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[ CAS No. 103028-33-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 103028-33-7
Chemical Structure| 103028-33-7
Chemical Structure| 103028-33-7
Structure of 103028-33-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 103028-33-7 ]

CAS No. :103028-33-7 MDL No. :MFCD28128367
Formula : C10H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :PUVNBWJBWQUILR-UHFFFAOYSA-N
M.W : 238.08 Pubchem ID :14566897
Synonyms :

Calculated chemistry of [ 103028-33-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.94
TPSA : 22.12 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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 2.85
Log Po/w (WLOGP) : 3.01
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.61
Solubility : 0.0578 mg/ml ; 0.000243 mol/l
Class : Soluble
Log S (Ali) : -2.97
Solubility : 0.253 mg/ml ; 0.00106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.69
Solubility : 0.00489 mg/ml ; 0.0000206 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 103028-33-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 103028-33-7 ]

* 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 [ 103028-33-7 ]

[ 103028-33-7 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 908094-01-9 ]
  • [ 84174-71-0 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
With methanol; diethyl ether
  • 2
  • [ 95836-49-0 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; water; sodium nitrite Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>;
  • 3
  • [ 19056-41-8 ]
  • [ 56-81-5 ]
  • [ 103028-33-7 ]
  • [ 36023-01-5 ]
  • 4
  • [ 106103-23-5 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
90% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.0833333h; Ambient temperature;
  • 5
  • [ 19056-41-8 ]
  • [ 7664-93-9 ]
  • [ 56-81-5 ]
  • sodium arsenic ate [ No CAS ]
  • [ 103028-33-7 ]
  • [ 36023-01-5 ]
  • 6
  • [ 106103-15-5 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) 2percent KOH 2) 0.5 N HCl / 1a) anodic oxidation 1b) H2O, brine, r.t., 4.5 h 2) acetone, r.t., 0.5 h 2: 90 percent / DDQ / benzene / 0.08 h / Ambient temperature
  • 7
  • [ 99-28-5 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphoric acid; sulfuric acid / 160 °C 2: methanol; diethyl ether
  • 8
  • [ 90-52-8 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid 2: acetic acid; bromine 3: aqueous HBr 4: sodium nitrite; water; sulfuric acid / Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>
Multi-step reaction with 5 steps 1: acetic acid 2: acetic acid; bromine 3: aqueous HCl 4: aqueous HBr; phenol 5: sodium nitrite; water; sulfuric acid / Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>
  • 9
  • [ 7148-88-1 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous HBr; phenol 2: sodium nitrite; water; sulfuric acid / Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>
  • 10
  • [ 19279-81-3 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; bromine 2: aqueous HBr 3: sodium nitrite; water; sulfuric acid / Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>
Multi-step reaction with 4 steps 1: acetic acid; bromine 2: aqueous HCl 3: aqueous HBr; phenol 4: sodium nitrite; water; sulfuric acid / Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>
  • 11
  • [ 95836-47-8 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous HBr 2: sodium nitrite; water; sulfuric acid / Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>
Multi-step reaction with 3 steps 1: aqueous HCl 2: aqueous HBr; phenol 3: sodium nitrite; water; sulfuric acid / Diazotization.anschliessend mit wss. Hypophosphorigsaeure <Phosphinsaeure>
  • 13
  • [ 51-66-1 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; bromine / Erhitzen des Reaktionsprodukts mit wss. Salzsaeure 2: sodium arsenic ate; sulfuric acid / 140 - 160 °C
  • 14
  • [ 103028-33-7 ]
  • (6-methoxyquinolin-7-yl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; Triisopropyl borate In tetrahydrofuran; n-heptane at -78 - 20℃; 6-1.2 Step 2: (6-Methoxyquinolin-7-yl)boronic acid Butyllithium (1.6 M in heptane, 1.90 ml_, 3.04 mmol) was added drop-wise over the course of one hour to a solution of 7-bromo-6-methoxyquinoline (0.603 g, 2.53 mmol) and triisopropyl borate (0.823 ml, 3.55 mmol) in THF (12.6 ml.) cooled to -78 °C. After the addition was complete, the cooling bath was removed and the slurry allowed to warm to room temperature. LC/MS analysis shows near quantitative conversion to the boronic acid. The mixture was concentrated, then the residue was concentrated sequentially from toluene and from heptane, to provide (6- methoxyquinolin-7-yl)boronic acid as an orange foam which was used immediately without purification. MS (M+1 ) = 204.2
  • 15
  • [ 64-17-5 ]
  • (2-amino-4-bromo-5-methoxyphenyl)methanol [ No CAS ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
603 mg With benzophenone; potassium <i>tert</i>-butylate In 1,4-dioxane at 80℃; for 2h; 6-1.1 Step 1: 7-Bromo-6-methoxyquinoline According to the general procedure of Martinez, R., et al, J. Org. Chem. 2008, 73, 9778-9780, in a 100 ml. round bottom flask, a mixture of (2-amino-4-bromo-5-methoxyphenyl)methanol (Intermediate 10, 2.36 g, 9.14 mmol), benzophenone (3.33 g, 18.3 mmol), KOtBu (2.05 g, 18.3 mmol), and ethanol (0.53 ml, 9.1 mmol) in 1 ,4-dioxane (30 ml.) was heated at 80 °C for 2 h. The reaction was diluted with EtOAc and extracted with 1 M HCI (3x). The acidic extracts were washed with ether, basified to pH 10 and extracted with EtOAc (5x). The extracts were washed with brine, dried over MgS04 and concentrated to an orange oil. Silica gel chromatography (2-60% EtOAc in DCM) provided 7-bromo-6-methoxyquinoline (603 mg) as a yellow solid. MS (M+1 ) = 238.1 . 1H NMR (400 MHz, CHLOROFORM-d) δ 8.80 (dd, J=4.5, 1 .5 Hz, 1 H), 8.44 (s, 1 H), 8.12 (d, J=8.1 Hz, 1 H), 7.43 (dd, J=8.3, 4.3 Hz, 1 H), 7.12 (s, 1 H), 4.04 (s, 3H).
  • 16
  • [ 153556-42-4 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sulfuric acid; potassium nitrate 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h 3: methanol 4: acetic acid; zinc / dichloromethane / 72 h / 20 °C 5: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -78 - 20 °C 6: benzophenone; potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 80 °C
  • 17
  • [ 1020717-99-0 ]
  • [ 103028-33-7 ]
  • 18
  • [ 1220886-29-2 ]
  • [ 103028-33-7 ]
  • 19
  • methyl 4-bromo-5-methoxy-2-nitrobenzoate [ No CAS ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; zinc / dichloromethane / 72 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -78 - 20 °C 3: benzophenone; potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 80 °C
  • 20
  • methyl 2-amino-4-bromo-5-methoxybenzoate [ No CAS ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -78 - 20 °C 2: benzophenone; potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 80 °C
  • 21
  • [ 19056-41-8 ]
  • [ 56-81-5 ]
  • [ 103028-33-7 ]
YieldReaction ConditionsOperation in experiment
57% With sulfuric acid; 3-Nitrobenzenesulfonic acid In water at 140℃; for 16h; B1.1 Step 1: Synthesis of 7-bromo-6-methoxyquinoline. A mixture of 3-bromo-4-methoxyaniline (10 g, 49.49 mmol), 3-nitrobenzenesulfonic acid (11.06 g, 54.4 mmol), propane-1,2,3-triol (45.6 g, 495 mmol) and H2SO4 (48.5 g, 495 mmol) in water (60 mL) was heated to 140 oC for 16 h. LCMS showed most of the starting material disappeared, and the mixture was poured into ice water (200 mL). NH3.H2O was added dropwise to the mixture to make the pH to about 8. The mixture was extracted with ethyl acetate (150 mL). The organic phase was washed with sodium chloride solution, dried, concentrated, and purified by silica gel chromatography (0-20% EtOAc/petroleum ether) to give 7-bromo-6-methoxyquinoline (6.81 g, 57% yield) as white solid. LCMS: m/z 237.9 [M+H]+; tR = 1.44 min.
  • 22
  • [ 103028-33-7 ]
  • [ 84174-71-0 ]
YieldReaction ConditionsOperation in experiment
8.2 g With boron tribromide In dichloromethane at -78 - 20℃; for 16h; B1.2 Step 2: Synthesis of 7-bromoquinolin-6-ol. To a mixture of 7-bromo-6-methoxyquinoline (6.3 g, 26.46 mmol) in DCM (80 mL) was added 1M BBr3 in DCM (66 mL) dropwise at -78 oC. The mixture was warmed to room temperature and stirred for 16 h. LCMS showed most of the starting material disappeared, and the mixture was quenched with ice water dropwise at 0 oC. Sodium hydroxide solution was added to the mixture to make the pH to about 7. The solid was filtered to give 8.2 g of 7-bromoquinolin-6-ol as white solid (contained boric acid). LCMS: m/z 224.0 [M+H]+; tR = 1.12 min.
  • 23
  • [ 103028-33-7 ]
  • 7-bromo-6-(methoxymethoxy)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 16 h / -78 - 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
  • 24
  • [ 103028-33-7 ]
  • 6-(methoxymethoxy)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: boron tribromide / dichloromethane / 16 h / -78 - 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
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