Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isoindoline-2-carboxylate

Base Information

• Chemical Name: Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isoindoline-2-carboxylate
• CAS No.: 905273-91-8
• Molecular Formula: C19H28 B N O4
• Molecular Weight: 345.247
• Hs Code.: 2934999090
• European Community (EC) Number: 887-483-9
• DSSTox Substance ID: DTXSID20582873
• Wikidata: Q82474374
• Mol file: 905273-91-8.mol

Synonyms:905273-91-8;TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLINE-2-CARBOXYLATE;TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,3-DIHYDROISOINDOLE-2-CARBOXYLATE;2-BOC-1H-Isoindoline-5-boronic acid pinacol ester;MFCD11226842;tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2h-isoindole-2-carboxylate;SCHEMBL2589826;DTXSID20582873;GVNKCVZBPCUBLS-UHFFFAOYSA-N;AMY21711;(2-(TERT-BUTOXYCARBONYL)ISOINDOLIN-5-YL)BORONIC ACID PINACOL ESTER;AKOS022173511;CS-W023015;DS-7479;MB09693;tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxyl;SY105398;2-Boc-5-isoindolineboronic Acid Pinacol Ester;F12814;EN300-4722462;Z2044772988;2-Boc-1,3-dihydro-isoindole-5-boronic acid pinacol ester;2-BOC-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1,3-DIHYDRO-ISOINDOLE;tert-butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindole-2-carboxylate;Tert-Butyl5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Isoindoline-2-Carboxylate;5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1,3-DIHYDRO-ISOINDOLE-2-CARBOXYLIC ACID TERT-BUTYL ESTER;tert-?Butyl 5-?(4,?4,?5,?5-?tetramethyl-?1,?3,?2-?dioxaborolan-?2-?yl)?isoindoline-?2-?carboxylate;tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate

Chemical Property of Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isoindoline-2-carboxylate

Chemical Property:

• Boiling Point: 442.5±45.0 °C(Predicted)
• PKA: -1?+-.0.20(Predicted)
• PSA: 48.00000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 3.17440
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 345.2111385
• Heavy Atom Count: 25
• Complexity: 512

Purity/Quality:

97% ^*data from raw suppliers

tert-?Butyl5-?(4,?4,?5,?5-?tetramethyl-?1,?3,?2-?dioxaborolan-?2-?yl)?isoindoline-?2-?carboxylate ^*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=CC3=C(CN(C3)C(=O)OC(C)(C)C)C=C2

Technology Process of Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isoindoline-2-carboxylate

There total 4 articles about Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isoindoline-2-carboxylate 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: 99.3%

5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (201940-08-1) + bis(pinacol)diborane (73183-34-3) → tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate (905273-91-8)

Guidance literature:

5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester; In 1,4-dioxane; for 0.166667h; Inert atmosphere;

bis(pinacol)diborane; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In 1,4-dioxane; at 80 ℃; for 12h; Solvent;

Reference yield:

5-Bromoisoindoline-1,3-dione (6941-75-9) → tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate (905273-91-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium borohydride; BF₃*Et₂O / 3 h / Heating

2: 600 mg / DMAP / dimethylformamide / 15 h / 20 °C

3: 80 percent / Pd(PPh₃)4; KOAc / dimethylsulfoxide / 80 °C

With dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; potassium acetate; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm060844e

Reference yield:

5-bromoisoindoline (127168-84-7) → tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate (905273-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 600 mg / DMAP / dimethylformamide / 15 h / 20 °C

2: 80 percent / Pd(PPh₃)4; KOAc / dimethylsulfoxide / 80 °C

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm060844e

upstream raw materials:

5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

bis(pinacol)diborane

5-Bromoisoindoline-1,3-dione

5-bromoisoindoline

Downstream raw materials:

(R)-tert-butyl 5-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)isoindoline-2-carboxylate

tert-butyl 5-hydroxyisoindoline-2-carboxylate