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1-Methylimidazole

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
MDL Number:
MFCD00005292
MOL File:
616-47-7.mol
MSDS File:
SDS
Last updated:2024-12-18 14:07:02

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 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.
InChIKey MCTWTZJPVLRJOU-UHFFFAOYSA-N
LogP -0.19 at 25℃
CAS DataBase Reference 616-47-7(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII P4617QS63Y
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)  GHS hazard pictogramsGHS hazard pictograms
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(49)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich MX1123 1-Methylimidazole 616-47-7 4L $1120 2024-03-01 Buy
Sigma-Aldrich 8.05852 1-Methylimidazole for synthesis 616-47-7 100mL $64.5 2024-03-01 Buy
Sigma-Aldrich 8.05852 1-Methylimidazole for synthesis 616-47-7 1L $404 2024-03-01 Buy
Sigma-Aldrich 336092 1-Methylimidazole ≥99%, purified by redistillation 616-47-7 1l $395 2024-03-01 Buy
Sigma-Aldrich 336092 1-Methylimidazole ≥99%, purified by redistillation 616-47-7 2l $584 2024-03-01 Buy
Product number Packaging Price Buy
MX1123 4L $1120 Buy
8.05852 100mL $64.5 Buy
8.05852 1L $404 Buy
336092 1l $395 Buy
336092 2l $584 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 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.

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.]

Toxicity evaluation

Acute toxicity:Harmful if swallowed. Toxic in contact with skin. LD50 Oral:1144 mg/kg, LD50 Dermal:400-640 mg/kg.

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.

35487-17-3
616-47-7
Synthesis of 1-Methylimidazole from BASIONIC(TM) AC 75
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1-Methylimidazole pictures 2024-12-18 1-Methylimidazole
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US $6.00 / kg 1kg More than 99% 2000KG/Month Hebei Longbang Technology Co., Ltd
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616-47-7
US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
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US $0.00 / Kg/Drum 1KG 99% 500mg/year Jinan Finer Chemical Co., Ltd
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  • 1-Methylimidazole
    616-47-7
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CAP B (1-METHYLIMIDAZOLE 12% IN ACETONIT 1-Methylimidazole, >=99%, purified by redistillation CAP B (1-METHYLIMIDAZOLE 10% IN THF)* CAP B (1-METHYLIMIDAZOLE 10% IN CAP B (1-METHYLIMIDAZOLE 16% IN THF)* 1-METHYLIMIDAZOLE, FOR DNA SYNTHESIS 1-METHYLIMIDAZOLE FOR SYNTHESIS Imidazole, 1-methyl- 1-Methylimdazole 1-methylimidazole solution 1-methyl-imidazo MethiMazole (ThiaMazole) IMpurity B 1-MethyliMidazole ReagentPlus(R), 99% 1-Methylimidazole Vetec(TM) reagent grade, 98% 1-METHYLIMIDAZOLE 1-Methylimidazole≥ 99% (GC) LUPRAGEN(R) NMI 1-methyl-imidazol Araldite DY 070 DY 070 N1-Methylimidazole NSC 88064 Methylimidazole, 1- Cap B (1-methylimidazole 10% in THF/pyridine 8 : 1),1-Methylimidazole solution 1-METHYLIMIDAZOLE/THF FOR ABI 1-Methylglyoxaline Cap B (1-methylimidazole 10% in THF/pyridine 8 : 1) Cap B (1-methylimidazole 12% in acetonitrile/pyridine 78 : 10) 56-37-1% 1-MethyliMidazole, 99% 100GR 1-MethyliMidazole, 99% 500GR Thiamazole EP Impuriy B SKL1561 Methimazole EP Impurity B 2-[4-[(2 1-Methylimidazole, 99%, J&KSeal Methimazole Impurity 2 Thiamazole EP Impurity B Thiamazole Impurity 2(Thiamazole Impurity B) Methimazole Impurity B 1-methyl-1H-imidazole TDS free sample MSDS N-Methylimidazole COA TDS free sample MSDS 1-methyl-1H-imidazole COA MSDS 1-Methylimidazole Standard@100 μg/mL in Toluene 1-Methylimidazole> N-methylimidazole (1-methylimidazole) N-methyl midazole N-methyl glyoxaline 1H-Imidazole, 1-methyl- MIM 1-methyl-1h-imidazole methyl imidazole N-METHYLIMIDAZOLE 1-methyl-1h-imidazol 1-methylmidazole MeIm 1-Methylimidazole (1-MI) 1-Methylimidazole MIm