2-Formylfuran-5-boronic acid supplier

Name
2-Formylfuran-5-boronic acid
EINECS 628-001-7
CAS No. 27329-70-0
Article Data7
CAS DataBase
Density 1.36 g/cm³
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;
PSA 70.67000
LogP -1.22810

Synthetic route

: 13529-27-6
2-(diethoxymethyl)furan

: 121-43-7
Trimethyl borate

: 27329-70-0
5-formylfurane-2-boronic acid

Conditions

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%

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

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

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

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;

: 5419-55-6
Triisopropyl borate

: C10H12O4Zn

: 27329-70-0
5-formylfurane-2-boronic acid

Conditions

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

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

: C22H25N5O4

Conditions

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

: ethyl 4-cyano-3-(5-formyl-2-furyl)benzoate

Conditions

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

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

: N-(4-([1,2,4]triazolo[4,3-c]pyrimidin-7-yloxy)-3-methylphenyl)-6-iodoquinazolin-4-amine

: 5-(4-((4-([1,2,4]triazolo[4,3-c]pyrimidin-7-yloxy)-3-methylphenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In tetrahydrofuran for 16h; Reflux;	99.9%

: 27329-70-0
5-formylfurane-2-boronic acid

: 696-62-8
para-iodoanisole

: 34070-33-2
5-(4-methoxyphenyl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 50℃; for 1h; Suzuki reaction;	99%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h; Suzuki Coupling;

: 626-55-1
3-Bromopyridine

: 27329-70-0
5-formylfurane-2-boronic acid

: 38588-49-7
5-(pyridin-3-yl)-furan-2-carbaldehyde

Conditions

Conditions	Yield
With PdCl2-[5-(1,1'-biphenyl-4-yl)isoxazole-3-carbaldehyde oxime]; potassium carbonate In methanol; water at 100℃; for 0.0833333h; Suzuki Coupling;	99%
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In chloroform; water at 80 - 100℃; for 0.166667h;	98%
With tetrabutylammomium bromide; potassium carbonate In methanol; water at 80℃; for 0.333333h; Suzuki Coupling; Reflux;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Suzuki cross-coupling; Heating;

: 27329-70-0
5-formylfurane-2-boronic acid

: 18179-39-0
methyl 4-iodosalicylate

: 1277116-14-9
methyl 4-(5-formylfuran-2-yl)-2-hydroxybenzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; Suzuki coupling; Inert atmosphere;	99%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling; Inert atmosphere;	96%
Stage #1: 5-formylfurane-2-boronic acid; methyl 4-iodosalicylate In ethanol; N,N-dimethyl-formamide for 0.166667h; Suzuki Coupling; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling; Inert atmosphere;	96%
Stage #1: 5-formylfurane-2-boronic acid; methyl 4-iodosalicylate In ethanol; N,N-dimethyl-formamide for 0.166667h; Suzuki Coupling; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	96%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	64%

: 27329-70-0
5-formylfurane-2-boronic acid

: 1393112-43-0
N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-iodoquinazoline-4-amine hydrochloride

: 1393112-44-1
5-[4-({3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}amino)quinazoline-6-yl]furan-2-carbaldehyde

Conditions

Conditions	Yield
With potassium carbonate; palladium diacetate In tetrahydrofuran; ethanol at 75℃; for 1h; Inert atmosphere;	98.8%
With palladium diacetate; potassium carbonate In tetrahydrofuran; ethanol at 75℃; for 1h; Inert atmosphere;	98.8%

: 27329-70-0
5-formylfurane-2-boronic acid

: 231278-20-9
N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

: 231278-84-5
5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With potassium carbonate; palladium diacetate In tetrahydrofuran; ethanol for 0.666667h; Product distribution / selectivity; Reflux;	98.7%
With palladium; triethylamine In tetrahydrofuran; ethanol at 65℃; for 7h; Temperature; Concentration; Inert atmosphere;	97.7%
With triethylamine; palladium 10% on activated carbon In methanol; 1,2-dimethoxyethane at 45 - 50℃; for 15h; Suzuki Coupling; Inert atmosphere;	96%

: 27329-70-0
5-formylfurane-2-boronic acid

: 132131-24-9
5-iodoanthranilonitrile

: 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile

Conditions

Conditions	Yield
With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane at 20 - 45℃; for 3h; Suzuki Coupling;	98.6%

: 537705-05-8
6-iodo-N-(3-methyl-4-((6-methylpyridin-3-yl)oxy)phenyl)quinazolin-4-amine

: 27329-70-0
5-formylfurane-2-boronic acid

: 1260402-39-8
5-(4-(4-(6-methylpyridin-3-yloxy)-3-methylphenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; ethanol at 75℃; for 4h; Inert atmosphere;	98%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In methanol for 12h; Suzuki Coupling; Reflux;

: 27329-70-0
5-formylfurane-2-boronic acid

: 51934-41-9
4-iodobenzoic acid ethyl ester

: 19247-87-1
5-(4-ethoxycarbonylphenyl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Suzuki-Miyaura Coupling; Sealed tube; Green chemistry;	98%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h;	73.8%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h; Suzuki Coupling;

: 27329-70-0
5-formylfurane-2-boronic acid

: 1121-86-4
1-Fluoro-3-iodobenzene

: 33342-18-6
5-(3'-fluorophenyl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 65℃; for 1h; Suzuki Coupling;	98%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling;

: 16064-08-7
6-iodoquinazolin-4(3H)-one

: 27329-70-0
5-formylfurane-2-boronic acid

: 1334953-71-7
5-(4-oxo-3,4-dihydroquinazolin-6-yl)furan-2-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 5-formylfurane-2-boronic acid With palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate In water; dimethyl sulfoxide at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 6-iodoquinazolin-4(3H)-one With potassium acetate In water; dimethyl sulfoxide at 75 - 85℃; for 0.333333h; Inert atmosphere;	97.6%
With tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate In water; dimethyl sulfoxide at 20 - 80℃; Product distribution / selectivity; Inert atmosphere;	97.6 %Chromat.

: 27329-70-0
5-formylfurane-2-boronic acid

: 360-01-0
1-iodo-4-((trifluoromethyl)sulfonyl)benzene

: 5-[4-(trifluoromethanesulfonyl)phenyl]-2-furaldehyde

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 50℃; for 1h; Suzuki reaction;	97%

: 25245-29-8
5-iodo-1,2,3-trimethoxybenzene

: 27329-70-0
5-formylfurane-2-boronic acid

: 62427-26-3
5-(3,4,5-trimethoxyphenyl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 65℃; for 1h; Suzuki Coupling;	97%

: 27329-70-0
5-formylfurane-2-boronic acid

: 108-90-7
chlorobenzene

: 13803-39-9
5-phenylfuran-2-carbaldehyde

Conditions

Conditions	Yield
With potassium phosphate; C75H58Cl2N4Pd In water; isopropyl alcohol at 25℃; for 24h; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique;	97%

: 27329-70-0
5-formylfurane-2-boronic acid

: 4-bromo-7-(11-butyl-11H-benzo[a]carbazol-5-yl)benzo[c][1,2,5]- thiadiazole

: 5-(7-(11-butyl-11H-benzo[a]carbazol-5-yl)benzo[c][1,2,5]- thiadiazol-4-yl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Suzuki Coupling; Reflux;	97%

: 27329-70-0
5-formylfurane-2-boronic acid

: 455-13-0
4-Iodobenzotrifluoride

: 55377-77-0
5-(4-(trifluoromethyl)phenyl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile	96.15%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h; Suzuki Coupling;

: 27329-70-0
5-formylfurane-2-boronic acid

: 585-76-2
m-bromobenzoic acid

: 304884-54-6
5-(3-carboxyphenyl)furane-2-carbaldehyde

Conditions

Conditions	Yield
With C11H8Cl4N2O3Pd; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki Coupling;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Suzuki cross-coupling; Heating;
With 2-[5-(4-methylphenyl)isoxazol-3-yl]-5-(5-phenylisoxazol-3-yl)-1,3,4-oxadiazole·2PdCl2; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 20℃; for 0.416667h; Suzuki Coupling;	0.21 g

: 27329-70-0
5-formylfurane-2-boronic acid

: 104-15-4
toluene-4-sulfonic acid

: 132131-24-9
5-iodoanthranilonitrile

: 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile p-toluenesulfonic acid

Conditions

Conditions	Yield
Stage #1: 5-formylfurane-2-boronic acid; 5-iodoanthranilonitrile With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane at 20 - 45℃; for 3h; Stage #2: toluene-4-sulfonic acid In water at 60℃;	96%

...Expand

: 27329-70-0
5-formylfurane-2-boronic acid

: 1352543-77-1
2-bromo-9-[4-(diphenylamino)phenyl]-5,12-dioctylquinolino[2,3-b]acridine-7,14-dione

: 1352543-79-3
5-{9-[4-(diphenylamino)phenyl]-5,12-dioctyl-7,14-dioxo-5,7,12,14-tetrahydroquinolino[2,3-b]acridin-2-yl}furan-2-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 2-bromo-9-[4-(diphenylamino)phenyl]-5,12-dioctylquinolino[2,3-b]acridine-7,14-dione With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In tetrahydrofuran for 0.5h; Suzuki Coupling; Reflux; Stage #2: 5-formylfurane-2-boronic acid In tetrahydrofuran for 12h; Suzuki Coupling; Reflux;	95.4%

: 637-87-6
1-Chloro-4-iodobenzene

: 27329-70-0
5-formylfurane-2-boronic acid

: 34035-03-5
5-(4-chlorophenyl)-2-furaldehyde

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 65℃; for 1h; Suzuki Coupling;	95%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling;

: 27329-70-0
5-formylfurane-2-boronic acid

: methyl 5-bromo-4-methoxy-2-methylbenzoate

: methyl 5-(5-formyl-2-furyl)-4-methoxy-2-methylbenzoate

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 50℃; for 18h; Suzuki-Miyaura Coupling;	95%

: 851684-46-3
N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-iodoquinazolin-4-amine hydrochloride

: 27329-70-0
5-formylfurane-2-boronic acid

: 231278-84-5
5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol for 2h; Heating / reflux;	94%

: 109-09-1
2-chloropyridine

: 27329-70-0
5-formylfurane-2-boronic acid

: 55484-36-1
5-(pyridin-2-yl)furan-2-carboxaldehyde

Conditions

Conditions	Yield
With potassium carbonate; sodium tetrachloropalladate(II) In water; butan-1-ol at 100℃; for 12h; Suzuki cross-coupling;	94%

: 27329-70-0
5-formylfurane-2-boronic acid

: 1351125-09-1
C20H15FINO3

: 1351125-22-8
C25H18FNO5

Conditions

Conditions	Yield
With palladium diacetate; potassium hydroxide In water; acetone at 35℃; Suzuki coupling;	94%

: 626-60-8
3-Chloropyridine

: 27329-70-0
5-formylfurane-2-boronic acid

: 38588-49-7
5-(pyridin-3-yl)-furan-2-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 3-Chloropyridine; 5-formylfurane-2-boronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;	94%

Yield

Stage #1: 3-Chloropyridine; 5-formylfurane-2-boronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;
Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;

94%

: 96-43-5
2-thienyl chloride

: 27329-70-0
5-formylfurane-2-boronic acid

: 32364-30-0
5-(thiophen-2-yl)furan-2-carboxaldehyde

Conditions

Conditions	Yield
Stage #1: 2-thienyl chloride; 5-formylfurane-2-boronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 1h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;	94%

Yield

Stage #1: 2-thienyl chloride; 5-formylfurane-2-boronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 1h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;
Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;

94%

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%.

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

Product Name

2-Formylfuran-5-boronic acid

Synthetic route

2-Formylfuran-5-boronic acid Specification

Related Products

Hot Products