| Identification | More | [Name]
E-PHENYLETHENYLBORONIC ACID | [CAS]
6783-05-7 | [Synonyms]
E-PHENYLETHENYLBORONIC ACID
RARECHEM AH PB 0201
STYRYLBORONIC ACID
TRANS-2-PHENYLVINYLBORONIC ACID
TRANS-BETA-STYRENEBORONIC ACID
TRANS-B-STYRENEBORONIC ACID
TRANS-PHENYLETHENYLBORONIC ACID
TRANS-PHENYLVINYLBORONIC ACID
Phenylethenylboronicacid | [Molecular Formula]
C8H9BO2 | [MDL Number]
MFCD00963621 | [Molecular Weight]
147.97 | [MOL File]
6783-05-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Brown granular powder | [Melting point ]
146-156 °C(lit.)
| [Boiling point ]
315.9±35.0 °C(Predicted) | [density ]
1.130±0.06 g/cm3(Predicted) | [storage temp. ]
0-6°C | [form ]
Powder and/or Chunks | [pka]
9.38±0.43(Predicted) | [color ]
Light yellow to beige | [CAS DataBase Reference]
6783-05-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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
| [HazardClass ]
IRRITANT | [HS Code ]
29310099 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Phenylacetylene-->CATECHOLBORANE-->1,3,2-Dioxaborolane, 2,2',2''-methylidynetris--->POTASSIUM BETA-STYRYLTRIFLUOROBORATE-->[(Z)-2-bromoethenyl]benzene-->TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE-->2,2'-Bis-1,3,2-benzodioxaborole-->Benzaldehyde-->1,3,2-Benzodioxaborole, 2-[(1E)-2-phenylethenyl]--->Water | [Preparation Products]
trans,trans-Dibenzylideneacetone-->(E)-2-Nitroethenylbenzene-->2-(2-Phenethenyl)pyridine |
| Hazard Information | Back Directory | [Chemical Properties]
Brown granular powder | [Uses]
Reagent used for
- Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions
- Rhodium (Rh)-catalyzed intramolecular amination of aryl azides
- Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction
- Copper (Cu)-mediated cyanation
- Rhodium (Rh)-catalyzed asymmetric addition
- Diastereoselective synthesis via iridium (Ir)-catalyzed addition
- Palladium (Pd)-catalyzed cascade cyclization
Reagent used in Preparation of
- Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction
- Amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization
| [Uses]
E-Phenylethenylboronic acid is a reagent used for• ;Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions
1 Rhodium (Rh)-catalyzed intramolecular amination of aryl azides
2 Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction
3 Copper (Cu)-mediated cyanation
4 Rhodium (Rh)-catalyzed asymmetric addition
5 Diastereoselective synthesis via iridium (Ir)-catalyzed addition
6 Palladium (Pd)-catalyzed cascade cyclization
7 Reagent used in Preparation of • ;Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reactio
| [Uses]
trans-beta-Styrylboronic acid as reagent is used for palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions, diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction and rhodium (Rh)-catalyzed intramolecular amination of aryl azides. It is also used as reagent in preparation of optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction and amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization. | [Synthesis]
The general procedure for the synthesis of trans-BETA-styrene boronic acid from (E)-(2-bromovinyl)benzene is as follows: in a 50 mL round-bottomed flask (equipped with a side arm, condenser, and stirring bar) triphenylphosphine (0.131 g, 0.5 mmol, 20 mol%), p-iodoanisole (0.585 g, 2.5 mmol), and triethylamine (1.78 mL. 12.5 mmol). The reaction system was degassed three times by alternating vacuum and argon filling. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol%) was added under positive argon atmosphere. After stirring for 15 minutes at room temperature, diisopropylaminoborane (5 mL, 1 M THF solution, 5 mmol) was added and the reaction mixture was again degassed three times by alternating vacuum and argon filling. The reaction mixture was heated to reflux and kept at reflux for 12 hours. Upon completion of the reaction, the reaction solution was cooled to 0 °C, and 6 mL of methanol was slowly added (note: this process is an exothermic reaction accompanied by hydrogen release). Stirring was continued for 15 minutes and then concentrated under reduced pressure to remove all solvent to give a black solid. The solid was dissolved in 3M sodium hydroxide solution (8 mL) and subsequently washed with hexane (3 x 10 mL). The aqueous phase was cooled to 0°C (ice bath) and acidified with concentrated hydrochloric acid to pH ≤ 1, at which point the boric acid precipitated as a white solid. The aqueous phase was extracted with ether (3 x 10 mL), the organic phases were combined, dried with magnesium sulfate and filtered. Finally, the solvent was removed by concentration under reduced pressure to obtain the target product, trans-BETA-styrene boronic acid, as a white solid. | [References]
[1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583 |
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