1-Methyl-1H-imidazole-2-carbaldehyde

Base Information

• Chemical Name: 1-Methyl-1H-imidazole-2-carbaldehyde
• CAS No.: 13750-81-7
• Molecular Formula: C5H6N2O
• Molecular Weight: 110.115
• Hs Code.: 29339900
• European Community (EC) Number: 629-142-7
• DSSTox Substance ID: DTXSID10160205
• Nikkaji Number: J132.807G
• Wikidata: Q72491540
• Mol file: 13750-81-7.mol

Synonyms:13750-81-7;1-Methyl-1H-imidazole-2-carbaldehyde;1-Methyl-2-imidazolecarboxaldehyde;1-methylimidazole-2-carbaldehyde;1-Methylimidazole-2-carboxaldehyde;1H-Imidazole-2-carboxaldehyde, 1-methyl-;MFCD01321308;Imidazole-2-carboxaldehyde, 1-methyl-;2-FORMYL-1-METHYLIMIDAZOLE;1-methyl-1H-imidazole-2-carboxaldehyde;2-formyl-l-methylimidazole;1-methyl-2-formylimidazole;1-methylimidazol-2-aldehyde;1-methyl-2-imidazolealdehyde;SCHEMBL202798;SCHEMBL4792546;N-methyl-2-imidazolecarbaldehyde;DTXSID10160205;1-methyl-imidazole-2-carbaldehyde;N-methylimidazole-2-carboxaldehyde;1-methyl-2-imidazole carboxaldehyde;N-methyl-imidazole-2-carboxaldehyde;1-methy-1H-imidazole-2-carbaldehyde;GEO-01857;STK510245;AKOS000122717;CS-W009259;PB12922;1-Methyl-1H-imidazole-2-carbaldehyde #;1-Methyl-2-imidazolecarboxaldehyde, 98%;AC-24711;AS-19537;BP-11897;SY001200;A2964;AM20080281;BB 0219739;FT-0636955;M2176;EN300-61999;W-200110;F2101-0177;Z363989438

Chemical Property of 1-Methyl-1H-imidazole-2-carbaldehyde

Chemical Property:

• Appearance/Colour: White to yellow crystalline mass
• Vapor Pressure: 0.0212mmHg at 25°C
• Melting Point: 36-39 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 250.8 °C at 760 mmHg
• PKA: 4.17±0.25(Predicted)
• Flash Point: 105.5 °C
• PSA: 34.89000
• Density: 1.14 g/cm³
• LogP: 0.23260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in water.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 110.048012819
• Heavy Atom Count: 8
• Complexity: 94.4

Purity/Quality:

99% ^*data from raw suppliers

1-Methyl-1H-imidazole-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C=CN=C1C=O
• Uses: It is an important raw material and intermediate used in organic synthesis, Pharmaceuticals, agrochemicals and dyestuffs. 1-Methyl-2-imidazolecarboxaldehyde may be used in the synthesis of:Schiff basesligand N,N-dimethyl-N′-(1-methylimidazole-2-ylmethyl)-ethylenediamine[(bis(1-methylimidazol-2-yl)methyl)(2-(pyridyl-2-yl)ethyl)amine]

Technology Process of 1-Methyl-1H-imidazole-2-carbaldehyde

There total 13 articles about 1-Methyl-1H-imidazole-2-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

1-methyl-1H-imidazole (616-47-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → N-methyl-2-imidazolcarboxaldehyde (13750-81-7)

Guidance literature:

1-methyl-1H-imidazole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -73 ℃; for 0.0833333h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - -73 ℃; for 0.0833333h; Inert atmosphere;

With hydrogenchloride; In water; at 20 ℃; for 1h;

DOI:10.1016/j.ica.2011.05.008

Reference yield: 79.0%

1-methyl-1H-imidazole (616-47-7) + methanol (67-56-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → methyl 1-methyl-1H-imidazole-2-carboxylate (62366-53-4) + N-methyl-2-imidazolcarboxaldehyde (13750-81-7)

Guidance literature:

1-methyl-1H-imidazole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;

methanol; Further stages;

DOI:10.1016/j.tet.2012.04.016

Reference yield: 76.1%

1H-imidazole (288-32-4) + methyl bromide (74-83-9) → N-methyl-2-imidazolcarboxaldehyde (13750-81-7)

Guidance literature:

1H-imidazole; With potassium hydroxide; In acetone; for 2h;

methyl bromide; In acetone;

upstream raw materials:

1-methyl-1H-imidazole

Methyl formate

N,N-dimethyl-formamide

formic acid ethyl ester

Downstream raw materials:

bis(1-methyl-2-imidazolyl)hydroxymethane

cis-3-(1-methyl-1H-imidazol-2-yl)acrylonitrile

trans-3-(1-methyl-1H-imidazol-2-yl)acrylonitrile

2-({[(1-methyl-2-imidazolyl)methyl]amino}methyl)phenol

Refernces

• 1、 Boulebd, Houssem,Zama, Sana,Insaf, Bataiche,Bouraiou, Abdelmalek,Bouacida, Sofiane,Merazig, Hocine,Romero, Alejandro,Chioua, Mourad,Marco-Contelles, José,Belfaitah, Ali. "Synthesis and biological evaluation of heterocyclic privileged medicinal structures containing (benz)imidazole unit". . p. 2209 - 2220. Retrieved 2016.
• 2、 Santagostini, Laura,Gullotti, Michele,Pagliarin, Roberto,Bianchi, Emanuela,Casella, Luigi,Monzani, Enrico. "Functional mimics of copper enzymes. Synthesis and stereochemical properties of the copper(II) complexes of a trinucleating ligand derived from L-histidine". . p. 281 - 295. Retrieved 1999.
• 3、 Szell, Patrick M. J.,Siiskonen, Antti,Catalano, Luca,Cavallo, Gabriella,Terraneo, Giancarlo,Priimagi, Arri,Bryce, David L.,Metrangolo, Pierangelo. "Halogen-bond driven self-assembly of triangular macrocycles". . p. 10467 - 10471. Retrieved 2018.
• 4、 -. "BICYCLIC COMPOUNDS". Paragraph 00717. . Retrieved 2020/06/01.