N-Boc-indole-2-boronic acid

Base Information

• Chemical Name: N-Boc-indole-2-boronic acid
• CAS No.: 213318-44-6
• Molecular Formula: C13H16BNO4
• Molecular Weight: 261.085
• Hs Code.: 2933990090
• European Community (EC) Number: 681-628-8
• DSSTox Substance ID: DTXSID20378354
• Nikkaji Number: J991.620B
• Wikidata: Q72449669
• Mol file: 213318-44-6.mol

Synonyms:213318-44-6;N-Boc-indole-2-boronic acid;1-Boc-indole-2-boronic acid;1-(tert-butoxycarbonyl)indole-2-boronic acid;(1-(TERT-BUTOXYCARBONYL)-1H-INDOL-2-YL)BORONIC ACID;1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid;1-N-BOC-indole-2-boronic acid;1-(TERT-BUTOXYCARBONYL)-1H-INDOL-2-YL-2-BORONIC ACID;[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid;MFCD02093045;1H-Indole-1-carboxylic acid, borono-, 1-(1,1-dimethylethyl) ester;1-T-BUTOXYCARBONYLINDOLE-2-BORONIC ACID;{1-[(tert-butoxy)carbonyl]-1H-indol-2-yl}boronic acid;1-BOC-1H-INDOLE-2-BORONIC ACID;[1-(tert-butoxycarbonyl)-1H-indol-2-yl]boronic acid;N-Boc-indole-2-boronicacid;N-BOC-INDOL-2-YL BORONIC ACID;22396-40-3;N-Boc-indoleboronic acid;N-(tert-butoxycarbonyl)indole-2-boronic acid;(1-tert-butoxycarbonylindol-2-yl)boronic acid;INDOLE-2-BORONIC ACID, N-BOC PROTECTED;SCHEMBL40961;1-N-boc-2-indole boronic acid;1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-2-BORONIC ACID;DTXSID20378354;SVIBPSNFXYUOFT-UHFFFAOYSA-N;STK689332;AKOS004116109;AB10718;AM86754;SB15062;N-Boc-indole-2-boronic acid, >=95%;AS-15070;SY009087;N-tert-butoxycarbonylindole-2-boronic acid;1-(t-butoxycarbonyl)-indole-2-boronic acid;1-(tert-butoxycarbonyl)indol-2-boronic acid;B5145;BB 0222350;CS-0002272;FT-0607417;N-tert-butyloxycarbonylindole-2-boronic Acid;tert-butyl 2-borono-1H-indole-1-carboxylate;1-(tert-butoxycarbonyl) indole-2-boronic acid;1-(tert-butoxycarbonyl)-indol-2-ylboronic acid;1-(tert-Butoxycarbonyl)-indole-2-boronic acid;1-(tert-butyloxycarbonyl)indole-2-boronic acid;A22446;EN300-299931;1-(tert-butoxycarbonyl)-1H-indo1-2-ylboronic acid;J-503637;1-(tert-Butoxycarbonyl)-2-(dihydroxyboryl)-1H-indole;(1-(tert-butoxycarbonyl)-1H-indol-2-yl) boronic acid;1-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)

Chemical Property of N-Boc-indole-2-boronic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Melting Point: 100 °C
• Refractive Index: 1.544
• Boiling Point: 443.5 °C at 760 mmHg
• PKA: 8.12±0.30(Predicted)
• Flash Point: 222 °C
• PSA: 71.69000
• Density: 1.17 g/cm³
• LogP: 1.10430
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 261.1172382
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=CC=CC=C2N1C(=O)OC(C)(C)C)(O)O
• Uses: Reactant involved in: Suzuki-Miyaura cross-coupling reactionsCopper-catalyzed trifluoromethylationPalladium-catalyzed benzylationHomocoupling reactions

Technology Process of N-Boc-indole-2-boronic acid

There total 11 articles about N-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: 97.0%

indole-1-carboxylic acid tert-butyl ester (75400-67-8) → N-Boc-indole-2-boronic acid (213318-44-6)

Guidance literature:

indole-1-carboxylic acid tert-butyl ester; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 2h;

With phosphate buffer; In tetrahydrofuran; pH=6.0; Further stages.;

DOI:10.1021/jo070206j

Reference yield: 96.0%

Triisopropyl borate (5419-55-6) + indole-1-carboxylic acid tert-butyl ester (75400-67-8) → N-Boc-indole-2-boronic acid (213318-44-6)

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: 37.0%

2,2,6,6-tetramethyl-piperidine (768-66-1) + indole-1-carboxylic acid tert-butyl ester (75400-67-8) → N-Boc-indole-2-boronic acid (213318-44-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane;

upstream raw materials:

indole-1-carboxylic acid tert-butyl ester

indole

di-tert-butyl dicarbonate

2,2,6,6-tetramethyl-piperidine

Downstream raw materials:

tert-Butyl 2-(3-methyl-2-pyridyl)-1H-indole-1-carboxylate

tert-butyl 2-(5-formyl-4-methoxy-1H-pyrrol-2-yl)-1H-indole-1-carboxylate

2-[N-(tert-butoxycarbonyl)-1H-indol-2-yl]benzoic acid

2-[N-(tert-butoxycarbonyl)-1H-indol-2-yl]phenyl isocyanate

Refernces

• 1、 -. "NITROGEN-CONTAINING AROMATIC COMPOUNDS AND ORGANIC ELECTROLUMINESCENT ELEMENTS". . . Retrieved 2014/02/15.
• 2、 Kassis, Pamela,Beneteau, Valerie,Merour, Jean-Yves,Routier, Sylvain. "Potassium [1-(tert-butoxycarbonyl)-1H-indol-2-yl]trifluoroborate as an efficient building block in palladium-catalyzed Suzuki-Miyaura cross couplings". experimental part. p. 2447 - 2453. Retrieved 2010/02/27.