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89095

Sigma-Aldrich

(R)-Tetrahydrofurfuryl alcohol

≥98.0% (sum of enantiomers, GC)

Sinonimo/i:

(R)-Tetrahydrofuran-2-methanol

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About This Item

Formula empirica (notazione di Hill):
C5H10O2
Numero CAS:
22415-59-4
Peso molecolare:
102.13
Beilstein:
79846
Numero MDL:
MFCD03093085
Codice UNSPSC:
12352005
ID PubChem:
57653325
NACRES:
NA.22

Saggio

≥98.0% (sum of enantiomers, GC)

Forma fisica

liquid

Purezza ottica

enantiomeric ratio: ≥97:3% (GC)

P. eboll.

178 °C (lit.)

Densità

1.054 g/mL at 20 °C (lit.)

Stringa SMILE

OC[C@H]1CCCO1

InChI

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

Applicazioni

(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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H319

Classi di pericolo

Eye Irrit. 2

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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)
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)
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)
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
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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