SKF 81297 hydrobromide

Base Information

• Chemical Name: SKF 81297 hydrobromide
• CAS No.: 67287-39-2
• Molecular Formula: C16H16ClNO2•BrH
• Molecular Weight: 370.673
• Hs Code.: 2933990090
• UNII: L86RFQ3NSD
• DSSTox Substance ID: DTXSID6042604
• Wikipedia: SKF-81,297
• Wikidata: Q278972
• Pharos Ligand ID: 5T1G6LQT41V2
• ChEMBL ID: CHEMBL553503
• Mol file: 67287-39-2.mol

Synonyms:SKF 81297 hydrobromide;67287-39-2;(+/-)-6-Chloro-PB hydrobromide;L86RFQ3NSD;SKF-81297 hydrobromide;SKF-81297C;UNII-L86RFQ3NSD;SKF 81297 (hydrobromide);9-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol;hydrobromide;1H-3-Benzazepine-7,8-diol, 6-chloro-2,3,4,5-tetrahydro-1-phenyl-, hydrobromide;1H-3-Benzazepine-7,8-diol, 6-chloro-2,3,4,5-tetrahydro-1-phenyl-, hydrobromide (1:1);CHEMBL553503;(+/-)-6-Chloro-2,3,4,5-tetrahydro-1-phenyl-1H-3-benzazepine hydrobromide;SKF-81,297;SR-01000075403;SKF81297 (hydrobromide);SKF-81297(hydrobromide);EU-0101162;C16H16ClNO2.HBr;MLS000860018;(y)-6-Chloro-PB hydrobromide;(?)-6-Chloro-PB hydrobromide;DTXSID6042604;SCHEMBL11253953;(5R)-9-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol;Tox21_501162;HB1858;AKOS024456604;CCG-222466;LP01162;NCGC00094421-01;NCGC00261847-01;BS162624;LS-27996;MS-25965;SMR000326876;NCG-C00094421-01;S-143;Q278972;( inverted question mark)-6-Chloro-PB hydrobromide;( inverted question mark)-SKF-81297 hydrobromide;SR-01000075403-1;SR-01000075403-3;(+/-)-6-Chloro-PB hydrobromide, >=98% (HPLC), solid;(+)-6-chloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-[1h]-3-benzazepine hydrobromide;(+/-)-6-Chloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro[1H]-3-benzazepine;6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol hydrobromide;6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol hydrobromide

Chemical Property of SKF 81297 hydrobromide

Chemical Property:

• Melting Point: >256°C (dec.)
• PSA: 52.49000
• LogP: 4.31570
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: H2O: 6 mg/mL
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 369.01312
• Heavy Atom Count: 21
• Complexity: 322

Purity/Quality:

99% ^*data from raw suppliers

SKF81297C ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CNCC(C2=CC(=C(C(=C21)Cl)O)O)C3=CC=CC=C3.Br
• Uses: SKF 81297C is a dopamine D1 agonist (1).

Technology Process of SKF 81297 hydrobromide

There total 17 articles about SKF 81297 hydrobromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (67287-38-1) → 6-chloro-7,8-dihydroxy-1phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (67287-39-2)

Guidance literature:

With boron tribromide; In hexane; dichloromethane; 1.) -70 deg C, 1 h, 2.) RT, 2 h;

DOI:10.1021/jm00116a004

Reference yield:

1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione hydrochloride → 9-chloro-1-phenyl-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide + 6-chloro-7,8-dihydroxy-1phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (67287-39-2)

Guidance literature:

In dichloromethane;

Reference yield:

isovanillin (621-59-0) → 6-chloro-7,8-dihydroxy-1phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (67287-39-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / Cl₂

2: 66 percent / K₂CO₃ / dimethylformamide / 0.08 h / Heating

3: 100 percent / NaBH₄ / aq. ethanol / 1 h / 25 °C

4: 97 percent / 12N aq. HCl

5: 96 percent / dimethylsulfoxide / 1.25 h

6: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating

7: 37 percent / 2.5 h / Heating

8: TFA, 36 N aq. H₂SO₄ / 3.5 h / 25 °C

9: BBr₃ / CH₂Cl₂ / 3 h / 25 °C

With hydrogenchloride; sodium tetrahydroborate; sulfuric acid; borane; chlorine; boron tribromide; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm00161a029

upstream raw materials:

6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

isovanillin

N-(2-Hydroxy-2-phenethyl)-N-<2-(2'-chlor-3',4'-dimethoxyphenyl)-ethyl>-amin

2-chloro-3,4-dimethoxybenzyl chloride

Downstream raw materials:

6-Chloro-1-phenyl-3-(4-trifluoromethyl-benzyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol

6-chloro-7,8-dihydroxy-3-(4-methoxybenzyl)-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

6-chloro-7,8-dihydroxy-3-(4-methoxybenzoyl)-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

6-chloro-7,8-dihydroxy-1-phenyl-3-(p-trifluoromethylbenzoyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Refernces

• 1、 Weinstock,Ladd,Wilson,Brush,Yim,Gallagher Jr.,McCarthy,Silvestri,Sarau,Flaim. "Synthesis and renal vasodilator activity of some dopamine agonist 1-aryl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diols: Halogen and methyl analogues of fenoldopam". . p. 2315 - 2325. Retrieved 2007/10/02.
• 2、 -. "Method for 6-bromination of 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds". . . Retrieved 2008/06/13.