54255-11-7

Basic information

• Product Name: 1H-IMidazole, 2-chloro-4,5-dihydro-
• Synonyms: 1H-IMidazole, 2-chloro-4,5-dihydro-
• CAS NO: 54255-11-7
• Molecular Formula: C₃H₅ClN₂
• Molecular Weight: 104.5382
• Mol File: 54255-11-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 141.4°Cat760mmHg
• Flash Point: 39.3°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 5.85mmHg at 25°C
• Refractive Index: 1.613
• PKA: 7.19±0.40(Predicted)
• CAS DataBase Reference: 1H-IMidazole, 2-chloro-4,5-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-IMidazole, 2-chloro-4,5-dihydro-(54255-11-7)
• EPA Substance Registry System: 1H-IMidazole, 2-chloro-4,5-dihydro-(54255-11-7)

Safety Data

• Hazardous Substances Data: 54255-11-7(Hazardous Substances Data)

Usage

General Description

1H-Imidazole, 2-chloro-4,5-dihydro- is a chemical compound with the molecular formula C3H5ClN2. It is a derivative of imidazole, a five-membered ring containing two nitrogen atoms. The addition of a chloro group to the 2nd position and a dihydro group to the 4th and 5th positions results in a compound that is commonly utilized in the synthesis of pharmaceuticals and agrochemicals. It is also used in the production of certain functional materials and as a reagent in chemical reactions. The compound's properties and structure make it a valuable building block for the creation of various complex organic molecules.

InChI:InChI=1/C3H5ClN2/c4-3-5-1-2-6-3/h1-2H2,(H,5,6)

Synthetic route

imidazolidone (120-93-4) → 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7)

Conditions	Yield
With phosphorus pentachloride In acetonitrile at 20℃; for 72h;	55%
With triethylamine; Dimethyl chlorophosphate In dichloromethane at 35℃; for 5h;

imidazolidone (120-93-4) + chlorophosphoric acid diphenyl ester (2524-64-3) → tetraphenyl pyrophosphate (10448-49-4) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 35℃; for 0.0666667h;

2-Chloro-4,5-dihydro-1H-imidazole sulfate (54255-12-8) → 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0℃;
With sodium hydroxide In water Cooling with ice;

N,N'-ethylenethiourea (96-45-7) → 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7)

Conditions	Yield
With chlorine In water at 45℃; for 2.5h;

isopropylamine (75-31-0) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → (4,5-dihydro-1H-imidazol-2-yl)-isopropyl-amine

Conditions	Yield
In dichloromethane	97%

4-[(4-methoxyphenyl)thio]benzenamine (14453-85-1) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → (4,5-dihydro-1H-imidazol-2-yl)-[4-(4-methoxyphenylsulfanyl)phenyl]amine hydrochloride

Conditions	Yield
In 2-methyl-propan-1-ol for 2h; Heating / reflux;	96%

2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 1,2,4,5-Tetrahydro-12bH-3,3b,6,6b,12c-pentaaza-dicyclopenta[a,c]phenanthrene (77737-90-7)

Conditions	Yield
With potassium carbonate at 5℃;	95%

aniline (62-53-3) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → N-phenyl-N-(4,5-dihydro-1H-imidazol-2-yl)amine (1848-75-5)

Conditions	Yield
In dichloromethane	95%

benzylamine (100-46-9) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → benzyl-(4,5-dihydro-1H-imidazol-2-yl)-amine (38941-36-5)

Conditions	Yield
In dichloromethane	95%

2,4-Dimethoxyaniline (2735-04-8) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → (4,5-dihydro-1H-imidazol-2-yl)-(2,4-dimethoxy-phenyl)-ammonium chloride

Conditions	Yield
In dichloromethane	94%

4-(4-(4-fluorobutoxy)benzyl)aniline + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → N-(4-(4-(4-fluorobutoxy)benzyl)phenyl)-4,5-dihydro-1H-imidazol-2-amine

Conditions	Yield
In isopropyl alcohol at 80 - 85℃; for 2h; Sealed tube;	90%

1H-imidazole (288-32-4) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → C6H9N4(1+)*Cl(1-)

Conditions	Yield
With propionaldehyde In dichloromethane for 1h; Ambient temperature;	88%

3-(4-Aminophenyl)-1-(4-morpholin-4-ylphenyl)-propan-1-one (427897-17-4) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 3-[4-(4,5-dihydro-1H-imidazol-2-yl-amino)-phenyl]-1-(4-morpholin-4-yl-phenyl)-propan-1-one

Conditions	Yield
In dichloromethane	88%

4-(4-isopropoxybenzyl)-3-(trifluoromethyl)aniline + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → N-(4-(4-isopropoxybenzyl)-3-(trifluoromethyl)phenyl)-4,5-dihydro-1H-imidazol-2-amine

Conditions	Yield
In isopropyl alcohol at 85℃; Inert atmosphere;	86%

1,2,4-Triazole (288-88-0) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 4-(4,5-dihydroimidazol-2-yl)triazole hydrochloride + C5H8N5(1+)*Cl(1-)

Conditions	Yield
With propionaldehyde In dichloromethane for 1h; Ambient temperature;	A 5% B 85%

1,2,3-Benzotriazole (95-14-7) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-(4,5-dihydro-1H-imidazol-2-yl)benzotriazole hydrochloride

Conditions	Yield
With acetaldehyde In dichloromethane for 0.0833333h; Ambient temperature;	85%

malononitrile (109-77-3) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 6-(2,3,4,5-tetrahydroimidazol-2-ylideneammonio)hexa-1,3,5-triene-1,1-dicarbonitrile chloride (112392-13-9)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 0.5h;	83%

benzoimidazole (51-17-2) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → C10H11N4(1+)*Cl(1-)

Conditions	Yield
With propionaldehyde In dichloromethane for 1h; Ambient temperature;	80%

7-methoxy-1H-indazole (133841-05-1) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-(4,5-dihydro-1H-imidazol-2-yl)-7-methoxy-2H-indazol hydrochloride

Conditions	Yield
With carbon disulfide In dichloromethane at 20℃; for 6h;	77%

1-(4-amino-2-fluorobenzyl)-4-isopropoxypyridin-2(1H)-one + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 1-(4-((4,5-dihydro-1H-imidazol-2-yl)amino)-2-fluorobenzyl)-4-isopropoxypyridin-2(1H)-one

Conditions	Yield
In isopropyl alcohol at 85℃; Sealed tube; Inert atmosphere;	77%

1-(4-aminobenzyl)-4-isopropoxypyridin-2(1H)-one + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 1-(4-((4,5-dihydro-1H-imidazol-2-yl)amino)benzyl)-4-isopropoxypyridin-2(1H)-one

Conditions	Yield
In isopropyl alcohol at 85℃; Sealed tube; Inert atmosphere;	76%

NH-pyrazole (288-13-1) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → C6H9N4(1+)*Cl(1-)

Conditions	Yield
With propionaldehyde In dichloromethane for 1h; Ambient temperature;	71%

2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-hydroxylamino-4,5-dihydroimidazolium-O-sulfonate (562075-24-5)

Conditions	Yield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water at 20℃; for 12h;	69%

3-fluoro-4-(4-isopropoxybenzyl)aniline + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → N-(3-fluoro-4-(4-isopropoxybenzyl)phenyl)-4,5-dihydro-1H-imidazol-2-amine

Conditions	Yield
In isopropyl alcohol at 85℃; Inert atmosphere;	68.8%

dmap (1122-58-3) + malononitrile (109-77-3) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → <2-(2,3-Dihydroimidazo<1,2-a>pyrimidin-5(1H)-ylidene)ethylidene>propanedinitrile (135504-87-9)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	68%

benzimidazole (271-44-3) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-(4,5-dihydro-1H-imidazol-2-yl)-1H-indazole hydrochloride

Conditions	Yield
With carbon disulfide In dichloromethane at 20℃; for 6h;	67%

4-methyl-1H-indazole (3176-63-4) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-(4,5-dihydro-1H-imidazol-2-yl)-4-methyl-2H-indazol hydrochloride

Conditions	Yield
With carbon disulfide In dichloromethane at 20℃; for 6h;	67%

phenyl isocyanate (103-71-9) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 5-Phenyl-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one (112392-03-7)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 0.5h;	65%

2-(3,4,5-trimethoxyphenoxy)aniline (74864-74-7) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-<2-(3,4,5-trimethoxyphenoxy)phenylimino>imidazolidine (76840-95-4)

Conditions	Yield
With carbon disulfide In dichloromethane for 3h;	65%

7-methylindazole (3176-66-7) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-(4,5-dihydro-1H-imidazol-2-yl)-7-methyl-2H-indazol hydrochloride

Conditions	Yield
With carbon disulfide In dichloromethane at 20℃; for 6h;	65%

6-methoxyquinoline N-oxide (6563-13-9) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 1-(6-methoxy-2-quinolyl)imidazolidin-2-one

Conditions	Yield
In dichloromethane at 20℃; for 12h;	65%

pyridine-2-carboxaldehyde methylhydrazone (5771-00-6) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → C10H13N5*ClH (1227298-90-9)

Conditions	Yield
In dichloromethane at 20 - 22℃; for 2h;	64%

1-isocyanato-3-trifluoromethyl-benzene (329-01-1) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 5-(3-Trifluoromethyl-phenyl)-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one (112392-06-0)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 0.5h;	63%

6-methyl-1H-indazole (698-24-8) + 2-chloro-4,5-dihydro-1H-imidazole (54255-11-7) → 2-(4,5-dihydro-1H-imidazol-2-yl)-6-methyl-2H-indazol hydrochloride

Conditions	Yield
With carbon disulfide In dichloromethane at 20℃; for 6h;	63%

Upstream product

• 120-93-4 imidazolidone 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 54255-12-8 2-Chloro-4,5-dihydro-1H-imidazole sulfate 
• 96-45-7 N,N'-ethylenethiourea 

Downstream Products

• 55107-60-3 3-(4,5-Dihydro-1H-imidazol-2-ylsulfanyl)-1H-indole; hydrochloride 
• 112418-16-3 5-(4-Chloro-phenyl)-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one 
• 112392-03-7 5-Phenyl-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one 
• 112392-04-8 5-(4-Methoxy-phenyl)-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one 
• 112392-05-9 5-(3-Chloro-phenyl)-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one 
• 112392-06-0 5-(3-Trifluoromethyl-phenyl)-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one 
• 112418-15-2 5-(3-Methoxy-phenyl)-2,3,5,5a-tetrahydro-1,3a,5,9a-tetraaza-cyclopenta[a]naphthalen-4-one 

Relevant articles and documents

C-N Bond forming reactions in the synthesis of substituted 2-aminoimidazole derivatives

Carbon-nitrogen bond forming reactions oriented to the synthesis of 2-amino-imidazolidines and imidazoles have been investigated. The C-2 amination of imidazolidinones, via the corresponding 2-chlorodihydroimidazoles, led to 2-benzylaminodihydroimidazole or bis(dihydroimidazole)amino derivatives by choosing the adequate experimental conditions. On the other hand, the use of N-acyl-2-methylsulfanyldihydroimidazoles allowed carrying out the reactions with aromatic amines, such as p-anisidine. Finally, palladium catalyzed Buchwald- Hartwig amination was the method of choice for C-N coupling between 2-haloimidazoles and aromatic amines in the synthesis of the corresponding imidazoles.

COMPOUNDS AND METHODS FOR THE RAPID QUANTITATIVE ANALYSIS OF PROTEINS AND POLYPEPTIDES

A polypeptide reactive reagent having the formula PRG-Z wherein "PRG" is a polypeptide reactive group which optionally binds to a capture reagent, and wherein "Z" is an aryl, substituted aryl, alkyl, substituted alkyl, lower alkyl or substituted lower alkyl group in which one or more atoms can be differentially labeled with one or more stable isotopes "X", wherein "X" is selected from the group consisting of H and D, is described.

Efficient synthesis of 2-(N-Substituted)-2-imidazolines and 2-(N-Substituted)-1,4,5, 6-tetrahydropyrimidines

A general method for the preparation of 2-(N-Substituted)-2-imidazolines and 2-(N-Substituted)-1,4,5,6-tetrahydropyrimidines is described. These heterocycles can be synthesized from their respective anilines with 2-chloro-2-imidazoline or 2-chloro-1,4,5,6-tetrahydropyrimidine, generated in situ from imidazolidin-2-one and tetrahydropyrimidin-2(1H)-one activated by dimethyl chlorophosphate, in good to excellent yields. Copyright Taylor & Francis, Inc.