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78917

Sigma-Aldrich

(R)-(+)-1-Phenyl-1,3-propanediol

≥99.0% (sum of enantiomers, GC)

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About This Item

Empirical Formula (Hill Notation):
C9H12O2
CAS Number:
103548-16-9
Molecular Weight:
152.19
Beilstein/REAXYS Number:
4741114
MDL number:
MFCD00145213
UNSPSC Code:
12352002
PubChem Substance ID:
57652761
NACRES:
NA.22

assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D +69±2°, c = 1% in chloroform

mp

62-66 °C

SMILES string

OCC[C@@H](O)c1ccccc1

InChI

1S/C9H12O2/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9-11H,6-7H2/t9-/m1/s1

InChI key

RRVFYOSEKOTFOG-SECBINFHSA-N

Application

(R)-(+)-1-Phenyl-1,3-propanediol can be used as a key intermediate:
  • For the enantioselective synthesis of (R)-fluoxetine, a potent serotonin reuptake inhibitor.[1]
  • To synthesize (S)-dapoxetine via Sharpless asymmetric epoxidation and Mitsunobu reaction.[2]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Chiral building block; e.g. synthesis of fluoxetine[3]; Equivalent of 2,4-dihydroxybutyric acid by oxidation with RuCl3/NaIO4[4]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM8964V
341653/1
1325572
1206797
1104706

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Simple and efficient synthesis of (S)-dapoxetine
Sasikumar M and Nikalje MD
Synthetic Communications, 42(20), 3061-3067 (2012)
A concise total synthesis of (R)-Fluoxetine, a potent and selective serotonin reuptake inhibitor
de Fatima, et al.
Journal of the Mexican Chemical Society, 49(2), 257-261 (2005)
F. Matsuura et al.
Tetrahedron, 49, 8211-8211 (1993)
R. Chenevert et al.
Tetrahedron, 48, 6769-6769 (1992)

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