2-Hydroxysaclofen

Base Information

• Chemical Name: 2-Hydroxysaclofen
• CAS No.: 117354-64-0
• Molecular Formula: C9H12 Cl N O4 S
• Molecular Weight: 265.718
• European Community (EC) Number: 634-206-2
• UNII: X5IFR0UF10
• DSSTox Substance ID: DTXSID30922408
• Nikkaji Number: J366.987D
• Wikidata: Q27071902
• Pharos Ligand ID: ZA6QZH3FAM5C
• ChEMBL ID: CHEMBL1256573
• Mol file: 117354-64-0.mol

Synonyms:2-hydroxy-saclofen;2-hydroxysaclofen;2-OH-saclofen;3-amino-2-(4-chlorophenyl)-2-hydroxypropane-1-sulfonic acid;3-amino-2-(4-chlorophenyl)-2-hydroxypropylsulfonic acid

Chemical Property of 2-Hydroxysaclofen

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 267-269 °C
• Refractive Index: 1.63
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 109.00000
• Density: 1.551 g/cm³
• LogP: 2.15520
• Storage Temp.: 2-8°C
• Solubility.: H2O: 1 mg/mL
• Water Solubility.: Soluble in water at 1mg/ml. Also soluble in DMSO, 0.1M HCl and methanol
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 265.0175567
• Heavy Atom Count: 16
• Complexity: 321

Purity/Quality:

98%Min ^*data from raw suppliers

2-Hydroxysaclofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(CN)(CS(=O)(=O)O)O)Cl
• Uses: 2-Hydroxysaclofen is a GABA-B receptor antagonist in the ventral tegmental area and may play a role in the mechanisms of cocaine usage. Affects specific acute nicotine responses in mice, abolishing hypolocomotion and increasing antinociception.

Technology Process of 2-Hydroxysaclofen

There total 11 articles about 2-Hydroxysaclofen 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:

2-(4-chlorophenyl)-3-hydroxypropene (45941-96-6) → 2-hydroxysaclofen (117354-64-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) diethyl D-(-)-tartrate, Ti(iPrO)4, 1A mol sieves, t-BuOOH / 1.) CH₂Cl₂, -20 deg C, 45 min, 2.) CH₂Cl₂, -20 deg C, 7 h then -12 deg C, 36 h and warmed to 0 deg C

2: 93 percent / NaN₃, NH₄Cl / methanol; H₂O / 15 h / Heating

3: 84 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature

4: 59 percent / methanol

5: 94 percent / hydrogen / PtO₂ / ethanol / 0.5 h / 2585.7 Torr

6: sodium sulfite

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium azide; molecular sieve; diethyl (2S,3S)-tartrate; hydrogen; ammonium chloride; sodium sulfite; platinum(IV) oxide; In methanol; ethanol; dichloromethane; water;

DOI:10.1016/0040-4020(95)00710-P

Reference yield:

4-Nitro-benzoic acid (S)-2-(4-chloro-phenyl)-oxiranylmethyl ester (172789-03-6) → 2-hydroxysaclofen (117354-64-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / K₂CO₃, MeOH / 0.17 h / 20 °C

2: 93 percent / NaN₃, NH₄Cl / methanol; H₂O / 15 h / Heating

3: 84 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature

4: 59 percent / methanol

5: 94 percent / hydrogen / PtO₂ / ethanol / 0.5 h / 2585.7 Torr

6: sodium sulfite

With pyridine; methanol; sodium azide; hydrogen; potassium carbonate; ammonium chloride; sodium sulfite; platinum(IV) oxide; In methanol; ethanol; dichloromethane; water;

DOI:10.1016/0040-4020(95)00710-P

Reference yield:

(2S)-3-azido-2-(4-chlorophenyl)-2-hydroxyprop-1-yl 4-toluenesulfonate (172788-94-2) → 2-hydroxysaclofen (117354-64-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / methanol

2: 94 percent / hydrogen / PtO₂ / ethanol / 0.5 h / 2585.7 Torr

3: sodium sulfite

With hydrogen; sodium sulfite; platinum(IV) oxide; In methanol; ethanol;

DOI:10.1016/0040-4020(95)00710-P

upstream raw materials:

<2-(4-chlorophenyl)prop-2-enyl>amine

N-<2-(4-chlorophenyl)prop-2-enyl>phthalimide

(2S)-1-amino-2-(4-chlorophenyl)-2,3-epoxypropane

2-(4-chlorophenyl)-3-hydroxypropene

Refernces

• 1、 Abbenante, Giovanni,Prager, Rolf H.. "Potential GabaB Receptor Antagonists. V. The Application of Radical Additions to Styrenes to Produce 2-Hydroxysaclofen". . p. 1791 - 1800. Retrieved 2007/10/02.