1-Methylimidazole
Synonym(s):1-Methylimidazole;N-Methylimidazole
- CAS NO.:616-47-7
- Empirical Formula: C4H6N2
- Molecular Weight: 82.1
- MDL number: MFCD00005292
- EINECS: 210-484-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-12-18 14:07:02
What is 1-Methylimidazole?
Chemical properties
1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colorless to yellow liquid, with an amine-like odor. It is miscible with water. N-methylimidazole is an important raw material for the synthesis of pharmaceutical intermediates, used in the preparation of losartan, nizofenone, 1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride and naphazoline hydrochloride, etc. It is also used as a specialty solvent, a base, and as a precursor to some ionic liquids.
The Uses of 1-Methylimidazole
1-Methylimidazole is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate. It is actively involved in removing acid during the production of diethoxyphenylphosphine. It is used as an intermediate in organic synthesis.
The Uses of 1-Methylimidazole
1-Methylimidazole is an aprotic solvent. It is a derivative of imidazole used in the production of pharmaceuticals, pesticides, ion exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors. It can also be used as a catalyst for the manufacture of polyurethane and a curing agent for epoxy resins. For example, when 1-methylimidazole is added to an aqueous diethylenetriamine (DETA) solution, high CO2 loading can be achieved through phase separation of the absorbent during CO2 absorption[1].
What are the applications of Application
1-Methylimidazole is a metabolite of 1-methyl-2-thioimidazole (methimazole)
Definition
ChEBI: 1-methyl-1H-imidazole is a 1H-imidazole having a methyl substituent at the N-1 position. It is a metabolite of 1-methyl-2-thioimidazole (methimazole). It inhibits bone resorption.
Preparation
1-Methylimidazole is prepared mainly by two routes industrially. The main one is acid-catalysed methylation of imidazole by methanol. The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine.
(CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O
The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation. Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation.
H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I
[H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI
General Description
This product has been enhanced for catalysis. 1-Methylimidazole is a derivative of imidazole that is utilized in the manufacture of such classes of items as pharmaceuticals, pesticides, ion-exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors. It is also used as a catalyst for manufacturing polyurethanes and a curing agent for epoxy resins.
Flammability and Explosibility
Not classified
Purification Methods
Dry it with sodium metal and then distil it. Store it at 0o under dry argon. The picrate has m 159.5-160.5o (from H2O). [Beilstein 23 III/IV 568.]
References
[1] You J, et al. Effect of 1-Methylimidazole on CO2 Absorption by Diethylenetriamine (DETA) Aqueous Solutions. Chemical Engineering & Technology, 2017; 40: 2238-2242.
Properties of 1-Methylimidazole
Melting point: | −60 °C(lit.) |
Boiling point: | 198 °C(lit.) |
Density | 1.03 g/mL at 25 °C(lit.) |
vapor pressure | 0.4 mm Hg ( 20 °C) |
refractive index | n |
Flash point: | 198 °F |
storage temp. | Store below +30°C. |
solubility | Chloroform (Slightly), Methanol (Slightly) |
pka | 6.95(at 25℃) |
form | Liquid |
color | Clear colorless to yellow |
Specific Gravity | 1.031 |
PH Range | 9.5 - 11.5 at 100 g/l at 20 °C |
PH | 9.5-10.5 (50g/l, H2O, 20℃) |
explosive limit | 2.7-15.7%(V) |
Water Solubility | Miscible with water. |
Sensitive | Hygroscopic |
BRN | 105197 |
Stability: | Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides. |
CAS DataBase Reference | 616-47-7(CAS DataBase Reference) |
NIST Chemistry Reference | 1H-Imidazole, 1-methyl-(616-47-7) |
EPA Substance Registry System | 1H-Imidazole, 1-methyl- (616-47-7) |
Safety information for 1-Methylimidazole
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H302:Acute toxicity,oral H311:Acute toxicity,dermal H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 1-Methylimidazole
InChIKey | MCTWTZJPVLRJOU-UHFFFAOYSA-N |
1-Methylimidazole manufacturer
SOLFYN INTERNATIONAL LLP
TRUUCHEM TECHNOLOGIES PRIVATE LIMITED
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