(S)-5-methoxychroman-3-amine

Base Information

• Chemical Name: (S)-5-methoxychroman-3-amine
• CAS No.: 117422-50-1
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID50441686
• Nikkaji Number: J1.624.344B
• Wikidata: Q82258563
• Mol file: 117422-50-1.mol

Synonyms:(S)-5-methoxychroman-3-amine;117422-50-1;(3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine;(3S)-5-methoxy-3,4-dihydro-2H-chromen-3-amine;SCHEMBL873500;2H-1-Benzopyran-3-amine, 3,4-dihydro-5-methoxy-, (S)-;DTXSID50441686;CS-0441680;(S)-3,4-Dihydro-5-methoxy-2H-1-benzopyran-3beta-amine

Chemical Property of (S)-5-methoxychroman-3-amine

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.545
• Boiling Point: 308.692°C at 760 mmHg
• PKA: 7.88±0.20(Predicted)
• Flash Point: 153.316°C
• PSA: 44.48000
• Density: 1.128g/cm³
• LogP: 1.65770
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 174

Purity/Quality:

98%min ^*data from raw suppliers

(S)-5-METHOXYCHROMAN-3-AMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1CC(CO2)N
• Isomeric SMILES: COC1=CC=CC2=C1C[C@@H](CO2)N

Technology Process of (S)-5-methoxychroman-3-amine

There total 8 articles about (S)-5-methoxychroman-3-amine 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:

1-methoxy-3-(methoxymethoxy)benzene (57234-28-3) → (3S)-3-amino-5-methoxy-3,4-dihydro-2H-1-benzopyran (117422-50-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / diethyl ether; hexane / 2 h / Heating

1.2: diethyl ether / 0.25 h / Heating

2.1: tetrahydrofuran / 26 h / Heating

3.1: Bu₃SnH; AIBN / toluene / 18 h / Heating

4.1: TMSBr / CH₂Cl₂ / 2 h / -30 °C

5.1: Ph₃P; DEAD / toluene / 1 h / 80 °C

6.1: TFA / CH₂Cl₂ / 9 h / 20 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylsilyl bromide; tri-n-butyl-tin hydride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1016/S0957-4166(01)00202-6

Reference yield:

(5-methoxy-chroman-3-yl)-carbamic acid tert-butyl ester → (3S)-3-amino-5-methoxy-3,4-dihydro-2H-1-benzopyran (117422-50-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 9h;

DOI:10.1016/S0957-4166(01)00202-6

Reference yield:

[2-(2-hydroxy-6-methoxy-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester → (3S)-3-amino-5-methoxy-3,4-dihydro-2H-1-benzopyran (117422-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Ph₃P; DEAD / toluene / 1 h / 80 °C

2: TFA / CH₂Cl₂ / 9 h / 20 °C

With triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In dichloromethane; toluene;

DOI:10.1016/S0957-4166(01)00202-6

upstream raw materials:

(R)-3-amino-5-methoxy-3,4dihydro-2H-1-benzopyran

1-methoxy-3-(methoxymethoxy)benzene

Downstream raw materials:

(3S)-N,N-dibenzyl-5-pyridin-2-ylchroman-3-amine

(3S)-N,N-dibenzyl-5-(4-methylpiperazin-1-yl)chroman-3-amine

(3S)-3-(dibenzylamino)chroman-5-ol

(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Refernces

• 1、 Hatzenbuhler, Nicole T.,Baudy, Reinhardt,Evrard, Deborah A.,Failli, Amedeo,Harrison, Boyd L.,Lenicek, Steven,Mewshaw, Richard E.,Saab, Annmarie,Shah, Uresh,Sze, Jean,Zhang, Minsheng,Zhou, Dahui,Chlenov, Michael,Kagan, Michael,Golembieski, Jeannette,Hornby, Geoffrey,Lai, Margaret,Smith, Deborah L.,Sullivan, Kelly M.,Schechter, Lee E.,Andree, Terrance H.. "Advances toward new antidepressants with dual serotonin transporter and 5-HT1A receptor affinity within a class of 3-aminochroman derivatives. Part 2". scheme or table. p. 6980 - 7004. Retrieved 2009/11/30.