5-Chloro-1-methyl-4-nitroimidazole

Description References

Product Name: 5-Chloro-1-methyl-4-nitroimidazole
CAS No.: 4897-25-0
Chemical Name: 5-Chloro-1-methyl-4-nitroimidazole
Synonyms: 5-CHLORO-1-METHYL-4-NITRO-1H-IMIDAZOLE;CMNI;pcmni;NSC-7852;S-50154-9;A(S50154-9);AZATHIOPRINUM;TIMTEC-BB SBB003949;Azathioprine Impurity 9;Azathioprine EP Impurity C
CBNumber: CB6151649
Molecular Formula: C4H4ClN3O2
Formula Weight: 161.55
MOL File: 4897-25-0.mol

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5-Chloro-1-methyl-4-nitroimidazole Property

Melting point:: 148-150 °C (lit.)
Boiling point:: 362.3±22.0 °C(Predicted)
Density: 1.9518 (rough estimate)
refractive index: 1.5500 (estimate)
storage temp.: Inert atmosphere,2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: -1.37±0.61(Predicted)
form: Powder
color: White
InChIKey: OSJUNMSWBBOTQU-UHFFFAOYSA-N
CAS DataBase Reference: 4897-25-0(CAS DataBase Reference)
NIST Chemistry Reference: 1H-imidazole, 5-chloro-1-methyl-4-nitro-(4897-25-0)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36-37/39
WGK Germany: 3
RTECS: NI4397100
HazardClass: IRRITANT
HS Code: 29332900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: BP965
Product name: 5-Chloro-1-methyl-4-nitroimidazole
Purity: British Pharmacopoeia (BP) Reference Standard
Packaging: 100 mg
Price: $272
Updated: 2025/07/31

Sigma-Aldrich

Product number: 367532
Product name: 5-Chloro-1-methyl-4-nitroimidazole
Purity: 98%
Packaging: 5g
Price: $112.32
Updated: 2025/07/31

TCI Chemical

Product number: C1646
Product name: 5-Chloro-1-methyl-4-nitroimidazole
Purity: >98.0%(N)
Packaging: 5g
Price: $102
Updated: 2025/07/31

TRC

Product number: C369270
Product name: 5-Chloro-1-methyl-4-nitroimidazole
Packaging: 5g
Price: $120
Updated: 2021/12/16

AK Scientific

Product number: A253
Product name: 5-Chloro-1-methyl-4-nitroimidazole
Packaging: 5g
Price: $13
Updated: 2021/12/16

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5-Chloro-1-methyl-4-nitroimidazole Chemical Properties,Usage,Production

Description

5-Chloro-1-methyl-4-nitroimidazole is an imidazole derivative. It is useful in the rapid mix experiments to investigate the mechanism of anomalous radiosensitization of mammalian cells. It can also be used in the synthesis of 5-aryl-1-methyl-4-nitroimidazoles, via Suzuki coupling with arylboronic acids, catalyzed by dichlorobis-(triphenylphosphine) palladium (II), K2CO3 and tetrabutylammonium bromide.

References

http://www.sigmaaldrich.com/catalog/product/aldrich/367532?lang=en&region=US
Watts, M. E., et al. "Rapid-mix studies on the anomalous radiosensitization of mammalian cells by 5-chloro-1-methyl-4-nitromidazole." Int J Radiat Biol Relat Stud Phys Chem Med 38.6(1980):673-675.
Saadeh, H. A, I. M. Mosleh, and M. M. Elabadelah. "New synthesis and antiparasitic activity of model 5-aryl-1-methyl-4-nitroimidazoles. "Molecules 14.8(2009):2758-67.

Description

5-Chloro-1-methyl-4-nitroimidazole is an intermediate in azathioprine synthesis, also present in the end product. It induced contact dermatitis in a man working on azathioprine synthesis. Cross reactivity is possible with imidazoles tioconazole, and econazole.

Chemical Properties

White Solid

Uses

5-Chloro-1-methyl-4-nitroimidazole (CMNI) is suitable for use in the rapid mix experiments to investigate the mechanism of anomalous radiosensitization of mammalian cells by CMNI. It may be used in the synthesis of 5-aryl-1-methyl-4-nitroimidazoles, via Suzuki coupling with arylboronic acids, catalyzed by dichlorobis-(triphenylphosphine)palladium(II), K₂CO₃ and tetrabutylammonium bromide.

General Description

5-Chloro-1-methyl-4-nitroimidazole is an 4-nitroimidazole derivative.

Contact allergens

This intermediate in azathioprine synthesis is also present in the end product. It induced contact dermatitis in a man working on azathioprine synthesis. Cross-reactivity is possible with imidazoles tioconazole and econazole.

Synthesis

872-49-1

4897-25-0

General procedure for the synthesis of 5-chloro-1-methyl-4-nitroimidazole from 5-chloro-1-methylimidazole: A mixed solution of 1-methyl-5-chloroimidazole (57.0 g, 0.50 mol) and dilute nitric acid (690 mL, 1.15 mol) was concentrated to dryness. The resulting light yellow oil (131.40 g) was slowly added dropwise to 214 mL of pre-cooled concentrated sulfuric acid over 85 minutes under nitrogen protection. Subsequently, the reaction mixture was stirred at 100 °C for 2 h under nitrogen atmosphere. Upon completion of the reaction, the reaction solution was slowly poured into 21 mL of ice water and precipitate was precipitated and collected by filtration. The precipitate was washed to neutrality with ice water to give 1-methyl-5-chloro-4-nitroimidazole (45.3 g, 62% yield) in white crystalline form. The melting point of the product was 147.5-148.9 °C. 1H NMR (400 MHz, d6-DMSO): δ= 7.50 (s, 1H, 2-H), 3.72 (s, 3H, CH3). 13C NMR (100 MHz, d6-DMSO): δ= 142.4 (C-4), 134.6 (C-2), 119.6 (C-5). 32.9 (CH3).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1369 - 1375
[2] Patent: US2017/281501, 2017, A1. Location in patent: Paragraph 0277-0280
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2690 - 2695
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1440 - 1444
[5] Patent: EP1066286, 2009, B1. Location in patent: Page/Page column 39-40

5-Chloro-1-methyl-4-nitroimidazole Preparation Products And Raw materials

Raw materials

Glass-lined reaction pot Phosphorus oxitrichloride Phosphorus pentachloride N,N'-Dimethyloxamide 5-Chloro-1-methylimidazole Potassium nitrate

Preparation Products

Azathioprine

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5-Chloro-1-methyl-4-nitroimidazole Suppliers

Americas 1 Belgium 3 Canada 3 China 200 Europe 4 Germany 4 India 22 Japan 3 Russia 2 Slovakia 1 Switzerland 2 The Netherlands 1 Ukraine 1 United Kingdom 19 United States 43 Global 309

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View Lastest Price from 5-Chloro-1-methyl-4-nitroimidazole manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: 5-Chloro-1-methyl-4-nitroimidazole 4897-25-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98.0%
Supply Ability: 10000KGS
Release date: 2025-05-26

Henan Aochuang Chemical Co.,Ltd.

Product: 5-Chloro-1-methyl-4-nitroimidazole 4897-25-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2022-09-29

airuikechemical co., ltd.

Product: 5-Chloro-1-methyl-4-nitroimidazole 4897-25-0
Price: US $0.00-0.00/Kg
Min. Order: 1Kg
Purity: 99.9%
Supply Ability: 200tons
Release date: 2024-04-08

4897-25-0, 5-Chloro-1-methyl-4-nitroimidazoleRelated Search:

Thiophanate-methyl Kresoxim-methyl Methyl acrylate Bensulfuron methyl Imidazole 4-Nitroimidazole Methylparaben 1-Methylimidazole Methyl Methyl bromide Difluorochloromethane nitrotoluene Parathion-methyl Imidazole, 1-methyl-4-nitro- 5-Chloro-1-methyl-4-nitroimidazole 5-CHLORO-4-NITRO-1-ISOBUTYL-2-ISOPROPYL-1H-IMIDAZOLE 5-CHLORO-2-ETHYL-4-NITRO-1-PROPYL-1H-IMIDAZOLE

5-chloro-1-methyl-4-nitroimidazole Solution, 100ppm

5-Chloro-1-methyl-4-nitroimidazole≥ 99% (HPLC)

Azathioprine EP Impurity C

Azathioprine Impurity Ⅰ: 5-Chloro-1-methyl-4-nitroimidazole

5-chloro-1-methyl-4-nitro-imidazol

A(S50154-9)

Imidazole, 5-chloro-1-methyl-4-nitro-

pcmni

TIMTEC-BB SBB003949

1-METHYL-5-CHLORO-4-NITRO IMIDAZOLE

1-METHYL-4-NITRO-5-CHLORO IMIDAZOLE

AZATHIOPRINUM

5-CHLORO-1-METHYL-4-NITRO-1H-IMIDAZOLE

5-CHLORO-1-METHYL-4-NITROIMIDAZOLE

5-Chloro-1-Methyl-4-NitroImidazole(ForAzathiopurine)

5-CHLORO-1-METHYL-4-NITROIMIDAZOLE (AZATHIOPRINUM)

1-Methyl-4-Nitro-5-Chloroimida

1H-Imidazole, 5-chloro-1-methyl-4-nitro-

S-50154-9

1-Methyl-5-chloro-4-nitro-1H-imidazole

CMNI

NSC-7852

5-Chloro-1-methyl-4-nitroimidazole,98%

Azathioprine Impurity 3（Azathioprine EP Impurity C）

5-Chloro-1-methyl-4-nitroimidazole &gt

Azathioprine Impurity 9

Azathioprine BP Impurity C

5-Chloro-1-methyl-4-nitroimidazole Solution in Methanol, 100μg/mL

5-Chloro-1-methyl-4-nitroimidazole (Azathioprine Impurity)

4897-25-0

C4H4ClN3O2

Building Blocks

Halogenated Heterocycles

Heterocyclic Building Blocks

Imidazoles

Heterocycles

Halogenated Heterocycles

Heterocyclic Building Blocks

Imidazoles

ImidazolesBuilding Blocks

Building Blocks

Chemical Synthesis

Halogenated Heterocycles

Heterocyclic Building Blocks

Heterocyclic Compounds

Imidaxoles