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551-92-8

Basic Information
CAS No.: 551-92-8
Name: 1,2-Dimethyl-5-nitroimidazole
Molecular Structure:
Molecular Structure of 551-92-8 (1,2-Dimethyl-5-nitroimidazole)
Formula: C5H7N3O2
Molecular Weight: 141.15
Synonyms: Imidazole,1,2-dimethyl-5-nitro- (7CI,8CI);5-Nitro-1,2-dimethylimidazole;Dimetridazol;Dimetridazole;Dimetrizadole;Dimetronidazole;Emtryl;Emtrylvet;Emtrymix;NSC 226253;
EINECS: 209-001-2
Density: 1.36 g/cm3
Melting Point: 177-182 °C
Boiling Point: 313.7 °C at 760 mmHg
Flash Point: 143.5 °C
Solubility: 9.69g/L(20 oC)
Appearance: solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-36/37-22
Transport Information:
PSA: 63.64000
LogP: 1.15990
Synthetic route
696-23-1

2-methyl-5-nitro-1H-imidazole

77-78-1

dimethyl sulfate

551-92-8

dimetridazole

Conditions
ConditionsYield
With formic acid for 4h; Reflux;87%
117836-28-9

2-bromomethyl-1-methyl-5-nitroimidazole

551-92-8

dimetridazole

Conditions
ConditionsYield
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

A

551-92-8

dimetridazole

B

6905-07-3

2-(chloromethyl)-1-methyl-5-nitroimidazole

Conditions
ConditionsYield
With sodium perborate; acetic acid for 14h; Ambient temperature;A 35%
B 25%
1739-84-0

1,2-dimethyl-1H-imidazole

A

13230-04-1

1,2-dimethyl-4-nitro-1H-imidazole

B

551-92-8

dimetridazole

Conditions
ConditionsYield
With sulfuric acid; nitric acid anfangs bei 0grad, dann bei 100grad;
696-23-1

2-methyl-5-nitro-1H-imidazole

77-78-1

dimethyl sulfate

A

13230-04-1

1,2-dimethyl-4-nitro-1H-imidazole

B

551-92-8

dimetridazole

696-23-1

2-methyl-4-nitro-1H-imidazole

77-78-1

dimethyl sulfate

A

13230-04-1

1,2-dimethyl-4-nitro-1H-imidazole

B

551-92-8

dimetridazole

175733-75-2

(1-Methyl-5-nitro-1H-imidazol-2-yl)-acetic acid

551-92-8

dimetridazole

Conditions
ConditionsYield
at 110℃;
1739-84-0

1,2-dimethyl-1H-imidazole

HNO3+H2SO4

HNO3+H2SO4

A

13230-04-1

1,2-dimethyl-4-nitro-1H-imidazole

B

551-92-8

dimetridazole

Conditions
ConditionsYield
beim Nitrieren;
696-23-1

2-methyl-5-nitro-1H-imidazole

551-92-8

dimetridazole

Conditions
ConditionsYield
With acetic acid; dimethyl sulfate In water
551-92-8

dimetridazole

762-70-9

2-chloroethanesulfonyl fluoride

C7H11FN3O4S(1+)*Cl(1-)

Conditions
ConditionsYield
In ethyl acetate for 2h; Menshutkin Reaction; Reflux;100%
551-92-8

dimetridazole

13230-04-1

1,2-dimethyl-4-nitro-1H-imidazole

Conditions
ConditionsYield
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%
551-92-8

dimetridazole

88-89-1

2,4,6-Trinitrophenol

24647-68-5

1,2-dimethyl-5-nitroimidazolium picrate

Conditions
ConditionsYield
In ethanol; water at 40℃; for 10h;92%
551-92-8

dimetridazole

98-88-4

benzoyl chloride

1448622-21-6

(Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-phenylvinylbenzoate

Conditions
ConditionsYield
With triethylamine In acetone at 20℃; for 4h; Cooling with ice;92%
551-92-8

dimetridazole

1188-33-6

N,N-dimethylformamide diethyl diacetal

57434-36-3

5-nitro-1-methyl-2-(2-dimethylaminovinyl)-imidazole

Conditions
ConditionsYield
With trifluoroacetic acid In N,N-dimethyl-formamide at 100℃; for 12h; Condensation;91%
551-92-8

dimetridazole

87-13-8

diethyl 2-ethoxymethylenemalonate

145837-15-6

5-[2,2-bis(ethoxycarbonyl)-1-vinylamino]-1,2-dimethylimidazole

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In 1,4-dioxane86%
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;
551-92-8

dimetridazole

cobalt(II) chloride hexahydrate

195046-62-9

bis(1,2-dimethyl-5-nitro-imidazole)cobalt(II) chloride

Conditions
ConditionsYield
In methanol stoichiometric ratio, refluxing (30 min); concn., crystn.; elem. anal.;85%
551-92-8

dimetridazole

122-04-3

4-nitro-benzoyl chloride

92478-52-9

4-Nitro-benzoic acid (Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-(4-nitro-phenyl)-vinyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile 1.) < 5 deg C, 2.) room temperature;84%
551-92-8

dimetridazole

352464-95-0

1,2-dimethyl-5-nitroimidazolium nitrate

Conditions
ConditionsYield
With nitric acid In ethanol; water at 40℃; for 10h;84%
10025-99-7

potassium tetrachloroplatinate(II)

551-92-8

dimetridazole

97747-63-2, 89918-00-3, 97747-64-3

[(1,2-dimethyl-5-nitro-1H-imidazole)2PtCl2]

Conditions
ConditionsYield
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%
551-92-8

dimetridazole

98-88-4

benzoyl chloride

35636-14-7

1-benzoyloxy-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-phenyl-ethene

Conditions
ConditionsYield
With triethylamine In acetonitrile 1.) < 5 deg C, 2.) room temperature;80%
With TEA In acetone at 20℃;
5271-67-0

2-Thiophenecarbonyl chloride

551-92-8

dimetridazole

92478-55-2

Thiophene-2-carboxylic acid (Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-thiophen-2-yl-vinyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile 1.) < 5 deg C, 2.) room temperature;79%
551-92-8

dimetridazole

C5H3(2)H4N3O2

Conditions
ConditionsYield
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;
551-92-8

dimetridazole

13750-81-7

N-methyl-2-imidazolcarboxaldehyde

1161926-14-2

1-methyl-2-[(E)-2-(1-methyl-1H-imidazol-2-yl)vinyl]-5-nitro-1H-imidazole

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 65℃; Aldol condensation;77%
551-92-8

dimetridazole

80912-09-0

5-amino-1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
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%
551-92-8

dimetridazole

7205-98-3

chloromethyl phenyl sulfone

116248-42-1

1,2-dimethyl-4-phenylsulfonylmethyl-5-nitroimidazole

Conditions
ConditionsYield
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 sulfoxide28%
551-92-8

dimetridazole

77-78-1

dimethyl sulfate

1,2,3-trimethyl-4-nitroimidazolium methyl sulfate

Conditions
ConditionsYield
In toluene at 20 - 25℃; for 48h;72%
551-92-8

dimetridazole

1122-91-4

4-bromo-benzaldehyde

1161925-98-9

2-[(E)-2-(4-bromophenyl)vinyl]-1-methyl-5-nitro-1H-imidazole

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 65℃; Aldol condensation;72%
551-92-8

dimetridazole

81172-89-6

terephthalaldehyde mono(diethylacetal)

223482-25-5

2-{(E)-2-[4-(diethoxymethyl)phenyl]vinyl}-1-methyl-5-nitro-1H-imidazole

Conditions
ConditionsYield
With sodium In ethanol at 60 - 65℃; for 3h;70%
With sodium ethanolate In ethanol at 65℃; Aldol condensation;24%
551-92-8

dimetridazole

87-13-8

diethyl 2-ethoxymethylenemalonate

A

145837-19-0

diethyl (5-amino-1,2-dimethylimidazol-4-yl)methylenemalonate

B

145837-15-6

5-[2,2-bis(ethoxycarbonyl)-1-vinylamino]-1,2-dimethylimidazole

C

145837-52-1

4,4'-bis(5-diethoxycarbonylethyleneamino-1,2-dimethylimidazole)

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanolA 5%
B 65%
C 1%
With hydrogen; palladium on activated charcoal In ethanolA 5%
B n/a
C 1%
551-92-8

dimetridazole

70-11-1

α-bromoacetophenone

1424382-15-9

C13H14N3O3(1+)*Br(1-)

Conditions
ConditionsYield
In acetonitrile for 48h; Reflux;65%
551-92-8

dimetridazole

54091-06-4

1-bromo-4-(chloromethylsulfonyl)benzene

4-(4-bromophenylsulfonyl)methyl-1,2-dimethyl-5-nitro-1H-imidazole

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.166667h;53%
With potassium hydroxide In dimethyl sulfoxide53%
98-01-1

furfural

551-92-8

dimetridazole

1161926-15-3

2-[(E)-2-(2-furyl)vinyl]-1-methyl-5-nitro-1H-imidazole

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 65℃; Aldol condensation;53%
551-92-8

dimetridazole

5943-04-4

chloromethyl p-chlorophenyl sulfone

4-(4-chlorophenylsulfonyl)methyl-1,2-dimethyl-5-nitro-1H-imidazole

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.166667h;49%
With potassium hydroxide In dimethyl sulfoxide49%
108-86-1

bromobenzene

551-92-8

dimetridazole

1197836-47-7

1,2-dimethyl-5-nitro-4-phenyl-1H-imidazole

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 120℃; for 18h; Inert atmosphere; regioselective reaction;44%
551-92-8

dimetridazole

433-13-6

1-chloromethanesulfonyl-4-fluoro-benzene

1146349-23-6

4-(4-fluorobenzenesulfonylmethyl)-1,2-dimethyl-5-nitro-1H-imidazole

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h;40%
551-92-8

dimetridazole

4750-57-6

1-methyl-5-nitro-1H-imidazole-2-carbaldehyde

Conditions
ConditionsYield
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;
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    CAS No.:551-92-8 EINECS No.:209-001-2 Other Names:1,2-Dimethy-5-Nitro Imidazole MF:C5H7N3O2 Type:Antibiotic and Antimicrobial Agents, Vitamins, Amino Acids and Coenzymes Grade Standard:Feed Grade, Medicine Grade Usage:Animal Pharmaceuti

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Chemistry

Molecular Formula:C5H7N3O2
Molar mass:141.12798 g/mol
Structure :
                                   
Synonyms of 1,2-Dimethyl-5-nitroimidazole(551-92-8):dimetridazole;Dimetridazol;1,2-dimethyl-5-nitro-1h-imidazole;1H-Imidazole, 1,2-dimethyl-5-nitro;Dimetridazolo;Dimetridazolum
Density:1.36 g/cm                  
Flash Point:143.5 °C         
Boiling Point:313.7 °C at 760 mmHg        
Index of Refraction:1.598     
Vapour Pressure:0.000901 mmHg at 25°C  
Melting point:177-182°C 
storage temp:2-8°C
Appearance:Light yellow needle-like crystalline powder

Uses

1,2-Dimethyl-5-nitroimidazole(551-92-8) is a livestock growth promoter and  broad-spectrum antiprotozoal drug with efficient and low toxicity. 
1,2-Dimethyl-5-nitroimidazole(551-92-8) can be used for pig feed, use 50-100g / t and also  for chicken feed, use 125-200g / t.

Production

1. Synthesized  with 2 - methyl-imidazole as the raw material, by nitration, esterification derived. 
2. Using glyoxal as starting material,then cyclizes with acetaldehyde and ammonia . Then nitrification. The end, dimethyl sulfate methylation of imidazole derived Metronidazole.

Toxicity Data With Reference

1.   

mmo-sat 25 µg/plate

   MUREAV    Mutation Research. 38 (1976),203.
2.   

bfa-rat/sat 800 mg/kg

   MUREAV    Mutation Research. 97 (1982),171.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:Xi
Risk Statements:
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
22:  Do not breathe dust
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing 
37:  Wear suitable gloves