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| CAS No.: | 87199-17-5 |
|---|---|
| Name: | 4-Formylphenylboronic acid |
| Article Data: | 39 |
| Molecular Structure: | |
|
|
|
| Formula: | C7H7BO3 |
| Molecular Weight: | 149.942 |
| Synonyms: | Boronic acid, (4-formylphenyl)-;(4-formylphenyl)boronic acid;(4-formylphenyl) Boronic acid;4-Formylphenyl Boronic Acid;4-Formylbenzeneboronic acid;4-(dihydroxyboryl)benzaldehyde; |
| EINECS: | 438-670-5 |
| Density: | 1.244 g/cm3 |
| Melting Point: | 237-242 °C(lit.) |
| Boiling Point: | 347.584 °C at 760 mmHg |
| Flash Point: | 164.013 °C |
| Solubility: | Slightly Soluble in water. |
| Appearance: | white to light yellow crystal powder |
| Hazard Symbols: |
 C, Xi
|
| Risk Codes: | 34-36/37/38 |
| Safety: | 22-26-36/37/39-45-37/39-36 |
| Transport Information: | UN 1759 8/PG 3 |
| PSA: | 57.53000 |
| LogP: | -0.82110 |
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- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| With iron(III) chloride; water In tetrahydrofuran at 20℃; for 1h; | 97% |
| With aluminum oxide; water at 70℃; for 0.25h; Microwave irradiation; | 92% |
| With water; silica gel at 20℃; for 24h; Inert atmosphere; | 88% |
- 59016-93-2
p-hydroxymethylphenylboronic acid
- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 5h; Inert atmosphere; | 90% |
| With o-iodoxybenzoic acid In dimethylsulfoxide reaction at room temp.; one phase-switch purification used; | 90% |
- 186497-79-0
4-allylphenylboronic acid
- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| With Triethoxysilane; iron(III) chloride In methanol for 12h; Reflux; | 88% |
- 61568-51-2
2-(4-bromophenyl)-1,3-dioxane
- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| Stage #1: 2-(4-bromophenyl)-1,3-dioxane With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: With Trimethyl borate In tetrahydrofuran; pentane at -78 - 20℃; for 3h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane | 81% |
| Stage #1: 2-(4-bromophenyl)-1,3-dioxane With magnesium; ethylene dibromide In tetrahydrofuran for 0.5h; Metallation; Heating; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - -45℃; for 7.5h; Grignard reaction; Stage #3: With hydrogenchloride; water for 0.25h; Hydrolysis; Heating; | 67% |
| Stage #1: 2-(4-bromophenyl)-1,3-dioxane With magnesium; ethylene dibromide In tetrahydrofuran for 1.66667h; Stage #2: With Trimethyl borate In tetrahydrofuran for 0.666667h; Stage #3: With hydrogenchloride In water for 1h; Reflux; | 48% |
- 10602-01-4
p-bromobenzaldehyde 1,3-dioxolane
- 5419-55-6
Triisopropyl borate
- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere; Schlenk technique; | 78% |
| With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; | 71% |
| Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; for 2h; | 64% |
| With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane n-C4H9Li/hexanes added dropwise to a soln. of 2-(4-bromophenyl)-1,3-dioxolane in THF at -78°C, stirred at -78°C for 45 min, B compd. added dropwise, warmed slowly to room temp. and stirred overnight, quenched with HCl at room temp. for 2 h; extd. (EtOAc), the combined org. layers washed (brine), dried (MgSO4), flash-chromd. (silica gel, EtOAc/petroleum ether, then MeOH); elem. anal.; | 64% |
- 688-74-4
boric acid tributyl ester
- 34421-94-8
4-bromobenzaldehyde diethyl acetal
- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| With Mg; aq. H2SO4; KOH In tetrahydrofuran; diethyl ether byproducts: BuOH, Mg(OH)2, MgBr2; dropwise addn. of the grignard compd. of the acetal in THF to mixt. of B(OC4H9)3 in THF (under N2, -68°C, under stirring), stirred after thawing (1 h), evapn. of volatiles (20°C, 1 Torr), addn. of 1 M H2SO4 to soln. of the residue in ether; extn. with ether, evapn. of ether (vac.), addn. of KOH to aq. phase, after addn. of water azeotropic distn. of H2O/ BuOH in vac., residue acidified with 1 M H2SO4, refluxed (30 min), filtered, cooling of the filtrate, recrystn. from hot H2O; elem. anal.; | 78% |
| Conditions | Yield |
|---|---|
| With montmorillonite K10 at 25℃; for 24h; | 75% |
- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| In water; dimethyl sulfoxide at 219.85℃; for 120h; | 72% |
| Conditions | Yield |
|---|---|
| In dimethyl sulfoxide thermolysis of mixt. of boron compound, DMSO and water at 493 K, 5 d, cooling; filtration, evapn. in vac., washing with ethyl acetate, drying; | 72% |
- 10602-01-4
p-bromobenzaldehyde 1,3-dioxolane
- 121-43-7
Trimethyl borate
- 87199-17-5
4-formylphenylboronic acid,
| Conditions | Yield |
|---|---|
| Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; | 63% |
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Specification
The 4-Formylphenylboronic acid is an organic compound with the formula C7H7BO3. The IUPAC name of this chemical is (4-formylphenyl)boronic acid. With the CAS registry number 87199-17-5, it is also named as Boronic acid, (4-formylphenyl)-. The product's categories are Aldehyde; Aldehydes; Blocks; Boronic Acids; Boronic Acid Series; Boron, Nitrile, Thio & TM-Cpds; Carbonyl Compounds; Substituted Boronic Acids; Pharmacetical; Boronic Acids & Esters; Phenyls & Phenyl-Het; Boronic Acids; Boronic Acid; Aryl; Organoborons; B (Classes of Boron Compounds); Chiral Chemicals; Boronic Acids & Esters; Phenyls & Phenyl-Het. Besides, it is a white to light yellow crystal powder, which should be stored in a closed and dry place.
Physical properties about 4-Formylphenylboronic acid are: (1)ACD/LogP: 0.51; (2)ACD/LogD (pH 5.5): 0.506; (3)ACD/LogD (pH 7.4): 0.183; (4)ACD/BCF (pH 5.5): 1.423; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 44.622; (7)ACD/KOC (pH 7.4): 21.187; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 57.53 Å2; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 38.257 cm3; (14)Molar Volume: 120.525 cm3; (15)Polarizability: 15.166×10-24cm3; (16)Surface Tension: 49.006 dyne/cm; (17)Density: 1.244 g/cm3; (18)Flash Point: 164.013 °C; (19)Enthalpy of Vaporization: 62.462 kJ/mol; (20)Boiling Point: 347.584 °C at 760 mmHg.
Uses of 4-Formylphenylboronic acid: it can be used to produce 4-iodo-benzaldehyde at temperature of 81 °C. It will need reagent NIS and solvent acetonitrile with reaction time of 14 hours. The yield is about 94%.
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When you are using this chemical, please be cautious about it as the following:
It can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection and do not breathe dust. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: B(c1ccc(cc1)C=O)(O)O
(2)InChI: InChI=1/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
(3)InChIKey: VXWBQOJISHAKKM-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
(5)Std. InChIKey: VXWBQOJISHAKKM-UHFFFAOYSA-N