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182163-96-8

Basic Information
CAS No.: 182163-96-8
Name: 3,4,5-Trimethoxyphenylboronic acid
Article Data: 11
Molecular Structure:
Molecular Structure of 182163-96-8 (3,4,5-Trimethoxyphenylboronic acid)
Formula: C9H13BO5
Molecular Weight: 212.01
Synonyms: Boronicacid, (3,4,5-trimethoxyphenyl)- (9CI);Boronicacid, B-(3,4,5-trimethoxyphenyl)-;
Density: 1.21 g/cm3
Melting Point: >230 °C(lit.)
Boiling Point: 370.6 °C at 760 mmHg
Flash Point: 177.9 °C
Appearance: beige crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 36/37/38-22-20/21/22
Safety: 37/39-26-36
PSA: 68.15000
LogP: -0.60780
Synthetic route
2675-79-8

1-bromo-3,4,5-trimethoxybenzene

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
Stage #1: 1-bromo-3,4,5-trimethoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
95%
Stage #1: 1-bromo-3,4,5-trimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -85℃; for 1h;
Stage #2: With Trimethyl borate In tetrahydrofuran at 20℃; for 18h; Further stages.;
64%
Stage #1: 1-bromo-3,4,5-trimethoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: With Trimethyl borate In tetrahydrofuran at -78℃; for 0.5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
121-43-7

Trimethyl borate

2675-79-8

1-bromo-3,4,5-trimethoxybenzene

182163-96-8

3,4,5-trimethoxyphenylboronic 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;95%
25245-29-8

5-iodo-1,2,3-trimethoxybenzene

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
Stage #1: 5-iodo-1,2,3-trimethoxybenzene With tert.-butyl lithium In tetrahydrofuran at -78℃;
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Further stages.;
69%
133095-91-7

3,4,5-trimethoxyphenylmagnesium bromide

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
Stage #1: 3,4,5-trimethoxyphenylmagnesium bromide With Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #2: With hydrogenchloride In water
65%
25245-29-8

5-iodo-1,2,3-trimethoxybenzene

121-43-7

Trimethyl borate

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
Stage #1: 5-iodo-1,2,3-trimethoxybenzene With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: Trimethyl borate In tetrahydrofuran at -78℃; for 1h;
Stage #1: 5-iodo-1,2,3-trimethoxybenzene In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #3: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 14h; Inert atmosphere;
24313-88-0

3,4,5-Trimethoxyaniline

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaNO2; concd. H2SO4 / H2O / 5 - 10 °C
1.2: 70 percent / aq. CuBr / 0.5 h / Heating
2.1: nBuLi / tetrahydrofuran; hexane / 1 h / -85 °C
2.2: 64 percent / trimethylborate / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium nitrite; potassium iodide / water; sulfuric acid / 5 h / 50 °C / Inert atmosphere
2.1: tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
2.3: 14 h / 20 °C / Inert atmosphere
View Scheme
1016971-56-4

C27H33B3O12

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
With water at 25℃; Equilibrium constant;
1016971-65-5

C27H33B3O8

A

301699-39-8

(4-methoxy-3,5-dimethylphenyl)boronic acid

B

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
With water at 25℃; Equilibrium constant;
1016971-67-7

C27H33B3O10

A

301699-39-8

(4-methoxy-3,5-dimethylphenyl)boronic acid

B

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

Conditions
ConditionsYield
With water at 25℃; Equilibrium constant;
1016971-69-9

C39H57B3O8

A

182163-96-8

3,4,5-trimethoxyphenylboronic Acid

B

233584-42-4

4-methoxy-3,5-di-tert-butylphenylboronic acid pinacol ester

Conditions
ConditionsYield
With water at 25℃; Equilibrium constant;
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Chemistry

Molecular structure of 3,4,5-Trimethoxyphenylboronic acid (CAS NO.182163-96-8):

IUPAC Name: (3,4,5-Trimethoxyphenyl)boronic acid
Molecular Formula: C9H13BO5
Molecular Weight: 212.01 g/mol
Density: 1.21 g/cm3
Melting Point: >230 °C(lit.)
Boiling Point: 370.6 °C at 760 mmHg 
Flash Point: 177.9 °C
Index of Refraction: 1.513 
Molar Refractivity: 52.38 cm3 
Molar Volume: 174 cm3 
Surface Tension: 43.6 dyne/cm 
Enthalpy of Vaporization: 65.15 kJ/mol 
Vapour Pressure: 3.79E-06 mmHg at 25 °C 
Storage temp.: refrigerator (+4 °C)
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Exact Mass: 212.085604
MonoIsotopic Mass: 212.085604
Topological Polar Surface Area: 68.2
Heavy Atom Count: 15 
Canonical SMILES: B(C1=CC(=C(C(=C1)OC)OC)OC)(O)O
InChI: InChI=1S/C9H13BO5/c1-13-7-4-6(10(11)12)5-8(14-2)9(7)15-3/h4-5,11-12H,1-3H3
InChIKey: RULQUTYJXDLRFL-UHFFFAOYSA-N
Product Categories: Substituted Boronic Acids; Alkoxy; Aryl; Organoborons; Boronic acid; Boronic acid series; Boronic Acids; Boronic Acids and Derivatives; Boronic Acids

Uses

 3,4,5-Trimethoxyphenylboronic acid (CAS NO.182163-96-8) is commonly used as fine chemical material and pharmaceutical intermediate.

Safety Profile

Hazard Codes: HarmfulXn, IrritantXi
Risk Statements: 36/37/38-22-20/21/22 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R22:Harmful if swallowed. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 37/39-26-36 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant

Specification

 3,4,5-Trimethoxyphenylboronic acid (CAS NO.182163-96-8) is also named as Boronicacid, B-(3,4,5-trimethoxyphenyl)- ; Boronicacid, (3,4,5-trimethoxyphenyl)- (9CI) ; 3,4,5-Trimethoxybenzeneboronic acid . 3,4,5-Trimethoxyphenylboronic acid (CAS NO.182163-96-8) is beige crystalline powder.