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METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE is an organic compound that is used in the design, synthesis, and biological evaluation of novel nonsteroidal farnesoid X receptor (FXR) antagonists. It is a derivative of 1,1'-biphenyl with a bromine atom at the 4' position and a carboxylate group at the 4 position, which gives it unique chemical properties and potential applications in various fields.

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  • 89901-03-1 Structure
  • Basic information

    1. Product Name: METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE
    2. Synonyms: AKOS BAR-2392;METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE;Methyl 4'-bromobiphenyl-4-carboxylate, 95%;Methyl 4-(4-bromophenyl)benzoate, 4'-Bromo-4-(methoxycarbonyl)biphenyl;4′-Bromobiphenyl-4-carboxylic acid methyl ester;Methyl 4-(4-bromophenyl)benzoate;[1,1'-Biphenyl]-4-carboxylicacid, 4'-bromo-, methyl ester
    3. CAS NO:89901-03-1
    4. Molecular Formula: C14H11BrO2
    5. Molecular Weight: 291.14
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 89901-03-1.mol
  • Chemical Properties

    1. Melting Point: 146-148°C
    2. Boiling Point: 382.7 °C at 760 mmHg
    3. Flash Point: 185.3 °C
    4. Appearance: /
    5. Density: 1.394 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. Water Solubility: Slightly soluble in water.
    10. CAS DataBase Reference: METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE(89901-03-1)
    12. EPA Substance Registry System: METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE(89901-03-1)
  • Safety Data

    1. Hazard Codes: Xi,N
    2. Statements: 36/37/38-50/53-41
    3. Safety Statements: 26-36/37/39-61-60-39
    4. RIDADR: UN 3077 9 / PGIII
    5. WGK Germany: 2
    6. RTECS:
    7. HazardClass: IRRITANT
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 89901-03-1(Hazardous Substances Data)

89901-03-1 Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE is used as a key intermediate in the synthesis of nonsteroidal FXR antagonists for the treatment of various liver diseases, such as nonalcoholic steatohepatitis (NASH), primary biliary cholangitis (PBC), and primary sclerosing cholangitis (PSC). FXR antagonists have shown potential in modulating bile acid synthesis and metabolism, reducing inflammation, and promoting liver regeneration.
Used in Medicinal Chemistry Research:
METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE is used as a building block in the development of novel FXR modulators with improved potency, selectivity, and pharmacokinetic properties. Researchers can use this compound to design and synthesize new chemical entities with potential therapeutic benefits in liver disease treatment and other related conditions.
Used in Drug Discovery and Development:
METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE is used in the biological evaluation of FXR antagonists to assess their efficacy, safety, and pharmacological profile. METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE can be used in various in vitro and in vivo assays to study the mechanism of action, target engagement, and potential side effects of FXR antagonists, ultimately contributing to the discovery of new drugs for liver disease treatment.

Check Digit Verification of cas no

The CAS Registry Mumber 89901-03-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,9,9,0 and 1 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 89901-03:
(7*8)+(6*9)+(5*9)+(4*0)+(3*1)+(2*0)+(1*3)=161
161 % 10 = 1
So 89901-03-1 is a valid CAS Registry Number.

89901-03-1 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (H51920)  Methyl 4'-bromobiphenyl-4-carboxylate, 95%   

  • 89901-03-1

  • 1g

  • 840.0CNY

  • Detail
  • Alfa Aesar

  • (H51920)  Methyl 4'-bromobiphenyl-4-carboxylate, 95%   

  • 89901-03-1

  • 5g

  • 3396.0CNY

  • Detail

89901-03-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 4-(4-bromophenyl)benzoate

1.2 Other means of identification

Product number -
Other names [1,1'-Biphenyl]-4-carboxylicacid,4'-bromo-,methyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:89901-03-1 SDS

89901-03-1Relevant articles and documents

The Development of Benzimidazole-Based Clickable Probes for the Efficient Labeling of Cellular Protein Arginine Deiminases (PADs)

Nemmara, Venkatesh V.,Subramanian, Venkataraman,Muth, Aaron,Mondal, Santanu,Salinger, Ari J.,Maurais, Aaron J.,Tilvawala, Ronak,Weerapana, Eranthie,Thompson, Paul R.

, p. 712 - 722 (2018)

Citrullination is the post-translational hydrolysis of peptidyl-arginines to form peptidyl-citrulline, a reaction that is catalyzed by the protein arginine deiminases (PADs), a family of calcium-regulated enzymes. Aberrantly increased protein citrullinati

“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

supporting information, 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.

Dihydropyrimidine compound and uses of dihydropyrimidine compound in drugs

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Paragraph 0556; 0557; 0558; 0559, (2019/01/16)

The present invention relates to a dihydropyrimidine compound and uses of the dihydropyrimidine compound as drugs, particularly as drugs for treatment and prevention of hepatitis B, particularly to acompound represented by a general formula (I) or (Ia) or an enantiomer, a diastereomer, a tautomer, a hydrate, a solvate or a pharmaceutically acceptable salt thereof, wherein each variable is definedin the specification. The invention further relates to uses of the compound represented by a general formula (I) or (Ia) or the enantiomer, the diastereomer, the tautomer, the hydrate, the solvate orthe pharmaceutically acceptable salt thereof as drugs, especially as drugs for treatment and prevention of hepatitis B. The formulas (I) and (Ia) are defined in the specification.

DIHYDROPYRIMIDINE COMPOUNDS AND USES THEREOF IN MEDICINE

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Paragraph 00224, (2019/01/17)

Provided herein are a dihydropyrimidine compound and a pharmaceutical application thereof, especially the application used for treating and preventing HBV diseases. Specifically, provided herein is a compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, wherein the variables of the formulas are as defined in the specification. Also provided herein is use of the compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof as a medicine, especially for treating and preventing HBV diseases.

GOLD-CATALYZED C-C CROSS-COUPLING OF BORON- AND SILICON-CONTAINING ARYL COMPOUNDS AND ARYLDIAZONIUM COMPOUNDS BY VISIBLE-LIGHT

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Page/Page column 45, (2018/07/29)

The present invention relates to a method for producing (functionalized) biaryls by employing a visible-light-driven, gold-catalyzed C-C cross-coupling reaction system involving boron- and silicon-containing aryl compounds and aryldiazonium compounds. Moreover, the present invention relates to the use of such boron- and silicon-containing aryl compounds and aryldiazonium compounds, as well as related gold catalysts, in the manufacture of (functionalized) biaryls.

Photosensitizer-Free, Gold-Catalyzed C–C Cross-Coupling of Boronic Acids and Diazonium Salts Enabled by Visible Light

Witzel, Sina,Xie, Jin,Rudolph, Matthias,Hashmi, A. Stephen K.

supporting information, p. 1522 - 1528 (2017/05/05)

The first photosensitizer-free visible light-driven, gold-catalyzed C–C cross-couplings of arylboronic acids and aryldiazonium salts are reported. The reactions can be conducted under very mild conditions, using a catalytic amount of tris(4-trifluoromethyl)phosphinegold(I) chloride [(4-CF3-C6H4)3PAuCl] with methanol as the solvent allowing an alternative access to a variety of substituted biaryls in moderate to excellent yields with broad functional group tolerance. (Figure presented.).

RETRACTED ARTICLE: Heterogeneous Titania-Photoredox/Nickel Dual Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Aryl Iodides

McTiernan, Christopher D.,Leblanc, Xavier,Scaiano, Juan C.

, p. 2171 - 2175 (2017/08/09)

The efficient, mild, and semiheterogeneous decarboxylative cross-coupling of a variety alkyl carboxylic acids with aryl iodides has been accomplished through a merger of TiO2 photoredox and nickel cross-coupling chemistries. The protocol is tolerant to a wide range of substituted aryl iodides and alkyl carboxylic acids. Through replacement of the commonly employed Ir transition-metal complexes with P25 TiO2 as photocatalyst, we show that these transformations can be heterogenized with little effect on the efficiency of these transformations, while at the same time decreasing the associated costs due to the reusability and inexpensive nature of the TiO2 photocatalyst.

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

A suite of activity-based probes for human cytochrome P450 enzymes

Wright, Aaron T.,Song, Joongyu D.,Cravatt, Benjamin F.

scheme or table, p. 10692 - 10700 (2009/12/08)

Cytochrome P450 (P450) enzymes regulate a variety of endogenous signaling molecules and play central roles in the metabolism of xenobiotics and drugs. We recently showed that an aryl alkyne serves as an effective activity-based probe for profiling mouse liver microsomal P450s in vitro and in vivo. However, individual P450s display distinct substrate and inhibitor specificities, indicating that multiple probe structures may be required to achieve comprehensive coverage of this large and diverse enzyme family. Here, we have synthesized a suite of P450-directed, activity-based protein profiling (ABPP) probes that contain: (1) varied chemical architectures validated as mechanism-based inhibitors of the P450 enzyme family, and (2) terminal alkyne groups for click chemistry conjugation of reporter tags. This set of probes was screened against a wide cross-section of human P450s, leading to the discovery of an optimal set of probes that provide broad coverage of this enzyme family. We used these probes to profile the effects on P450 activity of aromatase inhibitors in current clinical use for the treatment of breast cancer. We describe the surprising discovery that one of these aromatase inhibitors, anastrozole, significantly increases probe-labeling of P450 1A2, indicative of a heterotypic cooperativity effect on a central P450 isozyme involved in metabolizing numerous drugs and xenobiotics. The results presented herein greatly expand the suite of ABPP probes for profiling P450s and illuminate new applications for these tools to understand P450-drug interactions.

Synthesis and pharmacological testing of polyaminoquinolines as blockers of the apamin-sensitive Ca2+-activated K+ channel (SKCa)

Fletcher, David I.,Ganellin, C. Robin,Piergentili, Alessandro,Dunn, Philip M.,Jenkinson, Donald H.

, p. 5457 - 5479 (2008/09/18)

The synthesis and pharmacological testing of a series of non-peptidic blockers of the SKCa (SK-3) channel is described. Target compounds were designed to mimic the spatial relationships of selected key residues in the energy-minimised structure of the octadecapeptide apamin, which are a highly potent blocker of this channel. Structures consist of a central unit, either a fumaric acid or an aromatic ring, to which are attached two alkylguanidine or two to four alkylaminoquinoline substituents. Potency was tested by the ability to inhibit the SKCa channel-mediated after-hyperpolarization (AHP) in cultured rat sympathetic neurones. It was found that bis-aminoquinoline derivatives are significantly more potent as channel blockers than are the corresponding guanidines. This adds to the earlier evidence that delocalisation of positive charge through the more extensive aminoquinolinium ring system is important for effective channel binding. It was also found that an increase in activity can be gained by the addition of a third aminoquinoline residue to give non-quaternized amines which have submicromolar potencies (IC50 = 0.13-0.36 μM). Extension to four aminoquinoline residues increased the potency to IC50 = 93 nM.

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