R(+)-6-Bromo-APB hydrobromide

Base Information

• Chemical Name: R(+)-6-Bromo-APB hydrobromide
• CAS No.: 139689-19-3
• Molecular Formula: C19H21Br2NO2
• Molecular Weight: 455.189
• DSSTox Substance ID: DTXSID40474680
• ChEMBL ID: CHEMBL1256659
• Mol file: 139689-19-3.mol

Synonyms:R(+)-6-Bromo-APB hydrobromide;139689-19-3;R(+)-6-Bromo-APB HBr;1H-3-benzazepine hydrobromide;(R)-3-allyl-6-bromo-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol hydrobromide;EU-0100216;MLS000862194;R(+) 6 Bromo APB HBr;CHEMBL1256659;DTXSID40474680;R(+) 6 Bromo APB hydrobromide;(5R)-9-bromo-5-phenyl-3-prop-2-enyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol;hydrobromide;Tox21_500216;AKOS025294474;CCG-221520;LP00216;R(+)-6-Bromo-APB hydrobromide, solid;NCGC00093687-01;NCGC00260901-01;SMR000326957;B-135;SR-01000075357;J-007306;SR-01000075357-1;R(+)-6-Bromo-7,8-dihydroxy-3-allyl-1-phenyl-2,3,4,5-tetrahydro-

Chemical Property of R(+)-6-Bromo-APB hydrobromide

Chemical Property:

• PSA: 43.70000
• LogP: 4.93230
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 454.99185
• Heavy Atom Count: 24
• Complexity: 399

Purity/Quality:

97% ^*data from raw suppliers

R(+)-6-Bromo-APBHydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1CCC2=C(C(=C(C=C2C(C1)C3=CC=CC=C3)O)O)Br.Br
• Isomeric SMILES: C=CCN1CCC2=C(C(=C(C=C2[C@H](C1)C3=CC=CC=C3)O)O)Br.Br
• Uses: R(+)-6-Bromo-APB Hydrobromide is a D1 dopamine receptor agonist.

Technology Process of R(+)-6-Bromo-APB hydrobromide

There total 6 articles about R(+)-6-Bromo-APB 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: 20.0%

(R)-(+)-3-allyl-6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (139689-16-0) → (+)-6-Br-APB hydrobromide (139689-19-3)

Guidance literature:

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

DOI:10.1021/jm00086a016

Reference yield:

7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (20569-49-7) → (+)-6-Br-APB hydrobromide (139689-19-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / 88percent aq. formic acid / 4 h / Heating

3: 1.) canogenogen bromide, 2.) 3N aq. HCl, glacial acetic acid / 1.) benzene, 55-60 deg C, 4 h, 2.) reflux, 24 h

4: 62 percent / Br₂, glacial acetic acid / 3 h / Ambient temperature

5: 35 percent / K₂CO₃ / dimethylformamide; H₂O; CH₂Cl₂ / Ambient temperature

6: 20 percent / boron tribromide / CH₂Cl₂; hexane / 1.) -70 deg C, 1 h, 2.) RT, 2 h

With hydrogenchloride; formic acid; bromocyane; bromine; boron tribromide; potassium carbonate; acetic acid; In hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00086a016

Reference yield:

1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydro-3H-benzazepine (20012-08-2) → (+)-6-Br-APB hydrobromide (139689-19-3)

Guidance literature:

Multi-step reaction with 5 steps

2: 1.) canogenogen bromide, 2.) 3N aq. HCl, glacial acetic acid / 1.) benzene, 55-60 deg C, 4 h, 2.) reflux, 24 h

3: 62 percent / Br₂, glacial acetic acid / 3 h / Ambient temperature

4: 35 percent / K₂CO₃ / dimethylformamide; H₂O; CH₂Cl₂ / Ambient temperature

5: 20 percent / boron tribromide / CH₂Cl₂; hexane / 1.) -70 deg C, 1 h, 2.) RT, 2 h

With hydrogenchloride; bromocyane; bromine; boron tribromide; potassium carbonate; acetic acid; In hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00086a016

upstream raw materials:

(R)-(+)-3-allyl-6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

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

1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydro-3H-benzazepine

(+)-(R)-1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydro-3H-benzazepine

Refernces