4-AMino-3-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid Methyl ester

Base Information

• Chemical Name: 4-AMino-3-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid Methyl ester
• CAS No.: 524916-42-5
• Molecular Formula: C14H20BNO4
• Molecular Weight: 277.128
• Mol file: 524916-42-5.mol

Synonyms:

Chemical Property of 4-AMino-3-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid Methyl ester

Chemical Property:

• Melting Point: 167 - 169 °C (ethyl acetate)
• Boiling Point: 432.0±35.0 °C(Predicted)
• PKA: 1.76±0.10(Predicted)
• PSA: 70.78000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 1.93580

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-AMino-3-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid Methyl ester

There total 5 articles about 4-AMino-3-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid Methyl ester 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: 58.0%

4-amino-3-iodobenzoic acid methyl ester (19718-49-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (524916-42-5)

Guidance literature:

With N(CH₂CH₃)3; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; (Ar); addn. of triethylamine, palladium compd. and borane deriv. to dioxane soln. of aniline deriv., heating at 100°C for 5 h; cooling to room temp., filtration through celite with eluting by ethyl acetate, evapn., chromy. (silica gel, hexane/ethyl acetate (9/1 to 5/5)),NMR and MS;

DOI:10.1039/c2ob06695e

Reference yield: 35.0%

methyl 4-amino-3-bromobenzoate (106896-49-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (524916-42-5) + 4-methoxycarbonyl aniline (619-45-4)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine; In 1,4-dioxane; for 5h; Reflux;

DOI:10.1021/jo901930v

Reference yield: 33.0%

methyl 4-amino-3-bromobenzoate (106896-49-5) + bis(pinacol)diborane (73183-34-3) → methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (524916-42-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 100 ℃; Inert atmosphere;

upstream raw materials:

4-amino-3-iodobenzoic acid methyl ester

methyl 4-amino-3-bromobenzoate

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

Downstream raw materials:

methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-[(2-thienylacetyl)amino]benzoate

Refernces

• 1、 -. "FACTOR XIa INHIBITORS". Page/Page column 46. . Retrieved 2017/05/21.
• 2、 Inglis, Steven R.,Woon, Esther C. Y.,Thompson, Amber L.,Schofield, Christopher J.. "Observations on the deprotection of pinanediol and pinacol boronate esters via fluorinated intermediates". supporting information; experimental part. p. 468 - 471. Retrieved 2010/03/25.