135159-25-0 Usage
Description
2,4,6-TRIMETHOXYBENZENEBORONIC ACID is an organic compound that features a boronic acid functional group attached to a benzene ring with three methoxy substituents at the 2nd, 4th, and 6th positions. 2,4,6-TRIMETHOXYBENZENEBORONIC ACID is known for its reactivity and utility in various chemical reactions, particularly in the field of organic synthesis.
Uses
Used in Organic Synthesis:
2,4,6-TRIMETHOXYBENZENEBORONIC ACID is used as an intermediate in organic syntheses for the creation of various complex organic molecules. Its boronic acid group allows it to participate in a range of reactions, such as cross-coupling reactions, which are essential for constructing diverse molecular structures.
Used in Suzuki Reaction:
In the field of cross-coupling reactions, 2,4,6-TRIMETHOXYBENZENEBORONIC ACID is used as a key component in the Suzuki reaction. The Suzuki reaction is a widely employed method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds. The reaction involves the palladium-catalyzed coupling of an organoboron compound, such as 2,4,6-TRIMETHOXYBENZENEBORONIC ACID, with an organohalide or triflate, leading to the formation of the desired biaryl product. This reaction is highly valuable in the pharmaceutical and materials science industries for the synthesis of complex molecules and materials with specific properties.
Check Digit Verification of cas no
The CAS Registry Mumber 135159-25-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,5,1,5 and 9 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 135159-25:
(8*1)+(7*3)+(6*5)+(5*1)+(4*5)+(3*9)+(2*2)+(1*5)=120
120 % 10 = 0
So 135159-25-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H13BO5/c1-13-6-4-7(14-2)9(10(11)12)8(5-6)15-3/h4-5,11-12H,1-3H3
135159-25-0Relevant articles and documents
Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts
Dennis, Eric G.,Jeffery, David W.,Perkins, Michael V.,Smith, Paul A.
experimental part, p. 2125 - 2131 (2011/04/22)
Several functionalized biaryls and diarylmethanes containing the phloroglucinol subunit were synthesized in 55-85% yields using Negishi cross-couplings of 2,4,6-trimethoxyphenylzinc chloride with aryl and benzyl halides in the presence of catalytic quantities of Pd(DPEPhos)Cl2. These simple to prepare couplings were generally complete in 1-24 h depending on the halide, and were applicable to aryl and benzyl halides containing both electron-donating and electron-withdrawing groups.
Suzuki cross-coupling reaction of sterically hindered aryl boronates with 3-iodo-4-methoxybenzoic acid methylester
Chaumeil,Signorella,Le Drian
, p. 9655 - 9662 (2007/10/03)
The cross-coupling reaction of 3-iodo-4-methoxybenzoic acid methylester with sterically hindered arylboronic esters and especially 5,5-dimethyl-2-mesityl-1,3,2-dioxaborinane, is reported. The optimisation of the process in order to obtain biaryls in good yield by using anhydrous benzene at reflux and sodium phenoxide in the presence of 0.06 equiv. of Pd(PPh3)4 is described. (C) 2000 Elsevier Science Ltd.
