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5-Nitroimidazole

5-Nitroimidazole structure

CAS No:
3034-38-6
Formula:
C3H3N3O2
Chemical Name:
5-Nitroimidazole
Synonyms:
1H-Imidazole,5-nitro-;Imidazole,4-nitro-;1H-Imidazole,4-nitro-;Imidazole,4(or 5)-nitro-;5-Nitro-1H-imidazole;4-Nitroimidazole;5-Nitroimidazole;4(5)-Nitroimidazole;1H-5-Nitroimidazole;1H-4-Nitroimidazole;NSC 50359;4-Nitro-1H-imidazole;88054-21-1;196413-24-8;932779-11-8
Categories:
Organic Chemistry > Nitro Compounds

Description

WHITE TO LIGHT YELLOW POWDER

5-nitroimidazole is a C-nitro compound that is imidazole bearing a nitro substituent at position 5. It is a member of imidazoles and a C-nitro compound.

5-Nitroimidazole Basic Attributes

Molecular Weight：

113.076

Exact Mass：

113.07

EC Number：

221-224-7

UNII：

Y8U32AZ5O7

NSC Number：

50359

DSSTox ID：

DTXSID9062803

HScode：

2933290090

Characteristics

PSA：

74.5

XLogP3：

Appearance：

white powder

Density：

1.6±0.1 g/cm3

Melting Point：

303 °C (decomp)

Boiling Point：

404.8°C at 760 mmHg

Flash Point：

198.6±21.2 °C

Refractive Index：

1.612

Storage Conditions：

Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

2811

wgk germany：

hazard class code：

R22;R36/37/38

safety instructions：

S26-S36/37-S37/39

RTECS Number：

NI7892000

Marks：

Xn:Harmful;

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P280-P305 + P351 + P338

Hazard Statements：

H302 + H312 + H332-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 147 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4-nitroimidazole

5-Nitroimidazole Use and Manufacturing

Methods of Manufacturing

To a solution of the product of Preparation 4B (49.5 g, 181 mmol), stirring in dimethylformamide (500 mL) at room temperature, was added 4-nitroimidazole (20.5 g, 181 mmol) and potassium carbonate (75 g, 543 mmol). After 16 hours, the reaction mixture was filtered and concentrated. The resulting oil was partitioned between ethyl acetate and water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The resulting oil was purified by flash chromatography (silica gel, 30-70% ethyl acetates/hexanes gradient) to yield 33.6 g (61%) of the above-identified product as an orange oil that solidifies upon standing: 1H-NMR (d, DMSO) 1.17 (t, J=7.2 Hz, 3H), 3.78 (s, 3H), 4.25 (q, J=7.2 Hz, 2H), 6.57 (s, 1H), 7.02 (d, J=8.7 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H), 7.92 (s, 1H), 8.38 (s, 1H); MS (ion spray) 306 (M+1); Anal. Calc'd for C14H15N3O5: C, 55.08; H, 4.95; N, 13.76. Found: C, 54.93; H, 4.89; N, 13.82.To a solution of a compound of the formula (40 g, 200 mmol) in carbon tetrachloride (500 mL) is added N-bromosuccinimide (37 g, 206 mmol) and 4 drops of 48% HBr. The reaction mixture is refluxed for 5 h, filtered and concentrated to dryness. The resulting oil is flash chromatographed on silica gel using chloroform as eluant to afford 49.5 g (91%) of the bromide as a colorless oil. This material is immediately dissolved in DMF (500 mL) and to this is added 4-nitroimidazole (20.5 g, 181 mmol) and potassium carbonate (75 g, 543 mmol). The reaction mixture is stirred overnight at ambient temperature, filtered and concentrated to dryness. The resulting oil is partitioned between ethyl acetate and water and extracted with ethyl acetate. The combined organics are washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The resulting oil is absorbed onto a silica pad and flash chromatographed on silica gel using 30-70% ethyl acetates/hexanes to yield 8 (33.6 g, 61%) as an orange oil that solidifies upon sitting. 1H-NMR (300 MHz, DMSO): 1.17 (t, J=7.2 Hz, 3H), 3.78 (s, 3H), 4.25 (q, J=7.2 Hz, 2H), 6.57 (s, 1H), 7.02 2H), 7.46 (d, J=8.7 Hz, 2H), 7.92 (s, 1H), 8.38 (s, 1H); Anal. Calc'd for C14H15B3O5: C, 55.08; H, 4.95; N, 13.76. Found: C, 54.93; H, 4.89; N, 13.82; MS m/z 306 (M+).

Uses

Metronidazole (M338880) derivative, an antibacterial in the treatment of rosacea and inflammatory bowel disease.

Manufacturing Info：

1H-Imidazole, 5-nitro-: ACTIVE

Computed Properties

Molecular Weight:113.08
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

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