1-Pyrenecarboxaldehyde Chemical Properties

Melting point:

123-126 °C (lit.)

Boiling point:

312.25°C (rough estimate)

Density 

1.1350 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

yellow

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

1874889

InChI

InChI=1S/C17H10O/c18-10-14-7-6-13-5-4-11-2-1-3-12-8-9-15(14)17(13)16(11)12/h1-10H

InChIKey

RCYFOPUXRMOLQM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3029-19-4(CAS DataBase Reference)

NIST Chemistry Reference

1-Pyrene-carboxaldehyde(3029-19-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UR2450200

F 

10

HS Code 

29122990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Pyrenecarboxaldehyde Usage And Synthesis

Chemical Properties

Dark Yellow Solid

Uses

1-Pyrenecarboxaldehyde is a important intermediate used in agrochemical, pharmaceutical and dyestuff field. It is used as a highly polarity-sensitive fluorophore for SNP typing.

Uses

A novel base-discriminating fluorescent (BDF) compound: a highly polarity-sensitive fluorophore for SNP typing.

Synthesis

General procedure for the synthesis of 1-pyrenecarboxaldehyde from 1-pyrenemethanol: To a round-bottom flask were added 1-pyrenemethanol (2 mmol), copper trifluoromethanesulfonate (CuOTf, 0.1 mmol, 0.05 eq.), (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 eq.), 2,2,6,6-tetramethylpiperidine-1-yloxy ( TEMPO, 0.1 mmol, 0.05 eq.), 4-dimethylaminopyridine (DMAP, 0.15 mmol, 0.075 eq.) and acetonitrile (CH3CN, 5 mL). The reaction mixture was stirred and exposed to air at 25 °C until the reaction was completed, and the progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the acetonitrile was removed by evaporation under vacuum. The residue was diluted with dichloromethane (CH2Cl2, 5 mL) and filtered through a silica gel plug to obtain the target product 1-pyrenecarboxaldehyde.

Purification Methods

Recrystallise the aldehyde three times from aqueous EtOH. [Beilstein 7 IV 1821.]

References

[1] Chemical Communications, 2003, # 6, p. 758 - 759
[2] Inorganic Chemistry, 2016, vol. 55, # 12, p. 6114 - 6123
[3] Inorganic Chemistry, 2017, vol. 56, # 22, p. 14084 - 14100
[4] Tetrahedron, 2014, vol. 70, # 52, p. 9791 - 9796
[5] Chemistry - A European Journal, 2016, vol. 22, # 26, p. 8814 - 8822

1-Pyrenecarboxaldehyde(3029-19-4)Related Product Information

• Formaldehyde
• Pyrene
• Paraformaldehyde
• Benzaldehyde
• Formaldehyde catching agent
• Vat Orange 9
• Vat Orange 2
• 1-(BROMOACETYL)PYRENE
• 4-OXO-4-PYREN-1-YL-BUTYRIC ACID
• 1-ACETYLPYRENE
• 1-Pyrenecarboxaldehyde, diphenylhydrazone,1-Pyrenecarboxaldehyde,diphenylhydrazone
• 1-PYRENECARBOXYLIC ACID
• 1-Pyrenecarboxaldehyde
• CYCLOPENTA[CD]PYREN-3(4H)-ONE
• pyrene-1-carbonylcyanide
• 6,14-dichloropyranthrene-8,16-dione
• PYRENACYL OKADAATE
• RARECHEM AL BF 0667