4-[2-(Cyclopropylmethoxy)ethyl]phenol

Base Information

• Chemical Name: 4-[2-(Cyclopropylmethoxy)ethyl]phenol
• CAS No.: 63659-16-5
• Molecular Formula: C12H16O2
• Molecular Weight: 192.258
• Hs Code.: 2909500000
• European Community (EC) Number: 440-910-9,613-309-6,917-869-5
• UNII: QU56QY6BBB
• DSSTox Substance ID: DTXSID20453413
• Nikkaji Number: J2.562.992B
• Wikidata: Q82274550
• Mol file: 63659-16-5.mol

Synonyms:4-[2-(cyclopropylmethoxy)ethyl]phenol;63659-16-5;4-(2-(Cyclopropylmethoxy)ethyl)phenol;QU56QY6BBB;Phenol, 4-(2-(cyclopropylmethoxy)ethyl)-;Betaxolol Imp. D (EP);UNII-QU56QY6BBB;SCHEMBL3434728;DTXSID20453413;WNEQFDSWDCYKOE-UHFFFAOYSA-N;MFCD07787504;AKOS015951045;Betaxolol hydrochloride impurity D [EP];4-[(2-Cyclopropylmethoxy)-ethyl]-phenol;AC-30589;CS-0360023;FT-0665393;A1-17884;BETAXOLOL HYDROCHLORIDE IMPURITY D [EP IMPURITY];Betaxolol Hydrochloride Imp. D (EP);4-[2-(Cyclopropylmethoxy)ethyl]phenol;Betaxolol Hydrochloride Impurity D;Betaxolol Impurity D

Chemical Property of 4-[2-(Cyclopropylmethoxy)ethyl]phenol

Chemical Property:

• Appearance/Colour: Colourless oil
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.56
• Boiling Point: 304.439 °C at 760 mmHg
• PKA: 10.01±0.15(Predicted)
• Flash Point: 129.347 °C
• PSA: 29.46000
• Density: 1.112 g/cm³
• LogP: 2.36130
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 192.115029749
• Heavy Atom Count: 14
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

4-[2-(Cyclopropylmethoxy)ethyl]phenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1COCCC2=CC=C(C=C2)O
• Uses: An intermediate for the synthesis of Betaxolol 4-[2-(Cyclopropylmethoxy)ethyl]phenol (Betaxolol EP Impurity D) is an intermediate for the synthesis of Betaxolol.

Technology Process of 4-[2-(Cyclopropylmethoxy)ethyl]phenol

There total 10 articles about 4-[2-(Cyclopropylmethoxy)ethyl]phenol 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: 86.0%

1-benzyloxy-4-(2-cyclopropylmethoxyethyl)benzene (63659-15-4) → 4-[2-(cyclopropylmethoxy)-ethyl]-phenol (63659-16-5)

Guidance literature:

With hydrogen; nickel; In methanol; for 5h; under 3361.46 Torr;

DOI:10.1016/j.tetasy.2005.10.028

Reference yield: 50.0%

para-[2-(cyclopropylmethoxy)ethyl] aniline (890704-23-1) → 4-[2-(cyclopropylmethoxy)-ethyl]-phenol (63659-16-5)

Guidance literature:

With sulfuric acid; urea; sodium nitrite; In water; for 1h; Heating;

DOI:10.1021/jo0602367

Reference yield:

4-chlorobenzonitrile (100-00-5) → 4-[2-(cyclopropylmethoxy)-ethyl]-phenol (63659-16-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / [(t-Bu)3PH]BF₄; Cy₂NMe / Herrmann's palladacycle / dimethylformamide; H₂O / 1 h / 160 °C / microwave irradiation

2: 79 percent / ammonium formate / Pd on carbon / ethanol / 0.67 h / 80 °C / microwave irradiation

3: 50 percent / H₂SO₄; sodium nitrite; urea / H₂O / 1 h / Heating

With sulfuric acid; N-Methyldicyclohexylamine; ammonium formate; urea; tri tert-butylphosphoniumtetrafluoroborate; sodium nitrite; palladium on activated charcoal; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); In ethanol; water; N,N-dimethyl-formamide; 1: Heck reaction;

DOI:10.1021/jo0602367

upstream raw materials:

1-benzyloxy-4-(2-cyclopropylmethoxyethyl)benzene

para-[2-(cyclopropylmethoxy)ethyl] aniline

cyclopropylmethyl vinyl ether

1-(2-cyclopropylmethoxyethenyl)-4-nitrobenzene

Downstream raw materials:

(5S)-5-(4-((2-cyclopropylmethoxy)ethyl)phenoxy)methyl-3-isopropyl-2-phenyloxazolidine

(2S)-N-benzyl-3-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-2-hydroxypropylamine

1-[2-(cyclopropyl-methoxy)-ethyl]-4-(2,3-epoxypropoxy)-benzene

(R)-(+)-3-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-1,2-propanodiol acetonide

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF S-(-)-BETAXOLOL AND SALTS THEREOF". Page/Page column 3-5. . Retrieved 2010/02/15.
• 2、 Joshi, Ramesh A.,Garud, Dinesh R.,Muthukrishnan,Joshi, Rohini R.,Gurjar. "A convenient synthesis of the enantiomerically pure β-blocker (S)-betaxolol using hydrolytic kinetic resolution". . p. 3802 - 3806. Retrieved 2007/10/03.