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Methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is a chemical compound with the molecular formula C23H27BO4. It is a boronic ester, which means it contains a boron atom bonded to an alkyl or aryl group and an ester functional group. methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is a valuable building block for the production of complex organic molecules in chemical and pharmaceutical research.

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  • Methyl 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

    Cas No: 1381957-27-2

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  • 1381957-27-2 Structure
  • Basic information

    1. Product Name: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate
    2. Synonyms:
    3. CAS NO:1381957-27-2
    4. Molecular Formula:
    5. Molecular Weight: 338.211
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1381957-27-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 458.0±38.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: 1.12±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate(CAS DataBase Reference)
    10. NIST Chemistry Reference: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate(1381957-27-2)
    11. EPA Substance Registry System: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate(1381957-27-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1381957-27-2(Hazardous Substances Data)

1381957-27-2 Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is used as an intermediate in the synthesis of pharmaceuticals. It plays a crucial role in the development of new drugs and the improvement of existing ones.
Used in Agrochemical Industry:
methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is also used as an intermediate in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals.
Used in Materials Science:
Methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is used in the synthesis of various materials, including polymers and other advanced materials, for a wide range of applications.
Used in Organic Synthesis:
As a reagent for the Suzuki-Miyaura cross-coupling reaction, this compound is used for the formation of carbon-carbon bonds in organic synthesis. This reaction is widely used in the synthesis of complex organic molecules, making this compound an essential tool in chemical research.

Check Digit Verification of cas no

The CAS Registry Mumber 1381957-27-2 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,3,8,1,9,5 and 7 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1381957-27:
(9*1)+(8*3)+(7*8)+(6*1)+(5*9)+(4*5)+(3*7)+(2*2)+(1*7)=192
192 % 10 = 2
So 1381957-27-2 is a valid CAS Registry Number.

1381957-27-2Relevant articles and documents

Two-dimensional crystals from reduced symmetry analogues of trimesic acid

Barnard, Rachel A.,Dutta, Ananya,Schnobrich, Jennifer K.,Morrison, Christine N.,Ahn, Seokhoon,Matzger, Adam J.

, p. 5954 - 5961 (2015)

The two-dimensional assembly of multicarboxylated arenes is explored at the liquid-graphite interface using scanning tunneling microscopy. Symmetry variations were introduced via phenylene spacer addition and the influence of these perturbations on the formation of hydrogen-bonded motifs from an alkanoic acid solvent is observed. This work demonstrates the importance of symmetry in 2D crystal formation and draws possible links of this behavior to prediction of coordination modes in three-dimensional coordination polymers.

“Orthogonal-Twisted-Arm” Ligands for The Construction of Metal–Organic Frameworks (MOFs): New Topology and Catalytic Reactivity

He, Ying,Li, Guanghua,Ren, Junyu,Shan, Chuan,Shi, Xiaodong,Song, Zhiguang,Wang, Li,Wojtas, Lukasz,Zhao, Kai

, p. 16272 - 16276 (2020/11/30)

Extended tetratopic benzoic acid ligands with “orthogonal-twisted-arms” conformations were designed and synthesized for the construction of new MOF structures (OTA-MOF). Upon coordination with Cd2+ and Cu2+ cations, two well-defined new MOFs were prepared. X-ray single crystal structures were successfully obtained, demonstrating the formation of a new topology (4,4,4-c). The OTA2-MOF-Cu gave moderate stability in organic solvents and good gas sorption ability toward CO2. This new MOF showed superior catalytic reactivity toward the epoxide-CO2 cycloaddition, giving >50 folds yield enhancement over the controlled reaction without MOF. It is expected that this new ligand design, porous structure, and excellent CO2 catalytic reactivity will make OTA-MOF promising new materials for applications in catalysis and separation.

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Dai, Peng-Fei,Ning, Xiao-Shan,Wang, Hua,Cui, Xian-Chao,Liu, Jie,Qu, Jian-Ping,Kang, Yan-Biao

supporting information, p. 5392 - 5395 (2019/03/29)

Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.

A luminescent Zr-based metal-organic framework for sensing/capture of nitrobenzene and high-pressure separation of CH4/C2H6

Zou, Ruyi,Ren, Xueling,Huang, Fang,Zhao, Yifang,Liu, Jia,Jing, Xiping,Liao, Fuhui,Wang, Yinxia,Lin, Jianhua,Zou, Ruqiang,Sun, Junliang

supporting information, p. 23493 - 23500 (2015/11/28)

We present a novel luminescent metal-organic framework (LMOF) based on zirconium metal oxide cluster Zr6O8 bonding with a new tetratopic linker 1,3,6,8-tetrakis(4′-carboxy[1,1′-biphenyl]-4-yl-)pyrene. This (4,12)-connected ftw-a-type

Synthesis of trimethylstannyl arylboronate compounds by sandmeyer-type transformations and their applications in chemoselective cross-coupling reactions

Qiu, Di,Wang, Shuai,Tang, Shengbo,Meng, He,Jin, Liang,Mo, Fanyang,Zhang, Yan,Wang, Jianbo

, p. 1979 - 1988 (2014/04/03)

A synthetic method based on Sandmeyer-type reactions to access both tin- and boron-substituted arenes from nitroaniline derivatives is described. This transformation can be applied to the synthesis of a series of functionalized trimethylstannyl arylboronates. In addition, the chemoselective reaction of the Stille and Suzuki-Miyaura cross-coupling reactions is explored, and a series of m- and p-terphenyl derivatives have been synthesized by conducting consecutive one-pot Stille and Suzuki-Miyaura cross-coupling reactions.

Discovery of trifluoromethyl(pyrimidin-2-yl)azetidine-2-carboxamides as potent, orally bioavailable TGR5 (GPBAR1) agonists: Structure-activity relationships, lead optimization, and chronic in vivo efficacy

Phillips, Dean P.,Gao, Wenqi,Yang, Yang,Zhang, Guobao,Lerario, Isabelle K.,Lau, Thomas L.,Jiang, Jiqing,Wang, Xia,Nguyen, Deborah G.,Bhat, B. Ganesh,Trotter, Carol,Sullivan, Heather,Welzel, Gustav,Landry, Jannine,Chen, Yali,Joseph, Sean B.,Li, Chun,Gordon, W. Perry,Richmond, Wendy,Johnson, Kevin,Bretz, Angela,Bursulaya, Badry,Pan, Shifeng,McNamara, Peter,Seidel, H. Martin

, p. 3263 - 3282 (2014/05/20)

Activation of the G-protein coupled receptor (GPCR) Takeda G-protein receptor 5 (TGR5), also known as G-protein bile acid receptor 1 (GPBAR1), has been shown to play a key role in pathways associated with diabetes, metabolic syndrome, and autoimmune disease. Nipecotamide 5 was identified as an attractive starting point after a high-throughput screen (HTS) for receptor agonists. A comprehensive hit-to-lead effort culminated in the discovery of 45h as a potent, selective, and bioavailable TGR5 agonist to test in preclinical metabolic disease models. In genetically obese mice (ob/ob), 45h was as effective as a dipeptidyl peptidase-4 (DPP-4) inhibitor at reducing peak glucose levels in an acute oral glucose tolerance test (OGTT), but this effect was lost upon chronic dosing.

Synthesis of aryl trimethylstannanes from aryl amines: A sandmeyer-type stannylation reaction

Qiu, Di,Meng, He,Jin, Liang,Wang, Shuai,Tang, Shengbo,Wang, Xi,Mo, Fanyang,Zhang, Yan,Wang, Jianbo

, p. 11581 - 11584 (2013/11/06)

Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright

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