504-75-6

Basic information

• Product Name: 4,5-dihydro-1H-imidazole
• Synonyms: 4,5-dihydro-1H-imidazole;2-imidazoline
• CAS NO: 504-75-6
• Molecular Formula: C₃H₆N₂
• Molecular Weight: 70.09314
• EINECS: 207-999-4
• Mol File: 504-75-6.mol
• Article Data: 27

Chemical Properties

• Melting Point: 55°C
• Boiling Point: 111.55°C (rough estimate)
• Flash Point: 86.3°C
• Appearance: /
• Density: 0.8304 (rough estimate)
• Vapor Pressure: 0.122mmHg at 25°C
• Refractive Index: 1.4796 (estimate)
• PKA: 10.90±0.40(Predicted)
• CAS DataBase Reference: 4,5-dihydro-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-dihydro-1H-imidazole(504-75-6)
• EPA Substance Registry System: 4,5-dihydro-1H-imidazole(504-75-6)

Safety Data

• Hazardous Substances Data: 504-75-6(Hazardous Substances Data)

Usage

Uses

4,5-Dihydro-1H-imidazole possesses inhibition effect on the crevice corrosion of N80 carbon steel; Also, it is derived from Formamide (F691480), which is a compound that is used in biochemistry to prevent RNA samples from degradation due to RNAses. Formamide is also used as a plasticizer to prepare thermoplastic starch (TPS), a special type of starch that can be mixed with other synthetic polymers because of its unique ability to “flow”.

Definition

ChEBI: An imidazoline compound having the double bond at the 2-position.

InChI:InChI=1/C3H6N2/c1-2-5-3-4-1/h3H,1-2H2,(H,4,5)

Synthetic route

N,N'-ethylenethiourea (96-45-7) → 2-imidazoline (504-75-6) + imidazolidone (120-93-4)

Conditions	Yield
With 3,3-dimethyldioxirane In methanol; acetone at 25℃;	A 53% B 15%

carbon monoxide (201230-82-2) + ethylenediamine (107-15-3) → 2-imidazoline (504-75-6) + imidazolidone (120-93-4) + N-β-aminoethylcarbamic acid (109-58-0)

Conditions	Yield
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%

1,3,5-Triazine (290-87-9) + ethylenediamine (107-15-3) → 2-imidazoline (504-75-6)

N,N'-ethylenethiourea (96-45-7) → 2-imidazoline (504-75-6) + imidazolidone (120-93-4) + 4,5-dihydro-1H-imidazole-2-sulfonic acid (64205-92-1)

Conditions	Yield
With dihydrogen peroxide; trifluoroacetic acid at 25℃;

2-imidazoline (504-75-6) + N-butyl-2-iodobenzamide → C14H17N3O (1362191-54-5) + C14H15N3O (1362191-28-3)

Conditions	Yield
Stage #1: 2-imidazoline; N-butyl-2-iodobenzamide With caesium carbonate; L-proline In dimethyl sulfoxide for 0.333333h; Ullmann reaction; Inert atmosphere; Stage #2: With copper(l) iodide In dimethyl sulfoxide at 120℃; for 12h; Ullmann reaction; Inert atmosphere;	A 88% B n/a

2-imidazoline (504-75-6) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → cis-tetracarbonylbis(2-imidazoline-N)molybdenum(0) (64121-72-8) + fac-tricarbonyltris(2-imidazoline-N)molybdenum(0) (64121-75-1)

Conditions	Yield
In toluene byproducts: CO; N2-atmosphere; 3 equiv. of imidazoline, 100°C, 10 min (pptn.); filtration, washing (Et2O), drying (vac.); elem. anal.; bis(imidazoline)-complex from filtrate;	A 20% B 75%

2-imidazoline (504-75-6) + 2-methyl-5-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine (177662-53-2) → 2-methyl-5-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine (177660-80-9)

Conditions	Yield
With p-toluenesulfonic acid monohydrate In ethyl acetate; acetone; toluene	66%

thirane (420-12-2) + 2-imidazoline (504-75-6) → 2-imidazolinylethanethiol

Conditions	Yield
In toluene for 48h; Heating;	62%

2-imidazoline (504-75-6) + di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium (12092-47-6) → chloro(cyclo-octa-1,5-diene)(2-imidazoline-N)rhodium(I) (67012-40-2)

Conditions	Yield
In toluene N2-atmosphere; stoich. amts., refluxing for 1 h; crystn. (-20°C), addn. of hexane, collection (filtration), washing (Et2O), drying (vac.); elem. anal.;	55%

2-imidazoline (504-75-6) + 4-[4-hydroxy-1-[4-(methylsulfonyl) phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine (177662-51-0) → 4-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (177660-79-6)

Conditions	Yield
With p-toluenesulfonic acid monohydrate In ethyl acetate; acetone; toluene	41%

2-imidazoline (504-75-6) + 7-methoxy-1H-isochromene-1,3(4H)-dione (4702-29-8) → (10R,10aR)-1-[2-(2-Carboxy-4-methoxy-phenyl)-acetyl]-7-methoxy-5-oxo-1,2,3,5,10,10a-hexahydro-imidazo[1,2-b]isoquinoline-10-carboxylic acid

Conditions	Yield
In acetonitrile at 0℃; for 2h;

2-imidazoline (504-75-6) + 4-(4-fluorophenoxy)benzonitrile (215589-24-5) → 2-[4-(4-Fluorophenoxy)phenyl]-1H-imidazole (299206-79-4)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; p-toluenesulfonic acid monohydrate; ethylenediamine; palladium-carbon In methanol; ethylene glycol; ethyl acetate; toluene

2-imidazoline (504-75-6) + 4-ethylphenacyl bromide (2632-14-6) → 1-(4-ethylphenyl)-2-imidazolylethan-1-one (1094655-78-3)

Conditions	Yield
In acetonitrile

2-imidazoline (504-75-6) + CH3 + triethylamine (121-44-8) → 1H-imidazole (288-32-4)

Conditions	Yield
With manganese dioxide In dichloromethane; chloroform	370 mg (76%)
With manganese dioxide In dichloromethane; chloroform	370 mg (76%)

2-imidazoline (504-75-6) + 4-[2-Imidazolin-2-yl]-6-(2-chlorophenyl)-2,3,4,5-tetrahydro-8H-[1]benzothieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + methyl iodide (74-88-4) → 4-[1-Methyl-2-imidazolin-2-yl]-6-(2-chlorophenyl)-2,3,4,5-tetrahydro-8H-[1]benzothieno[3,2-f][1,2,4]triazolo [4,3-a][1,4]diazepine

Conditions	Yield
In tetrahydrofuran

2-imidazoline (504-75-6) + 3-methyl-6-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine (189297-36-7) → 5-methyl-2-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (177660-82-1)

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene

2-imidazoline (504-75-6) + amoxicillin (26787-78-0) → N-[6-[[2-(acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinylcarbonyl]amoxicillin

Conditions	Yield
With sodium hydroxide; triethylamine In N,N-dimethyl acetamide; water

2-imidazoline (504-75-6) → 1-acetyl-2-imidazoline (87604-75-9)

Conditions	Yield
In ethanol; acetic anhydride
In ethanol; acetic anhydride
In ethanol; acetic anhydride

Upstream product

• 96-45-7 N,N'-ethylenethiourea 
• 201230-82-2 carbon monoxide 
• 107-15-3 ethylenediamine 
• 290-87-9 1,3,5-Triazine 

Downstream Products

• 1362191-54-5 C₁₄H₁₇N₃O 
• 1362191-28-3 C₁₄H₁₅N₃O 
• 177660-82-1 5-methyl-2-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine 
• 177660-80-9 2-methyl-5-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine 
• 177660-79-6 4-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine 
• 288-32-4 1H-imidazole 
• 1094655-78-3 1-(4-ethylphenyl)-2-imidazolylethan-1-one 
• 299206-79-4 2-[4-(4-Fluorophenoxy)phenyl]-1H-imidazole 

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