Skip to Content
Merck
All Photos(1)

Key Documents

270148

Sigma-Aldrich

Methyl (R)-(−)-3-hydroxy-2-methylpropionate

99%

Synonym(s):

(−)-Methyl D-β-hydroxyisobutyrate, (R)-(−)-3-Hydroxy-2-methylpropionic acid methyl ester

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
HOCH2CH(CH3)CO2CH3
CAS Number:
Molecular Weight:
118.13
Beilstein:
3587507
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

liquid

optical activity

[α]19/D −26°, c = 4 in methanol

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.425 (lit.)

bp

76-77 °C/12 mmHg (lit.)

density

1.066 g/mL at 25 °C (lit.)

SMILES string

COC(=O)[C@H](C)CO

InChI

1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1

InChI key

ATCCIZURPPEVIZ-SCSAIBSYSA-N

Application

Methyl (R)-(-)-3-hydroxy-2-methylpropionate may be used in the preparation of (S)-(4-benzyloxy-3-methylbut-1-ynyl)triethylsilane. It may also be used as a starting material in the total synthesis of (-)-discodermolide, (-)-stemoamide and (-)-stemospironine.
The (R)- and (S)-isomers are bifunctional building blocks for the synthesis of a wide variety of optically active molecules.

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

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

Customers Also Viewed

Journal of the Chemical Society. Perkin Transactions 1, 759-759 (1993)
A convergent synthesis of (S)-?-methyl-2-aryltryptamine based gonadotropin releasing hormone antagonists.
Walsh TF, et al.
Tetrahedron, 57(24), 5233-5241 (2001)
Total Synthesis of (-)-Stemospironine.
Williams DR, et al.
Organic Letters, 3(17), 2721-2724 (2001)
Distinct binding and cellular properties of synthetic (+)-and (-)-discodermolides.
Hung DT, et al.
Chemistry & Biology, 1(1), 67-71 (1994)
Tetrahedron Letters, 34, 5939-5939 (1993)

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