| Identification | More | [Name]
N-Boc-indole-2-boronic acid | [CAS]
213318-44-6 | [Synonyms]
1-BOC-1H-INDOLE-2-BORONIC ACID
1-BOC-2-INDOLEBORONIC ACID
1-BOC-INDOLE-2-BORONIC ACID
1-(N-BOC)-INDOLE-2-BORONIC ACID
1-N-TERT-BUTOXYCARBONYLINDOLE-2-BORONIC ACID
1-T-BUTOXYCARBONYLINDOLE-2-BORONIC ACID
1-(TERT-BUTOXYCARBONYL)-1H-INDOL-2-YLBORONIC ACID
1-(TERT-BUTOXYCARBONYL)INDOLE-2-BORONIC ACID
AKOS BRN-0155
CBI-BB ZERO/004903
N-BOC-INDOLE-2-BORONIC ACID
N-(TERT-BUTOXYCARBONYL)-1H-INDOLE-2-BORONIC ACID
N-(TERT-BUTOXYCARBONYL)INDOLE-2-BORONIC ACID
Indole-2-boronic acid, N-BOC protected
Indole-2-boronic acid, N-BOC protected 98%
1-(tert-Butoxycarbonyl)-1H-indole-2-boronic acid
1H-Indole-2-boronic acid, N-BOC protected
1H-Indole-1-carboxylic acid, 2-borono-, 1-(1,1-dimethylethyl) ester
1-(tert-butoxycarbonyl)indole-2-boronic acid, N-(tert-butoxycarbonyl)indole-2-boronic acid | [EINECS(EC#)]
681-628-8 | [Molecular Formula]
C13H16BNO4 | [MDL Number]
MFCD02093045 | [Molecular Weight]
261.08 | [MOL File]
213318-44-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light yellow crystal powde | [Melting point ]
84-94 °C
85-90 °C (lit.) | [Boiling point ]
443.5±55.0 °C(Predicted) | [density ]
1.17±0.1 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [form ]
powder to crystal | [pka]
8.12±0.30(Predicted) | [color ]
White to Orange to Green | [BRN ]
8148683 | [InChI]
1S/C13H16BNO4/c1-13(2,3)19-12(16)15-10-7-5-4-6-9(10)8-11(15)14(17)18/h4-8,17-18H,1-3H3 | [InChIKey]
SVIBPSNFXYUOFT-UHFFFAOYSA-N | [SMILES]
CC(C)(C)OC(=O)n1c(cc2ccccc12)B(O)O | [CAS DataBase Reference]
213318-44-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [Hazard Note ]
IrritantKeep Cold | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 | [Storage Class]
4.1B - Flammable solid hazardous materials | [Hazard Classifications]
Flam. Sol. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light yellow crystal powde | [Uses]
Reactant involved in:
- Suzuki-Miyaura cross-coupling reactions
- Copper-catalyzed trifluoromethylation
- Palladium-catalyzed benzylation
- Homocoupling reactions
| [General Description]
May contain varying amounts of anhydride | [Synthesis]
Step 2: Synthesis of 1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid
Lithium diisopropylammonium (140 mL, 2.0 M in hexane) was slowly added dropwise to a solution of ethoxyethane (500 mL) containing tert-butyl 1H-indole-1-carboxylate (26 g, 119.67 mmol) and triisopropylboronate (30 g, 159.57 mmol) at -70 °C. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio ethyl acetate/petroleum ether = 1:5) during the reaction. Upon completion of the reaction, the reaction was quenched with 200 g of ice-water mixture, followed by adjusting the pH with 10% hydrochloric acid solution to 7. The reaction mixture was extracted with ethyl ether (100 mL x 1), and the organic layers were combined and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 13 g (67% yield) of the target compound 1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid as a white solid. | [References]
[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 8, p. 1218 - 1227
[2] Patent: US2008/139558, 2008, A1. Location in patent: Page/Page column 67
[3] Patent: EP2687530, 2014, A1. Location in patent: Paragraph 0096 |
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