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775351-57-0

775351-57-0 Structure

775351-57-0 Structure
IdentificationBack Directory
[Name]

3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER
[CAS]

775351-57-0
[Synonyms]

Bm369
3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER
3-Cyano-4-fluorobenzeneboronic acid pinacol ester, 96%
5-Cyano-2-fluorobenzeneboronic acid pinacol ester, 96%
3-Cyano-4-fluorophenylboronic acid, pinacol ester 95+%
2-fluoro-5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitri
2-fluoro-5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
2-(3-Cyano-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
Benzonitrile, 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
[Molecular Formula]

C13H15BFNO2
[MDL Number]

MFCD06795681
[MOL File]

775351-57-0.mol
[Molecular Weight]

247.07
Chemical PropertiesBack Directory
[Melting point ]

75-76℃
[Boiling point ]

334.5±32.0 °C(Predicted)
[density ]

1.12±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[form ]

Solid
[color ]

White to Almost white
[InChI]

1S/C13H15BFNO2/c1-12(2)13(3,4)18-14(17-12)10-5-6-11(15)9(7-10)8-16/h5-7H,1-4H3
[InChIKey]

RYJOVQGRIOURGT-UHFFFAOYSA-N
[SMILES]

FC1=C(C#N)C=C(B2OC(C)(C)C(C)(C)O2)C=C1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
[RIDADR ]

UN3439
[WGK Germany ]

WGK 3
[HazardClass ]

6.1
[HS Code ]

2931900090
[Storage Class]

11 - Combustible Solids
Spectrum DetailBack Directory
[Spectrum Detail]

3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER(775351-57-0)1HNMR
Hazard InformationBack Directory
[Synthesis]

5-Bromo-2-fluorobenzonitrile

179897-89-3

Bis(pinacolato)diboron

73183-34-3

3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER

775351-57-0

2-Fluoro-5-bromobenzonitrile (1000.00 mg, 5.00 mmol, 1.00 eq.) and pinacol ester of bisboronic acid (1396.61 mg, 5.50 mmol, 1.10 eq.) were added to potassium acetate (1472.07 mg, 15.00 mmol, 3.00 eq.) in a dioxane (10 mL) and DMF (1 mL) ) in a solvent mixture of dioxane (10 mL) and DMF (1 mL) for degassing. Subsequently, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride 1:1 complex with dichloromethane (366.85 mg, 0.50 mmol, 0.10 eq.) was added. The reaction mixture was placed in a sealed vial and the reaction was heated at 100 °C overnight. After completion of the reaction, it was cooled to room temperature and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, gradient 0 to 5%) to afford the target product 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.0 g, 81% yield).

[References]

[1] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 0504; 0505; 0506
[2] Patent: WO2011/25799, 2011, A1. Location in patent: Page/Page column 50
[3] Organic Letters, 2004, vol. 6, # 19, p. 3265 - 3268
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