2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

Base Information

• Chemical Name: 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
• CAS No.: 105650-23-5
• Molecular Formula: C13H12N4
• Molecular Weight: 224.265
• Hs Code.: 29333999
• European Community (EC) Number: 631-286-0
• UNII: 909C6UN66T
• DSSTox Substance ID: DTXSID3037628
• Nikkaji Number: J258.694K
• Wikipedia: 2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
• Wikidata: Q4596855
• NCI Thesaurus Code: C29792
• Metabolomics Workbench ID: 49227
• ChEMBL ID: CHEMBL1213271
• Mol file: 105650-23-5.mol

Synonyms:2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine;PhIP

Chemical Property of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 5.74E-09mmHg at 25°C
• Melting Point: 300 °C
• Refractive Index: 1.699
• Boiling Point: 468.94 °C at 760 mmHg
• PKA: 7.72±0.30(Predicted)
• Flash Point: 237.407 °C
• PSA: 56.73000
• Density: 1.3 g/cm³
• LogP: 2.79870
• Storage Temp.: Refrigerator
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 224.106196400
• Heavy Atom Count: 17
• Complexity: 264

Purity/Quality:

99%, ^*data from raw suppliers

PHIP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Rings
• Canonical SMILES: CN1C2=C(N=CC(=C2)C3=CC=CC=C3)N=C1N
• Recent ClinicalTrials: The Role of Meat-borne Carcinogens in Pancreatic Cancer
• Uses: Carcinogen

Technology Process of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

There total 38 articles about 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine 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: 90.2%

1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (125572-33-0) → 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (105650-23-5)

Guidance literature:

With sodium amide; In xylene; at 130 ℃; for 1.5h;

DOI:10.1021/jo00079a055

Reference yield: 38.0%

1-methyl-6-phenyl-2-N-(p-toluenesulfonyl)aminoimidazo[4,5-b]pyridine (1097725-70-6) → 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (105650-23-5)

Guidance literature:

With hydrogen fluoride; at 100 ℃; for 2.5h;

DOI:10.1002/jhet.5570450614

Reference yield: 35.0%

2-amino-1-methylbenzothieno[3,2-e]imidazo[4,5-b]pyridine (878996-00-0) → 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (105650-23-5)

Guidance literature:

With sodium hydroxide; nickel; In 1,4-dioxane; ethanol; Heating;

DOI:10.1002/jhet.5570430116

upstream raw materials:

bromocyane

3-methylamino-2-nitro-5-phenylpyridine

2-amino-3-methylamino-5-phenylpyridine

1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine

Downstream raw materials:

N-[6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-ylamino)-9H-purin-2-yl]-isobutyramide

6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)-9H-purine-2,8-diamine

Refernces

• 1、 Ghassem Zadeh, Raheleh,Yaylayan, Varoujan. "Indole: A Promising Scavenging Agent for Methylglyoxal and Related Carbonyls in Tryptophan Containing Maillard Model Systems". . p. 6359 - 6365. Retrieved 2019.
• 2、 Sajith, Ayyiliath M.,Muralidharan, Arayambath,Karuvalam, Ranjith P.,Haridas, Karickal R.. "Cross-coupling reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine offers a new synthetic route to mutagenic heterocyclic amine-PHIP and DMIP". supporting information. p. 361 - 364. Retrieved 2013/07/26.