| Identification | More | [Name]
1-Pyrenecarboxaldehyde | [CAS]
3029-19-4 | [Synonyms]
1-FORMYLPYRENE
1-PYRENECARBALDEHYDE
1-PYRENECARBOXALDEHYDE
PYRENE-1-CARBOXALDEHYDE
1-Pyrenealdehyde
3-Formylpyrene
3-Pyrenealdehyde
3-Pyrenecarboxaldehyde
3-Pyrenylaldehyde
4-Pyrenecarboxaldehyde
pyrene-1-aldehyde
NSC 30811
1-Pyrenaldehyde
Pyrenaldehyde | [EINECS(EC#)]
221-196-6 | [Molecular Formula]
C17H10O | [MDL Number]
MFCD00004139 | [Molecular Weight]
230.26 | [MOL File]
3029-19-4.mol |
| Chemical Properties | Back Directory | [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. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
yellow
| [Water Solubility ]
Insoluble in water. | [Sensitive ]
Air Sensitive | [Usage]
A novel base-discriminating fluorescent (BDF) compound: a highly polarity-sensitive fluorophore for SNP typing. | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [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 |
| Hazard Information | Back Directory | [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. | [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 |
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