Product Name

  • Name

    1,2-Dimethyl-5-nitroimidazole

  • EINECS 209-001-2
  • CAS No. 551-92-8
  • Article Data14
  • CAS DataBase
  • Density 1.36 g/cm3
  • Solubility 9.69g/L(20 oC)
  • Melting Point 177-182 °C
  • Formula C5H7N3O2
  • Boiling Point 313.7 °C at 760 mmHg
  • Molecular Weight 141.129
  • Flash Point 143.5 °C
  • Transport Information
  • Appearance solid
  • Safety 26-36-36/37-22
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 551-92-8 (1,2-Dimethyl-5-nitroimidazole)
  • Hazard Symbols IrritantXi
  • Synonyms Imidazole,1,2-dimethyl-5-nitro- (7CI,8CI);5-Nitro-1,2-dimethylimidazole;Dimetridazol;Dimetridazole;Dimetrizadole;Dimetronidazole;Emtryl;Emtrylvet;Emtrymix;NSC 226253;
  • PSA 63.64000
  • LogP 1.15990

Synthetic route

2-methyl-5-nitro-1H-imidazole
696-23-1

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

dimethyl sulfate
77-78-1

dimethyl sulfate

dimetridazole
551-92-8

dimetridazole

Conditions
ConditionsYield
With formic acid for 4h; Reflux;87%
2-bromomethyl-1-methyl-5-nitroimidazole
117836-28-9

2-bromomethyl-1-methyl-5-nitroimidazole

dimetridazole
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

3-(1-Methyl-5-nitro-1H-imidazol-2-yl)-2-oxo-propionic acid; hydrochloride

A

dimetridazole
551-92-8

dimetridazole

B

2-(chloromethyl)-1-methyl-5-nitroimidazole
6905-07-3

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

Conditions
ConditionsYield
With sodium perborate; acetic acid for 14h; Ambient temperature;A 35%
B 25%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

A

1,2-dimethyl-4-nitro-1H-imidazole
13230-04-1

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

B

dimetridazole
551-92-8

dimetridazole

Conditions
ConditionsYield
With sulfuric acid; nitric acid anfangs bei 0grad, dann bei 100grad;
2-methyl-5-nitro-1H-imidazole
696-23-1

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

dimethyl sulfate
77-78-1

dimethyl sulfate

A

1,2-dimethyl-4-nitro-1H-imidazole
13230-04-1

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

B

dimetridazole
551-92-8

dimetridazole

...Expand
2-methyl-4-nitro-1H-imidazole
696-23-1

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

dimethyl sulfate
77-78-1

dimethyl sulfate

A

1,2-dimethyl-4-nitro-1H-imidazole
13230-04-1

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

B

dimetridazole
551-92-8

dimetridazole

...Expand
(1-Methyl-5-nitro-1H-imidazol-2-yl)-acetic acid
175733-75-2

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

dimetridazole
551-92-8

dimetridazole

Conditions
ConditionsYield
at 110℃;
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

HNO3+H2SO4

HNO3+H2SO4

A

1,2-dimethyl-4-nitro-1H-imidazole
13230-04-1

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

B

dimetridazole
551-92-8

dimetridazole

Conditions
ConditionsYield
beim Nitrieren;
...Expand
2-methyl-5-nitro-1H-imidazole
696-23-1

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

dimetridazole
551-92-8

dimetridazole

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

dimetridazole

2-chloroethanesulfonyl fluoride
762-70-9

2-chloroethanesulfonyl fluoride

C7H11FN3O4S(1+)*Cl(1-)

C7H11FN3O4S(1+)*Cl(1-)

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

dimetridazole

1,2-dimethyl-4-nitro-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

1,2-dimethyl-5-nitroimidazolium picrate
24647-68-5

1,2-dimethyl-5-nitroimidazolium picrate

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

dimetridazole

benzoyl chloride
98-88-4

benzoyl chloride

(Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-phenylvinylbenzoate
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%
dimetridazole
551-92-8

dimetridazole

N,N-dimethylformamide diethyl diacetal
1188-33-6

N,N-dimethylformamide diethyl diacetal

5-nitro-1-methyl-2-(2-dimethylaminovinyl)-imidazole
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%
dimetridazole
551-92-8

dimetridazole

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

5-[2,2-bis(ethoxycarbonyl)-1-vinylamino]-1,2-dimethylimidazole
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;
dimetridazole
551-92-8

dimetridazole

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

bis(1,2-dimethyl-5-nitro-imidazole)cobalt(II) chloride
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%
dimetridazole
551-92-8

dimetridazole

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

4-Nitro-benzoic acid (Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-(4-nitro-phenyl)-vinyl ester
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%
dimetridazole
551-92-8

dimetridazole

1,2-dimethyl-5-nitroimidazolium nitrate
352464-95-0

1,2-dimethyl-5-nitroimidazolium nitrate

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

potassium tetrachloroplatinate(II)

dimetridazole
551-92-8

dimetridazole

[(1,2-dimethyl-5-nitro-1H-imidazole)2PtCl2]
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%
dimetridazole
551-92-8

dimetridazole

benzoyl chloride
98-88-4

benzoyl chloride

1-benzoyloxy-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-phenyl-ethene
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℃;
2-Thiophenecarbonyl chloride
5271-67-0

2-Thiophenecarbonyl chloride

dimetridazole
551-92-8

dimetridazole

Thiophene-2-carboxylic acid (Z)-2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1-thiophen-2-yl-vinyl ester
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%
dimetridazole
551-92-8

dimetridazole

C5H3(2)H4N3O2

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;
dimetridazole
551-92-8

dimetridazole

N-methyl-2-imidazolcarboxaldehyde
13750-81-7

N-methyl-2-imidazolcarboxaldehyde

1-methyl-2-[(E)-2-(1-methyl-1H-imidazol-2-yl)vinyl]-5-nitro-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

5-amino-1,2-dimethyl-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

chloromethyl phenyl sulfone
7205-98-3

chloromethyl phenyl sulfone

1,2-dimethyl-4-phenylsulfonylmethyl-5-nitroimidazole
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%
dimetridazole
551-92-8

dimetridazole

dimethyl sulfate
77-78-1

dimethyl sulfate

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

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

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

dimetridazole

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

2-[(E)-2-(4-bromophenyl)vinyl]-1-methyl-5-nitro-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

terephthalaldehyde mono(diethylacetal)
81172-89-6

terephthalaldehyde mono(diethylacetal)

2-{(E)-2-[4-(diethoxymethyl)phenyl]vinyl}-1-methyl-5-nitro-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

A

diethyl (5-amino-1,2-dimethylimidazol-4-yl)methylenemalonate
145837-19-0

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

B

5-[2,2-bis(ethoxycarbonyl)-1-vinylamino]-1,2-dimethylimidazole
145837-15-6

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

C

4,4'-bis(5-diethoxycarbonylethyleneamino-1,2-dimethylimidazole)
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%
...Expand
dimetridazole
551-92-8

dimetridazole

α-bromoacetophenone
70-11-1

α-bromoacetophenone

C13H14N3O3(1+)*Br(1-)
1424382-15-9

C13H14N3O3(1+)*Br(1-)

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

dimetridazole

1-bromo-4-(chloromethylsulfonyl)benzene
54091-06-4

1-bromo-4-(chloromethylsulfonyl)benzene

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

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%
furfural
98-01-1

furfural

dimetridazole
551-92-8

dimetridazole

2-[(E)-2-(2-furyl)vinyl]-1-methyl-5-nitro-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

chloromethyl p-chlorophenyl sulfone
5943-04-4

chloromethyl p-chlorophenyl sulfone

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

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%
bromobenzene
108-86-1

bromobenzene

dimetridazole
551-92-8

dimetridazole

1,2-dimethyl-5-nitro-4-phenyl-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

1-chloromethanesulfonyl-4-fluoro-benzene
433-13-6

1-chloromethanesulfonyl-4-fluoro-benzene

4-(4-fluorobenzenesulfonylmethyl)-1,2-dimethyl-5-nitro-1H-imidazole
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%
dimetridazole
551-92-8

dimetridazole

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

1,2-Dimethyl-5-nitroimidazole Chemical Properties

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/cm3                   
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

1,2-Dimethyl-5-nitroimidazole 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.

1,2-Dimethyl-5-nitroimidazole 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.

1,2-Dimethyl-5-nitroimidazole 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.

1,2-Dimethyl-5-nitroimidazole Consensus Reports

EPA Genetic Toxicology Program.

1,2-Dimethyl-5-nitroimidazole 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

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View