89095
(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:
Molecular Weight:
102.13
Beilstein:
79846
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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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.)
functional group
ether
hydroxyl
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.[1]
- As a starting material to synthesize naftidrofuryl isomers, used as potent 5-hydroxytryptamine 2A receptor antagonists.[2]
- As a building block for the preparation of (S)-2-tetrahydrofuran methyl ether 6-fluorophenyl ether analog, as an IGF-1R inhibitor.[3]
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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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
G Zarnt et al.
Journal of bacteriology, 183(6), 1954-1960 (2001-02-27)
The quinohemoprotein tetrahydrofurfuryl alcohol dehydrogenase (THFA-DH) from Ralstonia eutropha strain Bo was investigated for its catalytic properties. The apparent k(cat)/K(m) and K(i) values for several substrates were determined using ferricyanide as an artificial electron acceptor. The highest catalytic efficiency was
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