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Sigma-Aldrich

(R)-Tetrahydrofurfuryl alcohol

≥98.0% (sum of enantiomers, GC)

Synonym(s):

(R)-Tetrahydrofuran-2-methanol

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About This Item

Empirical Formula (Hill Notation):
C5H10O2
CAS Number:
22415-59-4
Molecular Weight:
102.13
Beilstein:
79846
MDL number:
MFCD03093085
UNSPSC Code:
12352005
PubChem Substance ID:
57653325
NACRES:
NA.22

Assay

≥98.0% (sum of enantiomers, GC)

form

liquid

optical purity

enantiomeric ratio: ≥97:3% (GC)

bp

178 °C (lit.)

density

1.054 g/mL at 20 °C (lit.)

SMILES string

OC[C@H]1CCCO1

InChI

1S/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2/t5-/m1/s1

InChI key

BSYVTEYKTMYBMK-RXMQYKEDSA-N

Application

(R)-Tetrahydrofurfuryl alcohol can be used:
  • To prepare (R)-tetrahydrofurfuryl aldehyde, which is employed as a building block to synthesize a fragment of pectenotoxin-4.
  • As a starting material to synthesize naftidrofuryl isomers, used as potent 5-hydroxytryptamine 2A receptor antagonists.
  • As a building block for the preparation of (S)-2-tetrahydrofuran methyl ether 6-fluorophenyl ether analog, as an IGF-1R inhibitor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor
Hao J, et al.
Bioorganic & Medicinal Chemistry Letters, 22(10), 3441-3444 (2012)
Rhodium-catalysed vinyl 1, 4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
Richardson MSW, et al.
Chemical Science, 10(25), 6336-6340 (2019)
Optimisation of a 5-[3-phenyl-(2-cyclic-ether)-methyl-ether]-4-aminopyrrolopyrimidine series of IGF-1R inhibitors
Fairhurst RA, et al.
Bioorganic & medicinal chemistry letters, 26(8), 2057-2064 (2016)
S M Bellm et al.
The Journal of chemical physics, 136(24), 244301-244301 (2012-07-05)
Cross section data for electron scattering from DNA are important for modelling radiation damage in biological systems. Triply differential cross sections for the electron impact ionization of the highest occupied outer valence orbital of tetrahydrofurfuryl alcohol, which can be considered
T Schräder et al.
Journal of bacteriology, 183(24), 7408-7411 (2001-11-22)
Different aldehyde dehydrogenases (AlDHs) were formed during growth of Ralstonia eutropha Bo on tetrahydrofurfuryl alcohol (THFA). One of these enzymes, AlDH 4, was purified and characterized as a homodimer containing no prosthetic groups, showing a strong substrate inhibition, and having
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