All Photos(1)
Synonym(s):
(1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol
Linear Formula:
4-(CH3S)C6H4CH(OH)CH(NH2)CH2OH
CAS Number:
Molecular Weight:
213.30
EC Number:
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
![(+)-Bis[(R)-1-phenylethyl]amine 99%](/deepweb/assets/sigmaaldrich/product/structures/188/828/177cd49c-056f-47d3-976c-c8cdcd5f62c5/640/177cd49c-056f-47d3-976c-c8cdcd5f62c5.png)
Assay
99%
optical activity
[α]25/D +25°, c = 1 in ethanol
mp
151-154 °C (lit.)
SMILES string
CSc1ccc(cc1)[C@H](O)[C@@H](N)CO
InChI
1S/C10H15NO2S/c1-14-8-4-2-7(3-5-8)10(13)9(11)6-12/h2-5,9-10,12-13H,6,11H2,1H3/t9-,10-/m0/s1
InChI key
IULJJGJXIGQINK-UWVGGRQHSA-N
Application
(1S,2S)-(+)-Thiomicamine can be used:
- As a starting material in the synthesis of 3,4-dihydroisoquinolinium salts, which are employed as promoters in asymmetric epoxidation and oxidation reactions.
- As a starting material in the synthesis of an α-amino acid named (3R,4R)-4-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, which is used to prepare modified peptides of biological importance.
- As a chiral base in the resolution of an angiotensin II type 2 receptor [AT2R] antagonist named EMA401.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Transformation of (+)-thiomicamine into chiral non-racemic 3, 4-dihydroisoquinolinium salts: application for catalytic asymmetric epoxidation of alkenes and oxidation of sulfides
Gluszynska A, et al.
Tetrahedron Asymmetry, 15(16), 2499-2505 (2004)
Stereoselective synthesis of 3-mono-and 1, 3-disubstituted 4-phenyl-1, 2, 3, 4-tetrahydroisoquinolines
Brozda D, et al.
Tetrahedron Asymmetry, 11(14), 3017-3025 (2000)
Synthesis of enantiopure angiotensin II type 2 receptor [AT2R] antagonist EMA401
Wakchaure PB, et al.
Tetrahedron, 71(38), 6881-6887 (2015)
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