3012-80-4

Basic information

• Product Name: 1-METHYL-2-FORMYLBENZIMIDAZOLE
• Synonyms: ZERENEX EZX001709;TIMTEC-BB SBB010051;1-METHYL-1H-BENZIMIDAZOLE-2-CARBALDEHYDE;1-METHYL-1H-BENZIMIDAZOLE-2-CARBOXALDEHYDE;1-METHYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE;1-METHYL-2-FORMYLBENZIMIDAZOLE;AKOS BC-1517;1-methylbenzimidazole-2-carboxaldehyde
• CAS NO: 3012-80-4
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17
• Product Categories: BENZIMIDAZOLE
• Mol File: 3012-80-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 114-116 °C
• Boiling Point: 286.07°C (rough estimate)
• Flash Point: 155.006 °C
• Appearance: Off-white to light beige/Crystalline Powder
• Density: 1.1846 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5570 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3?+-.0.10(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1-METHYL-2-FORMYLBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-FORMYLBENZIMIDAZOLE(3012-80-4)
• EPA Substance Registry System: 1-METHYL-2-FORMYLBENZIMIDAZOLE(3012-80-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 3012-80-4(Hazardous Substances Data)

Usage

Description

1-METHYL-2-FORMYLBENZIMIDAZOLE, also known as 1-Methyl-1H-benzimidazole-2-carboxaldehyde, is an organic compound that appears as an off-white to light beige crystalline powder. It is a reagent used in the synthesis of compounds that target dual protein kinase B alpha (AKT) and nuclear factor kappa-light-chain-enchancer of activated B cells (NF-κB) pathways, which are crucial in the development and progression of melanoma.

Uses

Used in Pharmaceutical Industry:
1-METHYL-2-FORMYLBENZIMIDAZOLE is used as a reagent for the synthesis of compounds that target dual protein kinase B alpha (AKT) and nuclear factor kappa-light-chain-enchancer of activated B cells (NF-κB) pathways. This is important for the development of potential therapeutic agents against melanoma, a type of skin cancer, by inhibiting the growth and progression of cancer cells through the modulation of these pathways.

InChI:InChI=1/C9H8N2O/c1-11-8-5-3-2-4-7(8)10-9(11)6-12/h2-6H,1H3

Upstream product

• 51-17-2 benzoimidazole 
• 1632-83-3 1-Methylbenzimidazole 
• 20461-86-3 2,2-diethoxy acetic acid 
• 13109-82-5 2-(diethoxymethyl)-1H-benzoimidazole 
• 95-54-5 1,2-diamino-benzene 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 3256-27-7 1,2-bis(1-methyl-1H-benzimidazole-2yl)ethane-1,2-diol 
• 68-12-2 N,N-dimethyl-formamide 
• 7467-35-8 (1-methyl-1H-benzimidazol-2-yl)methanol 
• 87-69-4 tartaric acid 
• 85510-65-2 1-methyl-2-(1-methyl-3-benzoyl-1,2-dihydro-2-benzimidazolyl)benzimidazole 
• 2876-08-6 1,2-dimethyl-1H-benzimidazole 
• 615-15-6 2-Methyl-1H-benzimidazole 

Downstream Products

• 5805-75-4 1-Methylbenzimidazole-2-carboxamide 
• 1357162-25-4 C₂₀H₁₈N₂O₃ 
• 1357162-33-4 C₂₀H₁₈N₂O₃ 
• 883448-42-8 C₁₆H₁₆N₄ 
• 943656-49-3 1-methyl-2-{2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-vinyl}-1H-benzoimidazole 
• 369654-59-1 2-(4-(N-Boc-N-2-picolylamino methyl) benzoyl)-5-((1-methylbenzimidazol-2-ylmethyl) amino) valerate 1-naphthalenemethylamide 
• 3013-07-8 1-methyl-1H-benzo[d]imidazole-2-carbaldehyde oxime 
• 4760-35-4 2-chloromethyl-1-methyl-1H-benzimidazole 

Relevant articles and documents

Cobalt(II) and nickel(II) complexes with 1-methyl-2-pyridin-2-yl-1H- and 1-methyl-2-phenyliminomethyl-1H-benzimidazoles and the closo-decaborate anion

Synthesis of cobalt(II) and nickel(II) complexes with the closo-decaborate anion and benzimidazole derivatives (L1 = C13N3H11, L2 = C15N3H13) of the general formula [ML3][B10H10] (M = Co, Ni) is described. Complexes have been characterized by elemental analysis, IR and UV spectroscopy. The structure of a [Ni(L1)3][B10H10] · 1.797CH3CN single crystal has been determined by X-ray diffraction. The imidazole and pyridine N atoms of three L1 molecules, two of which are disordered, form the distorted octahedral environment of the Ni atom. In the crystal, the majority of complexes [Ni(L1)3]2+ have the meridional configuration. The Ni-N bonds with the imidazole nitrogen atoms (2.010(4)-2.076(3) ?) are shorter than those with the pyridine atoms (2.132(4)-2.179(5) ?). This nonequivalence of the Ni-N bonds is responsible for the low magnetic susceptibility of the compound.

Metal-free oxidative decarbonylative halogenation of fused imidazoles

An efficient strategy has been developed for the deformylative halogenation of carbaldehyde imidazo-fused heterocycles in the presence of TBHP controlled by temperature. A convenient and sequential functionalization (C8 to C3) portrays the synthetic utility of the current method.N-Heterocycle benzamide products were also observedviathe ring opening of imidazopyridines through the cleavage of C-C bond at high temperatures. Features of this method include temperature-controlled excellent regioselectivity, mild conditions and functional group tolerance.

Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkylbenzimidazoles with arenes in the Br?nsted superacid TfOH resulted in the formation of the corresponding Friedel-Crafts reaction products, 2-diarylmethyl and 2-arylmethyl-substituted benzimidazoles, in yields up to 90%. The reaction intermediates, protonated species derived from starting benzimidazoles in TfOH, were thoroughly studied by means of NMR and DFT calculations and plausible reaction mechanisms are discussed.