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5720-07-0

Basic Information
CAS No.: 5720-07-0
Name: 4-Methoxyphenylboronic acid
Article Data: 130
Molecular Structure:
Molecular Structure of 5720-07-0 (4-Methoxyphenylboronic acid)
Formula: C7H9BO3
Molecular Weight: 151.958
Synonyms: Benzeneboronicacid, p-methoxy- (6CI,7CI,8CI);Boronic acid, (4-methoxyphenyl)- (9CI);(4-Methoxyphenyl)boric acid;(4-Methoxyphenyl)boronic acid;(p-Methoxyphenyl)boronic acid;4-Anisylboronic acid;4-Methoxybenzeneboronicacid;[4-(Methyloxy)phenyl]boronic acid;p-Anisylboronic acid;p-Methoxybenzeneboronic acid;
EINECS: 216-845-5
Density: 1.17 g/cm3
Melting Point: 204-206 °C(lit.)
Boiling Point: 306.8 °C at 760 mmHg
Flash Point: 139.3 °C
Appearance: white to light beige crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 49.69000
LogP: -0.62500
Synthetic route
171364-79-7

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride; polystyrene boronic acid In acetonitrile at 20℃; for 18h;99%
Stage #1: 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With potassium hydrogen difluoride In methanol at 20℃; for 0.25h;
Stage #2: With lithium hydroxide In acetonitrile at 20℃; for 20h;
95%
104-92-7

1-bromo-4-methoxy-benzene

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With iodine; magnesium In tetrahydrofuran at 20 - 80℃;
Stage #2: With Trimethyl borate In tetrahydrofuran at -10 - 20℃;
97%
Stage #1: 1-bromo-4-methoxy-benzene With diisobutylaluminium hydride; magnesium; lithium chloride In tetrahydrofuran; toluene at 20℃; for 15h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
92%
Stage #1: 1-bromo-4-methoxy-benzene With magnesium In tetrahydrofuran
Stage #2: With Trimethyl borate In tetrahydrofuran for 6h; Acidic conditions;
91%
104-92-7

1-bromo-4-methoxy-benzene

121-43-7

Trimethyl borate

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With Mg In tetrahydrofuran Mg (reflux), THF, B(OCH)3, bromobenzene-compound (-10°C) or n-butyllithium, B(OCH3)3, -78°C, THF;97%
Stage #1: 1-bromo-4-methoxy-benzene With magnesium In tetrahydrofuran
Stage #2: Trimethyl borate In tetrahydrofuran; diethyl ether at -70 - 20℃;
95%
With magnesium In tetrahydrofuran; diethyl ether aryl bromide soln. dropped to Mg in THF, filtered, Grignard soln. added dropwise to soln. of calcd. amt. of B compd. in Et2O at -70°C, warming to room temp. overnight; mixt. added to ice cold and concd. aq. H2SO4, stirred for 30 min, extd. with ether (repeatedly), dried with Na2SO4, evapn., dried in vac., elem.anal.;95%
7647-01-0

hydrogenchloride

883153-46-6

Pt(OB(C6H4OMe-4)OB(C6H4OMe-4)O)(dppe)

83095-83-4, 14647-25-7

[platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)]

B

7294-51-1

2,4,6-tris(4-methoxyphenyl)boroxine

C

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran under N2 or Ar; to a THF soln. of Pt-contg. compd. (0.05 mmol) was addedHCl (0.1 mmol); stirring at room temp. for 2 h; addn. of hexane; the complex was filtered off and dried under vac.; elem. anal.;A 97%
B n/a
C n/a
13139-86-1

4-methoxyphenyl magnesium bromide

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-methoxyphenyl magnesium bromide With Trimethyl borate In tetrahydrofuran at 20℃;
Stage #2: With acidic aq. solution
96%
Stage #1: 4-methoxyphenyl magnesium bromide With Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #2: With hydrogenchloride In water
71%
Stage #1: 4-methoxyphenyl magnesium bromide With Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran Further stages.;
4.37 g
With Trimethyl borate at -78℃; for 8h;
623-12-1

4-chloromethoxybenzene

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
96%
Stage #1: 4-chloromethoxybenzene With tetrahydroxydiboron; ethanol; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[(2-(2-aminoethyl)phenyl)]palladium(II); potassium acetate; sodium t-butanolate; XPhos at 80℃; for 18h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In ethyl acetate for 0.5h; Inert atmosphere;
82%
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos In ethanol at 80℃; for 2h; Inert atmosphere;
With methanol; tetrakis(dimethylamido)diborane; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; XPhos at 20 - 60℃; for 5.0833h; Inert atmosphere; Sealed tube;

potassium 4-(methoxy)phenyltrifluoroborate

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With aluminum oxide; water at 70℃; for 0.25h; Microwave irradiation;93%
With water; silica gel at 20℃; for 1h; Inert atmosphere;83%
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 0.5h;81%
With water In tetrahydrofuran at 55℃; Kinetics; Reagent/catalyst;
104-92-7

1-bromo-4-methoxy-benzene

13675-18-8

tetrahydroxydiboron

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran; methanol at 50℃; for 1h; Catalytic behavior; Reagent/catalyst; Concentration; Time; Inert atmosphere;92%
In methanol at 15℃; for 3h; Microwave irradiation;87%
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); tetramethyl ammonium acetate In 2-methyltetrahydrofuran; methanol; water at 40℃; for 8h; Schlenk technique; Inert atmosphere;70%
104-92-7

1-bromo-4-methoxy-benzene

5419-55-6

Triisopropyl borate

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃;
91%
With magnesium; iodine; hydrochloric acid In tetrahydrofuran; diethyl ether Mg and I2 heated under Ar, diethyl ether and soln. of 4-bromoanisole added, mixt. warmed to 40°C for 30 min, soln. transferred into soln.of (iso-PrO)3B in THF at -78°C, stirred overnight, warmed to roo m temp., HCl added, stirred for 1 h; extn. (aq. NH4Cl/NaOH and EtOAc), drying (MgSO4), evapn.;20%
With n-butyllithium In tetrahydrofuran; hexane
883153-46-6

Pt(OB(C6H4OMe-4)OB(C6H4OMe-4)O)(dppe)

76-05-1

trifluoroacetic acid

69005-06-7

Pt(CF3CO2)2(dppe)

B

7294-51-1

2,4,6-tris(4-methoxyphenyl)boroxine

C

5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran under N2 or Ar; to a THF soln. of Pt-contg. compd. (0.05 mmol) was addedCF3COOH (0.1 mmol); stirring at room temp. for 2 h; addn. of hexane; the complex was filtered off and dried under vac.; elem. anal.;A 91%
B n/a
C n/a
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Specification

This chemical is called Boronicacid, B-(4-methoxyphenyl)-, and it can also be named as Benzeneboronic acid, p-methoxy-. With the molecular formula of C7H9BO3, its product categories are Boronic Acid Series; Substituted Boronic Acids; Heterocyclic Compounds; Alkoxy; Aryl; Organoborons; B (Classes of Boron Compounds). The CAS registry number of this chemical is 5720-07-0. In addition, this chemical should be sealed in the cool and dry place.

Other characteristics of the Boronicacid, B-(4-methoxyphenyl)- can be summarised as followings: (1)#H bond acceptors: 3; (2)#H bond donors: 2; (3)#Freely Rotating Bonds: 4; (4)Polar Surface Area: 27.69 Å2; (5)Index of Refraction: 1.524; (6)Molar Refractivity: 39.65 cm3; (7)Molar Volume: 129.5 cm3; (8)Polarizability: 15.71×10-24cm3; (9)Surface Tension: 42.2 dyne/cm; (10)Density: 1.17 g/cm3; (11)Flash Point: 139.3 °C; (12)Enthalpy of Vaporization: 57.79 kJ/mol; (13)Boiling Point: 306.8 °C at 760 mmHg; (14)Vapour Pressure: 0.000329 mmHg at 25°C.

Uses of this chemical: The Boronicacid, B-(4-methoxyphenyl)- could react with vinylbenzene, and obtain the 1-methoxy-4-trans-styryl-benzene. This reaction needs the reagent of Pd(OAc)2, NaOAc, and the solvent of acetic acid. The yield is 97 %. In addition, this reaction should be taken for 20 hours at the temperature of 25 °C.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: O(c1ccc(B(O)O)cc1)C
2.InChI: InChI=1/C7H9BO3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3
3.InChIKey: VOAAEKKFGLPLLU-UHFFFAOYAN

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 200mg/kg (200mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00062,