1,3-Dimethyl-2-phenylbenzimidazoline

Base Information

• Chemical Name: 1,3-Dimethyl-2-phenylbenzimidazoline
• CAS No.: 3652-92-4
• Molecular Formula: C15H16N2
• Molecular Weight: 224.305
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90190025
• Nikkaji Number: J69.240I
• Wikidata: Q83062276
• Mol file: 3652-92-4.mol

Synonyms:3652-92-4;1,3-Dimethyl-2-phenylbenzimidazoline;1,3-Dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole;1,3-dimethyl-2-phenyl-2H-benzimidazole;Benzimidazoline, 1,3-dimethyl-2-phenyl-;1,3-Dimethyl-1,3-dihydro-2-phenyl-2H-benzimidazole;C15H16N2;ChemDiv3_000319;SCHEMBL993337;DTXSID90190025;HMS1473O11;AKOS021983201;CCG-103118;IDI1_019637;NCGC00176113-01;BS-51709;LS-33227;CS-0098800;FT-0699621;E77041;A902544;SR-01000389068;SR-01000389068-1;1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole

Chemical Property of 1,3-Dimethyl-2-phenylbenzimidazoline

Chemical Property:

• Vapor Pressure: 2.31E-05mmHg at 25°C
• Melting Point: 93-94 °C
• Boiling Point: 359.9°C at 760 mmHg
• PKA: 5.68±0.40(Predicted)
• Flash Point: 160.2°C
• PSA: 6.48000
• Density: 1.095g/cm³
• LogP: 3.40140
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 224.131348519
• Heavy Atom Count: 17
• Complexity: 242

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(N(C2=CC=CC=C21)C)C3=CC=CC=C3

Technology Process of 1,3-Dimethyl-2-phenylbenzimidazoline

There total 13 articles about 1,3-Dimethyl-2-phenylbenzimidazoline 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: 100.0%

benzaldehyde (100-52-7) + N,N'-dimethyl-1,2-phenylenediamine (3213-79-4) → 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole (3652-92-4)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In water; at 20 ℃; for 0.0333333h;

DOI:10.1039/d0gc01977a

Reference yield: 90.0%

1,3-dimethyl-2-phenylbenzimidazolium perchlorate → 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole (3652-92-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 1h;

DOI:10.1021/ja963768l

Reference yield: 89.0%

N,N’-dimethyl-2-phenyl-benzo[d]imidazolium iodide (3653-05-2) → 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole (3652-92-4)

Guidance literature:

With methanol; sodium tetrahydroborate; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.202102729

upstream raw materials:

N-methyl-2-(N-methyl-hydrazino)-aniline

benzaldehyde

acetic acid

N,N'-dimethyl-1,2-phenylenediamine

Downstream raw materials:

1-methyl-2-phenylbenzimidazole

methyl-phenyl-thioether

thiophenol

N-methyl-N-benzamide

Refernces

Primary kinetic isotope effects on hydride transfer from 1,3-dimethyl-2-phenylbenzimidazoline to NAD⁺ analogues

10.1021/ja004232+

The research investigates the primary kinetic isotope effects (KIE) for hydride transfer reactions between NAD+ analogues (pyridinium, quinolinium, phenanthridinium, and acridinium ions) and 1,3-dimethyl-2-phenylbenzimidazoline in a 4:1 mixture of 2-propanol and water at 25 °C. The study finds that the KIE values systematically vary from 6.27 to 4.06 as the equilibrium constant changes from around 10 to 10^12. This variation is consistent with Marcus theory, which assumes no high-energy intermediates and suggests that the perpendicular effect, arising from changes in bond distances and orders in critical complexes, is primarily responsible for the observed changes in KIE. The parallel effect (Leffler-Hammond effect) contributes less due to the high intrinsic barrier. The study supports Marcus theory's applicability to hydride transfer reactions and highlights the significant role of corner-cutting tunneling in hydrogen transfer reactions.