3-(4-Methylphenyl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene

Base Information

• Chemical Name: 3-(4-Methylphenyl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene
• CAS No.: 1159803-47-0
• Molecular Formula: C17H15BN2
• Molecular Weight: 258.13
• Mol file: 1159803-47-0.mol

Synonyms:3-(4-Methylphenyl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene

Chemical Property of 3-(4-Methylphenyl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(4-Methylphenyl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene

There total 7 articles about 3-(4-Methylphenyl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene 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: 98.0%

para-bromotoluene (106-38-7) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1214264-88-6) → 2-(p-tolyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1159803-47-0)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; XPhos; In 1,4-dioxane; at 60 ℃; for 12h; Reagent/catalyst; Temperature; Solvent; Time; chemoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1039/c5cc00231a

Reference yield: 94.0%

4-methylphenylboronic acid (5720-05-8) + naphthalene-1,8-diamine (479-27-6) → 2-(p-tolyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1159803-47-0)

Guidance literature:

With 1H-imidazole; iron(III) chloride; In water; acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0033-1340500

Reference yield: 93.0%

para-bromotoluene (106-38-7) + 2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (5656-71-3) → 2-(p-tolyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1159803-47-0)

Guidance literature:

para-bromotoluene; With iodine; magnesium; In tetrahydrofuran; at 20 ℃; for 1h; Schlenk technique; Inert atmosphere;

2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine; In tetrahydrofuran; at 20 ℃; for 3h; Schlenk technique; Inert atmosphere;

DOI:10.1039/d0cc02560g

upstream raw materials:

toluene

2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

4-methylphenylboronic acid

naphthalene-1,8-diamine

Downstream raw materials:

2-(4-methylphenyl)pyridine

4-Methylbiphenyl

4-(4-tolyl)anisole

4-chloro-4'-methylbiphenyl

Refernces

• 1、 Li, Jialun,Seki, Michinari,Kamio, Shintaro,Yoshida, Hiroto. "Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H-B(dan) as a B(dan) electrophile". supporting information. p. 6388 - 6391. Retrieved 2020/06/21.
• 2、 Miralles,Romero,Fernández,Mu?iz. "A mild carbon-boron bond formation from diaryliodonium salts". supporting information. p. 14068 - 14071. Retrieved 2015/09/15.