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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
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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.
Signal Word
Danger
Hazard Statements
Precautionary 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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