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Chemical Structure| 63927-22-0 Chemical Structure| 63927-22-0
Chemical Structure| 63927-22-0

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Product Details of 8-Bromoisoquinoline

CAS No. :63927-22-0
Formula : C9H6BrN
M.W : 208.06
SMILES Code : C1=NC=CC2=CC=CC(=C12)Br
MDL No. :MFCD04973298
InChI Key :DPRIHFQFWWCIGY-UHFFFAOYSA-N
Pubchem ID :9859134

Safety of 8-Bromoisoquinoline

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

Application In Synthesis of 8-Bromoisoquinoline

* 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 [ 63927-22-0 ]

[ 63927-22-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 63927-22-0 ]
  • (+/-)-[8,8']biisoquinolyl [ No CAS ]
  • 2
  • [ 23687-27-6 ]
  • [ 63927-22-0 ]
  • 3
  • [ 63927-22-0 ]
  • [ 7677-24-9 ]
  • [ 98-88-4 ]
  • [ 863290-47-5 ]
  • 4
  • [ 119-65-3 ]
  • polyethylene glycol PEG3400 [ No CAS ]
  • [ 63927-22-0 ]
  • 5
  • [ 34784-04-8 ]
  • [ 63927-22-0 ]
  • 6
  • [ 63927-22-0 ]
  • [ 863290-55-5 ]
  • 7
  • [ 63927-22-0 ]
  • 8-bromo-1-(3,4-dimethoxy-benzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
  • 8
  • [ 63927-22-0 ]
  • 2-benzoyl-8-bromo-1-(3,4-dimethoxy-benzyl)-1,2-dihydro-isoquinoline-1-carbonitrile [ No CAS ]
  • 9
  • [ 63927-22-0 ]
  • 8-bromo-1-(3,4-dimethoxy-benzyl)-2-methyl-isoquinolinium; iodide [ No CAS ]
  • 10
  • [ 63927-23-1 ]
  • [ 63927-22-0 ]
  • 11
  • [ 63927-22-0 ]
  • [ 444620-33-1 ]
  • 12
  • [ 63927-22-0 ]
  • [ 444620-35-3 ]
  • 13
  • [ 63927-22-0 ]
  • [ 444620-44-4 ]
  • 14
  • [ 63927-22-0 ]
  • [ 444620-48-8 ]
  • 15
  • [ 63927-22-0 ]
  • [ 444620-34-2 ]
  • 16
  • [ 63927-22-0 ]
  • [ 444620-47-7 ]
  • 17
  • [ 63927-22-0 ]
  • 4-(2-acetyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 18
  • [ 63927-22-0 ]
  • 4-(2-methanesulfonyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 19
  • [ 63927-22-0 ]
  • 4-[2-(propane-2-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-8-yl]-piperazine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 20
  • [ 63927-22-0 ]
  • 4-(2-benzenesulfonyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 21
  • [ 63927-22-0 ]
  • (R)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid [(R)-2-[4-(2-acetyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazin-1-yl]-1-(4-chloro-benzyl)-2-oxo-ethyl]-amide [ No CAS ]
  • 22
  • [ 63927-22-0 ]
  • (R)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid {(R)-1-(4-chloro-benzyl)-2-[4-(2-methanesulfonyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazin-1-yl]-2-oxo-ethyl}-amide [ No CAS ]
  • 23
  • [ 63927-22-0 ]
  • (R)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid ((R)-1-(4-chloro-benzyl)-2-oxo-2-{4-[2-(propane-2-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-8-yl]-piperazin-1-yl}-ethyl)-amide [ No CAS ]
  • 24
  • [ 63927-22-0 ]
  • (R)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid [(R)-2-[4-(2-benzenesulfonyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazin-1-yl]-1-(4-chloro-benzyl)-2-oxo-ethyl]-amide [ No CAS ]
  • 25
  • [ 63927-22-0 ]
  • 3-[2-[4-(2-acetyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazin-1-yl]-1-(4-chloro-benzyl)-2-oxo-ethylcarbamoyl]-3,4-dihydro-1<i>H</i>-isoquinoline-2-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 26
  • [ 63927-22-0 ]
  • 3-{1-(4-chloro-benzyl)-2-[4-(2-methanesulfonyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazin-1-yl]-2-oxo-ethylcarbamoyl}-3,4-dihydro-1<i>H</i>-isoquinoline-2-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 27
  • [ 63927-22-0 ]
  • 3-(1-(4-chloro-benzyl)-2-oxo-2-{4-[2-(propane-2-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-8-yl]-piperazin-1-yl}-ethylcarbamoyl)-3,4-dihydro-1<i>H</i>-isoquinoline-2-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 28
  • [ 63927-22-0 ]
  • 3-[2-[4-(2-benzenesulfonyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-piperazin-1-yl]-1-(4-chloro-benzyl)-2-oxo-ethylcarbamoyl]-3,4-dihydro-1<i>H</i>-isoquinoline-2-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 29
  • [ 63927-22-0 ]
  • [ 475994-60-6 ]
  • 30
  • [ 63927-22-0 ]
  • acetic acid 8-bromo-isoquinolin-1-yl ester [ No CAS ]
  • 31
  • [ 6630-33-7 ]
  • [ 63927-22-0 ]
  • 32
  • [ 63927-22-0 ]
  • [ 61563-43-7 ]
  • 33
  • [ 63927-22-0 ]
  • 8-isoquinolinecarboxylic acid methyl ester [ No CAS ]
  • 34
  • [ 63927-22-0 ]
  • [ 100-39-0 ]
  • [ 807330-23-0 ]
YieldReaction ConditionsOperation in experiment
59% To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 2.46 g (11.8 mmol) <strong>[63927-22-0]8-bromoisoquinoline</strong>, 1.68 mL (14.1 mmol) benzyl bromide, and 10 mL ethanol. The solution was heated at reflux for 6 hr, cooled, and evaporated. The oil was dissolved in 50 mL methanol, and 1.73 g (27.6 mmol) sodium cyanoborohydride was added. The solution was stirred at room temperature for 5 days, then diluted with water and extracted with three portions of ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate to afford 1.98 g (59percent) of an oil. 1H-NMR (delta, CDCl3): 2.68 (m, 2H), 2.88 (m, 2H), 3.68 (m, 2H), 3.75 (m, 2H), 7.0-7.1 (m, 2H), 7.2-7.4 (m, 6H).
  • 35
  • bromobenzalaminoacetal [ No CAS ]
  • [ 14000-31-8 ]
  • [ 645-36-3 ]
  • [ 6630-33-7 ]
  • [ 63927-22-0 ]
YieldReaction ConditionsOperation in experiment
In sulfuric acid; 8-bromoisoquinoline (24). To 7.0 mL (60.0 mmol) 2-bromobenzaldehyde (23) was added 10.0 mL (69.0 mmol) aminoacetaldehyde diethyl acetal. After 3 h at 100° C., the reaction mixture was cooled to room temperature and the layers separated. The organic layer was purified by vaccum distillation to give 15.89 g bromobenzalaminoacetal (b.p. 141-148° C. at approximately 1 mm Hg). To 143 g concentrated sulfuric acid at 0° C. was added 15.89 g bromobenzalaminoacetal. With mechanical stirring, the resulting mixture was added in portions over 5 min to 20 g phosphoric anhydride in 10 g concentrated sulfuric acid maintained at 160° C. After 25 min at 160° C., the reaction mixture was cooled, poured onto ice and washed with 300 mL ethyl ether. The aqueous layer was basified with solid NaOH to pH=10 and extracted with EtOAc repeatedly. The combined EtOAc layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (75*110 mm silica gel, linear gradient 0.5-3percent (10percent NH4H:MeOH):CH2CI2) produced 24. 1H NMR (CDCl3, 400 MHz) 89.627 (s, 1H, ArH); 8.622 (d, 1H, J=5.67 Hz, ArH); 7.858 (dd, 1H, J=0.87, 7.45 Hz, ArH); 7.799 (d, 1H, J=8.32 Hz, ArH); 7.631 (d, 1H, J=5.76 Hz, ArH); 7.538 (dd, 1H, J=7.50, 8.23 Hz, ArH); MS (Electrospray): m/z 207.9, 209.0 (M+H, 79Br, 81Br).
 

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