4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine
• CAS No.: 851883-08-4
• Molecular Formula: C12H21BN2O3
• Molecular Weight: 234.106
• Hs Code.: 2934999090
• European Community (EC) Number: 690-896-5
• DSSTox Substance ID: DTXSID50590380
• Wikidata: Q72462992
• Mol file: 851883-08-4.mol

Synonyms:851883-08-4;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine;3,4-DIAMINOPHENYLBORONIC ACID, PINACOL ESTER;3,4-Diaminophenylboronic acid pinacol ester;SCHEMBL189992;DTXSID50590380;SVUDHDDKOKWBNK-UHFFFAOYSA-N;BCP22376;MFCD09027073;AKOS016004645;AS-72019;CS-0096074;A22790;D75720;EN300-6785815;J-511130;Z2049760863;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene-1,2-diamine;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzenediamine;4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE-1,2-DIAMINE

Chemical Property of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

Chemical Property:

• Appearance/Colour: off-white solid
• PSA: 70.50000
• Density: 1.10
• LogP: 2.31260
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 234.1539580
• Heavy Atom Count: 17
• Complexity: 280

Purity/Quality:

97% ^*data from raw suppliers

3,4-diaminophenylboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C=C2)N)N

Technology Process of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

There total 8 articles about 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine 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: 91.0%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene-1,2-diamine (851883-08-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; under 3102.97 Torr;

DOI:10.1016/j.bmcl.2009.01.086

Reference yield: 87.0%

4-Bromo-benzene-1,2-diamine (1575-37-7) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene-1,2-diamine (851883-08-4)

Guidance literature:

With palladium⁽⁰⁾bis(tricyclohexylphosphine); potassium acetate; In 1,4-dioxane; at 80 ℃; for 5h;

DOI:10.1021/ja042849b

Reference yield: 85.0%

2-(3,4-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1075719-78-6) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene-1,2-diamine (851883-08-4)

Guidance literature:

With ammonium hydroxide; at 140 ℃; for 12h; Sealed tube;

upstream raw materials:

4-Bromo-benzene-1,2-diamine

bis(pinacol)diborane

4-amino-3-nitrophenylboronic acid pinacol ester

2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Downstream raw materials:

5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-amine