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Cas Database |
| Name |
2-Formylfuran-5-boronic acid |
EINECS | 628-001-7 |
| CAS No. | 27329-70-0 | Density | 1.36 g/cm3 |
| PSA | 70.67000 | LogP | -1.22810 |
| Solubility | Insoluble in water. | Melting Point |
136 °C (dec.)(lit.) |
| Formula | C5H5BO4 | Boiling Point | 379.3 °C at 760 mmHg |
| Molecular Weight | 139.903 | Flash Point | 183.2 °C |
| Transport Information | UN 3261 8/PG 3 | Appearance | beige to brown powder |
| Safety | 26-36/37/39-45-37/39-27 | Risk Codes | 34-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 C,  Xi
|
| Synonyms |
2-Furanboronicacid, 5-formyl- (8CI);Boronic acid, (5-formyl-2-furanyl)- (9CI);(2-Formylfuran-5-yl)boronic acid;(5-Formylfuran-2-yl)boronic acid;2-Formyl-5-furanboronic acid;2-Formylfuran-5-boric acid;5-Formyl-2-furanboronic acid;5-Formyl-2-furylboronic acid; |
Article Data | 7 |
2-Formylfuran-5-boronic acid Synthetic route
| Conditions | Yield |
|---|---|
| Stage #1: 2-(diethoxymethyl)furan With biphenyl; para-chlorotoluene; lithium In tetrahydrofuran at -65℃; for 9h; Stage #2: Trimethyl borate In tetrahydrofuran at -65℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water pH=6.3; | 81.5% |
| With n-butyllithium In tetrahydrofuran; hexane soln. of n-BuLi in hexane added dropwise to soln. of the acetal in THF at -78°C, stirred at -78°C for 5 h, dropwise addn. of trimethylborate, allowed to warm to 25°C with stirring overnight; aqueous workup, org. solvent removed under vac., aq. NaOH added to aq. phase (pH 10), washed with ether, aq. phase acidified carefully with 48% HBr (pH 4), ppt. filtered off, washed with ether; elem. anal.; | 52% |
- 1899-24-7
5-bromo-2-furancarboxaldehyde
- 5419-55-6
Triisopropyl borate
- 27329-70-0
5-formylfurane-2-boronic acid
| Conditions | Yield |
|---|---|
| Stage #1: 5-bromo-2-furancarboxaldehyde With n-butyllithium In tetrahydrofuran; hexane; toluene at -60 - -50℃; for 1.16667h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane; toluene | 78% |
- 13529-27-6
2-(diethoxymethyl)furan
- 27329-70-0
5-formylfurane-2-boronic acid
| Conditions | Yield |
|---|---|
| Stage #1: 2-(diethoxymethyl)furan With Triisopropyl borate; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -10 - 0℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; n-heptane; ethylbenzene; water at 30℃; | 75% |
| Stage #1: 2-(diethoxymethyl)furan With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 5h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 25℃; Stage #3: With sodium hydroxide pH=10; Further stages.; | 52% |
- 1708-41-4
2-(furan-2-yl)-1,3-dioxolane
- 27329-70-0
5-formylfurane-2-boronic acid
| Conditions | Yield |
|---|---|
| Stage #1: 2-(furan-2-yl)-1,3-dioxolane With biphenyl; Trimethyl borate; lithium; isoprene In tetrahydrofuran at 22 - 25℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity; | |
| Stage #1: 2-(furan-2-yl)-1,3-dioxolane With Trimethyl borate; lithium; isoprene In tetrahydrofuran at 25 - 30℃; for 4.16667h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity; | |
| Stage #1: 2-(furan-2-yl)-1,3-dioxolane With biphenyl; lithium; isoprene In tetrahydrofuran; toluene at 23 - 26℃; for 1.66667h; Stage #2: In tetrahydrofuran; water; toluene Product distribution / selectivity; Acidic conditions; | |
| Stage #1: 2-(furan-2-yl)-1,3-dioxolane With biphenyl; Triisopropyl borate; sodium In tetrahydrofuran at 5 - 25℃; for 3.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; Product distribution / selectivity; |
| Conditions | Yield |
|---|---|
| With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; |
- 27329-70-0
5-formylfurane-2-boronic acid
- 609-73-4
o-nitroiodobenzene
- 20000-96-8
5-(2-nitrophenyl)-2-furaldehyde
| Conditions | Yield |
|---|---|
| With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 50℃; for 3h; Suzuki reaction; | 100% |
| With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling; |
- 1009303-44-9
(3S)-4-[7-chloro-2-[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d] pyrimidin-4-yl] 3-methyl-morpholine
- 27329-70-0
5-formylfurane-2-boronic acid
| Conditions | Yield |
|---|---|
| With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 170℃; for 0.75h; Microwave radiation; | 100% |
- 27329-70-0
5-formylfurane-2-boronic acid
- 362527-61-5
ethyl 3-bromo-4-cyanobenzoate
| Conditions | Yield |
|---|---|
| With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 50℃; for 18h; Suzuki-Miyaura Coupling; | 100% |
- 27329-70-0
5-formylfurane-2-boronic acid
- 4068-75-1
methyl 5-iodosalicylate
- 330977-65-6
5-(5-formylfuran-2-yl)-2-hydroxybenzoic acid
| Conditions | Yield |
|---|---|
| With potassium carbonate In ethanol; water for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; Heating; | 100% |
- 27329-70-0
5-formylfurane-2-boronic acid
| Conditions | Yield |
|---|---|
| With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In tetrahydrofuran for 16h; Reflux; | 99.9% |
2-Formylfuran-5-boronic acid Specification
The IUPAC name of 2-Formylfuran-5-boronic acid is (5-formylfuran-2-yl)boronic acid. With the CAS registry number 27329-70-0, it is also named as Boronic acid, B-(5-formyl-2-furanyl)-. The product's categories are Aldehydes; Blocks; Boronic Acids; Heterocycles; Aldehyde; Furan; Organoborons; B (Classes of Boron Compounds); Boronic Acids and Derivatives; Heteroaryl. It is beige to brown powder which is sensitive to air. Additionally, this chemical should be stored at the temperature of 0-6 °C.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.09; (4)ACD/LogD (pH 7.4): -0.37; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 26.42; (8)ACD/KOC (pH 7.4): 9.11; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.51; (13)Molar Refractivity: 30.74 cm3; (14)Molar Volume: 102.6 cm3; (15)Polarizability: 12.18×10-24 cm3; (16)Surface Tension: 50.8 dyne/cm; (17)Enthalpy of Vaporization: 66.17 kJ/mol; (18)Vapour Pressure: 1.98E-06 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 140.028089; (21)MonoIsotopic Mass: 140.028089; (22)Topological Polar Surface Area: 70.7; (23)Heavy Atom Count: 10; (24)Complexity: 127.
Uses of 2-Formylfuran-5-boronic acid: It can react with iodobenzene to get 5-phenyl-furan-2-carbaldehyde. This reaction needs reagent tetrakistriphenylphosφne palladium(0), NaHCO3 and solvent ethanol, benzene, H2O by heating. The reaction time is 4.0 hours. The yield is 30%.
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When you are using this chemical, please be cautious about it as the following:
It can cause burns. And it is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
1. SMILES:O=Cc1oc(B(O)O)cc1
2. InChI:InChI=1/C5H5BO4/c7-3-4-1-2-5(10-4)6(8)9/h1-3,8-9H
3. InChIKey:JUWYQISLQJRRNT-UHFFFAOYAM
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