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(4-fluorophenyl)dichloroborane is an organoborane compound with the chemical formula C6H4BCl2F. It is a colorless liquid at room temperature and is derived from the reaction of 4-fluorophenylmagnesium bromide with boron trichloride. (4-fluorophenyl)dichloroborane is an important reagent in organic synthesis, particularly in the formation of carbon-carbon bonds through the Suzuki-Miyaura cross-coupling reaction. It is also used as a Lewis acid catalyst in various organic transformations. Due to its reactivity and sensitivity to moisture and air, it is typically handled under an inert atmosphere and stored in a sealed container.

31685-21-9

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31685-21-9 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 31685-21-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,6,8 and 5 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 31685-21:
(7*3)+(6*1)+(5*6)+(4*8)+(3*5)+(2*2)+(1*1)=109
109 % 10 = 9
So 31685-21-9 is a valid CAS Registry Number.

31685-21-9Relevant academic research and scientific papers

Synthesis of Fluorine-Containing Aryl(halo)boranes from Potassium Aryl(fluoro)borates

Bardin,Prikhod’ko,Shmakov,Shabalin, A. Yu.,Adonin, N. Yu.

, p. 50 - 61 (2020/04/09)

Fluorine-containing aryldihalogenoboranes have been obtained by the reaction of boron and aluminum chlorides and bromides with potassium aryltrifluoroborates K[ArBF3] under mild conditions. In a similar way, bis(pentafluorophenyl)halogenoboranes have been synthesized by the reaction with K[(C6F5)2BF2]. The reaction of K[C6F5BF3] with AlBr3 affords a mixture of C6F5BF2 and C6F5BCl2 due to fast conversion of AlBr3 to AlBrCl2. The inductive and resonance parameters of BCl2 and BBr2 groups were calculated.

Substituent Effects in the Cyclization of Yne-Diols Catalyzed by Gold Complexes Featuring L2/Z-Type Diphosphinoborane Ligands

Inagaki, Fuyuhiko,Nakazawa, Kenta,Maeda, Kakeru,Koseki, Tomoya,Mukai, Chisato

supporting information, p. 3005 - 3008 (2017/09/05)

Gold(I) complexes featuring Z-type ligands introducing electron-withdrawing groups (EWG), Au(DPBF)Cl (4a) and Au(DPBCl)Cl (4b) (DPB = diphosphine-boron), have been synthesized and structurally characterized. These studies suggest tha

Regioselective electrophilic borylation of haloarenes

Del Grosso, Alessandro,Ayuso Carrillo, Josue,Ingleson, Michael J.

supporting information, p. 2878 - 2881 (2015/02/19)

Haloarenes undergo direct borylation using amine:BCl3:AlCl3 in the ratio of 1:1:2. After esterification the pinacol boronate esters are isolated in good yield with regioselectivity controlled by steric and electronic effects.

Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions

Yasuike, Shuji,Nakata, Kazuhide,Qin, Weiwei,Matsumura, Mio,Kakusawa, Naoki,Kurita, Jyoji

, p. 9 - 16 (2015/05/13)

The reaction of triarylstibanes (1) with boron trihalides (BCl3, and BBr3) afforded arylboron dihalides (2) by utilizing all the three aryl groups on the antimony. Boron intermediates (2) were transformed to arylboronates (3) in good to excellent yields by treatment with methanol and 1,3-propanediol. Further, the Pd-catalyzed reactions of 2 with organic halides such as 1-bromonaphthalene and benzoyl chloride in the presence of H2O afforded the corresponding cross-coupling products, unsymmetrical biaryls (4) and ketones (5), in moderate to good yields. The potential energy surfaces for the transmetallations of triarylstibanes (1) with BCl3 affording 2 were determined by molecular orbital calculations. The analyses of substituent effects on theoretically calculated reactivities showed the importance of the resonance effects of the ring substituents on these transmetallations.

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