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Chemical Structure| 1899-24-7 Chemical Structure| 1899-24-7

Structure of 5-Bromo-2-furaldehyde
CAS No.: 1899-24-7

Chemical Structure| 1899-24-7

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Product Details of [ 1899-24-7 ]

CAS No. :1899-24-7
Formula : C5H3BrO2
M.W : 174.98
SMILES Code : O=CC1=CC=C(Br)O1
MDL No. :MFCD00159501
InChI Key :WJTFHWXMITZNHS-UHFFFAOYSA-N
Pubchem ID :600328

Safety of [ 1899-24-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 1899-24-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 31.8
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

30.21 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.26
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.81
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.85
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.27
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.13
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.46

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.46
Solubility 0.604 mg/ml ; 0.00345 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.06
Solubility 1.51 mg/ml ; 0.00863 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.41
Solubility 0.684 mg/ml ; 0.00391 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.08 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.01

Application In Synthesis of [ 1899-24-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1899-24-7 ]

[ 1899-24-7 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 186581-53-3 ]
  • [ 1899-24-7 ]
  • [ 3199-50-6 ]
  • 2
  • [ 1899-24-7 ]
  • [ 64-17-5 ]
  • [ 111252-31-4 ]
  • 4
  • [ 1899-24-7 ]
  • [ 13922-41-3 ]
  • [ 51792-36-0 ]
YieldReaction ConditionsOperation in experiment
95% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; at 70.0℃;Inert atmosphere; Sealed tube; General procedure: A bromo-aldehyde (1 mmol), boronic acid (1.1e1.3 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate(3 mmol), water (3 ml), ethanol (4 ml) and toluene (4 ml)were added to a round-bottomed flask. The reaction mixture wasflushed with argon, sealed under septa and heated at 70 C overnight.After cooling to room temperature, water (50 ml) was added,and product was extracted with ethyl acetate (3 x 50 ml). Combinedextracts were washed with brine, dried with anhydrousmagnesium sulfate and evaporated under reduced pressure. Theproduct was purified by column chromatography on silica withchloroform or a mixture of methanol and chloroform (1:9).
  • 5
  • [ 1899-24-7 ]
  • [ 145349-76-4 ]
  • [ 765937-68-6 ]
  • 6
  • [ 1899-24-7 ]
  • [ 42348-88-9 ]
  • [ 50-01-1 ]
  • 4-(5-bromo-furan-2-yl)-8-ethyl-5<i>H</i>-indeno[1,2-<i>d</i>]pyrimidin-2-ylamine [ No CAS ]
  • 7
  • [ 1899-24-7 ]
  • [ 118486-94-5 ]
  • [ 16303-60-9 ]
  • 8
  • [ 1899-24-7 ]
  • [ 163520-14-7 ]
  • [ 956316-48-6 ]
  • 9
  • [ 1455-20-5 ]
  • [ 1899-24-7 ]
  • [ 1062176-84-4 ]
  • 10
  • [ 1899-24-7 ]
  • [ 17626-75-4 ]
  • [ 1109226-45-0 ]
  • 11
  • [ 1899-24-7 ]
  • [ 133730-34-4 ]
  • [ 1001010-63-4 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃; for 72h;Reflux; General procedure for the Suzuki coupling. Method A To a solution of the halogen-substituted heteroaryl aldehyde (2.7 mmol) of formula (IV) and the corresponding boronic acid (3.2 mmol) of formula R2-B(OH)2 (R2 being as defined above) in THF (20.0 mL) a solution of sodium bicarbonate (8.0 mmol) in water (9.0 mL) was added. The reaction mixture was stirred at room temperature for 5 minutes, and a solution of Pd(PPh3)4 (0.2 mmol) in THF (5.0 mL) was added. The reaction mixture was refluxed at 80 C for three days, cooled to room temperature and diluted with ethyl acetate (150.0 mL) and water (50.0 mL). The aqueous layer was extracted with ethyl acetate (2 × 25.0 mL), and the combined organic layers were washed with brine, dried with anhydrous sulfate, filtered and concentrated under vacuum to afford the corresponding aldehyde of formula (II). Example 1. Synthesis of 5-(2,4-dimethoxy-phenyl)-furan-2-carbaldehyde [Show Image] Synthesized using method A. The compound did not need any further purification. 630.0 mg; 100% yield. MS (ES): M/z= 233 (M+H)+ 1H NMR (400 MHz, CDCl3, δ ppm): 9.59 (s, 1 H), 7.98 (d, J = 8.7 Hz, 1 H), 7.31 (d, J = 3.7 Hz, 1 H), 7.00 (d, J = 3.7 Hz, 1 H), 6.60 (dd, J = 8.7, 2.3 Hz, 1 H), 6.53 (d, J = 2.3 Hz, 1 H), 3.94 (s, 3H), 3.87 (s, 3H).
100% General procedure for the Suzuki coupling. Method A To a solution of the halogen-substituted heteroaryl aldehyde (2.7 mmol) of formula (IV) and the corresponding boronic acid (3.2 mmol) of formula R2-B(OH)2 (R2 being as defined above) in THF (20.0 ml.) a solution of sodium bicarbonate (8.0 mmol) in water (9.0 ml.) was added. The reaction mixture was stirred at room temperature for 5 minutes, and a solution of Pd(PPh3)4 (0.2 mmol) in THF (5.0 ml.) was added. The reaction mixture was refluxed at 80 C for three days, cooled to room temperature and diluted with ethyl acetate (150.0 ml.) and water (50.0 ml_). The aqueous layer was extracted with ethyl acetate (2 x 25.0 ml_), and the combined organic layers were washed with brine, dried with anhydrous sulfate, filtered and concentrated under vacuum to afford the corresponding aldehyde of formula (II).xample 1. Synthesis of 5-(2,4-dimethoxy-phenyl)-furan-2-carbaldehydeSynthesized using method A. The compound did not need any further purification. 630.0 mg; 100% yield.MS (ES): UIz= 233 (M+H)+1H NMR (400 MHz, CDCI3, d ppm): 9.59 (s, 1 H), 7.98 (d, J = 8.7 Hz, 1 H), 7.31 (d, J = 3.7 Hz, 1 H), 7.00 (d, J = 3.7 Hz, 1 H), 6.60 (dd, J = 8.7, 2.3 Hz, 1 H), 6.53 (d, J = 2.3 Hz, 1 H), 3.94 (s, 3H), 3.87 (s, 3H).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 90℃; General procedure: To a solution of substituted phenylboronic acid (3.87 mmol) in toluene/ethanol (50/50, 40 mL), 5-bromofuran-2-alsehyde (600 mg, 3.43 mmol), potassium carbonate (947.96 mg, 6.86 mmol) aq. solution (10.3 mL water), and tetrakis(triphenyphosphine)palladium(0) (35.78 mg, 0.03 mmol) were added slowly, after which the reaction mixture was stirred at 90 C. The mixture was acidified by 6 N hydrogen chloride solution, and extracted with dichloromethane. The organic layer was washed with brine, dried (MgSO4) and, filtered. The solvent was concentrated under reduced pressure to yield compound 10, 5(4-carboxaminophenyl)furan-2-aldehyde. Yield 60%; 1H NMR (300 MHz, DMSO-d6) δ: 9.65 (s, 1H), 8.11 (s, 1H), 8.02-7.94 (m, 4H), 7.69 (d, J = 3.7 Hz, 1H), 7.50 (s, 1H), 7.42 (d, J = 3.7 Hz, 1H).
  • 12
  • [ 1899-24-7 ]
  • [ 141-82-2 ]
  • [ 111252-31-4 ]
YieldReaction ConditionsOperation in experiment
60% With piperidine; In pyridine; for 3.0h;Inert atmosphere; Reflux; General Procedure: Piperidine was added to a solution of the appropriate aldehyde (4.97 mmol), malonic acid (5.96 mmol) and pyridine (10.94 mmol) under nitrogen atmosphere. The reaction mixture was heated to reflux under vigorous stirring for 3 hours, after which according to TLC the reaction was completed. The reaction mixture was allowed to cool and EtOAc (20 mL) was added, acidified to pH 5 with 1 M HCl, and the organic layer was sequentially washed with water, dried over MgSO4 and concentrated in vacuo. The pure desired product was obtained after purification by column chromatography.
  • 13
  • [ 1899-24-7 ]
  • [ 57497-39-9 ]
  • [ 1352327-49-1 ]
  • 14
  • [ 1899-24-7 ]
  • [ 13331-23-2 ]
  • [ 16303-60-9 ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; at 70℃;Inert atmosphere; Sealed tube; General procedure: A bromo-aldehyde (1 mmol), boronic acid (1.1e1.3 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate(3 mmol), water (3 ml), ethanol (4 ml) and toluene (4 ml)were added to a round-bottomed flask. The reaction mixture wasflushed with argon, sealed under septa and heated at 70 C overnight.After cooling to room temperature, water (50 ml) was added,and product was extracted with ethyl acetate (3 x 50 ml). Combinedextracts were washed with brine, dried with anhydrousmagnesium sulfate and evaporated under reduced pressure. Theproduct was purified by column chromatography on silica withchloroform or a mixture of methanol and chloroform (1:9).
  • 15
  • [ 1899-24-7 ]
  • [ 63558-65-6 ]
  • (5-bromo-2-furyl)(4-chloropyrimidin-5-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 0.166667h; Step 1: (5-Bromo-2-furyI)(4-chIoropyrimidin-5-yl)methanol [00984] A solution of <strong>[63558-65-6]4-chloro-5-iodopyrimidine</strong> (3.60 g, 14.80 mmol) in THF (40.0 mLl) was cooled to -78 C, at which point 2.50 M of n-BuLi in hexane (7.0 mL, 17.50 mmol) was added dropwise via syringe. At the conclusion of the addition, a solution of 5-bromo-2-furaldehyde (2.0 g, 1 1.40 mmol) in THF (10.0 mL) was next added dropwise, via syringe and the reaction was stirred at -78 C for 10 min. The reaction was quenched via addition of a saturated NaHC03 solution (20 mL), and then allowed to warm to RT and extracted with EtOAc (3X). Layers were separated and the combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with 0-50% EtOAc/Hex. over 25 mins) to give 2.5 g (75%) of product. NMR (400 MHz, Chloroform-d) delta 9.04 (s, 1 H), 8.95 (s, 1H), 6.28 (d, J = 3.2 Hz, 1 H), 6.19 (d, / = 3.2 Hz, 1H),6.08 (s, 1 H), 3.38 (s, 1H).
  • 16
  • [ 1899-24-7 ]
  • [ 105365-51-3 ]
  • 5-(4-butoxyphenyl)furan-2-carbaldehyde [ No CAS ]
 

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Technical Information

Categories

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[ 1899-24-7 ]

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