Home Cart 0 Sign in  
X

[ CAS No. 366445-82-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 366445-82-1
Chemical Structure| 366445-82-1
Chemical Structure| 366445-82-1
Structure of 366445-82-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 366445-82-1 ]

Related Doc. of [ 366445-82-1 ]

Alternatived Products of [ 366445-82-1 ]
Product Citations

Product Details of [ 366445-82-1 ]

CAS No. :366445-82-1 MDL No. :MFCD18254586
Formula : C10H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :UHAJOUKNSQWSDL-UHFFFAOYSA-N
M.W : 238.08 Pubchem ID :22226545
Synonyms :

Calculated chemistry of [ 366445-82-1 ]      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) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 2.76
Log Po/w (WLOGP) : 3.01
Log Po/w (MLOGP) : 1.92
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.56
Solubility : 0.0659 mg/ml ; 0.000277 mol/l
Class : Soluble
Log S (Ali) : -2.88
Solubility : 0.314 mg/ml ; 0.00132 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 : 1.35

Safety of [ 366445-82-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P280-P332+P313-P337+P313-P362+P364 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 366445-82-1 ]

* 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 [ 366445-82-1 ]

[ 366445-82-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 52986-70-6 ]
  • [ 366445-82-1 ]
YieldReaction ConditionsOperation in experiment
71% <strong>[52986-70-6]6-Methoxyisoquinoline</strong> 16 (5.32 g, 33.4 mmol) was slowly added at 0C to cone. H2SO4 (33.5 mL). The mixture was cooled to -25C and NBS (7.68 g, 43.2 mmol) was added at such a rate that the reaction temperature was kept between -25C and -22C. The mixture was stirred at -22C for 2 h and at -18C for 3 h, then poured onto crushed ice. The pH was adjusted to 9 using concentrated aqueous NH3 and the alkaline slurry was then extracted with diethyl ether. The combined organic fractions were washed with 1 N NaOH and water, dried (Na2SO4), filtered and evaporated to dryness to afford 5.65 g (71%) of the target product 17: m/z = 237.8 (M+H)+.
34% A: 5-Bromo-6-hvdroxy-2/-/-isoquinolin-1 -oneTo a solution of <strong>[52986-70-6]6-methoxyisoquinoline</strong> (2.38 g, 14.9 mmol) in dichloromethane (55 ml) was added AICI3 (4.4g, 33 mmol) under nitrogen at ambient temperature. The mixture was stirred for 30 min then Br2 (0.92 ml, 18 mmol) was added at 0 C. The mixture was stirred for 2 h, then poured into water and neutralised with solid Na2CO3. The mixture was filtered through celite and the filtrate extracted with dichloromethane and chloroform. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a residue. Flash chromatography of the residue on silica (eluent: 50-100 % ethyl acetate in heptane) gave 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (1.2 g, 34 % yield). m-Chloroperbenzoic acid (1.4 g, 75 %) was added in portions to a stirred solution of 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (1 ,2 g, 5.04 mmol) in dichloromethane (12 ml). The mixture was stirred for 1 h then further dichloromethane (10 ml) added and the mixture stirred for an additional 2 h. Methanol (12 ml) was added and the mixture concentrated in vacuo to ~9ml, then 1M hydrochloric acid in diethyl ether (10 ml) was added. The mixture was diluted with ether and filtered, the precipitated solid was washed with diethyl ether and dried in vacuo to give crude 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong>-?/-oxide hydrochloride (1.22 g). POCI3 (6.5 ml) was added to the 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong>-?/-oxide hydrochloride (1.22g) and the mixture heated at 90 C for 6h. Excess POCI3 was removed in vacuo and the remaining solid washed with water, filtered and dried in vacuo to give 5-bromo-1-chloro-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (1.26 g).A solution of 1 M BBr3 in dichloromethane (25.5 ml) was added dropwise to a stirred solution of 5-bromo-1-chloro-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (1.26 g) in dichloromethane at 10 C. The mixture was stirred at ambient temperature for 48 h then poured into ice- water and the pH adjusted to 8 by adding concentrated aqueous ammonia. The mixture was extracted with ethyl acetate (x 2) and the aqueous phase then acidified to pH ~ 4 using dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate (x 2), the combined organics were dried (Na2SO4) and concentrated in vacuo to give 5-bromo- 1-chloro-6-hydroxyisoquinoline (1.1 g), EI-MS: m/z = 257.9, 260.0 and 261.6 [M+H]+.
A: 5-Bromo-6-hydroxy-2H-isoquinolin-1-one To a solution of <strong>[52986-70-6]6-methoxyisoquinoline</strong> (2.38 g, 14.9 mmol) in dichloromethane (55 ml) was added AlCl3 (4.4 g, 33 mmol) under nitrogen at ambient temperature. The mixture was stirred for 30 min then Br2 (0.92 ml, 18 mmol) was added at 0 C. The mixture was stirred for 2 h, then poured into water and neutralised with solid Na2CO3. The mixture was filtered through celite and the filtrate extracted with dichloromethane and chloroform. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a residue. Flash chromatography of the residue on silica (eluent: 50-100% ethyl acetate in heptane) gave 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (1.2 g, 34% yield). m-Chloroperbenzoic acid (1.4 g, 75%) was added in portions to a stirred solution of 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (12 g, 5.04 mmol) in dichloromethane (12 ml). The mixture was stirred for 1 h then further dichloromethane (10 ml) added and the mixture stirred for an additional 2 h. Methanol (12 ml) was added and the mixture concentrated in vacuo to 9 ml, then 1M hydrochloric acid in diethyl ether (10 ml) was added. The mixture was diluted with ether and filtered, the precipitated solid was washed with diethyl ether and dried in vacuo to give crude 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong>-N-oxide hydrochloride (1.22 g). POCl3 (6.5 ml) was added to the 5-bromo-<strong>[52986-70-6]6-methoxyisoquinoline</strong>-N-oxide hydrochloride (1.22 g) and the mixture heated at 90 C. for 6 h. Excess POCl3 was removed in vacuo and the remaining solid washed with water, filtered and dried in vacuo to give 5-bromo-1-chloro-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (1.26 g). A solution of 1M BBr3 in dichloromethane (25.5 ml) was added dropwise to a stirred solution of 5-bromo-1-chloro-<strong>[52986-70-6]6-methoxyisoquinoline</strong> (1.26 g) in dichloromethane at 10 C. The mixture was stirred at ambient temperature for 48 h then poured into ice-water and the pH adjusted to 8 by adding concentrated aqueous ammonia. The mixture was extracted with ethyl acetate (x 2) and the aqueous phase then acidified to pH 4 using dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate (x 2), the combined organics were dried (Na2SO4) and concentrated in vacuo to give 5-bromo-1-chloro-6-hydroxyisoquinoline (1.1 g), El-MS: m/z=257.9, 260.0 and 261.6 [M+H]+.
  • 2
  • [ 366445-82-1 ]
  • [ 923586-13-4 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 5-bromo-6-methoxyisoquinoline With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 4h; Stage #2: With sodium hydroxide In dichloromethane; water 1.E Metachloroperbenzoic acid (6.73 g, 30 mmol) was added at O0C to a solution of 17 (5.65 g, 24 mmol) in CH2Cl2 (50 mL). After 30 min at 0°C for the reaction mixture was allowed to warm up to room temperature for 3.5 h. Then, additional CH2Cl2 (300 mL) was added and this mixture was successively washed with IN NaOH and with brine. The organic layer was dried (MgSO4), filtered and evaporated to afford 6.03 g (100%) of the target product 18 which was used as such in the next step: m/z = 253.9 (M+H)+.
  • 3
  • [ 366445-82-1 ]
  • [ 940890-88-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-bromo-6-methoxyisoquinoline With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 3h; Stage #2: With hydrogenchloride In methanol; diethyl ether; dichloromethane 29.A A: 5-Bromo-6-hydroxy-2H-isoquinolin-1-one To a solution of 6-methoxyisoquinoline (2.38 g, 14.9 mmol) in dichloromethane (55 ml) was added AlCl3 (4.4 g, 33 mmol) under nitrogen at ambient temperature. The mixture was stirred for 30 min then Br2 (0.92 ml, 18 mmol) was added at 0° C. The mixture was stirred for 2 h, then poured into water and neutralised with solid Na2CO3. The mixture was filtered through celite and the filtrate extracted with dichloromethane and chloroform. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a residue. Flash chromatography of the residue on silica (eluent: 50-100% ethyl acetate in heptane) gave 5-bromo-6-methoxyisoquinoline (1.2 g, 34% yield). m-Chloroperbenzoic acid (1.4 g, 75%) was added in portions to a stirred solution of 5-bromo-6-methoxyisoquinoline (12 g, 5.04 mmol) in dichloromethane (12 ml). The mixture was stirred for 1 h then further dichloromethane (10 ml) added and the mixture stirred for an additional 2 h. Methanol (12 ml) was added and the mixture concentrated in vacuo to 9 ml, then 1M hydrochloric acid in diethyl ether (10 ml) was added. The mixture was diluted with ether and filtered, the precipitated solid was washed with diethyl ether and dried in vacuo to give crude 5-bromo-6-methoxyisoquinoline-N-oxide hydrochloride (1.22 g). POCl3 (6.5 ml) was added to the 5-bromo-6-methoxyisoquinoline-N-oxide hydrochloride (1.22 g) and the mixture heated at 90° C. for 6 h. Excess POCl3 was removed in vacuo and the remaining solid washed with water, filtered and dried in vacuo to give 5-bromo-1-chloro-6-methoxyisoquinoline (1.26 g). A solution of 1M BBr3 in dichloromethane (25.5 ml) was added dropwise to a stirred solution of 5-bromo-1-chloro-6-methoxyisoquinoline (1.26 g) in dichloromethane at 10° C. The mixture was stirred at ambient temperature for 48 h then poured into ice-water and the pH adjusted to 8 by adding concentrated aqueous ammonia. The mixture was extracted with ethyl acetate (x 2) and the aqueous phase then acidified to pH 4 using dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate (x 2), the combined organics were dried (Na2SO4) and concentrated in vacuo to give 5-bromo-1-chloro-6-hydroxyisoquinoline (1.1 g), El-MS: m/z=257.9, 260.0 and 261.6 [M+H]+.
With m-chloroperoxybenzoic acid In dichloromethane for 3h; 29.A A: 5-Bromo-6-hvdroxy-2/-/-isoquinolin-1 -oneTo a solution of 6-methoxyisoquinoline (2.38 g, 14.9 mmol) in dichloromethane (55 ml) was added AICI3 (4.4g, 33 mmol) under nitrogen at ambient temperature. The mixture was stirred for 30 min then Br2 (0.92 ml, 18 mmol) was added at 0 C. The mixture was stirred for 2 h, then poured into water and neutralised with solid Na2CO3. The mixture was filtered through celite and the filtrate extracted with dichloromethane and chloroform. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a residue. Flash chromatography of the residue on silica (eluent: 50-100 % ethyl acetate in heptane) gave 5-bromo-6-methoxyisoquinoline (1.2 g, 34 % yield). m-Chloroperbenzoic acid (1.4 g, 75 %) was added in portions to a stirred solution of 5-bromo-6-methoxyisoquinoline (1 ,2 g, 5.04 mmol) in dichloromethane (12 ml). The mixture was stirred for 1 h then further dichloromethane (10 ml) added and the mixture stirred for an additional 2 h. Methanol (12 ml) was added and the mixture concentrated in vacuo to ~9ml, then 1M hydrochloric acid in diethyl ether (10 ml) was added. The mixture was diluted with ether and filtered, the precipitated solid was washed with diethyl ether and dried in vacuo to give crude 5-bromo-6-methoxyisoquinoline-?/-oxide hydrochloride (1.22 g). POCI3 (6.5 ml) was added to the 5-bromo-6-methoxyisoquinoline-?/-oxide hydrochloride (1.22g) and the mixture heated at 90 C for 6h. Excess POCI3 was removed in vacuo and the remaining solid washed with water, filtered and dried in vacuo to give 5-bromo-1-chloro-6-methoxyisoquinoline (1.26 g).A solution of 1 M BBr3 in dichloromethane (25.5 ml) was added dropwise to a stirred solution of 5-bromo-1-chloro-6-methoxyisoquinoline (1.26 g) in dichloromethane at 10 C. The mixture was stirred at ambient temperature for 48 h then poured into ice- water and the pH adjusted to 8 by adding concentrated aqueous ammonia. The mixture was extracted with ethyl acetate (x 2) and the aqueous phase then acidified to pH ~ 4 using dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate (x 2), the combined organics were dried (Na2SO4) and concentrated in vacuo to give 5-bromo- 1-chloro-6-hydroxyisoquinoline (1.1 g), EI-MS: m/z = 257.9, 260.0 and 261.6 [M+H]+.
  • 5
  • [ 1609581-37-4 ]
  • [ 366445-82-1 ]
  • [ 1609577-65-2 ]
YieldReaction ConditionsOperation in experiment
9% With palladium diacetate; potassium carbonate; triphenylphosphine In water; N,N-dimethyl-formamide at 80℃; for 0.333333h;
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 366445-82-1 ]

Bromides

Chemical Structure| 67335-10-8

[ 67335-10-8 ]

8-Bromo-7-methoxyisoquinoline

Similarity: 0.98

Chemical Structure| 666735-07-5

[ 666735-07-5 ]

7-Bromo-6-methoxyisoquinoline

Similarity: 0.97

Chemical Structure| 36023-01-5

[ 36023-01-5 ]

5-Bromo-6-methoxyquinoline

Similarity: 0.91

Chemical Structure| 90858-86-9

[ 90858-86-9 ]

4-Bromo-5-methoxy-1H-indole

Similarity: 0.89

Chemical Structure| 1620515-86-7

[ 1620515-86-7 ]

6-Bromo-7-methoxyquinoline

Similarity: 0.88

Related Parent Nucleus of
[ 366445-82-1 ]

Isoquinolines

Chemical Structure| 67335-10-8

[ 67335-10-8 ]

8-Bromo-7-methoxyisoquinoline

Similarity: 0.98

Chemical Structure| 666735-07-5

[ 666735-07-5 ]

7-Bromo-6-methoxyisoquinoline

Similarity: 0.97

Chemical Structure| 1220694-86-9

[ 1220694-86-9 ]

8-Bromo-6-methoxyisoquinoline

Similarity: 0.88

Chemical Structure| 679433-91-1

[ 679433-91-1 ]

5-Bromo-8-methoxyisoquinoline

Similarity: 0.88

Chemical Structure| 660398-06-1

[ 660398-06-1 ]

8-Bromoisoquinolin-7-ol

Similarity: 0.88