Skip to Content
Merck
All Photos(1)

Documents

361887

Sigma-Aldrich

(1S,2S)-(+)-Thiomicamine

99%

Synonym(s):

(1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol

Sign Into View Organizational & Contract Pricing


About This Item

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

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service