| Identification | More | [Name]
3-Cyanophenylboronic acid | [CAS]
150255-96-2 | [Synonyms]
3-CYANOBENZENEBORONIC ACID
3-CYANOPHENYLBORONIC ACID
AKOS BRN-0075
RARECHEM AH PB 0207
3-Boronobenzonitrile~3-Cyanophenylboronic acid
Boronic acid, (3-cyanophenyl)-(9CI)
3-Cyanophenylboronic
3-boronobenzonitrile
1-(2-Chlorophenyl)-1H-pyrazol-4-ylboronic acid
1-(2-Chlorophenyl)pyrazole-4-boronic acid
1-(3-Chlorophenyl)-1H-pyrazol-4-ylboronic acid
1-(3-Chlorophenyl)pyrazole-4-boronic acid
1-(4-Fluorophenyl)-1H-pyrazol-4-ylboronic acid
1-(4-Fluorophenyl)pyrazole-4-boronic acid
1-(6-Chloropyrimidin-4-yl)-1H-pyrazol-4-ylboronic acid
1-(6-Chloropyrimidin-4-yl)pyrazole-4-boronic acid
1,2-Bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethane
1,3-Bis(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea
1,3-Bis(4-boronophenyl)urea, dipinacol ester
1-Ethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)thiourea | [Molecular Formula]
C7H6BNO2 | [MDL Number]
MFCD01318967 | [Molecular Weight]
146.94 | [MOL File]
150255-96-2.mol |
| Chemical Properties | Back Directory | [Appearance]
light orange powder | [Melting point ]
298 °C (dec.) (lit.) | [Boiling point ]
347.4±44.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
soluble in Methanol | [form ]
solid | [pka]
7.17±0.10(Predicted) | [color ]
White to Light yellow | [BRN ]
6136720 | [InChI]
InChI=1S/C7H6BNO2/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,10-11H | [InChIKey]
XDBHWPLGGBLUHH-UHFFFAOYSA-N | [SMILES]
B(C1=CC=CC(C#N)=C1)(O)O | [CAS DataBase Reference]
150255-96-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,C | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns.
R36:Irritating to the eyes.
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust .
S39:Wear eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
UN3439 | [WGK Germany ]
3
| [Hazard Note ]
Harmful/Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29319099 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Tetrahydrofuran-->n-Butyllithium-->Triisopropyl borate-->3-Bromobenzonitrile-->3-Formylphenylboronic acid-->3-Iodobenzonitrile-->Hexane | [Preparation Products]
3-Cyanophenol-->3-Fluorobenzonitrile-->3-(2H-TETRAZOL-5-YL)-PHENYL-BORONIC ACID-->3-CYANOBENZYL ALCOHOL-->PF-06447475-->3'-(BENZYLOXY)[1,1'-BIPHENYL]-3-CARBONITRILE-->5-Methyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,2,4-oxadiazole-->3-[4-(TrifluoroMethoxy)phenyl]benzonitrile-->Benzonitrile,3-(2-pyridinyl)--->METHYL 3'-CYANO[1,1'-BIPHENYL]-4-CARBOXYLATE |
| Hazard Information | Back Directory | [Chemical Properties]
light orange powder | [Uses]
3-Cyanophenylboronic acid can be used:
- As an intermediate in the synthesis of piperidine-based MCH R1 antagonists.
- As a substrate in the Suzuki coupling reactions to prepare 4-aryl-1,8-naphthyridin-2(1H)-ones.
- As an intermediate in the synthesis of biaryl-based?phenylalanine?amino acid analogs, which are used as kainate receptors ligands.
- To prepare phenylimidazole-based?Ir(III) complexes for phosphorescent blue OLED applications.
| [Uses]
suzuki reaction | [Synthesis]
The general procedure for the synthesis of 3-cyanophenylboronic acid from triisopropyl borate and m-bromobenzonitrile was as follows: 20 g of 3-bromobenzonitrile was dissolved in 100 ml of anhydrous tetrahydrofuran (THF) and mixed with 37.6 ml of triisopropoxyborane under nitrogen protection. The reaction system was cooled to -78 °C, followed by the slow dropwise addition of 98.3 ml of 1.6 M n-butyllithium hexane solution under stirring for about 30 minutes. The reaction mixture was continued to be stirred at room temperature for 30 minutes, then cooled to 0°C and 220 ml of 4M sulfuric acid solution was added. The reaction solution was heated to reflux overnight, cooled again to 0°C, and 340 ml of 5M aqueous sodium hydroxide solution was added, followed by extraction with 200 ml of diethyl ether. The aqueous phase was separated and the pH was adjusted to 2 with 6 M hydrochloric acid and extracted twice with 300 ml ethyl acetate. The ethyl acetate layers were combined, dried with anhydrous magnesium sulfate (MgSO4) and the solvent was removed by distillation under reduced pressure. The resulting crude product was recrystallized by DMF-water system to give 11.6 g (72% yield) of 3-cyanophenylboronic acid as light yellow needle-like crystals. The product was characterized by 1H NMR (270 MHz, DMSO-d6): δ 8.5 (brs, 2H), 8.3-7.6 (m, 4H). | [References]
[1] Patent: EP1179527, 2002, A1. Location in patent: Page 19-20
[2] Patent: US6348478, 2002, B1. Location in patent: Page column 14
[3] Patent: US2012/295874, 2012, A1. Location in patent: Page/Page column 207
[4] Patent: US2002/45613, 2002, A1
[5] Patent: US6538137, 2003, B1 |
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