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382035

Sigma-Aldrich

3-Benzyloxy-1-propanol

97%

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About This Item

Fórmula lineal:
C6H5CH2O(CH2)3OH
Número de CAS:
4799-68-2
Peso molecular:
166.22
Beilstein/REAXYS Number:
1864016
MDL number:
MFCD00029659
UNSPSC Code:
12352100
PubChem Substance ID:
24863859
NACRES:
NA.22

assay

97%

form

liquid

bp

111-114 °C/2 mmHg (lit.)

density

1.049 g/mL at 25 °C (lit.)

SMILES string

OCCCOCc1ccccc1

InChI

1S/C10H14O2/c11-7-4-8-12-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2

InChI key

FUCYABRIJPUVAT-UHFFFAOYSA-N

General description

3-Benzyloxy-1-propanol is an organic building block. It undergoes cleavage selectively at the C3-O position in the presence of ruthenium catalyst.

Application

3-Benzyloxy-1-propanol may be used as starting reagent in the total synthesis of (+)-cocaine. It may be used in the synthesis of a series of galactosyl phosphate diester derivatives of 9-β-D-arabinofuranosyladenine and 1-β-D-arabinofuranosylcytosine.
3-Benzyloxy-1-propanol may be used for the synthesis of 1-benzyloxy-3-iodopropane.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

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Asymmetric synthesis of (R)-and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters.
Mu?oz L, et al.
Tetrahedron Asymmetry, 20(4), 420-424 (2009)
Cheng Chen et al.
Organic letters, 14(12), 2992-2995 (2012-06-06)
The ruthenium catalyzed selective sp(3) C-O cleavage with amide formation was reported in reactions of 3-alkoxy-1-propanol derivatives and amines. The cleavage only occurs at the C3-O position even with 3-benzyloxy-1-propanol. Based on the experimental results, O-bound and C-bound Ru enolate
Synthesis of galactosyl phosphate diester derivatives of nucleosides.
T W Ma et al.
Carbohydrate research, 257(2), 323-330 (1994-05-05)
Douglas M Mans et al.
Organic letters, 6(19), 3305-3308 (2004-09-10)
[reaction: see text] The total synthesis of (+)-cocaine is described. An extension of the recently reported proline catalyzed intramolecular enol-exo-aldol reaction to a meso-dialdehyde provided the tropane ring skeleton directly with good enantiomeric excess. The meso-dialdehyde was prepared using a

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