(R)-1-(4-bromophenyl)-2-fluoroethylamine

Base Information

• Chemical Name: (R)-1-(4-bromophenyl)-2-fluoroethylamine
• CAS No.: 1246567-36-1
• Molecular Formula: C₈H₉BrFN
• Molecular Weight: 218.069
• Mol file: 1246567-36-1.mol

Synonyms:(R)-1-(4-bromophenyl)-2-fluoroethylamine

Chemical Property of (R)-1-(4-bromophenyl)-2-fluoroethylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(4-bromophenyl)-2-fluoroethylamine

There total 4 articles about (R)-1-(4-bromophenyl)-2-fluoroethylamine 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: 39.0%

ethyl 2-methoxyacetate (3938-96-3) + (±)-1-(4-bromophenyl)-2-fluoro-ethanamine (1246567-29-2) → (R)-1-(4-bromophenyl)-2-fluoroethylamine (1246567-36-1) + (S)-N-(1-(4-bromophenyl)-2-fluoroethyl)-2-methoxyacetamide (1246567-50-9)

Guidance literature:

With immobilized Candida antarctica Lipase B; In hexane; at 60 ℃; for 6h; optical yield given as %ee; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.tet.2010.06.081

Reference yield:

(±)-1-(4-bromophenyl)-2-fluoro-ethanamine (1246567-29-2) → (S)-1-(4-bromophenyl)-2-fluoroethylamine (1246567-42-9) + (R)-1-(4-bromophenyl)-2-fluoroethylamine (1246567-36-1) + para-bromoacetophenone (99-90-1)

Guidance literature:

With pyridoxal 5'-phosphate; arthrobacter sp. transaminase; In aq. phosphate buffer; dimethyl sulfoxide; at 30 ℃; for 24h; pH=7.5; Enzymatic reaction;

DOI:10.1002/anie.201510554

Reference yield:

para-bromophenacyl bromide (99-73-0,132309-76-3) → (S)-1-(4-bromophenyl)-2-fluoroethylamine (1246567-42-9) + (R)-1-(4-bromophenyl)-2-fluoroethylamine (1246567-36-1) + para-bromoacetophenone (99-90-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium fluoride; zinc(II) fluoride / acetonitrile / 24 h / 100 °C

2: ammonium acetate; sodium cyanoborohydride / methanol / 24 h / 20 °C

3: arthrobacter sp. transaminase; pyridoxal 5'-phosphate / aq. phosphate buffer; dimethyl sulfoxide / 24 h / 30 °C / pH 7.5 / Enzymatic reaction

With potassium fluoride; zinc(II) fluoride; pyridoxal 5'-phosphate; arthrobacter sp. transaminase; ammonium acetate; sodium cyanoborohydride; In methanol; aq. phosphate buffer; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/anie.201510554

upstream raw materials:

ethyl 2-methoxyacetate

(±)-1-(4-bromophenyl)-2-fluoro-ethanamine

para-bromophenacyl bromide

1-(4-bromophenyl)-2-fluoroethan-1-one

Refernces

• 1、 Thvedt, Thor Hkon Krane,Fuglseth, Erik,Sundby, Eirik,Hoff, Brd Helge. "Enantioenriched 1-aryl-2-fluoroethylamines. Efficient lipase-catalysed resolution and limitations to the Mitsunobu inversion protocol". experimental part. p. 6733 - 6743. Retrieved 2010/09/30.