551-92-8

Basic information

• Product Name: 1,2-Dimethyl-5-nitroimidazole
• Synonyms: DIMETRIDAZOLE;1,2-dimethyl-5-nitro-1h-imidazole;1,2-DIMETHYL-5-NITROIMIDAZOLE;TIMTEC-BB SBB006915;1,2-dimethy-5-nitroimidazole;1,2-dimethyl-5-nitro-1h-imidazol;1,2-dimethyl-5-nitro-imidazol;1H-Imidazole, 1,2-dimethyl-5-nitro-
• CAS NO: 551-92-8
• Molecular Formula: C₅H₇N₃O₂
• Molecular Weight: 141.13
• EINECS: 209-001-2
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;nitro-compound;EMTRYL;Broad spectrum peptides anaerobic bacteria and drug resistance;Pharmaceutical intermediates
• Mol File: 551-92-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 177-182°C
• Boiling Point: 258.15°C (rough estimate)
• Flash Point: 143.5 °C
• Appearance: white to yellow with a green cast/Crystalline Powder
• Density: 1.3818 (rough estimate)
• Vapor Pressure: 0.000901mmHg at 25°C
• Refractive Index: 1.6190 (estimate)
• Storage Temp.: 2-8°C
• Solubility: ethanol: soluble50mg/mL
• PKA: 2.81±0.25(Predicted)
• Water Solubility: 9.69g/L(20 oC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,3265
• BRN: 130665
• CAS DataBase Reference: 1,2-Dimethyl-5-nitroimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dimethyl-5-nitroimidazole(551-92-8)
• EPA Substance Registry System: 1,2-Dimethyl-5-nitroimidazole(551-92-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37-22
• WGK Germany: 3
• RTECS: NI5075000
• Hazardous Substances Data: 551-92-8(Hazardous Substances Data)

Usage

Chemical Properties

solid

InChI:InChI=1/C5H7N3O2/c1-4-6-3-5(7(4)2)8(9)10/h3H,1-2H3

Synthetic route

2-methyl-5-nitro-1H-imidazole (696-23-1) + dimethyl sulfate (77-78-1) → dimetridazole (551-92-8)

Conditions	Yield
With formic acid for 4h; Reflux;	87%

2-bromomethyl-1-methyl-5-nitroimidazole (117836-28-9) → dimetridazole (551-92-8)

Conditions	Yield
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In toluene for 5h; Mechanism; Irradiation;	63%

3-(1-Methyl-5-nitro-1H-imidazol-2-yl)-2-oxo-propionic acid; hydrochloride → dimetridazole (551-92-8) + 2-(chloromethyl)-1-methyl-5-nitroimidazole (6905-07-3)

Conditions	Yield
With sodium perborate; acetic acid for 14h; Ambient temperature;	A 35% B 25%

1,2-dimethyl-1H-imidazole (1739-84-0) → 1,2-dimethyl-4-nitro-1H-imidazole (13230-04-1) + dimetridazole (551-92-8)

Conditions	Yield
With sulfuric acid; nitric acid anfangs bei 0grad, dann bei 100grad;

2-methyl-5-nitro-1H-imidazole (696-23-1) + dimethyl sulfate (77-78-1) → 1,2-dimethyl-4-nitro-1H-imidazole (13230-04-1) + dimetridazole (551-92-8)

2-methyl-4-nitro-1H-imidazole (696-23-1) + dimethyl sulfate (77-78-1) → 1,2-dimethyl-4-nitro-1H-imidazole (13230-04-1) + dimetridazole (551-92-8)

(1-Methyl-5-nitro-1H-imidazol-2-yl)-acetic acid (175733-75-2) → dimetridazole (551-92-8)

Conditions	Yield
at 110℃;

1,2-dimethyl-1H-imidazole (1739-84-0) + HNO3+H2SO4 → 1,2-dimethyl-4-nitro-1H-imidazole (13230-04-1) + dimetridazole (551-92-8)

Conditions	Yield
beim Nitrieren;

2-methyl-5-nitro-1H-imidazole (696-23-1) → dimetridazole (551-92-8)

Conditions	Yield
With acetic acid; dimethyl sulfate In water

dimetridazole (551-92-8) + 2-chloroethanesulfonyl fluoride (762-70-9) → C7H11FN3O4S(1+)*Cl(1-)

Conditions	Yield
In ethyl acetate for 2h; Menshutkin Reaction; Reflux;	100%

dimetridazole (551-92-8) → 1,2-dimethyl-4-nitro-1H-imidazole (13230-04-1)

Conditions	Yield
With methyl iodide In various solvent(s) at 156℃; for 48h;	97%
With methyl iodide In various solvent(s) at 156℃; for 48h; Product distribution; Mechanism; variation of reagents, solvent, reaction time, and temperature;;	97%

dimetridazole (551-92-8) + 2,4,6-Trinitrophenol (88-89-1) → 1,2-dimethyl-5-nitroimidazolium picrate (24647-68-5)

Conditions	Yield
In ethanol; water at 40℃; for 10h;	92%

dimetridazole (551-92-8) + benzoyl chloride (98-88-4) → (Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-phenylvinylbenzoate (1448622-21-6)

Conditions	Yield
With triethylamine In acetone at 20℃; for 4h; Cooling with ice;	92%

dimetridazole (551-92-8) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → 5-nitro-1-methyl-2-(2-dimethylaminovinyl)-imidazole (57434-36-3)

Conditions	Yield
With trifluoroacetic acid In N,N-dimethyl-formamide at 100℃; for 12h; Condensation;	91%

dimetridazole (551-92-8) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 5-[2,2-bis(ethoxycarbonyl)-1-vinylamino]-1,2-dimethylimidazole (145837-15-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In 1,4-dioxane	86%
Pd on carbon In 1,4-dioxane; hydrogenchloride; hydrogen
With hydrogen; 5%-palladium/activated carbon In 1,4-dioxane under 1810.07 - 2068.65 Torr; for 29h;

dimetridazole (551-92-8) + cobalt(II) chloride hexahydrate → bis(1,2-dimethyl-5-nitro-imidazole)cobalt(II) chloride (195046-62-9)

Conditions	Yield
In methanol stoichiometric ratio, refluxing (30 min); concn., crystn.; elem. anal.;	85%

dimetridazole (551-92-8) + 4-nitro-benzoyl chloride (122-04-3) → 4-Nitro-benzoic acid (Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-(4-nitro-phenyl)-vinyl ester (92478-52-9)

Conditions	Yield
With triethylamine In acetonitrile 1.) < 5 deg C, 2.) room temperature;	84%

dimetridazole (551-92-8) → 1,2-dimethyl-5-nitroimidazolium nitrate (352464-95-0)

Conditions	Yield
With nitric acid In ethanol; water at 40℃; for 10h;	84%

potassium tetrachloroplatinate(II) (10025-99-7) + dimetridazole (551-92-8) → [(1,2-dimethyl-5-nitro-1H-imidazole)2PtCl2] (97747-63-2, 89918-00-3, 97747-64-3)

Conditions	Yield
In water solid ligand added to aq. soln. of K2(PtCl4), stirred at 50 °C for 1 h; ppt. filtered, washed with EtOH/Et2O, Et2O, dried in vac.; elem. anal.;	83%

dimetridazole (551-92-8) + benzoyl chloride (98-88-4) → 1-benzoyloxy-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-phenyl-ethene (35636-14-7)

Conditions	Yield
With triethylamine In acetonitrile 1.) < 5 deg C, 2.) room temperature;	80%
With TEA In acetone at 20℃;

2-Thiophenecarbonyl chloride (5271-67-0) + dimetridazole (551-92-8) → Thiophene-2-carboxylic acid (Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-thiophen-2-yl-vinyl ester (92478-55-2)

Conditions	Yield
With triethylamine In acetonitrile 1.) < 5 deg C, 2.) room temperature;	79%

dimetridazole (551-92-8) → C5H3(2)H4N3O2

Conditions	Yield
With water-d2; sodium carbonate at 200℃; for 0.5h; Microwave irradiation;	77%
With water-d2; aluminium; platinum on carbon at 200℃; for 1h; Microwave irradiation;	57.2%
With deuteriated sodium hydroxide; 1,1,1-trideuteromethanol; water-d2 at 60℃; Rate constant; NaD2PO4-NaDCO3-K2CO3 buffer; half-live time;

dimetridazole (551-92-8) + N-methyl-2-imidazolcarboxaldehyde (13750-81-7) → 1-methyl-2-[(E)-2-(1-methyl-1H-imidazol-2-yl)vinyl]-5-nitro-1H-imidazole (1161926-14-2)

Conditions	Yield
With sodium ethanolate In ethanol at 65℃; Aldol condensation;	77%

dimetridazole (551-92-8) → 5-amino-1,2-dimethyl-1H-imidazole (80912-09-0)

Conditions	Yield
With palladium on carbon (10%) In 1,4-dioxane at 20℃; Cooling with ice; Inert atmosphere;	76%
With hydrogen; palladium on activated charcoal In 1,4-dioxane under 760 Torr;	74%
With hydrogen; 5%-palladium/activated carbon In 1,4-dioxane under 760 Torr;	74%

dimetridazole (551-92-8) + chloromethyl phenyl sulfone (7205-98-3) → 1,2-dimethyl-4-phenylsulfonylmethyl-5-nitroimidazole (116248-42-1)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 0.25h;	73%
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.166667h;	28%
With potassium hydroxide In dimethyl sulfoxide	28%

dimetridazole (551-92-8) + dimethyl sulfate (77-78-1) → 1,2,3-trimethyl-4-nitroimidazolium methyl sulfate

Conditions	Yield
In toluene at 20 - 25℃; for 48h;	72%

dimetridazole (551-92-8) + 4-bromo-benzaldehyde (1122-91-4) → 2-[(E)-2-(4-bromophenyl)vinyl]-1-methyl-5-nitro-1H-imidazole (1161925-98-9)

Conditions	Yield
With sodium ethanolate In ethanol at 65℃; Aldol condensation;	72%

dimetridazole (551-92-8) + terephthalaldehyde mono(diethylacetal) (81172-89-6) → 2-{(E)-2-[4-(diethoxymethyl)phenyl]vinyl}-1-methyl-5-nitro-1H-imidazole (223482-25-5)

Conditions	Yield
With sodium In ethanol at 60 - 65℃; for 3h;	70%
With sodium ethanolate In ethanol at 65℃; Aldol condensation;	24%

dimetridazole (551-92-8) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl (5-amino-1,2-dimethylimidazol-4-yl)methylenemalonate (145837-19-0) + 5-[2,2-bis(ethoxycarbonyl)-1-vinylamino]-1,2-dimethylimidazole (145837-15-6) + 4,4'-bis(5-diethoxycarbonylethyleneamino-1,2-dimethylimidazole) (145837-52-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	A 5% B 65% C 1%
With hydrogen; palladium on activated charcoal In ethanol	A 5% B n/a C 1%

dimetridazole (551-92-8) + α-bromoacetophenone (70-11-1) → C13H14N3O3(1+)*Br(1-) (1424382-15-9)

Conditions	Yield
In acetonitrile for 48h; Reflux;	65%

dimetridazole (551-92-8) + 1-bromo-4-(chloromethylsulfonyl)benzene (54091-06-4) → 4-(4-bromophenylsulfonyl)methyl-1,2-dimethyl-5-nitro-1H-imidazole

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.166667h;	53%
With potassium hydroxide In dimethyl sulfoxide	53%

furfural (98-01-1) + dimetridazole (551-92-8) → 2-[(E)-2-(2-furyl)vinyl]-1-methyl-5-nitro-1H-imidazole (1161926-15-3)

Conditions	Yield
With sodium ethanolate In ethanol at 65℃; Aldol condensation;	53%

dimetridazole (551-92-8) + chloromethyl p-chlorophenyl sulfone (5943-04-4) → 4-(4-chlorophenylsulfonyl)methyl-1,2-dimethyl-5-nitro-1H-imidazole

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.166667h;	49%
With potassium hydroxide In dimethyl sulfoxide	49%

bromobenzene (108-86-1) + dimetridazole (551-92-8) → 1,2-dimethyl-5-nitro-4-phenyl-1H-imidazole (1197836-47-7)

Conditions	Yield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 120℃; for 18h; Inert atmosphere; regioselective reaction;	44%

dimetridazole (551-92-8) + 1-chloromethanesulfonyl-4-fluoro-benzene (433-13-6) → 4-(4-fluorobenzenesulfonylmethyl)-1,2-dimethyl-5-nitro-1H-imidazole (1146349-23-6)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h;	40%

dimetridazole (551-92-8) → 1-methyl-5-nitro-1H-imidazole-2-carbaldehyde (4750-57-6)

Conditions	Yield
With selenium(IV) oxide at 140℃; for 0.0833333h;	39%
With selenium(IV) oxide at 140℃; for 0.0833333h;	39%
With selenium(IV) oxide at 140℃; for 0.0833333h; Inert atmosphere;	22.1%
Multi-step reaction with 2 steps 1.1: 91 percent / trifluoroacetic acid / dimethylformamide / 12 h / 100 °C 2.1: ozone / CH2Cl2; methanol / 2 h / -78 °C 2.2: 51 percent / dimethyl sulfide / CH2Cl2; methanol / -78 - 20 °C View Scheme
With selenium(IV) oxide at 140℃; for 0.0833333h; chemoselective reaction;

Upstream product

• 1739-84-0 1,2-dimethyl-1H-imidazole 
• 696-23-1 2-methyl-5-nitro-1H-imidazole 
• 77-78-1 dimethyl sulfate 
• 696-23-1 2-methyl-4-nitro-1H-imidazole 
• 117836-28-9 2-bromomethyl-1-methyl-5-nitroimidazole 
• 175733-75-2 (1-Methyl-5-nitro-1H-imidazol-2-yl)-acetic acid 

Downstream Products

• 22544-26-9 iodure de trimethyl-1,2,3 nitro-5 imidazolium 
• 223482-25-5 2-{(E)-2-[4-(diethoxymethyl)phenyl]vinyl}-1-methyl-5-nitro-1H-imidazole 
• 7664-41-7 ammonia 
• 56-40-6 glycine 
• 74-89-5 methylamine 
• 66962-38-7 1-methyl-2-(phenylsulfanylmethyl)-5-nitroimidazole 
• 1146349-23-6 4-(4-fluorobenzenesulfonylmethyl)-1,2-dimethyl-5-nitro-1H-imidazole 
• 1424382-15-9 C₁₃H₁₄N₃O₃⁽¹⁺⁾*Br^(1-) 
• 1424382-22-8 C₉H₁₄N₃O₄⁽¹⁺⁾*Br^(1-) 
• 13230-22-3 2-Methyl-4-nitroimidazole-1-acetic acid ethyl ester 
• 14766-63-3 2-(1-methyl-5-nitro-1H-imidazol-2-yl)ethanol 
• 32097-42-0 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-phenylethan-1-ol 
• 1575651-47-6 C₁₂H₁₁N₃O₂ 
• 1575651-46-5 C₁₂H₁₃N₃O₃ 

Relevant articles and documents

Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.

Oxidative decarbonylation of β-arylpyruvic acids using sodium perborate

Oxidation of β-aryl- and β-heteroarylpyruvic acids using sodium perborate tetrahydrate (SPB) in aqueous solution at ambient temperature gives the corresponding arylacetic acids in good yield (68-86%). The mild conditions are convenient for the preparation of thermally unstable acids. In particular the method has been applied to the preparation of an unstable 5- nitroimidazol-2-yl ethanoic acid which could not be obtained using other reagents apparently due to enolisation of the pyruvic acid precursor. Attempts to achieve decarbonylation using calcium hypochlorite or SPB in acidic solution lead to the 2 chloromethyl derivatives. The novel 5- nitroimidazol-2-yl ethanoic acid, which was required as a precursor of molecules of biological interest, has been fully characterised and converted to a known amide. Reaction of this acid with Vilsmeier's reagent gave an enamine derivative and not the expected vinamidinium salt. This novel mode of reaction is attributable to intramolecular hydrogen-bonding and favourable conjugation.

Reduction of Substituted Nitro Compounds with Tri-n-butyltin Hydride

α-Substituted nitro compounds have been reduced with tri-n-butyltin hydride to give replacement of the α-substituent by hydrogen (2-bromo, 2-chloro- and 2-nitro-2-phenylsulphonylpropane to 2-nitropropane; p-nitrobenzyl chloride, bromide, iodide and thiocyanate to p-nitrotoluene; 5-nitrofurfuryl nitrate to 2-methyl-5-nitrofuran and 2-hydroxymethyl-5-nitrofuran; 2-(bromomethyl)-1-methyl-5-nitroimidazole to 1,2-dimethylimidazole). 2-Bromo-2-nitrohept-6-ene and 1-bromo-1-nitrohex-5-ene were reduced to 2-nitrohept-6-ene and 1-nitrohex-5-ene,5-bromo- and 5-phenylsulphonyl-5-nitro-6-phenyl-norborn-6-ene to 5-nitro-6-phenylnorborn-6-ene and 2-iodo-2-nitro-3-(endo-norborn-2-en-5-yl)propane to 2-nitro-3-(endo-norborn-2-en-5-yl)propane without cyclisation of the intermediate alkenyl α-nitroalkyl radicals. 2-Bromo-2-nitrohex-5-ene and 1-bromo-1-nitropent-4-ene were reduced to the respective nitroalkenes at high but at lower cyclisation to 1-methyl-1-nitrocyclopentane and 1-nitrocyclopentane took place.Inhibition studies of the reductions of 2-bromo-2-nitrohex-5-ene and p-nitrobenzyl bromide showed a radical chain mechanism.In some of the reductions at low , radical rearrangement of the intermediate α-nitroalkyl radicals gave the respective ketones.Mechanisms involving (a) addition/elimination and (b) dissociation of intermediate radical anions, are proposed.