5-Benzyloxy-1-boc-indole-2-boronic acid

Base Information

• Chemical Name: 5-Benzyloxy-1-boc-indole-2-boronic acid
• CAS No.: 850568-62-6
• Molecular Formula: C20H22BNO5
• Molecular Weight: 367.209
• Hs Code.: 2933990090
• European Community (EC) Number: 639-277-3
• DSSTox Substance ID: DTXSID80583083
• Nikkaji Number: J2.794.574K
• Wikidata: Q72441799
• Mol file: 850568-62-6.mol

Synonyms:850568-62-6;5-BENZYLOXY-1-BOC-INDOLE-2-BORONIC ACID;(5-(Benzyloxy)-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid;[1-[(2-methylpropan-2-yl)oxycarbonyl]-5-phenylmethoxyindol-2-yl]boronic acid;1-(TERT-BUTOXYCARBONYL)-5-(BENZYLOXY)-1H-INDOL-2-YL-2-BORONIC ACID;5-Benzyloxy-1H-indole-2-boronic acid, N-BOC protected;1H-INDOLE-1-CARBOXYLIC ACID, 2-BORONO-5-(PHENYLMETHOXY)-, 1-(1,1-DIMETHYLETHYL) ESTER;[5-(Benzyloxy)-1-(tert-butoxycarbonyl)-1H-indol-2-yl]boronic acid;5-Benzyloxyindole-2-boronic acid, N-BOC protected;SCHEMBL1180319;DTXSID80583083;IQKGFXDPCFAYFP-UHFFFAOYSA-N;5-(benzyloxy)-1-(tert-butoxycarbonyl)-1h-indol-2-ylboronic acid;5-(Benzyloxy)-1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid;MFCD06659824;AKOS004113907;AB26406;PS-9663;CS-0002250;J-503646;5-benzyloxy-1-Boc-indole-2-boronic acid, AldrichCPR;{1-{[(1,1-dimethylethyl)oxy]carbonyl}-5-[(phenylmethyl)oxy]-1H-indol-2-yl}boronic acid

Chemical Property of 5-Benzyloxy-1-boc-indole-2-boronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 106-110 °C
• Refractive Index: 1.561
• Boiling Point: 564.744 °C at 760 mmHg
• PKA: 7.97±0.30(Predicted)
• Flash Point: 295.347 °C
• PSA: 80.92000
• Density: 1.176 g/cm³
• LogP: 2.68330
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 367.1591030
• Heavy Atom Count: 27
• Complexity: 503

Purity/Quality:

97% ^*data from raw suppliers

5-Benzyloxy-1-BOC-indole-2-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(N1C(=O)OC(C)(C)C)C=CC(=C2)OCC3=CC=CC=C3)(O)O

Technology Process of 5-Benzyloxy-1-boc-indole-2-boronic acid

There total 4 articles about 5-Benzyloxy-1-boc-indole-2-boronic acid 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: 100.0%

tert-butyl 5-(benzyloxy)-1H-indole-1-carboxylate (170147-29-2) → 1-tert-butyloxycarbonyl-5-benzyloxy-indole-2-boronic acid (850568-62-6)

Guidance literature:

With Triisopropyl borate; In tetrahydrofuran; n-heptane; ethylbenzene; for 2.41667h; Cooling with ice;

Reference yield: 99.0%

Triisopropyl borate (5419-55-6) + tert-butyl 5-(benzyloxy)-1H-indole-1-carboxylate (170147-29-2) → 1-tert-butyloxycarbonyl-5-benzyloxy-indole-2-boronic acid (850568-62-6)

Guidance literature:

With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; addn. of boron compd. to a soln. of indole deriv. in THF, cooling to 0°C, dropwise addn. of Li salt in THF/heptane/ethylbenzene over 1 h,stirring for 30 min, addn. of 2 M HCl, stirring at room temp. for 10 mi n; sepn., extn. aq. layer with ethyl acetate, drying org layer with Na2SO4,filtration, evapn. in vac.;

DOI:10.1039/b700433h

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) → 1-tert-butyloxycarbonyl-5-benzyloxy-indole-2-boronic acid (850568-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / (dimethylamino)pyridine / tetrahydrofuran / 20 °C

2.1: triisopropyl borate / tetrahydrofuran / 0 °C

2.2: 99 percent / lithium diisopropylamide / heptane; tetrahydrofuran; ethylbenzene / 0.5 h / 0 °C

With dmap; Triisopropyl borate; In tetrahydrofuran;

DOI:10.1039/b700433h

upstream raw materials:

tert-butyl 5-(benzyloxy)-1H-indole-1-carboxylate

5-benzyloxy-1H-indole

di-tert-butyl dicarbonate

Triisopropyl borate

Downstream raw materials:

C₂₀H₁₅FN₂O

C₂₁H₁₅F₃N₂O

C₃₂H₄₀N₂O₄Si

C₂₆H₂₈N₂O₃Si

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