4-bromo-1-methyl-1H-imidazole-5-carbaldehyde

Base Information

• Chemical Name: 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde
• CAS No.: 141524-74-5
• Molecular Formula: C5H5BrN2O
• Molecular Weight: 189.011
• Hs Code.: 2933290090
• European Community (EC) Number: 686-958-6
• DSSTox Substance ID: DTXSID90378321
• Nikkaji Number: J618.467G
• Wikidata: Q82167866
• Mol file: 141524-74-5.mol

Synonyms:141524-74-5;4-Bromo-1-methyl-1H-imidazole-5-carboxaldehyde;4-bromo-1-methyl-1H-imidazole-5-carbaldehyde;5-bromo-3-methylimidazole-4-carbaldehyde;SCHEMBL2456342;DTXSID90378321;MBLIXONXVCDFMO-UHFFFAOYSA-N;MFCD01632216;AKOS015850985;PB33964;AS-50430;CS-0053922;FT-0643327;EN300-133623;P10191;A807772;W-205557;4-Bromo-1-methyl-1H-imidazole-5-carboxaldehyde, 95%;Z1255373007

Chemical Property of 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde

Chemical Property:

• Vapor Pressure: 4.81E-05mmHg at 25°C
• Melting Point: 60-64 °C
• Refractive Index: 1.621
• Boiling Point: 349.115 °C at 760 mmHg
• PKA: 1.12±0.61(Predicted)
• Flash Point: 164.939 °C
• PSA: 34.89000
• Density: 1.738 g/cm³
• LogP: 0.99510
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 187.95853
• Heavy Atom Count: 9
• Complexity: 120

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Bromo-1-methyl-1H-imidazole-5-carboxaldehyde 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C=NC(=C1C=O)Br

Technology Process of 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde

There total 6 articles about 4-bromo-1-methyl-1H-imidazole-5-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: 99.0%

1-methyl-4-bromo-5-hydroxymethyl-1H-imidazole (141524-73-4) → 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde (141524-74-5)

Guidance literature:

With manganese(IV) oxide; In chloroform; Reflux; Inert atmosphere;

DOI:10.1002/ejoc.201601384

Reference yield: 95.0%

N-methyl-2,4,5-tribromoimidazole (1003-91-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde (141524-74-5)

Guidance literature:

N-methyl-2,4,5-tribromoimidazole; With ethylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

N,N-dimethyl-formamide; In diethyl ether; hexane; at -78 ℃; for 0.75h;

Reference yield: 65.0%

4-bromo-1H-imidazole-5-carbaldehyde + methyl iodide (74-88-4) → 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde (141524-74-5)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

upstream raw materials:

1-methyl-4-bromo-5-hydroxymethyl-1H-imidazole

N,N-dimethyl-formamide

1-Methyl-4,5-dibromoimidazole-2-carboxylic acid

5-hydroxymethyl-2-mercapto-1-methyl-1H-imidazole

Downstream raw materials:

5-benzenesulfonyl-3-methyl-3H-imidazole-4-carbaldehyde

(5S,10aS)-6,8-dimethoxy-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

(5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

1-methyl-4-(phenylthio)-1H-imidazole-5-carbaldehyde

Refernces

• 1、 -. "MATRIX METALLOPROTEINASE (MMP) INHIBITORS AND METHODS OF USE THEREOF". Paragraph 0658; 0660. . Retrieved 2019/12/02.
• 2、 Ohba,Mukaihira,Fujii. "Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines". . p. 1784 - 1790. Retrieved 2007/10/02.