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[ CAS No. 1427438-58-1 ] {[proInfo.proName]}

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Chemical Structure| 1427438-58-1
Chemical Structure| 1427438-58-1
Structure of 1427438-58-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1427438-58-1 ]

CAS No. :1427438-58-1 MDL No. :MFCD23705518
Formula : C8H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XXDBEJYASPBHLS-UHFFFAOYSA-N
M.W : 215.04 Pubchem ID :90893513
Synonyms :

Calculated chemistry of [ 1427438-58-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.52
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 2.64
Log Po/w (WLOGP) : 2.28
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 2.63
Consensus Log Po/w : 2.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.144 mg/ml ; 0.00067 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.181 mg/ml ; 0.000843 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.207 mg/ml ; 0.000962 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 1427438-58-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1427438-58-1 ]

* 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 [ 1427438-58-1 ]

[ 1427438-58-1 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 24078-12-4 ]
  • C8H7BrO2 [ No CAS ]
  • 2
  • [ 1427438-58-1 ]
  • [ 2520349-41-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h 2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere
  • 3
  • [ 1427438-58-1 ]
  • [ 105-39-5 ]
  • [ 1427356-25-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 2h; Intermediate INT-26: (4704) 6-Bromo-4-methyl-1-benzofuran-2-carboxylic acid According to GP3, commercially available 4-bromo-2-hydroxy-6-methylbenzaldehyde (4707) (CAS: 1427438-58-1, 100 mg, 465 µmol), ethyl chloroacetate (50 µL, 470 µmol), potassium carbonate (630 mg, 4.56 mmol) were stirred in DMF (2.2 mL) for 2 h. After reaction completion and workup the desired residue was obtained as a dark brown solid (4708) (80 mg, 57%, 60% pure) which was used directly in the next step. H-NMR (400 MHz, (4709) DMSO-d6) d [ppm]: 10.16 (bs, 1 H), 7.57, 7.46, 7.45 (3 mc, 1 H each), 2.45 (s, 3 H).
  • 4
  • [ 1427438-58-1 ]
  • [ 2760558-03-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C
  • 5
  • [ 1427438-58-1 ]
  • [ 2760558-04-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice
  • 6
  • [ 1427438-58-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C
  • 7
  • [ 1427438-58-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C 5: lithium hydroxide monohydrate; hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C
  • 8
  • [ 1427438-58-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C 5: lithium hydroxide monohydrate; hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 6: 1,1'-(azodicarboxylic)dipiperidide; tributylphosphine / toluene / 1 h / 60 °C / Inert atmosphere
Multi-step reaction with 6 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C 5: lithium hydroxide monohydrate; hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 6: 1,1'-(azodicarboxylic)dipiperidide; tributylphosphine / toluene / 1 h / 60 °C / Inert atmosphere
  • 9
  • [ 1427438-58-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C 5: lithium hydroxide monohydrate; hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 6: 1,1'-(azodicarboxylic)dipiperidide; tributylphosphine / toluene / 1 h / 60 °C / Inert atmosphere 7: sodium tertiary butoxide; methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C 5: lithium hydroxide monohydrate; hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 6: 1,1'-(azodicarboxylic)dipiperidide; tributylphosphine / toluene / 1 h / 60 °C / Inert atmosphere 7: sodium tertiary butoxide; methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere
  • 10
  • [ 1427438-58-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C 5: lithium hydroxide monohydrate; hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 6: 1,1'-(azodicarboxylic)dipiperidide; tributylphosphine / toluene / 1 h / 60 °C / Inert atmosphere 7: sodium tertiary butoxide; methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 8: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
Multi-step reaction with 8 steps 1: potassium carbonate / acetonitrile / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: potassium carbonate; potassium iodide / acetonitrile / 3 h / 80 °C 5: lithium hydroxide monohydrate; hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 6: 1,1'-(azodicarboxylic)dipiperidide; tributylphosphine / toluene / 1 h / 60 °C / Inert atmosphere 7: sodium tertiary butoxide; methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 8: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 11
  • [ 13057-17-5 ]
  • [ 1427438-58-1 ]
  • [ 2760558-02-7 ]
YieldReaction ConditionsOperation in experiment
38.18% With potassium carbonate In acetonitrile at 20℃; for 3h; 22.1 4-Bromo-2-(methoxymethoxy)-6-methylbenzaldehyde 22b Compound 4-bromo-2-hydroxy-6-methylbenzaldehyde 22a (500 mg, 2.33 mmol, Prepared by the well-known method "Organic Letters, 2017, vol.19, no.23, p.6280-6283") was dissolved in acetonitrile (20 mL),Anhydrous potassium carbonate (1.0 g, 3.11 mmol, Chinese medicine) and bromomethyl methyl ether (350 mg, 2.80 mmol) were added, and the reaction was stirred at room temperature for 3 hours,The reaction solution was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with eluent system A to obtain the title product 22b (230 mg, yield: 38.18%).
38.18% With potassium carbonate In acetonitrile at 20℃; for 3h; 22.1 4-Bromo-2-(methoxymethoxy)-6-methylbenzaldehyde 22b Compound 4-bromo-2-hydroxy-6-methylbenzaldehyde 22a (500 mg, 2.33 mmol, Prepared by the well-known method "Organic Letters, 2017, vol.19, no.23, p.6280-6283") was dissolved in acetonitrile (20 mL),Anhydrous potassium carbonate (1.0 g, 3.11 mmol, Chinese medicine) and bromomethyl methyl ether (350 mg, 2.80 mmol) were added, and the reaction was stirred at room temperature for 3 hours,The reaction solution was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with eluent system A to obtain the title product 22b (230 mg, yield: 38.18%).
  • 12
  • [ 1427438-58-1 ]
  • [ 2834094-20-9 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In N,N-dimethyl acetamide 2; 3; 4 Into a three-necked flask, inject 60g of 4-bromo-2-hydroxyl-6-methylbenzaldehyde and 480g of DMAC, then slowly add 180g of concentrated sulfuric acid (98%) dropwise, and continue the reaction for 3h after the addition, and separate and purify to obtain 2-bromo -4-Hydroxy-5-formyl-6-methylbenzenesulfonic acid.Inject 40g of 2-bromo-4-hydroxy-5-formyl-6-methylbenzenesulfonic acid and 120g of tetrahydrofuran into a water-free and oxygen-free glass bottle, and slowly add 17g of butyl to the reaction system dropwise at -78°C Lithium (1mol/L), then add 80g triethylamine, rise to room temperature and continue to react for 6h, separate and purify to obtain 2-(diethylamino)-4-hydroxy-5-formyl-6-ethylbenzenesulfonic acid.Dissolve 40g of 2-(diethylamino)-4-hydroxy-5-formyl-6-methylbenzenesulfonic acid, 360g of acetic anhydride and 2g of calcium acetate in DMF, raise the temperature to 160°C for 30min to obtain the extraction modifier 5-methyl-6-sulfono-7-(diethylamino)benzofuran.
  • 13
  • [ 1427438-58-1 ]
  • [ 2834094-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / N,N-dimethyl acetamide / 3 h 2: n-butyllithium / tetrahydrofuran / 6 h / -78 - 20 °C
  • 14
  • [ 1427438-58-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfuric acid / N,N-dimethyl acetamide / 3 h 2: n-butyllithium / tetrahydrofuran / 6 h / -78 - 20 °C 3: calcium acetate / N,N-dimethyl-formamide / 30 min / 160 °C
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