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Merck
CN

270148

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

99%

Synonym(s):

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

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About This Item

Linear Formula:
HOCH2CH(CH3)CO2CH3
CAS Number:
72657-23-9
Molecular Weight:
118.13
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
24856357
MDL number:
MFCD00063450
Beilstein/REAXYS Number:
3587507
Assay:
99%
Form:
liquid

Key Documents

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InChI

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

SMILES string

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

InChI key

ATCCIZURPPEVIZ-SCSAIBSYSA-N

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.)

functional group

ester, hydroxyl

Quality Level

200

Related Categories

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

3 - Flammable liquids

wgk

WGK 3

flash_point_f

176.0 °F - closed cup

flash_point_c

80 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL4024
MKCK4748
MKCJ8958
1450439V
MKBJ7268V

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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)
Recent progress in the chemistry of the Stemona alkaloids.
Pilli RA and de Oliveira MDCF.
Natural Product Reports, 17(1), 117-127 (2000)
Total Synthesis of (-)-Stemospironine.
Williams DR, et al.
Organic Letters, 3(17), 2721-2724 (2001)
Journal of the Chemical Society. Perkin Transactions 1, 759-759 (1993)
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