Salsolinol hydrobromide

Base Information

• Chemical Name: Salsolinol hydrobromide
• CAS No.: 38221-21-5
• Molecular Formula: C10H14BrNO2
• Molecular Weight: 179.2157
• DSSTox Substance ID: DTXSID60191600
• ChEMBL ID: CHEMBL553751
• Mol file: 38221-21-5.mol

Synonyms:1-methyl-6,7-dihydroxytetrahydroisoquinoline;salsolinol;salsolinol hydrobromide;salsolinol, (+-)-isomer;salsolinol, (S)-isomer

Chemical Property of Salsolinol hydrobromide

Chemical Property:

• Melting Point: 186-187oC(lit.)
• Boiling Point: 362.6°Cat760mmHg
• Flash Point: 175.4°C
• PSA: 52.49000
• Density: 1.201g/cm³
• LogP: 2.59140
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 259.02079
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

98% ^*data from raw suppliers

Salsolinol hydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=CC(=C(C=C2CCN1)O)O.Br
• Isomeric SMILES: C[C@H]1C2=CC(=C(C=C2CCN1)O)O.Br
• Uses: Salsolinol Hydrobromide is a salt of Salsolinol, a tetrahydroisoquinoline neurotoxin that has been speculated to contribute to pathophysiology of parkinson’s disease and chronic alcoholism.

Technology Process of Salsolinol hydrobromide

There total 4 articles about Salsolinol 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:

6,7-Dihydroxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline monohydrobromide (59709-57-8) → (S)-salsolinol hydrobromide (38221-21-5) + (+)-Salsolinol hydrobromide (38221-22-6)

Guidance literature:

With N-isopropylcarbamoyl-derivatized cyclofructan-6 column; In methanol; acetic acid; triethylamine; acetonitrile; at 20 ℃; Resolution of racemate;

DOI:10.1021/ac902257a

Reference yield:

(6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) (493-48-1,5784-74-7,38520-68-2,54193-08-7) → (S)-salsolinol hydrobromide (38221-21-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2) 10percent NaOH / methanol; diethyl ether / 24 h / Ambient temperature

2: 0 °C

3: 1) 2M Na/BuOH, 2) 48percent HBr / 1) reflux, 2 h, 2) reflux, 6 h

With sodium hydroxide; hydrogen bromide; sodium; butan-1-ol; In methanol; diethyl ether;

Reference yield:

(1S)-2<<(R)-1-phenylethyl>carbamoyl>salsolidine (110691-51-5) → (S)-salsolinol hydrobromide (38221-21-5)

Guidance literature:

With hydrogen bromide; sodium; butan-1-ol; Yield given; 1) reflux, 2 h, 2) reflux, 6 h;

upstream raw materials:

(1S)-2<<(R)-1-phenylethyl>carbamoyl>salsolidine

(S)-salsolidine

(6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline)

6,7-Dihydroxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline monohydrobromide

Refernces

• 1、 Sun, Ping,Wang, Chunlei,Breitbach, Zachary S.,Zhang, Ying,Armstrong, Daniel W.. "Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans". experimental part. p. 10215 - 10226. Retrieved 2010/05/01.