1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol

Base Information

• Chemical Name: 1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol
• CAS No.: 4199-09-1
• Molecular Formula: C16H21 N O2
• Molecular Weight: 259.348
• European Community (EC) Number: 224-095-5
• UNII: 74MLR03FLC
• DSSTox Substance ID: DTXSID90873366
• Nikkaji Number: J224.993F
• Wikidata: Q63390536
• Pharos Ligand ID: ABUYDR54X2J4
• Metabolomics Workbench ID: 135125
• ChEMBL ID: CHEMBL452861
• Mol file: 4199-09-1.mol

Synonyms:4199-09-1;(S)-propranolol;Propranolol, L-;(-)-propranolol;1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol;Levopropranolol;s-(-)-propranolol;(S)-1-(Isopropylamino)-3-(naphthyloxy)propan-2-ol;(2S)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol;74MLR03FLC;CHEMBL452861;EINECS 224-095-5;(S)-1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-ol;l-propranolol;(2S)-1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol;(S)-(-)-PROPRANOLOL;s-propranolol;1-propranolol;2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, (S)-;propranolol-(S);2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-, (S)-;(-)-propanolol;propranolol (S-);S-(-)-propanolol;Tocris-0834;(-)-(S)-Propranolol;Prestwick0_001081;Prestwick1_001081;Prestwick2_001081;Prestwick3_001075;Prestwick3_001081;(2S)-PROPRANOLOL;GTPL63;UNII-74MLR03FLC;SCHEMBL3956;PROPRANOLOL, (S)-;Lopac0_001023;BSPBio_001040;BSPBio_001090;BSPBio_001122;KBioGR_000380;KBioSS_000380;SPBio_003021;BPBio1_001200;BPBio1_001236;BCBcMAP01_000208;KBio2_000380;KBio2_002948;KBio2_005516;KBio3_000739;KBio3_000740;DTXSID90873366;Bio2_000360;Bio2_000840;HMS1362D21;HMS1792D21;HMS1990D21;HMS2089B07;BDBM50246936;MFCD00066276;PDSP1_000768;PDSP2_000756;AKOS040768709;CCG-205103;SDCCGSBI-0050996.P004;IDI1_002115;NCGC00024813-01;NCGC00024813-02;NCGC00024813-03;NCGC00024813-04;NCGC00024813-05;NCGC00024813-06;NCGC00024813-07;NCGC00024813-08;NCGC00024813-16;NCGC00024813-17;SBI-0050996.P003;LS-122524;AB00514695;AB00514695-07;AB00514695_08;A903061;BRD-K13994703-001-02-0;BRD-K13994703-003-04-2;BRD-K13994703-003-10-9;Q63390536;(2S)-1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol;S-(-)-1-ISOPROPYLAMINO-3-(1-NAPHTHOXY)-2-PROPANOL;1-((1-methylethyl)amino) 3-(1-naphthalenyloxy) 2-propanol;[2-Hydroxy-3-(naphthalen-1-yloxy)-propyl]-isopropyl-ammonium((-)-propranolol);2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-, (2S)-

Chemical Property of 1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol

Chemical Property:

• Vapor Pressure: 2.48E-08mmHg at 25°C
• Boiling Point: 434.9°C at 760 mmHg
• Flash Point: 216.8°C
• PSA: 41.49000
• Density: 1.093g/cm³
• LogP: 2.96840
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

(-)-PROPRANOLOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O
• Isomeric SMILES: CC(C)NC[C@@H](COC1=CC=CC2=CC=CC=C21)O

Technology Process of 1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol

There total 147 articles about 1-(Isopropylamino)-3-(1-naphthyloxy)-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: 95.0%

(S)-(+)-1-chloro-2-acetoxy-3-(1-naphthyloxy)propane (132076-77-8) + isopropylamine (75-31-0) → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2004.05.084

Reference yield: 93.0%

C26H41NO4Si (228704-16-3) → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo990272o

Reference yield: 90.0%

[(R)-2-Benzyloxy-3-(naphthalen-1-yloxy)-propyl]-isopropyl-amine → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 24h; Ambient temperature;

DOI:10.1016/0957-4166(96)00337-0

upstream raw materials:

(S)-3-(1-naphthyloxy)-1,2-propanediol

isopropylamine

(S)-propranolol O-acetyl ester

(S)-O-acetyl propranolol hydrochloride

Downstream raw materials:

(-)-Desisopropylpropranolol

(S)-(-)-propanolol hydrochloride

Refernces

• 1、 Ge, Li,Zhao, Qiongqiong,Yang, Kedi,Liu, Shishi,Xia, Fan. "Optical resolution and optimization of (R, S) - Propranolol using dehydroabietic acid via diastereomeric crystallization". . p. 131 - 136. Retrieved 2015.
• 2、 Katsuki, Tsutomu. "THE SYNTHESIS OF E-(2S,3S)-3-TRIMETHYLSILYLGLYCIDOL AND ITS CONVERSION TO (-)-PROPRANOLOL". . p. 2821 - 2822. Retrieved 1984.
• 3、 Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng. "Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC". . p. 168 - 184. Retrieved 2019/11/25.
• 4、 Zhao, Baojing,Li, Lan,Wang, Yuting,Zhou, Zhiming. "Preparation of polar group derivative β-cyclodextrin bonded hydride silica chiral stationary phases and their chromatography separation performances". . p. 643 - 649. Retrieved 2018/11/27.