| Identification | More | [Name]
3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE | [CAS]
214360-46-0 | [Synonyms]
3-(4,4,5,5-tetraMethy
3-cyanphenylboronic acid pinacol ester
3-CYANOPHENYLBORONIC ACID, PINACOL ESTER
3-Cyanobenzeneboronic acid, pinacol ester
(3-Cyanophenyl)boronic acid pinalol ester
3-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
1,1,2,2-Tetramethyldimethylene (3-cyanophenyl)boronate
2-(3-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
3-(4,4,5,5-tetraMethyl-1,3,2-dioxoborolan-2-yl)-benzonitrile
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrilele
Benzonitrile, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
(3-cyanophenyl)-(3-hydroxy-2,3-dimethylbutan-2-yl)oxyborinic acid
(3-Cyanophenyl)boronic acid pinacol ester
1,1,2,2-Tetramethyldimethylene (3-cyanophenyl)boronate
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, 2-(3-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | [Molecular Formula]
C13H16BNO2 | [MDL Number]
MFCD03789262 | [Molecular Weight]
229.08 | [MOL File]
214360-46-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
78-82 °C (lit.) | [Boiling point ]
341.0±25.0 °C(Predicted) | [density ]
1.06±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Solid | [color ]
White | [InChI]
InChI=1S/C13H16BNO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-6-10(8-11)9-15/h5-8H,1-4H3 | [InChIKey]
FIGQEPXOSAFKTA-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1 | [CAS DataBase Reference]
214360-46-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
3-Cyanophenylboronic acid pinacol ester can be used as a reactant to synthesize:
- 3-Cyano aryl/ heteroaryl derivatives by forming a C?C bond via palladium-catalyzed Suzuki-Miyaura reaction.
- 3-(Phenylamino)benzonitrile by copper-catalyzed Chan-Evans-Lam amination reaction.
- 3-(Trifluoromethyl)benzonitrile using potassium (trifluoromethyl)trimethoxyborate.
| [Synthesis]
To a solution of 3-aminobenzonitrile (0.5 g, 4.23 mmol) in acetonitrile (30 mL) was added tert-butyl nitrite (0.7 mL, 6.34 mmol) and pinacol ester of bis(boronic acid) (1.29 g, 5.076 mmol) sequentially at 0 °C. The reaction mixture was warmed to 80 °C and stirred continuously for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (combiflash system) with the eluent being a 4% ethyl acetate/hexane solvent mixture, resulting in pinacol ester of 3-cyanobenzeneboronic acid (0.35 g, 99.8% yield). The molecular weight of the product was confirmed by LCMS analysis: m/z 294 ([M+H]+). | [References]
[1] Patent: WO2015/105779, 2015, A1. Location in patent: Page/Page column 17; 18
[2] Patent: US2016/333005, 2016, A1. Location in patent: Paragraph 0064-0065
[3] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933
[4] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(214360-46-0)1HNMR
3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(214360-46-0)IR
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