(S)-2-Hydroxypropyl benzoate

Base Information

• Chemical Name: (S)-2-Hydroxypropyl benzoate
• CAS No.: 141396-05-6
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• UNII: Y15C47H14D
• Nikkaji Number: J72.420C
• Wikidata: Q27294122
• Mol file: 141396-05-6.mol

Synonyms:(S)-2-Hydroxypropyl benzoate;141396-05-6;2-Hydroxypropyl benzoate, (S)-;Y15C47H14D;(2S)-1,2-Propanediol 1-benzoate;1,2-Propanediol, 1-benzoate, (S)-;J72.420C;UNII-Y15C47H14D;1,2-PROPANEDIOL, 1-BENZOATE, (2S)-;[(2S)-2-hydroxypropyl] benzoate;Q27294122

Chemical Property of (S)-2-Hydroxypropyl benzoate

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 180.078644241
• Heavy Atom Count: 13
• Complexity: 162

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(COC(=O)C1=CC=CC=C1)O
• Isomeric SMILES: C[C@@H](COC(=O)C1=CC=CC=C1)O

Technology Process of (S)-2-Hydroxypropyl benzoate

There total 6 articles about (S)-2-Hydroxypropyl benzoate 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: 92.0%

2-oxopropyl benzoate (6656-60-6) → (S)-1-O-benzoyl-1,2-dihydroxypropane (141396-05-6)

Guidance literature:

With glucose dehydrogenase; ketoreductase; NADPH; D-glucose; In dimethyl sulfoxide; at 34 ℃; for 13h; pH=6.8 - 6.9;

DOI:10.1016/j.tetasy.2005.10.002

Reference yield:

propylene glycol (57-55-6,63625-56-9) + benzaldehyde (100-52-7) → (S)-1,2-Propanediol (4254-15-3,63625-56-9) + (S)-1-O-benzoyl-1,2-dihydroxypropane (141396-05-6) + (2R)-propane-1,2-diol (4254-14-2,63625-56-9) + (R)-1-O-benzoyl-1,2-dihydroxypropane (103548-13-6)

Guidance literature:

With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; BF₄^(1-)*C₂₁H₂₄N₃O⁽¹⁺⁾; caesium carbonate; In tetrahydrofuran; at -5 ℃; for 20h; enantioselective reaction; Molecular sieve; Schlenk technique; Sealed tube; Inert atmosphere; Resolution of racemate;

DOI:10.1021/acs.orglett.8b01029

Reference yield:

propylene glycol (57-55-6,63625-56-9) + benzoyl chloride (98-88-4) → (S)-1-O-benzoyl-1,2-dihydroxypropane (141396-05-6) + [(1R)-2-hydroxy-1-methyl-ethyl]benzoate (113566-74-8) + (S)-1-hydroxypropan-2-yl benzoate (113566-73-7) + (R)-1-O-benzoyl-1,2-dihydroxypropane (103548-13-6)

Guidance literature:

With N-benzyl[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}methanamine; N-ethyl-N,N-diisopropylamine; copper(l) chloride; In dichloromethane; at -40 ℃; for 33h; optical yield given as %ee; Resolution of racemate; Inert atmosphere;

DOI:10.3987/COM-08-S(N)59

upstream raw materials:

2-oxopropyl benzoate

propylene glycol

vinyl benzoate

2-hydroxypropyl benzoate

Downstream raw materials:

(S)-1,2-Propanediol

Benzoic acid (S)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-propyl ester