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2-Nitroimidazole

2-Nitroimidazole structure

CAS No:
527-73-1
Formula:
C3H3N3O2
Chemical Name:
2-Nitroimidazole
Synonyms:
1H-Imidazole,2-nitro-;Imidazole,2-nitro-;2-Nitro-1H-imidazole;2-Nitroimidazole;Azomycin;Amicin;Ro 05-9129;Azomycin (antiprotozoal);116421-32-0;151223-78-8
Categories:
Organic Chemistry > Nitro Compounds

Description

Azomycin is an antibiotic which can be active against aerobic Gram-positive and Gram-negative bacteria.

2-nitroimidazole is an imidazole that is 1H-imidazole substituted at position 2 by a nitro group. It has a role as an antitubercular agent. It is a C-nitro compound and a member of imidazoles. It derives from a 1H-imidazole.

2-Nitroimidazole Basic Attributes

Molecular Weight：

113.07

Exact Mass：

113.07

BRN：

116444

EC Number：

208-425-5

UNII：

K8E96XL55D

NSC Number：

105831

DSSTox ID：

DTXSID7060178

HScode：

29332990

Characteristics

PSA：

74.5

XLogP3：

0.1

Appearance：

Light yellow to khaki-green Powder

Density：

1.6±0.1 g/cm3

Melting Point：

287 °C (decomp)

Boiling Point：

373.6ºC at 760 mmHg

Flash Point：

179.7±23.2 °C

Refractive Index：

1.612

Water Solubility：

H2O: insoluble ;NH4OH: soluble 50mg/mL, clear, yellow to orange

Storage Conditions：

Refrigerator

Toxicity：

LD50 i.v. in mice: 80 mg/kg (Maeda)

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

22-36/37/38-23/24/25-20/21/22

safety instructions：

26-36-45-36/37/39

RTECS Number：

NI7875000

Marks：

Xn,T

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

Drug Information

MeSH Entry Terms：

azomycin

2-Nitroimidazole Use and Manufacturing

Methods of Manufacturing

Mix amino acetal S-methyl isosulfide with water, stir and heat, evaporate to dryness under reduced pressure, the residue is dissolved in methanol, and then acetone is added dropwise to obtain white crystal N-(2, 2-diethoxyeth Base) guanidine sulfate, yield 84.4%. Take N-(2, 2-diethoxyethyl)guanidine sulfate and concentrated hydrochloric acid, stir and heat to reflux, complete the reaction, add distilled water to dry under reduced pressure, then add water to dry, the residue is dissolved with absolute ethanol, Then add anhydrous ether dropwise to obtain a white solid 2-aminoimidazole with a yield of 64.5%. 2-Aminoimidazole, add fluoroboric acid and water, cool to below -15℃, and add a solution of sodium nitrate and water dropwise with stirring. After finishing, continue stirring. Pour the brown-green solution produced by the reaction into copper sulfate pentahydrate solution, stir while adding, then add sodium nitrite to continue stirring, after the reaction is completed, add concentrated hydrochloric acid to adjust the pH to 2, extract with acetate, the extract is free of After drying with sodium sulfate, the ethyl acetate was recovered to the end, and the residue was recrystallized from ethanol to obtain 2-nitroimidazole.

Uses

Antibiotic substance produced by an unidentified Streptomyces

Manufacturing Info：

1H-Imidazole, 2-nitro-: ACTIVE

Computed Properties

Molecular Weight:113.08
XLogP3:0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:113.022526347
Monoisotopic Mass:113.022526347
Topological Polar Surface Area:74.5
Heavy Atom Count:8
Complexity:99.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethyl acetate

SODIUM SULFATE

Tetrafluoroboric acid

Ethanol

Sodium nitrite

Nitric acid

Sodium sulfate

PETROLEUM ETHER

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