51067-38-0

Basic information

• Product Name: 4-PHENOXYPHENYLBORONIC ACID
• Synonyms: 4-PHENOXYBENZENEBORONIC ACID;4-PHENOXYPHENYLBORONIC ACID;AKOS BRN-0132;RARECHEM AH PB 0260;(P-PHENOXYPHENYL)BORONIC ACID;TIMTEC-BB SBB003409;4-Phenoxybenzeneboronic acid 98%;4-Phenoxyphenylboronic acid,97%
• CAS NO: 51067-38-0
• Molecular Formula: C₁₂H₁₁BO₃
• Molecular Weight: 214.02
• Product Categories: blocks;BoronicAcids;Heterocyclic Compounds;Aryl;Organoborons;Boronic Acids;Boronic Acids and Derivatives;Boronic Acids
• Mol File: 51067-38-0.mol

Chemical Properties

• Melting Point: 141-145 °C(lit.)
• Boiling Point: 377 °C at 760 mmHg
• Flash Point: 181.8 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.23 g/cm³
• Vapor Pressure: 2.36E-06mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 8.76±0.10(Predicted)
• CAS DataBase Reference: 4-PHENOXYPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENOXYPHENYLBORONIC ACID(51067-38-0)
• EPA Substance Registry System: 4-PHENOXYPHENYLBORONIC ACID(51067-38-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 51067-38-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenoxyphenylboronic acid is used as an intermediate for the preparation of biphenyl derivatives of nitrotrifluoromethoxybenzyloxydihydroimidazooxazines, which possess antitubercular activity. It plays a crucial role in the development of new drugs to combat tuberculosis.
Used in Chemical Synthesis:
4-Phenoxyphenylboronic acid is used as a reactant in the Suzuki-Miyaura coupling reaction, a widely employed method for the synthesis of aryl derivatives via C-C bond formation. This reaction involves the use of a palladium catalyst and different aryl halides, allowing for the creation of various organic compounds.
Used in the Synthesis of Pyrrolo Pyrimidines:
4-Phenoxyphenylboronic acid is used in the synthesis of pyrrolo pyrimidines, which are potent inhibitors of Lck kinase. These compounds have potential applications in the development of drugs for the treatment of various diseases, including cancer.
Used in the Synthesis of Evobrutinib:
4-Phenoxyphenylboronic acid is utilized in the synthesis of evobrutinib, a potent Bruton's tyrosine kinase (BTK) inhibitor. Evobrutinib has been approved for the treatment of certain autoimmune diseases, such as multiple sclerosis, and is under investigation for other therapeutic applications.
Used in the Preparation of 1-Phenoxy-4-(trifluoromethyl)benzene:
4-Phenoxyphenylboronic acid can be used to prepare 1-phenoxy-4-(trifluoromethyl)benzene via oxidative trifluoromethylation using Chan-Lam-type reaction conditions. 4-PHENOXYPHENYLBORONIC ACID may have potential applications in various chemical and pharmaceutical processes.

InChI:InChI=1/C12H11BO3/c14-13(15)10-6-8-12(9-7-10)16-11-4-2-1-3-5-11/h1-9,14-15H

Upstream product

• 101-55-3 4-Bromodiphenyl ether 
• 5419-55-6 Triisopropyl borate 
• 150-46-9 triethyl borate 
• 7025-06-1 1-bromo-2-phenoxybenzene 
• 101-84-8 diphenylether 
• 121-43-7 Trimethyl borate 
• 2050-47-7 4,4'-dibromodiphenyl ether 
• 7732-18-5 water 
• 13675-18-8 tetrahydroxydiboron 
• 688-74-4 boric acid tributyl ester 

Downstream Products

• 490030-16-5 4-chloro-5-(4-phenoxyphenyl)-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 330786-01-1 1-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 41280-37-9 1-phenoxy-4-methylphenylsulfanyl-benzene 
• 934273-82-2 N-(3,5-dimethyl-4'-phenoxybiphenyl-4-yl)-2,2,2-trifluoroacetamide 

Relevant articles and documents

Preparation method of 4-phenoxy phenylboronic acid

The invention discloses a preparation method of 4-phenoxy phenylboronic acid, which belongs to the technical field of organic boric acid chemistry. The preparation method comprises the following steps: starting from diphenyl ether, reacting with NBS to generate 4,4'-dibromo diphenyl ether, reacting with borate and butyl lithium by a one-pot method, and hydrolyzing to obtain 4-phenoxy phenylboronicacid. According to the method, dibromides which are easy to purify are generated during bromination, monosubstituted products are generated by controlling the using amount of a lithiation reagent andthe boric acid ester during lithiation, the method is verified on the scale of 100 kg, and the method has the prospect of industrial methods.

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis

Flow chemistry processes for boronic acid syntheses utilizing lithiation-borylation have been developed. The side reactions in the lithiation step that occur in batch were suppressed, and unstable lithium intermediates were handled safely. Flow technology was applied to several kinds of boronic acid syntheses, and scale-up was successfully conducted to allow kilogram-scale production. Some of the key benefits of flow flash chemistry were utilized, both to avoid side reactions and to enable dianion chemistry that is difficult to perform successfully in batch reactions. The examples showed further perspectives on the utility of flow technologies for process development.

Anthracene compound, preparing method of anthracene compound and organic light-emitting device

The invention provides an anthracene compound. The anthracene compound has a structure in the formula (I), wherein Q is the C1-60 alkyl group or the C6-60 aryl group or the C5-60 condensed ring group or the C5-60 heterocyclic group; Ar is the C6-60 aryl group or the C5-60 condensed ring group or the C5-60 heterocyclic group; and Ar1 is H, the C1-60 alkyl group, the C1-60 alkoxy group, the C1-60 ether group, the C6-60 aryl group, the C6-60 condensed ring group, the C6-60 heterocyclic group and the C6-60 arylamine group. Compared with the prior art, the anthracene compound is connected with an aromatic compound through anthracene, and the Q, Ar and Ar1 groups are introduced, so that a device emits blue light after the organic compound is applied to the organic light-emitting device; and meanwhile, the means that the above groups are used for adjusting the light-emitting wavelength is adopted, the light-emitting efficiency of the organic light-emitting device is high, and the service life is long.

Preparation method of 4-phenoxyphenylboronic acid

The invention discloses a preparation method of 4-phenoxyphenylboronic acid, and relates to the technical field of organic synthesis. The preparation method comprises the steps that 4-bromodiphenyl ether is taken as a raw material to react with magnesium sheets to prepare a Grignard reagent by taking tetrahydrofuran as a solvent, the obtained Grignard reagent reacts with trimethyl borate, hydrochloric acid hydrolysis is conducted to prepare coarse 4-phenoxyphenylboronic acid, and then purifying is conducted to obtain the finished 4-phenoxyphenylboronic acid. According to the preparation method, the adopted raw materials are low in cost and easy to obtain, the reaction conditions are mild, aftertreatment operation is easy, the production cost is low, the yield is high, and the method is suitable for industrialized production.

Pyrazolopyrimidine derivative, preparation method, pharmaceutical composition and application

The invention discloses a pyrazolopyrimidine derivative, a preparation method, a pharmaceutical composition and application. The invention provides the pyrazolopyrimidine derivative as shown in a formula I and stereoisomer or solvate or pharmaceutically acceptable salts or active metabolite or prodrug thereof. The pyrazolopyrimidine derivative as shown in the formula I has good inhibitory activity on Bruton's tyrosine kinase (Btk) and particularly has good in vitro and in vivo inhibitory activity on growth of tumor cells, and a good marketization prospect is achieved. Please see the formula I in the description.

Platinum(II) cyclometallates featuring broad emission bands and their applications in color-tunable OLEDs and high color-rendering WOLEDs

Two phosphorescent platinum(ii) cyclometallated complexes with phenoxy groups (1 and 2) have been developed. The modified organic ligands derived by combining the phenoxy moiety and 2-phenylpyridine conferred them with a more flexible structure, leading to superior intermolecular interaction properties of the resulting Pt(ii) metallophosphors. Because of the excimer formation induced by Pt(ii) complexes 1 and 2, the emission color can be tuned over a wide range from cyan to orange by simply increasing the concentration of the Pt(ii) metallophosphors. Inspired by their broad emission band, color tunability and outstanding electroluminescence (EL) performance, these two Pt(ii) phosphors complemented with blue fluorescent emitter 4,4′-bis(9-ethyl-3-carbazovinylene)-1,1′-biphenyl (BCzVBi) were employed in manufacturing high color-rendering white organic light-emitting devices (WOLEDs). In such simple two-emitter systems, 1-based WOLEDs exhibited reasonable EL performance with an external quantum efficiency (ηext) of 11.7%, luminance efficiency (ηL) of 29.1 cd A-1, power efficiency (ηp) of 16.9 lm W-1 and color rendering index (CRI) of 77, whereas 2-based WOLEDs demonstrated an ηext of 10%, ηL of 21.7 cd A-1, ηp of 10.7 lm W-1 and CRI of 88.

Compound containing anthracene and pyrene and preparing method and application thereof

The invention provides a compound containing anthracene and pyrene and a preparing method and application thereof. The compound has a structure shown in formula I, wherein R1 and R3 are independently selected from substituted or unsubstituted C1-C60 alkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C10-C60 condensed ring groups or substituted or unsubstituted C5-C60 heterocyclic groups; R2 is selected from hydrogen, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C5-C60 heterocyclic groups, substituted or unsubstituted C10-C60 condensed ring groups or substituted or unsubstituted C5-C60 arylamine groups; n is 0 or 1. When current density is 20 mA/cm2, the current efficiency of the compound with the structure shown in formula I is as high as 8.9 cd/A, and service life is as long as 8500 h which is much longer than that of existing electroluminescent materials.

New organic electroluminescent material, preparation method and applications thereof

The invention relates to a new organic electroluminescent material, a preparation method and applications thereof, and provides a new anthracene derivative, wherein an ether structure is introduced into an anthracene compound to link Y1, Ar1, Ar2 and R1 so as to improve the stereo skill of the compound, adjust the molecular weight of the ligand R1, carry out performance improving and skill improving according to ligand type performance, and provide other advantages. The device prepared by using the new anthracene derivative of the present invention has characteristics of high brightness, excellent heat resistance, long service life, high efficiency, and the like.