248886
(1R,2R)-(−)-2-Amino-1-phenyl-1,3-propanediol
98%
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About This Item
Linear Formula:
C6H5CH(OH)CH(NH2)CH2OH
CAS Number:
Molecular Weight:
167.21
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352116
EC Number:
256-250-8
MDL number:
Product Name
(1R,2R)-(−)-2-Amino-1-phenyl-1,3-propanediol, 98%
InChI key
JUCGVCVPNPBJIG-RKDXNWHRSA-N
InChI
1S/C9H13NO2/c10-8(6-11)9(12)7-4-2-1-3-5-7/h1-5,8-9,11-12H,6,10H2/t8-,9-/m1/s1
SMILES string
N[C@H](CO)[C@H](O)c1ccccc1
assay
98%
optical activity
[α]23/D −37°, c = 1 in 1 M HCl
mp
112-118 °C (lit.)
functional group
amine
hydroxyl
phenyl
Application
(1R,2R)-(−)-2-Amino-1-phenyl-1,3-propanediol can be used as a starting material to prepare:
- Diaryl sulfides, used to synthesize sulfimides and N-tosylsulfimides, applicable as chiral ligands.
- (S,S)-Reboxetine, a selective norepinephrine reuptake inhibitor (NRI).
- L-2-Mercaptosuccinic acid, used in the synthesis of polyester with mercapto group.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Syntheses of (S,S)-reboxetine via a catalytic stereospecific rearrangement of beta-amino alcohols
Metro T, et al.
The Journal of Organic Chemistry, 73(2), 707-710 (2008)
Direct enzymatic synthesis of a polyester with free pendant mercapto groups
Kato M, et al.
Biomacromolecules, 10(2), 366-373 (2009)
H Takada et al.
Chirality, 12(5-6), 299-312 (2000-05-29)
The copper-catalyzed diastereoselective imidation of diaryl sulfides bearing a chiral oxazolinyl moiety at the ortho-position with [N-(p-toluenesulfonyl) imino]phenyliodinane (TsN=IPh) or Chloramine-T trihydrate [TsN(Cl)Na.3H2O] was successfully carried out to give the corresponding optically active N-tosylsulfimides in good yields. For example, the
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