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469602

Sigma-Aldrich

4-Benzyloxybutyric acid

95%

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About This Item

Linear Formula:
C6H5CH2O(CH2)3CO2H
CAS Number:
Molecular Weight:
194.23
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

refractive index

n20/D 1.512 (lit.)

bp

135 °C/0.3 mmHg (lit.)

density

1.097 g/mL at 25 °C (lit.)

functional group

carboxylic acid
ether
phenyl

SMILES string

OC(=O)CCCOCc1ccccc1

InChI

1S/C11H14O3/c12-11(13)7-4-8-14-9-10-5-2-1-3-6-10/h1-3,5-6H,4,7-9H2,(H,12,13)

InChI key

CXEFZVVLTJQWBF-UHFFFAOYSA-N

Related Categories

General description

4-Benzyloxybutyric acid can be synthesized from γ-butyrolactone. It participates in the asymmetric total synthesis of erythromycin.

Application

4-Benzyloxybutyric acid may be used in the synthesis of benzyloxybutyryl (BOB) esters of alcohols by standard acylation techniques or by the Jacobsen asymmetric nucleophilic ring opening of epoxides.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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

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Synthesis of tylonolide, the aglycone of tylosin.
Masamune S, et al.
Journal of the American Chemical Society, 104(20), 5523-5526 (1982)
What about BOB? A synthetically useful protecting group.
Clark MA and Ganem B.
Tetrahedron Letters, 41(49), 9523-9526 (2000)
Asymmetric total synthesis of erythromcin. 1. Synthesis of an erythronolide A secoacid derivative via asymmetric induction.
Woodward RB, et al.
Journal of the American Chemical Society, 103(11), 3210-3213 (1981)

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