Product Name

  • Name

    alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol

  • EINECS 222-134-0
  • CAS No. 3366-95-8
  • Article Data9
  • CAS DataBase
  • Density 1.39 g/cm3
  • Solubility
  • Melting Point 76 °C
  • Formula C7H11N3O3
  • Boiling Point 396.1 °C at 760 mmHg
  • Molecular Weight 185.183
  • Flash Point 193.4 °C
  • Transport Information
  • Appearance Crystalline solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 3366-95-8 (alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol)
  • Hazard Symbols
  • Synonyms Imidazole-1-ethanol, alpha,2-dimethyl-5-nitro-;PM 185184;Secnidazol [INN-Spanish];1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-ol;1-(2-Methyl-5-nitro-1-imidazolyl)-2-propanol;Secnidazole [BAN:DCF:INN];alpha,2-Dimethyl-5-nitroimidazole-1-ethanol;1-(2-Hydroxypropyl)-2-methyl-5-nitroimidazol;Secnidazolum [INN-Latin];1H-Imidazole-1-ethanol,R,2-dimethyl-5- nitro-;RP 14539;
  • PSA 83.87000
  • LogP 1.00370

Synthetic route

1-bromo-2-propanol
19686-73-8

1-bromo-2-propanol

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

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

secnidazole
3366-95-8

secnidazole

Conditions
ConditionsYield
With potassium carbonate In acetone at 70℃; for 5h; Reagent/catalyst; Temperature;89.1%
2-methyl-5-nitro-1H-imidazole
696-23-1

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

methyloxirane
75-56-9, 16033-71-9

methyloxirane

secnidazole
3366-95-8

secnidazole

Conditions
ConditionsYield
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(dimethylamino)cyclohexyl]thiourea In ethyl acetate at 25 - 30℃; for 6h; Solvent; Temperature; Reagent/catalyst;80.5%
With aluminum (III) chloride In ethyl acetate at 45 - 50℃; for 1.5h; Temperature;75%
1-(2-methyl-imidazol-1-yl)-propan-2-ol
34091-34-4

1-(2-methyl-imidazol-1-yl)-propan-2-ol

secnidazole
3366-95-8

secnidazole

Conditions
ConditionsYield
With magnesium(II) perchlorate; N–nitrosaccharin In [D3]acetonitrile at 85℃; for 19h; Inert atmosphere; Sealed tube;44%
water
7732-18-5

water

secnidazole
3366-95-8

secnidazole

copper(ll) bromide
7789-45-9

copper(ll) bromide

[Cu(secnidazole)2Br2]*0.5H2O

[Cu(secnidazole)2Br2]*0.5H2O

Conditions
ConditionsYield
In ethanol for 4h; Reflux;96%
...Expand
copper(II) choride dihydrate

copper(II) choride dihydrate

secnidazole
3366-95-8

secnidazole

[Cu(secnidazole)2Cl2]
1429662-19-0

[Cu(secnidazole)2Cl2]

Conditions
ConditionsYield
In ethanol for 4h; Reflux;96%
water
7732-18-5

water

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

secnidazole
3366-95-8

secnidazole

[Co2(secnidazole)6(O2C2H3)2(μ2-O2 H5C3)2]·H2O

[Co2(secnidazole)6(O2C2H3)2(μ2-O2 H5C3)2]·H2O

Conditions
ConditionsYield
In ethanol for 4h; Reflux;95%
...Expand
nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

secnidazole
3366-95-8

secnidazole

[Ni2(secnidazole)4(μ2-O2C2H3)4]

[Ni2(secnidazole)4(μ2-O2C2H3)4]

Conditions
ConditionsYield
In ethanol for 4h; Reflux;93%
oxalyl dichloride
79-37-8

oxalyl dichloride

secnidazole
3366-95-8

secnidazole

bis(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl) oxalate

bis(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl) oxalate

Conditions
ConditionsYield
Stage #1: secnidazole With pyridine In toluene at 40℃; for 0.5h; Green chemistry;
Stage #2: oxalyl dichloride In toluene at 40℃; for 2.5h; Green chemistry;		91%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

secnidazole
3366-95-8

secnidazole

1-methyl-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl (4-chlorophenyl)carbamate

1-methyl-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl (4-chlorophenyl)carbamate

Conditions
ConditionsYield
With ammonium chloride; triethylamine In toluene at 110℃; for 17h; Inert atmosphere;91%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

secnidazole
3366-95-8

secnidazole

(NO2CCHNC(CH3)N(CH2CH(OH)CH3))2PtCl2
84431-19-6

(NO2CCHNC(CH3)N(CH2CH(OH)CH3))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.;90%
secnidazole
3366-95-8

secnidazole

1-(2-chloropropyl)-2-methyl-5-nitro-1H-imidazole
1393310-68-3

1-(2-chloropropyl)-2-methyl-5-nitro-1H-imidazole

Conditions
ConditionsYield
With thionyl chloride at 60℃; for 6h;90%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl 4-methylbenzenesulfonate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 25h; Reagent/catalyst;87%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

secnidazole
3366-95-8

secnidazole

1-(5-methyl-2-nitro-1H-imidazol-1-yl)propan-2-yl benzenesulfonate

1-(5-methyl-2-nitro-1H-imidazol-1-yl)propan-2-yl benzenesulfonate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 25h; Reagent/catalyst;85%
secnidazole
3366-95-8

secnidazole

2-Naphthalenesulfonyl chloride
93-11-8

2-Naphthalenesulfonyl chloride

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl naphthalene-2-sulfonate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl naphthalene-2-sulfonate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 25h; Reagent/catalyst;85%
C17H13ClN2O2

C17H13ClN2O2

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1-(4-chlorophenyl)-5-(p-tolyl)-1H-pyrazole-3- carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1-(4-chlorophenyl)-5-(p-tolyl)-1H-pyrazole-3- carboxylate

Conditions
ConditionsYield
Stage #1: C17H13ClN2O2 With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		85%
secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-one
31876-69-4

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-one

Conditions
ConditionsYield
With dipyridinium dichromate In dichloromethane at 20℃; for 48h; Reagent/catalyst;84%
1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid
477712-01-9

1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: 1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		84%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

secnidazole
3366-95-8

secnidazole

[Co(secnidazole)3(H2O)Cl2]
1429662-20-3

[Co(secnidazole)3(H2O)Cl2]

Conditions
ConditionsYield
In ethanol for 4h; Reflux;83%
C16H10ClIN2O2

C16H10ClIN2O2

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1-(4-chlorophenyl)-5-(4-iodophenyl)-1H-3-carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1-(4-chlorophenyl)-5-(4-iodophenyl)-1H-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10ClIN2O2 With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		82%
zinc(II) nitrate hexahydrate

zinc(II) nitrate hexahydrate

water
7732-18-5

water

secnidazole
3366-95-8

secnidazole

[Zn(secnidazole)3(NO3)][NO3]*2H2O

[Zn(secnidazole)3(NO3)][NO3]*2H2O

Conditions
ConditionsYield
In ethanol for 4h; Reflux;81%
...Expand
C18H16N2O2

C18H16N2O2

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1,5-di-p-tolyl-1H-pyrazole-3-carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1,5-di-p-tolyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C18H16N2O2 With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		81%
4-chlorobenzenesulfonyl chloride
98-60-2

4-chlorobenzenesulfonyl chloride

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl 4-chlorobenzenesulfonate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl 4-chlorobenzenesulfonate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 25h; Reagent/catalyst;80%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl methanesulfonate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl methanesulfonate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 25h; Reagent/catalyst;79%
C16H11IN2O2

C16H11IN2O2

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-5-(4-iodophenyl)-1-phenyl-1H-pyrazole-3-carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-5-(4-iodophenyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H11IN2O2 With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		79%
5-(4-methoxy-phenyl)-1-phenyl-1H-pyrazole-3-carboxylic acid
47209-42-7

5-(4-methoxy-phenyl)-1-phenyl-1H-pyrazole-3-carboxylic acid

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3- carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3- carboxylate

Conditions
ConditionsYield
Stage #1: 5-(4-methoxy-phenyl)-1-phenyl-1H-pyrazole-3-carboxylic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		78%
C17H14N2O2

C17H14N2O2

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1-phenyl-5-(m-tolyl)-1H-pyrazole-3-carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1-phenyl-5-(m-tolyl)-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C17H14N2O2 With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		78%
3,4-dichlorophenylisocyanate
102-36-3

3,4-dichlorophenylisocyanate

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl (3,4-dichlorophenyl)carbamate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl (3,4-dichlorophenyl)carbamate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 1.16667h;77.2%
4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl 4-methylbenzoate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl 4-methylbenzoate

Conditions
ConditionsYield
Stage #1: secnidazole With pyridine In toluene at 70℃; for 0.5h; Green chemistry;
Stage #2: 4-methyl-benzoyl chloride In toluene at 70℃; for 4.5h; Green chemistry;		77%
1,5-diphenylpyrazole-3-carboxylic acid
13599-22-9

1,5-diphenylpyrazole-3-carboxylic acid

secnidazole
3366-95-8

secnidazole

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1,-5-diphenyl-1H-pyrazole-3-carboxylate

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-1,-5-diphenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: 1,5-diphenylpyrazole-3-carboxylic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 0.5h;
Stage #2: secnidazole In 1,2-dichloro-ethane Reflux;		77%
benzaldehyde
100-52-7

benzaldehyde

secnidazole
3366-95-8

secnidazole

1-(5-nitro-2-styryl-1H-imidazol-1-yl)propan-2-ol
1448528-37-7

1-(5-nitro-2-styryl-1H-imidazol-1-yl)propan-2-ol

Conditions
ConditionsYield
With sodium methylate In methanol; dimethyl sulfoxide at 20℃;76.1%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

water
7732-18-5

water

secnidazole
3366-95-8

secnidazole

[Ni(secnidazole)2(H2O)2Cl2]*5H2O

[Ni(secnidazole)2(H2O)2Cl2]*5H2O

Conditions
ConditionsYield
In ethanol for 4h; Reflux;76%
...Expand

Secnidazole Chemical Properties

Molecular Formula: C7H11N3O3
Molecular Weight: 185.18
EINECS: 222-134-0
 Index of Refraction: 1.597
Density: 1.39 g/cm3
Flash Point: 193.4 °C
Enthalpy of Vaporization: 68.17 kJ/mol
Boiling Point: 396.1 °C at 760 mmHg
Vapour Pressure: 5.49E-07 mmHg at 25 °C
Melting point: 76 °C
Appearance: Crystalline solid
Structure of Secnidazole (CAS NO.3366-95-8):
                         
IUPAC Name: 1-(2-Methyl-5-nitroimidazol-1-yl)propan-2-ol
Canonical SMILES: CC1=NC=C(N1CC(C)O)[N+](=O)[O-]
InChI: InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
InChIKey: KPQZUUQMTUIKBP-UHFFFAOYSA-N
Product Category of Secnidazole (CAS NO.3366-95-8): Active Pharmaceutical Ingredients;Heterocycles;Intermediates & Fine Chemicals

Secnidazole Uses

 Secnidazole (CAS NO.3366-95-8) has been used for analog of metronidazole.

Secnidazole Specification

 Secnidazole , its cas register number is 3366-95-8. It also can be called alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol .

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