N-TIPS indole-3-boronic acid pinacol ester

Base Information

• Chemical Name: N-TIPS indole-3-boronic acid pinacol ester
• CAS No.: 476004-82-7
• Molecular Formula: C23H38BNO2Si
• Molecular Weight: 399.457
• Mol file: 476004-82-7.mol

Synonyms:3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)indole;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[triisopropylsilyl]indole;

Chemical Property of N-TIPS indole-3-boronic acid pinacol ester

Chemical Property:

• PSA: 23.39000
• LogP: 5.96410

Purity/Quality:

97% ^*data from raw suppliers

1-Triisopropylsilanyl-1H-indole-3-boronicacidpinacolester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of N-TIPS indole-3-boronic acid pinacol ester

There total 12 articles about N-TIPS indole-3-boronic acid pinacol 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: 95.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + C6Cl4O2BN(C2H5)3(1+)*AlCl4(1-)=C6Cl4O2BN(C2H5)3[AlCl4] + 1-(triisopropylsilyl)-1H-indole (123191-00-4) → 3?(4,4,5,5?tetramethyl?1,3,2?dioxaborolan?2?yl)?1?(triisopropylsilyl)?1H?indole (476004-82-7)

Guidance literature:

With Et₃N; In dichloromethane; byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added Cl4CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excessEt3N added; pinacol added; stirred for 4 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;;

DOI:10.1002/anie.201006196

Reference yield: 83.0%

1-(triisopropylsilyl)-1H-indole (123191-00-4) + bis(pinacol)diborane (73183-34-3) → 3?(4,4,5,5?tetramethyl?1,3,2?dioxaborolan?2?yl)?1?(triisopropylsilyl)?1H?indole (476004-82-7)

Guidance literature:

bis(1,5-cyclooctadiene)diiridium(I) dichloride; 4,4'-di-tert-butyl-2,2'-bipyridine; In octane; at 80 ℃; for 16h;

DOI:10.1016/S0040-4039(02)01135-8

Reference yield: 81.0%

→ 3?(4,4,5,5?tetramethyl?1,3,2?dioxaborolan?2?yl)?1?(triisopropylsilyl)?1H?indole (476004-82-7)

Guidance literature:

upstream raw materials:

1-(triisopropylsilyl)-1H-indole

bis(pinacol)diborane

2,3-dimethyl-2,3-butane diol

2-chloro-1,3,2-benzodioxaborole

Downstream raw materials:

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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