Skip to Content
Merck
All Photos(1)

Key Documents

460516

Sigma-Aldrich

Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate

96%

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
ClCH2CH(OH)CH2CO2C2H5
CAS Number:
Molecular Weight:
166.60
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

optical activity

[α]23/D +14°, neat

optical purity

ee: 97% (GLC)

refractive index

n20/D 1.453 (lit.)

bp

93-95 °C/5 mmHg (lit.)

density

1.19 g/mL at 25 °C (lit.)

functional group

chloro
ester
hydroxyl

SMILES string

CCOC(=O)C[C@@H](O)CCl

InChI

1S/C6H11ClO3/c1-2-10-6(9)3-5(8)4-7/h5,8H,2-4H2,1H3/t5-/m1/s1

InChI key

ZAJNMXDBJKCCAT-RXMQYKEDSA-N

Application

Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate is a chiral building block that can be used:
  • To prepare allyl stannane, a precursor for the total synthesis of macrolide iriomoteolide-1b.
  • As a starting material for the synthesis of a chiral g-αmino acid fragment, which in turn is used to prepare the immunosuppressive agent FR252921.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

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

Visit the Document Library

Enantioselective total synthesis of the proposed structure of macrolide iriomoteolide-1b
Ye Z, et al.
Tetrahedron, 67(33), 5979-5989 (2011)
A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants
Chen Y, et al.
Journal of the American Chemical Society, 141(35), 13772-13777 (2019)

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