(2R,3R)-(+)-2,3-Epoxy-3-(4-bromophenyl)-1-propanol

Base Information

• Chemical Name: (2R,3R)-(+)-2,3-Epoxy-3-(4-bromophenyl)-1-propanol
• CAS No.: 115362-13-5
• Molecular Formula: C9H9 Br O2
• Molecular Weight: 229.073
• DSSTox Substance ID: DTXSID401262154
• Nikkaji Number: J413.986K
• Mol file: 115362-13-5.mol

Synonyms:(2R,3R)-(+)-2,3-Epoxy-3-(4-bromophenyl)-1-propanol;115362-13-5;BRN 5258931;3-(4-Bromophenyl)oxiranemethanol (2R-trans)-;[(2R,3S)-3-(4-bromophenyl)oxiran-2-yl]methanol;Oxiranemethanol, 3-(4-bromophenyl)-, (2R-trans)-;SCHEMBL8897358;DTXSID401262154;LS-101056;(2R,3R)-3-(4-Bromophenyl)-2-oxiranemethanol;(2R,3R)-3-(4-Bromophenyl)oxirane-2-methanol

Chemical Property of (2R,3R)-(+)-2,3-Epoxy-3-(4-bromophenyl)-1-propanol

Chemical Property:

• Vapor Pressure: 8.08E-05mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• Boiling Point: 327.6°Cat760mmHg
• Flash Point: 151.9°C
• PSA: 32.76000
• Density: 1.599g/cm³
• LogP: 1.88130
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 227.97859
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2C(O2)CO)Br
• Isomeric SMILES: C1=CC(=CC=C1[C@@H]2[C@H](O2)CO)Br

Technology Process of (2R,3R)-(+)-2,3-Epoxy-3-(4-bromophenyl)-1-propanol

There total 7 articles about (2R,3R)-(+)-2,3-Epoxy-3-(4-bromophenyl)-1-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: 79.0%

(2E)-3-(4-bromophenyl)prop-2-en-1-ol (105515-33-1) → [(2R,3R)-3-(4-bromophenyl)oxiran-2-yl]methanol (115362-13-5)

Guidance literature:

With tert.-butylhydroperoxide; titanium(III) triisopropoxide; D-(-)-diisopropyl tartrate; In hexane; dichloromethane; Molecular sieve; Inert atmosphere;

DOI:10.1039/b802819b

Reference yield:

3-(4-bromophenyl)oxirane-2-carbaldehyde → [(2R,3R)-3-(4-bromophenyl)oxiran-2-yl]methanol (115362-13-5) + [(2S,3S)-3-(4-bromophenyl)oxiran-2-yl]methanol (106948-05-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2016.02.009

Reference yield:

(2S,3R)-3-(4-bromophenyl)oxirane-2-carbaldehyde (1020746-20-6) → [(2R,3R)-3-(4-bromophenyl)oxiran-2-yl]methanol (115362-13-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; chloroform; at 0 ℃;

DOI:10.1055/s-2006-956488

upstream raw materials:

(2S,3R)-3-(4-bromophenyl)oxirane-2-carbaldehyde

trans-4-bromocinnamaldehyde

(2E)-3-(4-bromophenyl)prop-2-en-1-ol

4-bromocinnamaldeyde

Downstream raw materials:

(2R,3S)-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propane-1,2-diol

Refernces

• 1、 Xu, Ming-Hui,Tu, Yong-Qiang,Tian, Jin-Miao,Zhang, Fu-Min,Wang, Shao-Hua,Zhang, Shi-Heng,Zhang, Xiao-Ming. "Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst". supporting information. p. 294 - 300. Retrieved 2017/03/01.
• 2、 Jobson, Nicola K.,Spike, Rosemary,Crawford, Andrew R.,Dewar, Deborah,Pimlott, Sally L.,Sutherland, Andrew. "Stereoselective synthesis of (2S,3R)- and (2R,3S)-iodoreboxetine; Potential SPECT imaging agents for the noradrenaline transporter". experimental part. p. 2369 - 2376. Retrieved 2009/02/02.