172975-69-8

Basic information

• Product Name: 3,5-Dimethylphenylboronic acid
• Synonyms: RARECHEM AH PB 0186;M-XYLENE-5-BORONIC ACID;TIMTEC-BB SBB004076;3,5-DIMETHYLBENZENEBORONIC ACID;3,5-DIMETHYLPHENYLBORONIC ACID;AKOS BRN-0067;3,5-Dimethyl benzene;3,5-DIMETHYLBENZENEBORONIC ACID 98%
• CAS NO: 172975-69-8
• Molecular Formula: C₈H₁₁BO₂
• Molecular Weight: 149.98
• EINECS: 1312995-182-4
• Product Categories: blocks;BoronicAcids;Boric Acid;Heterocyclic Compounds;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Pyridines
• Mol File: 172975-69-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 261-265 °C(lit.)
• Boiling Point: 312.7 °C at 760 mmHg
• Flash Point: 142.9 °C
• Appearance: /solid
• Density: 1.07 g/cm³
• Storage Temp.: 0-6°C
• PKA: 8.72±0.10(Predicted)
• Water Solubility: Slightly soluble in water
• BRN: 7368658
• CAS DataBase Reference: 3,5-Dimethylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethylphenylboronic acid(172975-69-8)
• EPA Substance Registry System: 3,5-Dimethylphenylboronic acid(172975-69-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 37/39-26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 172975-69-8(Hazardous Substances Data)

Usage

Description

3,5-Dimethylphenylboronic acid, also known as DMPBA, is an organic compound with the chemical formula C8H11BO2. It is an off-white to light yellow crystalline powder that serves as a versatile intermediate in organic synthesis due to its unique chemical properties.

Uses

Used in Organic Synthesis:
3,5-Dimethylphenylboronic acid is used as a research intermediate for organic synthesis, allowing chemists to create a wide range of compounds with various applications in different industries.
Used in Suzuki Reaction:
In the field of organic chemistry, 3,5-Dimethylphenylboronic acid is used as a reactant in the palladium-catalyzed Suzuki coupling reactions. This reaction is a powerful method for forming carbon-carbon bonds, which are essential in the synthesis of complex organic molecules.
Used in Extraction Processes:
3,5-Dimethylphenylboronic acid is used as a co-extractant in combination with modified Aliquat 336 for the extraction of xylose, glucose, and fructose from aqueous solutions. This application is particularly relevant in the biotechnology and food industries, where the separation and purification of these sugars are crucial.
Used in Pharmaceutical Industry:
As a reactant, 3,5-Dimethylphenylboronic acid is used to prepare the penultimate methyl ester, which can be further utilized in the synthesis of various pharmaceutical compounds. This application highlights the importance of DMPBA in the development of new drugs and therapeutic agents.

Synthetic route

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + 5-bromo-1,3-xylene (556-96-7) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 5-bromo-1,3-xylene In tetrahydrofuran at 70℃; Stage #3: methanol Further stages;	89%

Trimethyl borate (121-43-7) + 5-bromo-1,3-xylene (556-96-7) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With Mg; H2SO4 In tetrahydrofuran; diethyl ether aryl bromide in THF was added to Mg turnings, filtered, added dropwise with stirring to trimethyl borate in ether at -70°C, the suspn. was allowed to warm to room temp. overnight, added with stirring to ice, concd. H2SO4, stirred for 30 min (Ar); shaken with ether, dried over Na2SO4, evapd., filtered, dried in vac.; elem. anal.;	85.6%
With Mg; iodomethane In diethyl ether under Ar atm. 1,3-dimethyl-5-bromobenzene in Et2O was added slowly to Mgturning in the presence of MeI, react. mixt. was refluxed for 6 h and a dded at -60°C to soln. B(OMe)3 in Et2O, allowed to warm slowly toroom temp. with stirring; react. mixt. was poured into 20% H2SO4, org. phase was separated, washedwith water and dried over MgSO4, solvent was removed in vacuo;	82%

Trimethyl borate (121-43-7) + water (7732-18-5) + 3,5-dimethyphenylmagnesium bromide (34696-73-6) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
Stage #1: Trimethyl borate; 3,5-dimethyphenylmagnesium bromide In tetrahydrofuran at 20℃; Stage #2: water With hydrogenchloride In tetrahydrofuran; diethyl ether	74%

Trimethyl borate (121-43-7) + 5-bromo-1,3-xylene (556-96-7) + water (7732-18-5) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
Stage #1: Trimethyl borate; 5-bromo-1,3-xylene With magnesium In tetrahydrofuran at -78 - 20℃; Stage #2: water With hydrogenchloride In tetrahydrofuran; diethyl ether	74%

5-bromo-1,3-xylene (556-96-7) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With Trimethyl borate
Stage #1: 5-bromo-1,3-xylene With magnesium In tetrahydrofuran Stage #2: With Trimethyl borate Stage #3: With hydrogenchloride Further stages.;
Stage #1: 5-bromo-1,3-xylene With magnesium; methyl iodide In diethyl ether Inert atmosphere; Reflux; Stage #2: With Trimethyl borate In diethyl ether at -60 - 20℃; Inert atmosphere;
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: -78 - 20 °C 2.1: water; hydrogenchloride / tetrahydrofuran; hexane / 20 °C / pH 3 - 5 View Scheme

2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (325142-93-6) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
Stage #1: 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water for 0.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 4h;
Stage #1: 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 17h;

m-xylene (108-38-3) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4,4'-di-tert-butyl-2,2'-bipyridine / [Ir(COD)(OMe)]2 / tetrahydrofuran / 16 h / 80 °C 2.1: sodium periodate / tetrahydrofuran; H2O / 0.25 h 2.2: HCl / H2O; tetrahydrofuran / 4 h View Scheme
Multi-step reaction with 2 steps 1.1: 4,4'-di-tert-butyl-2,2'-bipyridine; pinacolborane / [(COD)Ir(OMe)]2 / cyclohexane / 24 h / 80 °C 2.1: sodium periodate / tetrahydrofuran; H2O / 0.5 h 2.2: hydrochloric acid / tetrahydrofuran; H2O / 17 h / 20 °C View Scheme

Triisopropyl borate (5419-55-6) + 5-bromo-1,3-xylene (556-96-7) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With N2 In tetrahydrofuran	2.41 g (29.7%)
With N2 In tetrahydrofuran	2.41 g (29.7%)
With sodium hydroxide; n-butyllithium In tetrahydrofuran; hydrogenchloride; hexane; dichloromethane
Stage #1: 5-bromo-1,3-xylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 25℃; for 0.333333h; Inert atmosphere;

C26H31B3O5 (1016971-57-5) → (4-methoxy-3,5-dimethylphenyl)boronic acid (301699-39-8) + 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With water at 25℃; Equilibrium constant;

C25H29B3O4 (1016971-59-7) → (4-methoxy-3,5-dimethylphenyl)boronic acid (301699-39-8) + 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With water at 25℃; Equilibrium constant;

C38H55B3O5 (1016971-63-3) → 3,5-dimethylphenyl boronic acid (172975-69-8) + 4-methoxy-3,5-di-tert-butylphenylboronic acid pinacol ester (233584-42-4)

Conditions	Yield
With water at 25℃; Equilibrium constant;

C31H41B3O4 (1016971-64-4) → 3,5-dimethylphenyl boronic acid (172975-69-8) + 4-methoxy-3,5-di-tert-butylphenylboronic acid pinacol ester (233584-42-4)

Conditions	Yield
With water at 25℃; Equilibrium constant;

C25H29B3O6 (1016971-54-2) → 3,5-dimethylphenyl boronic acid (172975-69-8) + 3,4,5-trimethoxyphenylboronic Acid (182163-96-8)

Conditions	Yield
With water at 25℃; Equilibrium constant;

C26H31B3O9 (1016971-55-3) → 3,5-dimethylphenyl boronic acid (172975-69-8) + 3,4,5-trimethoxyphenylboronic Acid (182163-96-8)

Conditions	Yield
With water at 25℃; Equilibrium constant;

tris(3.5-dimethyl phenyl)boroxine (34907-38-5) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With water at 25℃; Equilibrium constant;

3,5-dimethyphenylmagnesium bromide (34696-73-6) → B,B-bis(3,5-dimethylphenyl)borinic acid + 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With Triisopropyl borate In tetrahydrofuran at -55 - 20℃; Temperature;

(3,5-dimethylphenyl)lithium (95070-94-3) → B,B-bis(3,5-dimethylphenyl)borinic acid + 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With Triisopropyl borate In tetrahydrofuran at -70 - 20℃;

C10H15BO2 → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; pH=3 - 5;
With hydrogenchloride; water In tetrahydrofuran	114.6 g

3,5-dimethyphenylmagnesium bromide (34696-73-6) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / -78 - 20 °C 2: hydrogenchloride; water / tetrahydrofuran View Scheme

2,6-dimethylaniline (87-62-7) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine / methanol / 20 °C 2.1: sulfuric acid / ethanol / 1 h / 7 - 20 °C 2.2: 1.5 h / 20 °C / Cooling 2.3: 20 °C / Inert atmosphere 3.1: magnesium / tetrahydrofuran / -78 - 20 °C View Scheme

3,5-dimethylphenyl boronic acid (172975-69-8) + methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate (246219-75-0) → methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate (246219-76-1)

Conditions	Yield
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol; toluene at 85℃; for 15h; Suzuki-Miayura cross-coupling;	100%

3,5-dimethylphenyl boronic acid (172975-69-8) + (S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-iodo-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methyl propan-1-one (292600-31-8) → (S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methylpropan-1-one (292600-32-9)

Conditions	Yield
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol; toluene at 90℃; for 15h; Suzuki-Miayura cross-coupling;	100%

3,5-dimethylphenyl boronic acid (172975-69-8) → 3,3',5,5'-tetramethyl-1,1'-biphenyl (25570-02-9)

Conditions	Yield
With air; palladium diacetate In methanol at 20℃;	100%
With potassium acetate; silver(l) oxide In methanol at 40℃; for 15h;	99%
With bromo-phenyl-acetic acid methyl ester; potassium fluoride; dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) In 1,4-dioxane; water at 100℃; for 24h;	95%

4-(4-bromo-2-formylphenyl)piperazine-1-carboxylic acid tert-butyl ester (628326-05-6) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 4-(3-formyl-3',5'-dimethylbiphenyl-4-yl)piperazine-1-carboxylic acid tert-butyl ester (628325-65-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane Suzuki coupling; Heating;	100%

7-chloro-2-cyclohexylmethylindan-1-one (1147270-21-0) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 7-(3',5'-dimethylphenyl)-2-cyclohexylmethylindan-1-one (1147270-27-6)

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate In water; ethylene glycol at 125℃; for 4h; Inert atmosphere;	100%

N-(2-(4-bromo-5-(4-(tert-butyl)phenyl)-3-phenylthiophen-2-yl)-2-(p-tolyl)ethyl)-4-methylbenzenesulfonamide + 3,5-dimethylphenyl boronic acid (172975-69-8) → N-(2-(5-(4-(tert-butyl)phenyl)-4-(3,5-dimethylphenyl)-3-phenylthiophen-2-yl)-2-(p-tolyl)ethyl)-4-methylbenzenesulfonamide

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium hydroxide; tri-t-butylphosphonium tetraphenylborate complex In tetrahydrofuran; water at 65℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	100%

bromobenzene (108-86-1) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 3,5-dimethylbiphenyl (17057-88-4)

Conditions	Yield
With Pd/C; potassium carbonate In water; N,N-dimethyl-formamide at 40℃; for 5h; Suzuki Coupling;	99%
With potassium carbonate In ethanol; water at 80℃; for 7h; Suzuki Coupling;	90%
With tris-(o-tolyl)phosphine; microencapsulated Pd(PPh3) In acetonitrile for 6h; Heating;	83%
With potassium phosphate tribasic trihydrate In water at 80℃; for 15h; Suzuki-Miyaura Coupling; Green chemistry;	82%

(Ra)-3,3’-dibromo-2,2’-dimethoxy-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene (78229-12-6) + 3,5-dimethylphenyl boronic acid (172975-69-8) → (R)-3,3'-bis-(3,5-dimethylphenyl)-2,2'-dimethoxy-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In tetrahydrofuran at 75℃; for 22h;	99%
Stage #1: (Ra)-3,3’-dibromo-2,2’-dimethoxy-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 0.166667h; Suzuki coupling; Stage #2: 3,5-dimethylphenyl boronic acid With sodium carbonate In ethanol at 90℃; for 18h; Further stages.;	97%

para-bromotoluene (106-38-7) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 1-(4-methylphenyl)-3,5-dimethylbenzene (7383-87-1)

Conditions	Yield
With bis-(1-methylimidazole)palladium(II) dichloride; sodium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;	99%
With sodium carbonate; 1,2-bis(2'-pyrazineethynyl)benzene palladium dichloride In water; acetonitrile at 70℃; for 6h; Suzuki coupling;	91%

3,5-dimethylphenyl boronic acid (172975-69-8) + 3-bromoaniline (591-19-5) → 3-amino-3',5'-dimethylbiphenyl (783325-73-5)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; cesium fluoride In tetrahydrofuran at 20℃; for 2h; Suzuki coupling;	99%
With cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 2h; Suzuki Coupling;	99%

indole-2,3-dione (91-56-5) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 3-(3',5'-dimethylphenyl)-3-hydroxy-1,3-dihydro-indol-2-one

Conditions	Yield
With triphenyl phosphite; [(C2H4)2Rh(acac)] In acetone for 4h; Heating;	99%

6-chloro-2-picoline (18368-63-3) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 2-(3',5'-dimethylphenyl)-6-methylpyridine

Conditions	Yield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 16h; Suzuki-Miyaura coupling;	99%

N-(5'-bromo-3'-phenylpyraz-2'-yl)pyridinium aminide (910791-84-3) + 3,5-dimethylphenyl boronic acid (172975-69-8) → N-[5-(3,5-dimethylphenyl)-3-phenylpyrazin-2-yl]pyridinium aminide (1011793-95-5)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 8h; Suzuki coupling reaction; Heating;	99%

3'-Chloroacetophenone (99-02-5) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 1-(3',5'-dimethylbiphenyl-3-yl)ethanone

Conditions	Yield
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling;	99%

iodobenzene (591-50-4) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 3,5-dimethylbiphenyl (17057-88-4)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; acetone at 35℃; for 0.5h; Inert atmosphere;	99%
With bis-(1-methylimidazole)palladium(II) dichloride; sodium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;	99%
With potassium carbonate In water at 80℃; for 1.5h; Suzuki Coupling; Green chemistry;	90%

4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole] (130755-46-3) + 3,5-dimethylphenyl boronic acid (172975-69-8) → C19H13Cl2F3N4S (1158997-64-8)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; oxygen In water; dimethyl sulfoxide at 100℃; for 36h;	99%

C19H15NO4 + 3,5-dimethylphenyl boronic acid (172975-69-8) → C27H25NO4 (1204518-49-9)

Conditions	Yield
With C52H36F8O2Rh2 In 1,4-dioxane; water at 50℃; for 12h; optical yield given as %ee; enantioselective reaction;	99%

cyclohexenone (930-68-7) + 3,5-dimethylphenyl boronic acid (172975-69-8) → (R)-3-(3,5-dimethyl-phenyl)cyclohexanone (1220531-61-2)

Conditions	Yield
With chlorobis(ethylene)rhodium(I) dimer; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine; potassium hydroxide In water; toluene at 20 - 40℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
Stage #1: 3,5-dimethylphenyl boronic acid With chlorobis(ethylene)rhodium(I) dimer; C8H16N2O4S2 In 1,4-dioxane at 50℃; for 0.25h; Inert atmosphere; Stage #2: cyclohexenone With potassium hydroxide In 1,4-dioxane; methanol at 10℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
With potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (R,Z)-1-(tert-butylsulfinyl)-2-(prop-1-enyl)benzene In methanol; water at 40℃; for 3h; Hayashi-Miyaura reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction;	99%

3-Bromopyridine (626-55-1) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 3,5-dimethyl-1-(3-pyridyl)benzene

Conditions	Yield
With bis-(1-methylimidazole)palladium(II) dichloride; sodium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;	99%
With sodium carbonate In methanol at 60℃; for 0.5h; Suzuki-Miyaura cross-coupling;	> 99 %Chromat.

para-bromoacetophenone (99-90-1) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 1-(3’,5’-dimethylbiphenyl-4-yl)ethanone (677022-27-4)

Conditions	Yield
With potassium carbonate In water at 80℃; for 10h; Suzuki-Miyaura Coupling; Green chemistry;	99%
With potassium carbonate; palladium dichloride; 3,3'-dimethyl-1,1’-(1,3-phenylenedimethylene)-bis(1H-imidazolium) dichloride In water; N,N-dimethyl-formamide for 3h; Suzuki Coupling; Reflux;	97%
With sodium acetate In water; N,N-dimethyl-formamide for 12h; Suzuki coupling; Reflux;	94%

(E)-2-fluorovinyl 4-methylbenzenesulfonate (1262431-28-6) + 3,5-dimethylphenyl boronic acid (172975-69-8) → (E)-1-(2-fluorovinyl)-3,5-dimethylbenzene (1262431-30-0)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; tricyclohexylphosphine In 1,4-dioxane at 100℃; for 14h; Suzuki-Miyaura reaction; Inert atmosphere; stereoselective reaction;	99%

1-methoxy-4-(2-nitro-vinyl)-benzene (3179-10-0) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 1-methoxy-4-(1-(3,5-dimethylphenyl)-2-nitroethyl)benzene

Conditions	Yield
With chlorobis(ethylene)rhodium(I) dimer; tert-butanesulfinylphosphine; triethylamine In ethanol at 40℃; for 10h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

9-Chloroacridine (1207-69-8) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 9-(3,5-dimethylphenyl)acridine (1352136-18-5)

Conditions	Yield
With potassium phosphate In toluene at 100℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	99%
With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene Reflux;

benzil (134-81-6) + 3,5-dimethylphenyl boronic acid (172975-69-8) → C22H20O2

Conditions	Yield
With bis(ethylene)rhodium(I) chloride dimer; C19H23NOS; potassium hydroxide In 1,4-dioxane; water at 20 - 50℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

benzoic acid anhydride (93-97-0) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 3,5-dimethylbenzophenone (13319-70-5)

Conditions	Yield
With NHC-Pd(II)-Im; sodium hydrogencarbonate In water at 20℃; for 12h; Inert atmosphere;	99%
Stage #1: benzoic acid anhydride; 3,5-dimethylphenyl boronic acid With sodium hydrogencarbonate In water at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With C19H25Br2N5Pd In water at 20℃; for 36h; Inert atmosphere;	86%

3,5-dimethylphenyl boronic acid (172975-69-8) + 1,3-diphenyl-propen-3-one (614-47-1) → (S)-3-(3, 5-dimethylphenyl)-1,3-diphenylpropan-1-one (1383843-81-9)

Conditions	Yield
With potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine In water; isopropyl alcohol at 40℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

3-butyl-1,2-benzisothiazole-1,1-dioxide (55379-09-4) + 3,5-dimethylphenyl boronic acid (172975-69-8) → (R)-3-butyl-3-(3,5-dimethylphenyl)-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide

Conditions	Yield
With palladium(II) trifluoroacetate; (S)-methyl 6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinate; oxygen In 2,2,2-trifluoroethanol at 40℃; for 12h; enantioselective reaction;	99%

methyl o-formylbenzoate (4122-56-9) + 3,5-dimethylphenyl boronic acid (172975-69-8) → (S)-3-(3,5-dimethylphenyl)-1,3-dihydro-2-benzofuran-1-one (1227504-98-4)

Conditions	Yield
With (R)-Me-BIPAM; tris(triphenylphosphine)ruthenium(II) chloride; potassium carbonate In water; toluene at 50℃; for 18h; Inert atmosphere; enantioselective reaction;	99%

2-methylbenzyl carbamate + 3,5-dimethylphenyl boronic acid (172975-69-8) → C16H18

Conditions	Yield
With NHC-Pd(II)-Im; lithium tert-butoxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;	99%

3-methylbenzyl N,N-dimethylcarbamate (16605-27-9) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 3,3',5-Trimethyl-diphenylmethan (16134-73-9)

Conditions	Yield
With NHC-Pd(II)-Im; lithium tert-butoxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;	99%

Upstream product

• 556-96-7 5-bromo-1,3-xylene 
• 87-62-7 2,6-dimethylaniline 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 67-56-1 methanol 
• 55124-35-1 diisopropylamine borane 
• 95070-94-3 (3,5-dimethylphenyl)lithium 
• 34907-38-5 tris(3.5-dimethyl phenyl)boroxine 
• 1016971-55-3 C₂₆H₃₁B₃O₉ 
• 1016971-54-2 C₂₅H₂₉B₃O₆ 
• 1016971-64-4 C₃₁H₄₁B₃O₄ 
• 1016971-63-3 C₃₈H₅₅B₃O₅ 
• 1016971-59-7 C₂₅H₂₉B₃O₄ 

Downstream Products

• 638352-48-4 2-chloro-5-(3,5-dimethylphenyl)pyridine 
• 388631-92-3 methyl (E)-3-(3,5-dimethylphenyl)prop-2-enoate 
• 852171-78-9 4-(3,5-dimethylphenyl)-2H-chromen-2-one 
• 259267-02-2 4-(3,5-dimethyl-phenyl)-5H-furan-2-one 
• 852042-25-2 1-(3,5-dimethyl-phenyl)-7-nitro-1H-indole 
• 852042-41-2 1-(3,5-dimethyl-phenyl)-2-methyl-5-nitro-1H-indole 
• 852042-10-5 1-(3,5-dimethyl-phenyl)-5-nitro-1H-indole 
• 445262-64-6 2-(3,5-dimethylphenyl)-4,5-methylenedioxy-benzaldehyde 
• 884323-17-5 4-(3',5'-dimethylphenyl)-2-chlorobenzoic acid 
• 61172-35-8 1-(1-chlorovinyl)-3,5-dimethylbenzene 
• 916235-53-5 3,5,3''',5'''-tetramethyl-[1,3';1',1'';3'',1''']quaterphenyl-2',2''-dicarboxylic acid diisopropyl ester 
• 1402852-05-4 C₃₆H₃₈O₂ 

Relevant articles and documents

Suzuki reaction of a diarylborinic acid: One-pot preparation and cross-coupling of bis(3,5-dimethylphenyl)borinic acid

3,5-Dimethylphenylmagnesium bromide reacts with triisopropyl borate to give 3,5-dimethylphenylboronic acid and bis(3,5-dimethylphenyl)borinic acid. Conditions were found which allowed the clean preparation of bis(3,5-dimethylphenyl)borinic acid, which was coupled with a vinyl triflate using Suzuki cross-coupling conditions. Both aryl groups were efficiently transferred from boron in the Suzuki step.

Meso-substituted boron-dipyrromethene compounds: synthesis, tunable solid-state emission, and application in blue-driven LEDs

In this work, we depict the synthesis and characterization of a series of meso-substituted boron-dipyrromethene (BODIPY) compounds. Their optical and electrochemical properties were investigated systematically. All these compounds exhibited intense absorption bands in the ultraviolet (UV) and visible regions, which arise from the π–π* transitions based on their BODIPY core segments. By comparing electron-withdrawing substituents and electron-donating substituents, we found that these compounds exhibited some similar photophysical properties but exhibited different fluorescence in the solid state. All compounds were highly emissive in dichloromethane at room temperature (λem = 512–523 nm, ΦPL > 0.9). When these compounds were applied in blue-driven light-emitting diodes (LEDs) as light-emitting materials, the devices showed luminescence efficiency ranging from 1.09 to 34.13 lm/W. Their luminescence and electrochemical properties could be used for understanding the structure–property relationship of BODIPY compounds and developing functional fluorescent materials.

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.