification of cas no

The CAS Registry Mumber 120-93-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 120-93:
(5*1)+(4*2)+(3*0)+(2*9)+(1*3)=34
34 % 10 = 4
So 120-93-4 is a valid CAS Registry Number.
InChI:InChI=1/C2H4.CH4N2O/c1-2;2-1(3)4/h1-2H2;(H4,2,3,4)

120-93-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Aldrich

  • (I601)  2-Imidazolidone  96%

  • 120-93-4

  • I601-25G

  • 745.29CNY

  • Detail
  • Aldrich

  • (I601)  2-Imidazolidone  96%

  • 120-93-4

  • I601-500G

  • 3,105.18CNY

  • Detail
  • Aldrich

  • (I601)  2-Imidazolidone  96%

  • 120-93-4

  • I601-1KG

  • 4,595.76CNY

  • Detail
  • Sigma-Aldrich

  • (31534)  2-Imidazolidone  PESTANAL®, analytical standard

  • 120-93-4

  • 31534-250MG

  • 299.52CNY

  • Detail

120-93-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name imidazolidin-2-one

1.2 Other means of identification

Product number -
Other names imidazolidinone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adhesives and sealant chemicals,Processing aids, not otherwise listed
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:120-93-4 SDS

120-93-4Synthetic route

1-carboxy-2-imidazolidinone
32682-96-5

1-carboxy-2-imidazolidinone

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
In water-d2 at 25℃; Rate constant; Mechanism;100%
carbon dioxide
124-38-9

carbon dioxide

ethylenediamine
107-15-3

ethylenediamine

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With 2-pyrrolidinon; caesium carbonate at 200℃; under 37503.8 Torr; for 2h; Temperature; Pressure; Reagent/catalyst; Solvent; Autoclave;99%
With caesium carbonate at 200℃; under 37503.8 Torr; for 2h; Reagent/catalyst; Temperature; Pressure; Autoclave;99%
at 180℃; under 75007.5 Torr; for 24h; Autoclave;96.9%
methanol
67-56-1

methanol

1,1'-(2-oxoimidazolidine-1,3-diyl)bis(propan-1-one)
40424-08-6

1,1'-(2-oxoimidazolidine-1,3-diyl)bis(propan-1-one)

A

imidazolidone
120-93-4

imidazolidone

B

propanoic acid methyl ester
554-12-1

propanoic acid methyl ester

Conditions
ConditionsYield
With C17H23BN2O at 50℃; under 760.051 Torr; for 15h; Inert atmosphere; chemoselective reaction;A 97%
B n/a
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

ethylenediamine
107-15-3

ethylenediamine

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
In acetonitrile for 8h; Ambient temperature;90%
ethylenediamine
107-15-3

ethylenediamine

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With sodium methylate In methanol; toluene at 55 - 90℃; for 3h; Temperature; Concentration; Solvent; Time; Inert atmosphere;90%
With sodium methylate In methanol; toluene at 23 - 90℃; for 3h; Inert atmosphere;90%
methanol
67-56-1

methanol

carbon dioxide
124-38-9

carbon dioxide

ethylenediamine
107-15-3

ethylenediamine

A

imidazolidone
120-93-4

imidazolidone

B

1-methyl-2-imidazolidone
694-32-6

1-methyl-2-imidazolidone

Conditions
ConditionsYield
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Temperature;A 86.3%
B n/a
ethanol
64-17-5

ethanol

carbon dioxide
124-38-9

carbon dioxide

ethylenediamine
107-15-3

ethylenediamine

A

imidazolidone
120-93-4

imidazolidone

B

1-ethylimidazolidine-2-one
872-69-5

1-ethylimidazolidine-2-one

Conditions
ConditionsYield
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h;A 82.5%
B n/a
propan-1-ol
71-23-8

propan-1-ol

carbon dioxide
124-38-9

carbon dioxide

ethylenediamine
107-15-3

ethylenediamine

A

imidazolidone
120-93-4

imidazolidone

B

1-propyl-2-imidazolidone
40424-27-9

1-propyl-2-imidazolidone

Conditions
ConditionsYield
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h;A 80.5%
B n/a
S,S-dimethyl dithiocarbonate
868-84-8

S,S-dimethyl dithiocarbonate

ethylenediamine
107-15-3

ethylenediamine

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
In methanol at 60℃; for 24h;80%
C3H8N2O

C3H8N2O

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane In acetonitrile at 20℃; for 0.583333h; chemoselective reaction;80%
ethylenediamine
107-15-3

ethylenediamine

urea
57-13-6

urea

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With water for 3h; Heating;75%
With water for 3h; Mechanism; Product distribution; Heating; (15)N-labelled urea, N-alkylated 1,2-diaminoethane, toluene as a moderator;75%
In ethylene glycol at 130 - 180℃; for 6h;68.3%
(-)-3-[2-(S)-(1-amino-3,3,3-trifluoropropyl)]-[4-(R)-phenyl]-oxazolidin-2-one
909002-34-2

(-)-3-[2-(S)-(1-amino-3,3,3-trifluoropropyl)]-[4-(R)-phenyl]-oxazolidin-2-one

ethylenediamine
107-15-3

ethylenediamine

A

imidazolidone
120-93-4

imidazolidone

B

2-(1-aminomethyl-2,2,2-trifluoroethylamino)-2-phenylethanol
909002-37-5

2-(1-aminomethyl-2,2,2-trifluoroethylamino)-2-phenylethanol

Conditions
ConditionsYield
for 18h; Heating;A n/a
B 75%
N,N'-ethylenethiourea
96-45-7

N,N'-ethylenethiourea

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid at 25℃; for 0.0166667h;73%
With potassium hydroxide; dihydrogen peroxide
N-(2-chloroethyl)urea
6296-42-0

N-(2-chloroethyl)urea

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With triethylamine In diethyl ether at 18 - 20℃; for 12h;70%
ethylenediamine
107-15-3

ethylenediamine

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

imidazolidone
120-93-4

imidazolidone

B

1-methyl-2-imidazolidone
694-32-6

1-methyl-2-imidazolidone

Conditions
ConditionsYield
Stage #1: ethylenediamine; carbonic acid dimethyl ester With aminosulfonic acid at 50℃; for 3h; Green chemistry;
Stage #2: at 160℃; for 15h; Green chemistry;
A 70%
B n/a
N-(2-formylaminoethyl)formamide
4938-92-5

N-(2-formylaminoethyl)formamide

ethylenediamine
107-15-3

ethylenediamine

A

imidazolidone
120-93-4

imidazolidone

B

N-(2-aminoethyl)formamide
69219-13-2

N-(2-aminoethyl)formamide

Conditions
ConditionsYield
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;A 67%
B 19%
4-(trifluoromethoxy)benzonitrile
332-25-2

4-(trifluoromethoxy)benzonitrile

ethylenediamine
107-15-3

ethylenediamine

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; Sealed tube;65%
2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

A

morpholine
110-91-8

morpholine

B

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In water at 1 - 95℃; for 15.5h; Temperature;A 54.4%
B 7.9%
N,N'-ethylenethiourea
96-45-7

N,N'-ethylenethiourea

A

2-imidazoline
504-75-6

2-imidazoline

B

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In methanol; acetone at 25℃;A 53%
B 15%
carbon monoxide
201230-82-2

carbon monoxide

ethylenediamine
107-15-3

ethylenediamine

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
Stage #1: carbon monoxide; ethylenediamine With potassium carbonate; sulfur In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 4h;
Stage #2: With oxygen In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 2h;
51%
With iodine; potassium carbonate; tungsten hexacarbonyl In dichloromethane at 20℃; under 60804.1 Torr; for 24h;40%
With iodine; potassium carbonate; tungsten hexacarbonyl In dichloromethane at 20℃; under 76005.1 Torr; for 24h;40%
With dichloro[2-(β-diphenylphosphinoethyl)pyridine]palladium(II); oxygen In water at 100℃; under 30003 Torr; for 4h; Autoclave; Green chemistry;90 %Chromat.
phenylmagnesium bromide

phenylmagnesium bromide

1-methoxycarbonyl-2-imidazolidinone
41730-78-3

1-methoxycarbonyl-2-imidazolidinone

A

imidazolidone
120-93-4

imidazolidone

B

benzophenone
119-61-9

benzophenone

C

triphenylmethyl alcohol
76-84-6

triphenylmethyl alcohol

D

1-benzoyl-2-imidazolidinone
27034-77-1

1-benzoyl-2-imidazolidinone

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Product distribution; Ambient temperature; other imidazolone substrates; var. ratios;A 22%
B 42%
C 15%
D 5%
N-(2-aminoethyl)formamide
69219-13-2

N-(2-aminoethyl)formamide

A

imidazolidone
120-93-4

imidazolidone

B

N-(2-formylaminoethyl)formamide
4938-92-5

N-(2-formylaminoethyl)formamide

Conditions
ConditionsYield
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;A 38%
B 19%
methanol
67-56-1

methanol

ethylenediamine
107-15-3

ethylenediamine

A

imidazolidone
120-93-4

imidazolidone

B

N-(2-aminoethyl)formamide
69219-13-2

N-(2-aminoethyl)formamide

Conditions
ConditionsYield
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;A 33%
B 18%
carbon monoxide
201230-82-2

carbon monoxide

ethylenediamine
107-15-3

ethylenediamine

A

2-imidazoline
504-75-6

2-imidazoline

B

imidazolidone
120-93-4

imidazolidone

C

N-β-aminoethylcarbamic acid
109-58-0

N-β-aminoethylcarbamic acid

Conditions
ConditionsYield
With tetracarbonyl nickel In ethanol at 160℃; for 18h;A 28%
B 10.6%
C 31.7%
With tetracarbonyl nickel In ethanol at 160℃; for 18h;A 28%
B 10.6%
C 31.7%
benzamide
55-21-0

benzamide

A

imidazolidone
120-93-4

imidazolidone

B

benzaldehyde
100-52-7

benzaldehyde

C

benzonitrile
100-47-0

benzonitrile

D

diphenyl acetylene
501-65-5

diphenyl acetylene

Conditions
ConditionsYield
With titanium In tetrahydrofuran for 20h; Heating;A 30%
B 12%
C 15%
D 5%
carbon dioxide
124-38-9

carbon dioxide

ethylenediamine
107-15-3

ethylenediamine

acetonitrile
75-05-8

acetonitrile

A

imidazolidone
120-93-4

imidazolidone

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h;A 27%
B n/a
carbon dioxide
124-38-9

carbon dioxide

ethylenediamine
107-15-3

ethylenediamine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

imidazolidone
120-93-4

imidazolidone

B

N-(2-formylaminoethyl)formamide
4938-92-5

N-(2-formylaminoethyl)formamide

Conditions
ConditionsYield
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h;A 13.8%
B n/a
methanol
67-56-1

methanol

ethylenediamine
107-15-3

ethylenediamine

imidazolidone
120-93-4

imidazolidone

Conditions
ConditionsYield
With (6-di-tert-butylphosphinomethyl-2,2’-bipyridyl)Ru(CO)HCl; potassium tert-butylate In 1,4-dioxane at 150℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;13%
imidazolidone
120-93-4

imidazolidone

1,3-dinitroimidazolidin-2-one
2536-18-7

1,3-dinitroimidazolidin-2-one

Conditions
ConditionsYield
With nitric acid100%
With dinitrogen pentoxide In carbon dioxide at 0 - 5℃; under 45004.5 - 60006 Torr; for 1h; liquid CO2;93%
With ammonium nitrate; trifluoroacetic anhydride In nitromethane Ambient temperature;41%
imidazolidone
120-93-4

imidazolidone

allyl alcohol
107-18-6

allyl alcohol

1,3-diallyl-2-imidazolidinone
33532-95-5

1,3-diallyl-2-imidazolidinone

Conditions
ConditionsYield
With silver hexafluoroantimonate; 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride In 1,4-dioxane at 60℃; for 24h; Inert atmosphere;100%
imidazolidone
120-93-4

imidazolidone

pyridin-2-yl tosylate
57785-86-1

pyridin-2-yl tosylate

1,3-di-(pyridin-2-yl)imidazolidin-2-one

1,3-di-(pyridin-2-yl)imidazolidin-2-one

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;99%
imidazolidone
120-93-4

imidazolidone

isobutyraldehyde
78-84-2

isobutyraldehyde

1,3-di(1-hydroxy-2-methylpropyl)-2-imidazolidinone

1,3-di(1-hydroxy-2-methylpropyl)-2-imidazolidinone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 15℃;98%
imidazolidone
120-93-4

imidazolidone

allyl bromide
106-95-6

allyl bromide

1,3-diallyl-2-imidazolidinone
33532-95-5

1,3-diallyl-2-imidazolidinone

Conditions
ConditionsYield
With sodium sulfite In tetrahydrofuran; methanol; hexane98%
imidazolidone
120-93-4

imidazolidone

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

[Co(2-imidazolidone)4(H2O)2]Cl2*2(2-imidazolidone)

[Co(2-imidazolidone)4(H2O)2]Cl2*2(2-imidazolidone)

Conditions
ConditionsYield
In acetone ligand was added to soln. of Co salt in acetone; mixt. was stirred for 5min; concd. (vac.); mixt. was stirred for 15 min; filtered; dried with hexane; elem. anal.;96%
imidazolidone
120-93-4

imidazolidone

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2-oxoimidazolidine-1-carbonyl chloride
13214-53-4

2-oxoimidazolidine-1-carbonyl chloride

Conditions
ConditionsYield
In tetrahydrofuran at 55 - 60℃; for 2h; chloroformylation;95.6%
imidazolidone
120-93-4

imidazolidone

N-Methoxymethylmonoaza-15-crown-5 ether
91043-70-8

N-Methoxymethylmonoaza-15-crown-5 ether

N,N'-(2-Oxotetrahydroimidazol-1,3-diyldimethyl)-bis
91043-74-2

N,N'-(2-Oxotetrahydroimidazol-1,3-diyldimethyl)-bis

Conditions
ConditionsYield
In tetrachloromethane for 3h; Heating;95%
imidazolidone
120-93-4

imidazolidone

1,12-dodecanedioic acid
693-23-2

1,12-dodecanedioic acid

poly[N,N-(1,10-decanedicarboxyl)-2-imidazolidone], Mw 22000, Mn 8100, DP 34; monomer(s): 1,10-decanedicarboxylic acid; 2-imidazolidone

poly[N,N-(1,10-decanedicarboxyl)-2-imidazolidone], Mw 22000, Mn 8100, DP 34; monomer(s): 1,10-decanedicarboxylic acid; 2-imidazolidone

Conditions
ConditionsYield
With 3,5-bis-trifluromethylphenylboronic acid In 1,3,5-trimethyl-benzene for 24h; Heating;95%
2-chloropyridine
109-09-1

2-chloropyridine

imidazolidone
120-93-4

imidazolidone

1,3-di-(pyridin-2-yl)imidazolidin-2-one

1,3-di-(pyridin-2-yl)imidazolidin-2-one

Conditions
ConditionsYield
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; palladium diacetate In 1,4-dioxane at 100℃; for 6h;95%
imidazolidone
120-93-4

imidazolidone

2-bromoanisole
578-57-4

2-bromoanisole

1,3-bis(2-methoxyphenyl)imidazolidin-2-one
1040129-85-8

1,3-bis(2-methoxyphenyl)imidazolidin-2-one

Conditions
ConditionsYield
With potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; copper(l) iodide In toluene for 24h; Goldberg-Buchwald-Nandakumar reaction; Heating;95%
imidazolidone
120-93-4

imidazolidone

acetyl iodide
507-02-8

acetyl iodide

1-acetylimidazolidin-2-one hydroiodide

1-acetylimidazolidin-2-one hydroiodide

Conditions
ConditionsYield
at 20 - 60℃; for 24h;95%
imidazolidone
120-93-4

imidazolidone

ethene
74-85-1

ethene

1,3-diethyl-imidazolidin-2-one
40424-21-3

1,3-diethyl-imidazolidin-2-one

Conditions
ConditionsYield
With 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride; silver trifluoromethanesulfonate In 1,4-dioxane at 100℃; under 6205.94 Torr; for 20h; Autoclave;95%
imidazolidone
120-93-4

imidazolidone

butyraldehyde
123-72-8

butyraldehyde

1,3-bis(1-hydroxybutyl)-2-imidazolidinone

1,3-bis(1-hydroxybutyl)-2-imidazolidinone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 15℃;94%
imidazolidone
120-93-4

imidazolidone

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

1,3-bis-(4-phenyl-butyryl)-imidazolidin-2-one

1,3-bis-(4-phenyl-butyryl)-imidazolidin-2-one

Conditions
ConditionsYield
With 3,5-bis-trifluromethylphenylboronic acid In 1,3,5-trimethyl-benzene for 23h; Heating;94%
imidazolidone
120-93-4

imidazolidone

formaldehyd
50-00-0

formaldehyd

tetramethylcucurbit[6]uril

tetramethylcucurbit[6]uril

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 0.5h;94%
imidazolidone
120-93-4

imidazolidone

1,2-diaminoethane dihydrochloride
333-18-6

1,2-diaminoethane dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 0.0333333h; microwave irradiation;94%
imidazolidone
120-93-4

imidazolidone

acetyl iodide
507-02-8

acetyl iodide

1,3-diacetylimidazolidin-2-one dihydroiodide

1,3-diacetylimidazolidin-2-one dihydroiodide

Conditions
ConditionsYield
at 20 - 65℃; for 24h;94%
imidazolidone
120-93-4

imidazolidone

phosgene
75-44-5

phosgene

2-oxoimidazolidine-1-carbonyl chloride
13214-53-4

2-oxoimidazolidine-1-carbonyl chloride

Conditions
ConditionsYield
In tetrahydrofuran at 10℃; for 3h;93%
In 1,2-dichloro-ethane at 70 - 75℃; for 1h;41.5 g
In tetrahydrofuran at 0℃; for 3h;
imidazolidone
120-93-4

imidazolidone

formaldehyd
50-00-0

formaldehyd

hemicucurbit[12]uril

hemicucurbit[12]uril

Conditions
ConditionsYield
With hydrogenchloride at 55℃; for 3h;93%
imidazolidone
120-93-4

imidazolidone

chloromethyl trimethyl benzene
51958-58-8

chloromethyl trimethyl benzene

epichlorohydrin
106-89-8

epichlorohydrin

N,N'-bis(glycidyl)-ethyleneurea
15336-78-4

N,N'-bis(glycidyl)-ethyleneurea

Conditions
ConditionsYield
With sodium hydroxide93%
imidazolidone
120-93-4

imidazolidone

3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-iodophenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester
1208318-04-0

3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-iodophenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester

3-[1-(4-carbamoyl-2-methylphenyl)-5-[4-(2-oxo-imidazolidin-1-yl)phenyl]-1H-pyrrol-2-yl]propionic acid ethyl ester
1208318-17-5

3-[1-(4-carbamoyl-2-methylphenyl)-5-[4-(2-oxo-imidazolidin-1-yl)phenyl]-1H-pyrrol-2-yl]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: imidazolidone; 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-iodophenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester With potassium phosphate; copper(l) iodide; N,N-dimethylethylenediamine In N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave irradiation; Inert atmosphere;
Stage #2: imidazolidone With copper(l) iodide In N,N-dimethyl-formamide at 130℃; for 0.333333h; Microwave irradiation; Inert atmosphere;
93%
With copper(l) iodide; potassium phosphate tribasic trihydrate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 120 - 130℃; for 0.666667h; Inert atmosphere; Microwave irradiation; Sealed tube;93%
imidazolidone
120-93-4

imidazolidone

1,3-dinitroso-imidazolidin-2-one
54850-18-9

1,3-dinitroso-imidazolidin-2-one

Conditions
ConditionsYield
With dinitrogen tetroxide impregnated on activated charcoal In dichloromethane at 20℃; for 4.33333h;92%
With cross-linked polyvinylpyrrolidone*N2O4; dinitrogen tetraoxide In dichloromethane at 20℃; for 4h;90%
With nitric acid; sodium nitrite
imidazolidone
120-93-4

imidazolidone

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

1,3-bis(3'-methoxyphenyl)-2-imidazolidone

1,3-bis(3'-methoxyphenyl)-2-imidazolidone

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 44h;92%
imidazolidone
120-93-4

imidazolidone

1-chloro-2-formyl-3,4-dihydronaphthalene
3262-03-1

1-chloro-2-formyl-3,4-dihydronaphthalene

1,3-bis(3',4'-dihydro-2'-formylnaphthyl)-2-imidazolidone

1,3-bis(3',4'-dihydro-2'-formylnaphthyl)-2-imidazolidone

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate In toluene at 90℃; Buchwald-Hartwig amination;92%
imidazolidone
120-93-4

imidazolidone

para-bromotoluene
106-38-7

para-bromotoluene

1,3-di-4-tolylimidazolidin-2-one
5584-36-1

1,3-di-4-tolylimidazolidin-2-one

Conditions
ConditionsYield
With potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; copper(l) iodide In toluene for 24h; Goldberg-Buchwald-Nandakumar reaction; Heating;92%
imidazolidone
120-93-4

imidazolidone

7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylic acid tert-butyl ester
258515-65-0

7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylic acid tert-butyl ester

C17H23N3O3

C17H23N3O3

Conditions
ConditionsYield
With copper(l) iodide; potassium tert-butylate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In N,N-dimethyl-formamide at 120℃;92%

120-93-4Relevant articles and documents

-

Naumov et al.

, (1973)

-

-

Staudinger,Niessen

, p. 75,87 (1955)

-

Kinetics and mechanism for CO2 scrambling in a N-carboxyimidazolidone analogue for N1-carboxybiotin

Lihs, Fiona J.,Caudle, M. Tyler

, p. 11334 - 11341 (2002)

The N-carboxyimidazolidone anion, 2-, was prepared as an analogue for N1-carboxybiotin, and the kinetics of its CO2-dependent chemistry were studied in polar aprotic media. The objective was to assess the viability of unimolecular CO2 elimination from N1-carboxybiotin as a microscopic step in biotin-dependent carboxyl transfer enzymes. The anionic 2- was prepared as its lithium salt by first deprotonating 2-imidazolidone with phenyllithium, followed by direct reaction with carbon dioxide. This procedure also permitted isolation of the 13C enriched derivative 2-{13C} by reaction with 13 CO2. Proton and 13C NMR and isotope-dependent FTIR measurements confirmed that carboxylation had occurred at the nitrogen atom of 2-imidazolidone to give 2-. Time-dependent FTIR spectroscopy showed that Li2 undergoes carboxyl exchange with free carbon dioxide, with kinetics indicative of rate-limiting unimolecular dissociation of the N-CO2 bond. Under these conditions, the weak Lewis acid Mg2+ catalyses the exchange of 2- with free CO2, which appears to be related to the ability of the metal ion to coordinate to 2-. Reaction of Li2 with carboxylic acids in DMSO results in acid-dependent decarboxylation of 2- with a rate that is dependent on the concentration of the acid and its pKa. A common mechanistic framework is presented for both Lewis acid catalyzed carboxyl exchange and acid-dependent decarboxylation that involves initial interaction at the carbonyl oxygen and which has the effect of polarizing the nitrogen lone pair toward the imidazolidone ring rather than the carboxyl group. Lewis acid interaction with the carbonyl oxygen thus weakens the N-CO2- bond and functions as a trigger for dissociation of CO2. In the context of biotin-dependent enzymes, this suggests a means by which the kinetically stable N1-carboxybiotin cofactor intermediate might be triggered for dissociation of CO2.

ALKALINE HYDROLYSIS OF N-NITROSO-2-IMIDAZOLIDONE

Castro, Albino,Leis, J. Ramon,Pena, M. Elena,Tato, Jose Vazquez

, p. 117 - 122 (1986)

The hydrolysis of N-nitroso-2-imidazolidone has been studied kinetically between pH 8.3 and 12.6.This nitroso compound has an acid-base equilibrium whose constant has been determined spectrophotometrically (pKa 11.45).Only the acid form is reactive.At pH - and is subject to general base catalysis.These results are interpreted in terms of a mechanism involving an initial steady-state hydrate whose decomposition by base leads to the final products.At pH > 10 reaction paths of orders one and two in OH- appear.The second-order term reflects general base catalysis superimposed on a first-order term in OH- (the bases dimethylamine, sarcosine, piperidine, and HPO42- have been used).The results are interpreted by an initial OH- attack on the carbonyl group of the nitroso compound to give an intermediate which in the rate-controlling step reacts with bases, among them water (which explains the first-order term with respect to OH-).The low value of the Broensted relation (β ca.O) and the fact that the intermediate possesses no proton yielding a low pKa value suggest that there is inverse classical general base catalysis.

-

Schweitzer

, p. 471,472 (1950)

-

CO2-Fixation on Aliphatic α,ω-Diamines to Form Cyclic Ureas, Catalyzed by Ceria Nanoparticles that were Obtained by Templating with Alginate

Primo, Ana,Aguado, Eric,Garcia, Hermenegildo

, p. 1020 - 1023 (2013)

Ceria nanoparticles (average particle size: 8nm) have been obtained by the calcination of alginate aerogel beads that were precipitated from aqueous solutions of (NH4)2Ce(NO3)6. These nanoparticles were considerably more active as a catalyst for CO2-insertion into aliphatic α,ω-diamines than the analogous commercial CeO2 with larger particle size (40nm). CeO2 that was obtained by templating with the natural alginate biopolymer afforded the cyclic urea of ethylenediamine in EtOH solvent at 160°C in 37% yield. This yield is remarkable for a process that involves CO2 as a feedstock. Other α,ω-diamines, such as diethylenetriamine, N,N′-dimethylethylenediamine, N-(2-aminoethyl)acetamide, and 1,4-diaminobutane, also formed their corresponding cyclic ureas in 4-36% yield. The catalyst lost activity upon reuse, thereby leading to severe deactivation that was only partially recovered by washing with aqueous acidic solutions.

Efficient and Green Preparation of 2-Imidazolidinone using Sulfamic Acid as Acidic Catalyst

Liu, Jianshe,Xie, Yaqiang,Ye, Liyi,Yan, Huidong,Tu, Song

, p. 453 - 456 (2014)

-

-

McKay et al.

, p. 3205 (1950)

-

Weinberger,McKay

, p. 1321 (1955)

SBA-15 Supported Dendritic ILs as a Green Catalysts for Synthesis of 2-Imidazolidinone from Ethylenediamine and Carbon Dioxide

Liu, Jinghan,Ma, Jianjun,Miao, Penghua,Min, Qingwang,Qi, Meijuan,Shamsa, Farzaneh

, (2021/07/26)

In this work, a simple and facile approach is conducted for preparing many new SBA-15 supported dendritic imidazolium ILs heterogeneous catalysts SBA-15/IL(1–3) having high ionic density from SBA-15. SBA-15/IL(3) as a green heterogeneous catalyst can be used for synthesis of 2-imidazolidinone from ethylenediamine and carbon dioxide and considering solvent-free condition. SBA-15/IL(3) showed to have the highest catalytic activity besides a positive dendritic influence on the yields of the synthesis of 2-imidazolidinone in the presence of CO2 is seen because of existing the high-density peripheral zwitterionic ionic liquid functional groups on the biobased SBA-15/IL(3) catalyst surfaces. Graphical Abstract: [Figure not available: see fulltext.]

Rational design of bifunctional catalyst from KF and ZnO combination on alumina for cyclic urea synthesis from CO2 and diamine

John, Crowny,Kulal, Nagendra,Shanbhag, Ganapati V.

, (2020/04/22)

This study is mainly focused on the design of stable, active and selective catalyst for direct synthesis of 2-imidazolidinone (cyclic urea) from ethylenediamine and CO2. Based on the rationale for the catalyst properties needed for this reaction, KF, ZnO and Al2O3 combination was selected to design the catalyst. ZnO/KF/Al2O3 catalyst was prepared by stepwise wet-impregnation followed by the removal of physisorbed KF from the surface. High product yield could be achieved by tuning acid-base sites by varying the composition and calcination temperature. The catalysts were characterized by various techniques like XRD, N2-sorption, NH3-TPD, CO2-TPD, TEM, XPS and FT-IR measurements. It is shown that acidic and basic properties of the solvent can influence the activity and product selectivity for this reaction. Under optimized condition; 180 °C, 10 bar and 10 wt.% catalyst in batch mode, 96.3 % conversion and 89.6 % selectivity towards the 2-imidazolidinone were achieved.

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