1-PYRENEMETHANOL Chemical Properties

Melting point:

123-126 °C (lit.)

Boiling point:

455.2±14.0 °C(Predicted)

Density 

1.321±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

14.36±0.10(Predicted)

color 

Pale Green to Yellow

InChI

InChI=1S/C17H12O/c18-10-14-7-6-13-5-4-11-2-1-3-12-8-9-15(14)17(13)16(11)12/h1-9,18H,10H2

InChIKey

NGDMLQSGYUCLDC-UHFFFAOYSA-N

SMILES

C1(CO)=C2C3=C4C(C=C2)=CC=CC4=CC=C3C=C1

CAS DataBase Reference

24463-15-8(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

WGK Germany 

3

RTECS 

UR2457242

HS Code 

29062990

MSDS

• Language:English Provider:SigmaAldrich

1-PYRENEMETHANOL Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

1-Pyrenemethanol (cas# 24463-15-8) is a compound useful in organic synthesis.

Uses

1-Pyrenemethanol can be used:

• For the synthesis of pincer-like benzene-bridged fluorescent selective sensor for adenosine-5′-triphosphate (ATP) detection.
• As a starting material for the synthesis of pyrene-end poly(glycidyl methacrylate) polymer.
• As an initiator for the synthesis of pyrene core star polymers.
• For the synthesis of 1-pyrenecarboxaldehyde, an important intermediate in pharmaceutical and agrochemical fields.

Synthesis

General procedure for the synthesis of 1-pyrenemethanol from 1-pyrenecarboxaldehyde: 1-pyrenecarboxaldehyde (1 g, 4.3 mmol) and dry tetrahydrofuran (20 mL) were placed in a round bottom flask. Sodium borohydride (165 mg, 4.3 mmol) was added in small portions and a small amount of methanol was added to promote dissolution (cumulative volume of methanol added was 10 mL) to obtain an orange solution. Upon completion of the reaction, the reaction was quenched with a 2% hydrochloric acid solution. Subsequently, the solvent was removed by distillation under reduced pressure. The resulting white powder was dissolved in dichloromethane, the organic phase was washed with water and dried with magnesium sulfate. The solvent was again removed by distillation under reduced pressure. Finally, the product was purified by silica gel column chromatography in 88% yield using dichloromethane as eluent. The structure of the product was confirmed by the following characterization: 1H NMR (300 MHz, CDCl3, 300K): δ (ppm) = 1.87 (s, 1H); 5.39 (s, 2H); 7.9-8.4 (m, 9H). 13C NMR {1H} (75 MHz, CDCl3, 300K): δ (ppm) = 64.03; 123.15 ; 124.87; 124.93; 125.13; 125.42; 125.45; 126.14; 126.19; 127.54; 127.63; 128.07; 128.97; 130.95; 131.42; 131.44; 133.94. ESI-MS: m/z = 254.97 [M + Na]+ , 214.99 [M-OH]+ (calculated values C17H12O: 232.09 (exact mass); 232.28 (molecular weight)).UV-Vis (DCM): λmax (nm) = 314; 327; 344.

References

[1] Molecules, 2011, vol. 16, # 8, p. 6950 - 6968
[2] Journal of the American Chemical Society,
[3] Journal of the American Chemical Society, 2008, vol. 130, p. 12846 - 12847
[4] Analytical Chemistry, 2018, vol. 90, # 2, p. 1402 - 1407
[5] Journal of Physical Chemistry A, 2003, vol. 107, # 40, p. 8363 - 8370

1-PYRENEMETHANOL(24463-15-8)Related Product Information

• 1-PYRENEMETHANOL
• Pyrene
• 1-(1-PYRENYL)ETHANOL
• 1-PYRENYLMETHYL METHACRYLATE
• BIS(1-PYRENYLMETHYL) ETHER
• BPDE-III
• 6-sulfooxymethylbenzo(a)pyrene
• 1-PYRENECARBOXYLIC ACID
• 9,10-dihydro-9,10-dihydroxybenzo(a)pyrene
• 6-(hydroxymethyl)benzo(a)pyrene
• benzo(a)pyrene 9,10-oxide
• 1-PYRENEMETHYL 3BETA-(CIS-9-OCTADECENOYLOXY)-22,23-BISNOR-5-CHOLENATE
• 1-PYRENEMETHYL IODOACETATE
• PYRENYLMETHYL OKADAATE
• RARECHEM AL BF 0667
• 3-Hydroxy-3,4-dihydrocyclopenta(cd)pyrene
• 6-acetoxymethylbenzo(a)pyrene
• 6-BENZOYLOXYMETHYLBENZO(A)PYRENE