2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With hydrogenchloride; polystyrene boronic acid In acetonitrile at 20℃; for 18h; | 95% |
Conditions | Yield |
---|---|
With Mg In tetrahydrofuran Mg (reflux), THF, B(OCH)3, bromobenzene-compound (-10°C) or n-butyllithium, B(OCH3)3, -78°C, THF; | 78% |
Stage #1: 4-Bromoveratrole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; for 2h; pH=1; Inert atmosphere; | 64% |
Stage #1: 4-Bromoveratrole With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at -78℃; for 1h; | |
Stage #1: 4-Bromoveratrole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 25℃; Inert atmosphere; |
4-Bromoveratrole
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 4-Bromoveratrole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 78% |
Stage #1: 4-Bromoveratrole With tert.-butyl lithium In tetrahydrofuran at -78℃; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Further stages.; | 39% |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / tetrahydrofuran; water / -20 - 20 °C / Inert atmosphere View Scheme |
Triisopropyl borate
4-Bromoveratrole
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 4-Bromoveratrole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 74% |
3,4-dimethoxyaniline
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3,4-dimethoxyaniline With hydrogenchloride; sodium nitrite In methanol; water at 0 - 5℃; for 0.5h; Stage #2: With tetrahydroxydiboron In methanol; water at 20℃; for 1h; | 65% |
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at 22℃; | |
With hydrogenchloride In tetrahydrofuran; water at -20 - 20℃; Inert atmosphere; | 17.2 g |
1,2-dimethoxybenzene
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; silica gel / dichloromethane / 24 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / tetrahydrofuran; water / -20 - 20 °C / Inert atmosphere View Scheme |
3,4-Dimethoxyphenylboronic acid
1-[2-(4-methoxy-phenyl)-ethyl]-3,4-bis-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 20h; Suzuki cross-coupling; Heating; | 100% |
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 85℃; for 24h; Suzuki-Miyaura reaction; | 100% |
2,5-dibromothiophen
3,4-Dimethoxyphenylboronic acid
2,5-bis(3',4'-dimethoxyphenyl)thiophene
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 90℃; Inert atmosphere; | 100% |
With sodium carbonate; Pd(PPh3)4 In 1,4-dioxane |
N,N,N-trimethyl-1-phenylmethanaminium trifluoromethanesulfonate
3,4-Dimethoxyphenylboronic acid
(3,4-dimethoxyphenyl)phenylmethane
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; cyclohexyldiphenylphosphine In 1,4-dioxane at 40℃; for 24h; Reagent/catalyst; Inert atmosphere; Glovebox; | 100% |
3,4-Dimethoxyphenylboronic acid
Glyoxilic acid
Conditions | Yield |
---|---|
Stage #1: 3,4-Dimethoxyphenylboronic acid; Glyoxilic acid In dichloromethane at 20℃; Petasis Reaction; Stage #2: (S)-(+)-(1,2,3,4-tetrahydronaphth-1-ylamino)acetaldehyde dimethyl acetal In dichloromethane at 20℃; for 72h; Petasis Reaction; diastereoselective reaction; | 100% |
3,4-Dimethoxyphenylboronic acid
Glyoxilic acid
Conditions | Yield |
---|---|
Stage #1: 3,4-Dimethoxyphenylboronic acid; Glyoxilic acid In dichloromethane at 20℃; Petasis Reaction; Stage #2: (R)-(-)-(1-indanamino)acetaldehyde dimethyl acetal In dichloromethane at 20℃; for 72h; Petasis Reaction; diastereoselective reaction; | 100% |
4-bromo-5-cyano-2-carbethoxypyrrole
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 110℃; for 2h; Suzuki-Miyaura Coupling; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide; toluene for 16h; Reflux; Molecular sieve; Dean-Stark; | 100% |
In N,N-dimethyl-formamide at 120℃; Molecular sieve; Inert atmosphere; |
5-amino-2-bromobenzonitrile
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 1h; Inert atmosphere; | 100% |
Stage #1: 5-amino-2-bromobenzonitrile; 3,4-Dimethoxyphenylboronic acid With potassium carbonate In 1,2-dimethoxyethane; water for 0.0833333h; Suzuki Coupling; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane; water at 100℃; for 1h; Suzuki Coupling; | 100% |
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 12h; Suzuki Coupling; Inert atmosphere; | 100% |
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 12h; Suzuki Coupling; Inert atmosphere; | 100% |
3,4-Dimethoxyphenylboronic acid
7-iodo-2-trimethylsilanyl-imdole-1-carboxylic acid diethylamide
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 15h; Suzuki-Miyaura cross coupling; | 99% |
3,4-Dimethoxyphenylboronic acid
para-nitrophenyl bromide
4-nitro-3',4'-dimethoxy-2,2'-biphenyl
Conditions | Yield |
---|---|
With 18-crown-6 ether; 10% Pd/C; potassium carbonate In methanol; water at 45℃; for 0.5h; Suzuki-Miyaura Coupling; | 99% |
With potassium carbonate; amino-imidate palladium(II) complexes In water; N,N-dimethyl-formamide at 100℃; for 6h; Suzuki cross-coupling reaction; | 87% |
2,3-dimethyl-2,3-butane diol
3,4-Dimethoxyphenylboronic acid
2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 16h; Heating; | 99% |
iodobenzene
3,4-Dimethoxyphenylboronic acid
3,4-dimethoxy-1,1'-biphenyl
Conditions | Yield |
---|---|
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 99% |
With potassium carbonate In water at 80℃; under 760.051 Torr; for 14h; Suzuki Coupling; Green chemistry; | 98% |
With potassium carbonate In dimethyl sulfoxide at 80℃; for 6h; Suzuki-Miyaura Coupling; | 98% |
3,4-Dimethoxyphenylboronic acid
Glyoxilic acid
tert-butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate
C24H30N2O6
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide; acetonitrile at 100℃; for 0.166667h; Microwave irradiation; | 99% |
7-aminophthalazin-1(2H)-one
3,4-Dimethoxyphenylboronic acid
Glyoxilic acid
C18H17N3O5
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide; acetonitrile at 100℃; for 0.166667h; Microwave irradiation; | 99% |
In water; N,N-dimethyl-formamide; acetonitrile Microwave irradiation; Heating; |
benzyl bromide
3,4-Dimethoxyphenylboronic acid
(3,4-dimethoxyphenyl)phenylmethane
Conditions | Yield |
---|---|
With [(1,7-bis{(pyridin-2′-yl)hydroxymethyl}-1,7-dicarba-closo-dodecaborane(-1H))PdCl]*DMF; potassium carbonate In water at 110℃; for 10h; Reagent/catalyst; Suzuki Coupling; | 99% |
With [2-(1H-pyrazolyl-κN2)-6-((diphenylphosphino)amine-κP)phenyl-κCl]palladium(II) chloride; sodium carbonate In water at 100℃; for 3h; Suzuki coupling; | 81% |
With caesium carbonate In water at 110℃; for 18h; Suzuki-Miyaura Coupling; | 41% |
With potassium phosphate; Br(1-)*C21H21BrN5O6(1+) In water at 100℃; for 3h; Suzuki-Miyaura coupling; | 65 %Spectr. |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane for 48h; Suzuki coupling; Inert atmosphere; Reflux; Darkness; | 99% |
4,4‘-(2,5-dibromo-1,4-phenylene)bis(2-methylbut-3-yn-2-ol)
3,4-Dimethoxyphenylboronic acid
C32H34O6
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Suzuki coupling; Inert atmosphere; Reflux; Darkness; | 99% |
trifluoromethanesulfonic acid 6-methoxy-2-oxo-2H-chromen-4-yl ester
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; toluene Suzuki coupling; Reflux; | 99% |
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water for 14h; Suzuki Coupling; Inert atmosphere; Reflux; | 61% |
dimethyl N-benzyl-3,4-bis(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate
3,4-Dimethoxyphenylboronic acid
dimethyl N-benzyl-3,4-bis(3,4-dimethoxyphenyl)pyrrole-2,5-dicarboxylate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 20℃; Suzuki-Miyaura coupling; Reflux; Inert atmosphere; | 99% |
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane; water at 80℃; for 18h; Inert atmosphere; |
3-O-(4-bromobenzyl)-4,5-di-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol
3,4-Dimethoxyphenylboronic acid
4,5-di-O-benzyl-3-O-(4-(3,4-dimethoxyphenyl)benzyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol
Conditions | Yield |
---|---|
With potassium phosphate; tetrabutylammomium bromide; palladium diacetate In ethanol at 20℃; for 3h; Suzuki-Miyaura coupling; Inert atmosphere; | 99% |
4-bromo-benzaldehyde
3,4-Dimethoxyphenylboronic acid
3',4'-dimethoxy-[1,1'-biphenyl]-4-carbaldehyde
Conditions | Yield |
---|---|
With 18-crown-6 ether; 10% Pd/C; potassium carbonate In methanol; water at 45℃; for 0.5h; Suzuki-Miyaura Coupling; | 99% |
With C14H8F6O4; nickel trifluoroacetate; potassium carbonate; triphenylphosphine; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In water at 80℃; for 18h; Suzuki-Miyaura Coupling; Green chemistry; | 90.2% |
1-bromo-4-methoxy-benzene
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 99% |
With 18-crown-6 ether; 10% Pd/C; potassium carbonate In methanol; water at 45℃; for 1h; Suzuki-Miyaura Coupling; | 98% |
With C14H8F6O4; nickel trifluoroacetate; potassium carbonate; triphenylphosphine; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In water at 80℃; for 18h; Suzuki-Miyaura Coupling; Green chemistry; | 85% |
3,4-Dimethoxyphenylboronic acid
methyl 2-isocyano-3,3-diphenyl acrylate
Conditions | Yield |
---|---|
With oxygen; manganese(II) acetylacetonate dihydrate In toluene at 80℃; for 2h; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With N-iodo-succinimide; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,1,2,2,2-hexamethyldisilane; oxygen; copper diacetate; diisopropylamine at 20 - 150℃; Schlenk technique; | 99% |
6,8-dibromo-2-phenyl-4H-chromen-4-one
3,4-Dimethoxyphenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 15h; Suzuki-Miyaura Coupling; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 80℃; Suzuki-Miyaura Coupling; Inert atmosphere; | 99% |
Systematic Name: (3,4-Dimethoxyphenyl)boronic acid
Synonyms of 3,4-Dimethoxyphenylboronic acid (CAS NO.122775-35-3): 3,4-Dimethoxyphenylboronic acid,97%
CAS NO: 122775-35-3
Molecular Formula: C8H11BO4
Molecular Weight: 181.98
Molecular Structure:
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 5
Polar Surface Area: 36.92 Å2
Index of Refraction: 1.517
Molar Refractivity: 46.01 cm3
Molar Volume: 151.8 cm3
Surface Tension: 43 dyne/cm
Density: 1.19 g/cm3
Flash Point: 157.4 °C
Enthalpy of Vaporization: 61.21 kJ/mol
Boiling Point: 336.7 °C at 760 mmHg
Vapour Pressure: 4.31E-05 mmHg at 25°C
Melting Point: 245-250 °C(lit.)
Storage temp: Keep Cold
Water Solubility: 25 g/L
Appearance: white to light beige powder and granules
Product Categories of of 3,4-Dimethoxyphenylboronic acid (CAS NO.122775-35-3): blocks;BoronicAcids;Boronic Acid series;Substituted Boronic Acids;Boronic Acid;Alkoxy;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives
SMILES: O(c1ccc(cc1OC)B(O)O)C
InChI: InChI=1/C8H11BO4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5,10-11H,1-2H3
InChIKey: RCVDPBFUMYUKPB-UHFFFAOYAB
Std. InChI: InChI=1S/C8H11BO4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5,10-11H,1-2H3
Std. InChIKey: RCVDPBFUMYUKPB-UHFFFAOYSA-N
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant/Keep Cold
HazardClass: IRRITANT
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store 3,4-Dimethoxyphenylboronic acid (CAS NO.122775-35-3) in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4°C/39°F.)
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