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2-Methylimidazole

CAS No.
693-98-1
Chemical Name:
2-Methylimidazole
Synonyms
2-Methyl-1H-imidazole;2MI;2MZ;Ondansetron EP Impurity F;Actiron 2MI;2-methyl-imidazol;2-methyl-1h-imidazol;2MZ-H;2MZ-PW;NSC 21394
CBNumber:
CB6146227
Molecular Formula:
C4H6N2
Molecular Weight:
82.1
MDL Number:
MFCD00005190
MOL File:
693-98-1.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-04-10 10:27:21
Product description Number Pack Size Price
2-Methylimidazole 99% M50850 100g $68.2
Ondansetron impurity F European Pharmacopoeia (EP) Reference Standard Y0001320 10 mg $254
2-Methylimidazole 99% M50850 500g $304
2-Methylimidazole >97.0%(GC)(T) M0345 25g $18
2-Methylimidazole >97.0%(GC)(T) M0345 100g $26
More product size

2-Methylimidazole Properties

Melting point 142-143 °C (lit.)
Boiling point 267-268 °C (lit.)
bulk density 550kg/m3
Density 1.0500 (rough estimate)
vapor pressure <1 mm Hg ( 0 °C)
refractive index 1.4970 (estimate)
Flash point 155 °C
storage temp. 2-8°C
solubility 780g/l
pka 14.44±0.10(Predicted)
form Crystalline Powder
color White to light yellow
PH 10.5-11.5 (100g/l, H2O, 20℃)
PH Range 10.5
Water Solubility Soluble in water and ethanol.
BRN 1368
Henry's Law Constant 8.1×102 mol/(m3Pa) at 25℃, Du et al. (2017)
InChI 1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
InChIKey LXBGSDVWAMZHDD-UHFFFAOYSA-N
SMILES Cc1ncc[nH]1
LogP 0.22 at 25℃
Toxicology and Carcinogenesis Toxicology and Carcinogenesis Studies of 2-Methylimidazole (CASRN 693-98-1) in F344/N Rats and B6C3F1 Mice (Feed Studies)
Substances of Very High Concern (SVHC) Candidate List 2-methylimidazole (693-98-1)
CAS DataBase Reference 693-98-1(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII T0049Z45LZ
IARC 2B (Vol. 101) 2013
NIST Chemistry Reference 1H-Imidazole, 2-methyl-(693-98-1)
Proposition 65 List 2-Methylimidazole
EPA Substance Registry System 2-Methylimidazole (693-98-1)
UNSPSC Code 41116107
NACRES NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H314-H351-H360Df
Precautionary statements  P260-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
PPE Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes  C
Risk Statements  22-34
Safety Statements  26-36/37/39-45-25
RIDADR  UN 3259 8/PG 2
WGK Germany  2
RTECS  NI7175000
Autoignition Temperature >600 °C DIN 51794
Hazard Note  Harmful/Corrosive
TSCA  TSCA listed
HazardClass  8
PackingGroup  III
HS Code  29332990
Storage Class 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard Classifications Acute Tox. 4 Oral
Carc. 2
Eye Dam. 1
Repr. 1B
Skin Corr. 1C
Hazardous Substances Data 693-98-1(Hazardous Substances Data)
Toxicity LD50 orally in Rabbit: 1500 mg/kg
Limited Quantities 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
NFPA 704
0
3 0

2-Methylimidazole price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich M50850 2-Methylimidazole 99% 693-98-1 100g $68.2 2026-03-19 Buy
Sigma-Aldrich Y0001320 Ondansetron impurity F European Pharmacopoeia (EP) Reference Standard 693-98-1 10 mg $254 2026-03-19 Buy
Sigma-Aldrich M50850 2-Methylimidazole 99% 693-98-1 500g $304 2026-03-19 Buy
TCI Chemical M0345 2-Methylimidazole >97.0%(GC)(T) 693-98-1 25g $18 2026-03-19 Buy
TCI Chemical M0345 2-Methylimidazole >97.0%(GC)(T) 693-98-1 100g $26 2026-03-19 Buy
Product number Packaging Price Buy
M50850 100g $68.2 Buy
Y0001320 10 mg $254 Buy
M50850 500g $304 Buy
M0345 25g $18 Buy
M0345 100g $26 Buy

2-Methylimidazole Chemical Properties,Uses,Production

Detection method

Fluorescence detection method: Using o-phenylenediamine as the carbon source and phytic acid as the phosphorus source, two P-rich carbon quantum dots RCD and BCD were successfully synthesized by changing the reaction temperature and time of the hydrothermal method. The study found that the red-emitting RCD can achieve sensitive detection of 2-Methylimidazole, while 2-methylimidazole has no obvious quenching effect on the blue-emitting BCD, which makes RCD a sensitive, fast and selective fluorescence sensor for 2-methylimidazole detection. Under the optimal experimental conditions, the fluorescence intensity of RCDs decreases with the increase of 2-methylimidazole concentration; the carbon quantum dot sensor shows a good linear relationship in the detection of 2-methylimidazole concentration in the range of 5 ~ 110 µM, and the minimum detection limit is 0.61 µM (S/N = 3). The sensor can detect 2-methylimidazole in lake water and can be used for the detection of actual samples[2].

Chemical Properties

2-Methylimidazole is a white to light yellow crystalline powder with an amine-like odor. It is highly soluble in polar organic solvents. Insoluble in ether and cold benzene, easily soluble in water, alcohols and ketones. Irritating to skin and mucous membranes. Mice orally LD50 1400mg/kg.

Chemical Properties

The 2-methylimidazole molecule is approximately planar, and the maximum deviation of all non-H atoms from the plane of the least squares imidazole is 0.006(2). N–H··· N hydrogen bonds link molecules together to form infinite chains of hydrogen bond pattern C(4). The crystal of 2-methylimidazole is in orthorhombic crystal system with space group P212121 (Z = 4), lattice parameters: a = 5.9957(12) , b = 8.1574(16) and c = 9.7010(19) , V = 474.47(16) [1].

Uses

2-Methylimidazole is a monomethylated imidazole that can be used as a building block in the preparation of a wide range of biologically active compounds. 2-Methylimidazole as well as other imidazoles can be use as catalyst for refolding of enhanced coloured fluorescent protein. 2-Methylimidazole has been identified as a byproduct of fermentation and is detected in foods and mainstream and side-str eam tobacco smoke.

Uses

2-Methylimidazole is used as a raw material for the preparation of nitroimidazole antibiotics, which is useful in combat anaerobic bacterial and parasitic infections. It acts as a ligand in coordination chemistry. It is also employed as a hardener or accelerator for epoxy resin and auxiliary agent for textile dyes. Further, it acts as a catalyst for refolding of enhanced colored fluorescent protein. It is also useful as a building block in the synthesis of biologically active compounds. In addition to this, it is used as an active pharmaceutical ingredient intermediate such as metronidazole and dimetridazole.

Preparation

2-Methylimidazole is prepared by condensation of glyoxal, ammonia and acetaldehyde, a Radziszewski reaction. It is widely used as a polymeriza tion cross-linking accelerator and a hardener for epoxy resin systems for semiconductor potting compounds and soldering masks.
It is obtained by eliminating dehydrogenation of 2-methylimidazoline. 2-methylimidazoline heated to melt (melting point 107 ℃), carefully add active nickel, raise the temperature to 200-210 ℃ reaction 2h. cool down to below 150 ℃, add water to dissolve, while hot pressure filtration, separation of active nickel, the filter Chemicalbook liquid concentrated to a temperature of 140 ℃ or more, put the material cooling that 2-methylimidazole. Use the method to produce purity of ≥ 98% of the product, 1t product consumption of ethylenediamine (95%) 1095kg, acetonitrile 975kg. better method is to use glyoxal and aldehyde as raw materials.

General Description

It is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and is a ligand in coordination chemistry.

Hazard

Possible carcinogen.

Flammability and Explosibility

Not classified

Purification Methods

Recrystallise 2-methylimidazole from *benzene or pet ether. The picrate has m 215o (from H2O). [Beilstein 23 III/IV 594, 23/5 V 35.]

Toxicity evaluation

2-Methylimidazole is harmful if swallowed and may cause severe skin burns and eye damage from exposure. It is also associated with adverse effects such as neurotoxins, reproductive toxins and toxic pneumonia. In vitro studies have shown a mouse LD50: 480 mg/kg (intraperitoneal); 1400 mg/kg (oral).

References

[1] Hachua B, et al. Crystal and Molecular Structure Analysis of 2-Methylimidazole. Journal of Chemical Crystallography, 2009; 40: 201–206.
[2] ZHENGYUAN DAI. Synthesis of P-Rich Carbon Quantum Dots for Sensitive Fluorescent Detection of 2-Methylimidazole.[J]. Journal of Fluorescence, 2024. DOI:10.1007/s10895-024-03946-9.

13750-62-4
693-98-1
Synthesis of 2-Methylimidazole from 1-Benzyl-2-methyl-1H-imidazole
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1H-Imidazole,2-methyl- 2-methyl-1h-imidazol 2-methyl-imidazol 2MZ 1H-2-MethyliMidazole 2MZ-H 2MZ-PW Actiron 2MI Curezol 2MZ-P Epicure MI 2 Epikure MI 2 IMicure AMI 2 NSC 21394 Ondansetron HCl IMpurity-F Ondansetron impurity F Ondansetron impurity F (PhEur) 2-Methyl Limidazole Ondansetron EP Impurity F 2-methyl-1H-imidazole analogue 2-Methylimidazole (Ondansetron Impurity F) 2-Methylimidazole Solution, 100ppm 2-METHYL-3-NITROBENZOTRIFLUORIDE 2-NITRO-6-(TRIFLUOROMETHYL)TOLUENE 2-NITRO-5-TRIFLUOROMETHYLTOLUENE Benzene, 2-methyl-1-nitro-3-(trifluoromethyl)- alpha,alpha,alpha-trifluoro-3-nitro-o-xylene 3-Trifluoromethyl-2-methyl-1-nitrobenzene 2- 2-Methylimidazole 693-98-1 693-98-1 2-Methylimidazole 2-Methylimidazo Ondansetron Impurity 6(Ondansetron EP Impurity F) Ondansetron Hydrochloride Dihydrate EP Impurity F Glyoxalethyline Imidazole, 2-methyl- p-Oxal-methyline 2-METHYLIMIDAZOLE 2-METHYLGLYOXALINE 2MI AKOS BBS-00004447 Flucythrinate PESTANAL 2-Methylimidazole,97% RESICURE(TM) 46 2-METHYLIMIDAZOLE pure 2-MethyliMidazole, 99% 100GR 2-MethyliMidazole, 99% 500GR Curezol 2MZ Denka CN 25 2-Methylimidazole,99% JACS-693-98-1 2-Methylimidazole > 2-Methylimidazole Standard@100 μg/mL in Toluene 2-Methylimidazole Reference Material Ondansetron impurity F CRS 2-Methylimidazole,98% 2-METHYLIMIDAZOLE FOR SYNTHESIS 2-Methylimidazole USP/EP/BP Ondansetron impurity F (Y0001320) 2-METHYLIMIDAZOLE Extra Pure 2-Methylimidazole flakes (2-MI Flakes) 2-Methylimidazole pure (2-MI Pure) Ondansetron Hydrochloride Dihydrate Impurity F 2-Methylimidazole 98% Extrapure 2-Methylimidazole in methanol