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1-Methylimidazole

1-Methylimidazole Structure
CAS No.
616-47-7
Chemical Name:
1-Methylimidazole
Synonyms
N-METHYLIMIDAZOLE;1-methyl-1h-imidazole;MIM;MeIm;methyl imidazole;1H-Imidazole, 1-methyl-;N-methylimidazole (1-methylimidazole);1-methylmidazole;N-methyl midazole;N-methyl glyoxaline
CBNumber:
CB1316726
Molecular Formula:
C4H6N2
Molecular Weight:
82.1
MOL File:
616-47-7.mol
MSDS File:
SDS
Modify Date:
2024/8/8 18:06:34

1-Methylimidazole Properties

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 n20/D 1.495(lit.)
Flash point 198 °F
storage temp. Store below +30°C.
solubility Chloroform (Slightly), Methanol (Slightly)
form Liquid
pka 6.95(at 25℃)
Specific Gravity 1.031
color Clear colorless to yellow
PH 9.5-10.5 (50g/l, H2O, 20℃)
PH Range 9.5 - 11.5 at 100 g/l at 20 °C
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.
InChIKey MCTWTZJPVLRJOU-UHFFFAOYSA-N
LogP -0.19 at 25℃
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

Risk and Safety Statements

Symbol(GHS) 
GHS05,GHS06
Signal word  Danger
Hazard statements  H302-H311-H314
Precautionary statements  P270-P280-P301+P312-P301+P330+P331-P303+P361+P353-P305+P351+P338
Hazard Codes  C,Xn,F,T
Risk Statements  21/22-34-19-11-20/21/22-52/53-24-22-40-37-21
Safety Statements  26-36-45-1/2-36/37/39-16-33-29-61
RIDADR  UN 3267 8/PG 2
WGK Germany  1
RTECS  NI7000000
3-10
Autoignition Temperature 977 °F
TSCA  Yes
HazardClass  8
PackingGroup  III
HS Code  29332990
Toxicity LD50 orally in Rabbit: 1144 mg/kg LD50 dermal Rabbit > 400 - < 640 mg/kg
NFPA 704
2
3 1

1-Methylimidazole price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) M50834 1-Methylimidazole ReagentPlus?, 99% 616-47-7 100G ₹1960 2022-06-14 Buy
Sigma-Aldrich(India) 8.05852 1-Methylimidazole for synthesis 616-47-7 25ML ₹3620 2022-06-14 Buy
Sigma-Aldrich(India) M50834 1-Methylimidazole ReagentPlus?, 99% 616-47-7 500G ₹7980 2022-06-14 Buy
Sigma-Aldrich(India) 8.05852 1-Methylimidazole for synthesis 616-47-7 100ML ₹8710 2022-06-14 Buy
Sigma-Aldrich(India) 8.05852 1-Methylimidazole for synthesis 616-47-7 1L ₹40520 2022-06-14 Buy
Product number Packaging Price Buy
M50834 100G ₹1960 Buy
8.05852 25ML ₹3620 Buy
M50834 500G ₹7980 Buy
8.05852 100ML ₹8710 Buy
8.05852 1L ₹40520 Buy

1-Methylimidazole Chemical Properties,Uses,Production

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.

Uses

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.

Uses

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].

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

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.

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.

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.

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