ChemicalBook Product Catalog Chemical Reagents Organic reagents Tricyclic compound 1-Pyrenecarboxaldehyde

1-Pyrenecarboxaldehyde

Product Name1-Pyrenecarboxaldehyde
CAS3029-19-4
MFC17H10O
MW230.26
EINECS221-196-6
MOL File3029-19-4.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Description

1-Pyrenecarboxaldehyde (PCA) is a bifunctional molecule containing a pyrene moiety and an aldehyde group. PCA can serve as a reducing agent capable of replacing toxic hydrazine in the chemical reduction of graphene oxide (GO). Numerous PCA molecules can be adsorbed onto the GO surface via strong π–π stacking and hydrophobic interactions between the pyrene moiety and the graphite plane. This successfully removes most of the oxygen-containing groups (such as epoxy and alkoxy groups) from the GO, thereby restoring the conjugated structure and electrical conductivity of graphene[6].

Chemical Properties

Dark Yellow Solid

Uses

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

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.

Synthesis

24463-15-8

3029-19-4

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
[6] Yinjie Kuang. (2013). Synthesis of carboxylate-functionalized graphene nanosheets for high dispersion of platinum nanoparticles based on the reduction of graphene oxide via 1-pyrenecarboxaldehyde. Nanotechnology, 24 39, 395604. https://doi.org/10.1088/0957-4484/24/39/395604

1-Pyrenecarboxaldehyde

Chemical Properties

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MSDS

Usage And Synthesis

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