1-Chloro-3-(1-naphthoxy)-2-propanol

Base Information

• Chemical Name: 1-Chloro-3-(1-naphthoxy)-2-propanol
• CAS No.: 20133-93-1
• Molecular Formula: C13H13ClO2
• Molecular Weight: 236.698
• Hs Code.: 2909499000
• European Community (EC) Number: 243-538-3
• NSC Number: 91519
• DSSTox Substance ID: DTXSID101273366
• Nikkaji Number: J280.456E
• Mol file: 20133-93-1.mol

Synonyms:1-chloro-3-(1-naphthyloxy)-2-propanol;1-Cl-3-NP

Chemical Property of 1-Chloro-3-(1-naphthoxy)-2-propanol

Chemical Property:

• Vapor Pressure: 1.46E-07mmHg at 25°C
• Refractive Index: 1.616
• Boiling Point: 413.1 °C at 760 mmHg
• PKA: 13.07±0.20(Predicted)
• Flash Point: 203.6 °C
• PSA: 29.46000
• Density: 1.246 g/cm³
• LogP: 2.81830
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 236.0604073
• Heavy Atom Count: 16
• Complexity: 210

Purity/Quality:

99%, ^*data from raw suppliers

1-Chloro-3-(1-naphthyloxy)-2-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2OCC(CCl)O
• Uses: 1-Chloro-3-(1-naphthyloxy)-2-propanol is an intermediates in the synthesis of β-adrenergic blocking agents and antihypertensive drugs such as propranolol and nadoxolol. Also used in the kinetic resolution studies of (±)-1-chloro-3-(1-naphthyloxy)-2-propanol in nonaqueous media using lipase-catalyzed esterification.

Technology Process of 1-Chloro-3-(1-naphthoxy)-2-propanol

There total 12 articles about 1-Chloro-3-(1-naphthoxy)-2-propanol 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: 92.5%

α-naphthol (90-15-3) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 1-chloro-3-(1-naphthoxy)-2-propanol (20133-93-1)

Guidance literature:

α-naphthol; epichlorohydrin; With 1,8-diazabicyclo[5.4.0]undec-7-ene; for 0.333333h; Heating;

With hydrogenchloride; In dichloromethane; at 5 ℃; for 2h;

DOI:10.1016/S0045-2068(03)00050-6

Reference yield: 69.0%

α-naphthol (90-15-3) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 3-(1-naphthyloxy)-1,2-epoxypropane (2461-42-9) + 1-chloro-3-(1-naphthoxy)-2-propanol (20133-93-1)

Guidance literature:

With sodium hydroxide; In water; for 6h; Heating;

DOI:10.1016/j.tet.2006.08.067

Reference yield: 29.0%

allyl naphthyl ether (20009-25-0) → 1-chloro-3-(1-naphthoxy)-2-propanol (20133-93-1)

Guidance literature:

With μ-(R)-BINAP μ-1-phenylhexane-1,3,5-triketone bis[(acetonitrile)palladium(II)] tetrafluoroborate; oxygen; lithium chloride; copper dichloride; In tetrahydrofuran; water; at 23 ℃; for 240h; under 760.051 Torr; Reagent/catalyst; Sealed tube;

DOI:10.1021/acs.orglett.5b02650

upstream raw materials:

α-naphthol

epichlorohydrin

3-(1-naphthyloxy)-1,2-epoxypropane

1-chloro-3-(1-naphthyloxy)-propan-2-one

Downstream raw materials:

1-(3,4-dimethoxyphenethylamino)-3-(naphthalen-1-yloxy)propan-2-ol

(+/-)-dimethyl<2-hydroxy-3-(1-naphthyloxy)propyl>amine

1-benzylamino-3-(naphth-1-yloxy)-2-propanol

1-[3-(1-Naphthoxy)-2-hydroxyprop-1-yl]-4-benzamidopiperidine

Refernces

• 1、 Kapoor,Anand,Koul,Chimni,Manhas,Raina,Parshad,Taneja,Qazi. "Kinetic resolution of 1-chloro-3-(1-naphthyloxy)-2-propanol, an intermediate in the synthesis of β-adrenergic receptor blockers". . p. 259 - 269. Retrieved 2003.
• 2、 Pchelka, Beata K.,Loupy, Andre,Petit, Alain. "Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism". . p. 10968 - 10979. Retrieved 2007/10/03.