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248886

Sigma-Aldrich

(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:
46032-98-8
Molecular Weight:
167.21
EC Number:
256-250-8
MDL number:
MFCD00069617
UNSPSC Code:
12352116
PubChem Substance ID:
24854958
NACRES:
NA.22

assay

98%

optical activity

[α]23/D −37°, c = 1 in 1 M HCl

mp

112-118 °C (lit.)

functional group

amine
hydroxyl
phenyl

SMILES string

N[C@H](CO)[C@H](O)c1ccccc1

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

InChI key

JUCGVCVPNPBJIG-RKDXNWHRSA-N

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.[1]
  • (S,S)-Reboxetine, a selective norepinephrine reuptake inhibitor (NRI).[2]
  • L-2-Mercaptosuccinic acid, used in the synthesis of polyester with mercapto group.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF9264
MKBW0340V
MKBQ6407V
MKBP7716V
MKBF5527V

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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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