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5-Chloro-1-methyl-4-nitroimidazole

5-Chloro-1-methyl-4-nitroimidazole structure

CAS No.: 4897-25-0

Chemical Name:: 5-Chloro-1-methyl-4-nitroimidazole

Synonyms: 5-CHLORO-1-METHYL-4-NITRO-1H-IMIDAZOLE;Azathioprine EP Impurity C;CMNI;pcmni;NSC-7852;S-50154-9;A(S50154-9);AZATHIOPRINUM;TIMTEC-BB SBB003949;Azathioprine Impurity 9

CBNumber:: CB6151649

Molecular Formula:: C4H4ClN3O2

Molecular Weight:: 161.55

MDL Number:: MFCD00233664

MOL File:: 4897-25-0.mol

MSDS File:: SDS

TDS File:: TDS

Last updated:2026-05-28 03:18:53

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5-Chloro-1-methyl-4-nitroimidazole Properties

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
InChI	1S/C4H4ClN3O2/c1-7-2-6-4(3(7)5)8(9)10/h2H,1H3
InChIKey	OSJUNMSWBBOTQU-UHFFFAOYSA-N
SMILES	Cn1cnc(c1Cl)[N+]([O-])=O
CAS DataBase Reference	4897-25-0(CAS DataBase Reference)
EWG's Food Scores	1
FDA UNII	P917JW98BD
NIST Chemistry Reference	1H-imidazole, 5-chloro-1-methyl-4-nitro-(4897-25-0)
UNSPSC Code	41116107
NACRES	NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P305+P351+P338-P280a-P304+P340-P405-P501a

PPE

dust mask type N95 (US), Eyeshields, Gloves

Hazard Codes

Risk Statements

36/37/38

Safety Statements

26-36-37/39

WGK Germany

RTECS

NI4397100

HazardClass

IRRITANT

HS Code

29332900

Storage Class

11 - Combustible Solids

REACH Registrations

Active

NFPA 704

	1
2		0

5-Chloro-1-methyl-4-nitroimidazole price More Price(57)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	BP965	5-Chloro-1-methyl-4-nitroimidazole British Pharmacopoeia (BP) Reference Standard	4897-25-0	100 mg	$292	2026-04-30	Buy
Sigma-Aldrich	367532	5-Chloro-1-methyl-4-nitroimidazole 98%	4897-25-0	5g	$151	2026-04-30	Buy
TCI Chemical	C1646	5-Chloro-1-methyl-4-nitroimidazole >98.0%(N)	4897-25-0	5g	$108	2026-04-30	Buy
Usbiological	C5028-52	5-Chloro-1-methyl-4-nitroimidazole		1g	$333	2026-06-03	Buy
Biosynth	FC19985	5-Chloro-1-methyl-4-nitroimidazole	4897-25-0	0.1kg	$150	2026-06-04	Buy

Product number	Packaging	Price	Buy
BP965	100 mg	$292	Buy
367532	5g	$151	Buy
C1646	5g	$108	Buy
C5028-52	1g	$333	Buy
FC19985	0.1kg	$150	Buy

5-Chloro-1-methyl-4-nitroimidazole Chemical Properties, Uses, 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

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Preparation Products

Azathioprine 1H-Imidazol-5-amine,1-methyl-4-nitro-(9CI)

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

Global Suppliers ( 314)

Supplier	Tel	Email	Country	ProdList	Advantage
J & K SCIENTIFIC LTD.	18210857532 18210857532	jkinfo@jkchemical.com	China	96815	76
Alfa Aesar	400-6106006	saleschina@alfa-asia.com	China	30103	84
TCI (Shanghai) Development Co., Ltd.	021-67121386	Sales-CN@TCIchemicals.com	China	24512	81
Energy Chemical	400-0056266	sales8178@energy-chemical.com	China	44850	61
Wuhan Chemwish Technology Co., Ltd	86-027-67849912	sales@chemwish.com	China	35884	56
Beijing Ouhe Technology Co., Ltd	13552068683 13522913783	2355560935@qq.com	China	11777	60
Shanghai Sinch Parmaceuticals Tech. Co. Ltd.	+86-21-54098501	sales@sinch.com.cn	China	11592	64
Jia Xing Isenchem Co.,Ltd	0573-85285100 18627885956	isenchem@163.com	China	9389	66
Pure Chemistry Scientific Inc.	001-857-928-2050 or 1-888-588-9418	sales@chemreagents.com	United States	10174	62
Shanghai Hanhong Scientific Co.,Ltd.	021-54306202 13764082696	info@hanhongsci.com	China	42917	64

Supplier	Advantage
J & K SCIENTIFIC LTD.	76
Alfa Aesar	84
TCI (Shanghai) Development Co., Ltd.	81
Energy Chemical	61
Wuhan Chemwish Technology Co., Ltd	56
Beijing Ouhe Technology Co., Ltd	60
Shanghai Sinch Parmaceuticals Tech. Co. Ltd.	64
Jia Xing Isenchem Co.,Ltd	66
Pure Chemistry Scientific Inc.	62
Shanghai Hanhong Scientific Co.,Ltd.	64

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

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2026-08-07	5-Chloro-1-methyl-4-nitroimidazole 4897-25-0	$1.00-2.10	1KG	99%	20000KG	Shaanxi Dideu Medichem Co. Ltd
2026-06-30	5-Chloro-1-methyl-4-nitroimidazole 4897-25-0		1KG	98.0%	10000KGS	Shaanxi Dideu New Materials Co. Ltd
2025-04-04	5-Chloro-1-methyl-4-nitroimidazole 4897-25-0		1KG	98%	1ton	Henan Aochuang Chemical Co.,Ltd.

5-Chloro-1-methyl-4-nitroimidazole
4897-25-0
$1.00-2.10
99%
Shaanxi Dideu Medichem Co. Ltd

5-Chloro-1-methyl-4-nitroimidazole
4897-25-0
98.0%
Shaanxi Dideu New Materials Co. Ltd

5-Chloro-1-methyl-4-nitroimidazole
4897-25-0
98%
Henan Aochuang Chemical Co.,Ltd.

5-Chloro-1-methyl-4-nitroimidazole Spectrum

5-Chloro-1-methyl-4-nitroimidazole(4897-25-0)MS 5-Chloro-1-methyl-4-nitroimidazole(4897-25-0)¹HNMR 5-Chloro-1-methyl-4-nitroimidazole(4897-25-0)IR1 5-Chloro-1-methyl-4-nitroimidazole(4897-25-0)IR2

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5-chloro-1-methyl-4-nitroimidazole Solution, 100ppm 5-Chloro-1-methyl-4-nitroimidazole≥ 99% (HPLC) 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-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 > 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) 5-Chloro-1-methyl-4-nitroimidazole (Standard) 5-CHLORO-1-METHYL-4-NITRO-1H-IMIDAZOLE Azathioprine EP Impurity C 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