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Name	3,5-Dimethylphenylboronic acid	EINECS	605-655-1
CAS No.	172975-69-8	Density	1.07 g/cm³
PSA	40.46000	LogP	-0.01680
Solubility	Slightly soluble in water	Melting Point	261-265 °C(lit.)
Formula	C₈H₁₁BO₂	Boiling Point	312.7 °C at 760 mmHg
Molecular Weight	149.985	Flash Point	142.9 °C
Transport Information	N/A	Appearance	off-white to light yellow crystalline powder
Safety	37/39-26-36/37	Risk Codes	22-36/37/38
Molecular Structure		Hazard Symbols	Xn
Synonyms	Boronic acid, (3,5-dimethylphenyl)- (9CI);(3,5-Dimethylphenyl)boronic acid;(3,5-Dimethylphenyl)dihydroxyborane;3,5-Dimethylbenzeneboronicacid;	Article Data	20

3,5-Dimethylphenylboronic acid Synthetic route

: 67-56-1
methanol

: 55124-35-1
diisopropylamine borane

: 556-96-7
5-bromo-1,3-xylene

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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%

: 121-43-7
Trimethyl borate

: 556-96-7
5-bromo-1,3-xylene

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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%

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%

: 121-43-7
Trimethyl borate

: 7732-18-5
water

: 34696-73-6
3,5-dimethyphenylmagnesium bromide

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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

: 121-43-7
Trimethyl borate

: 556-96-7
5-bromo-1,3-xylene

: 7732-18-5
water

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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%

: 556-96-7
5-bromo-1,3-xylene

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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

: 325142-93-6
2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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;

: 108-38-3
m-xylene

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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

: 5419-55-6
Triisopropyl borate

: 556-96-7
5-bromo-1,3-xylene

: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

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;

: 1016971-57-5
C26H31B3O5

A: 301699-39-8
(4-methoxy-3,5-dimethylphenyl)boronic acid

B: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

Conditions	Yield
With water at 25℃; Equilibrium constant;

: 1016971-59-7
C25H29B3O4

A: 301699-39-8
(4-methoxy-3,5-dimethylphenyl)boronic acid

B: 172975-69-8
3,5-dimethylphenyl boronic acid

Conditions

Conditions	Yield
With water at 25℃; Equilibrium constant;

3,5-Dimethylphenylboronic acid Chemical Properties

MF: C₈H₁₁BO₂
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%
MW: 149.98
mp: 261-265 °C(lit.)
storage temp.: 0-6°C
BRN : 7368658

3,5-Dimethylphenylboronic acid Safety Profile

Risk Statements : R36/37/38:Irritating to eyes, respiratory system and skin.;
Safety Statements : S26:In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice.;
S37/39:Wear suitable gloves and eye/face protection.;
Hazard Codes : Xn,Xi
WGK Germany : 3
Hazard Note : Irritant

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