Pyrene information

Pyrene
Names
	Preferred IUPAC name Pyrene
	Other names Benzo[def]phenanthrene
Identifiers
CAS Number	129-00-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1307225
ChEBI	CHEBI:39106 ;
ChEMBL	ChEMBL279564 ;
ChemSpider	29153 ;
ECHA InfoCard	100.004.481
Gmelin Reference	84203
KEGG	C14335 ;
PubChem CID	31423;
RTECS number	UR2450000;
UNII	9E0T7WFW93 ;
CompTox Dashboard (EPA)	DTXSID3024289 ;
	InChI InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H Key: BBEAQIROQSPTKN-UHFFFAOYSA-N ; InChI=1/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H Key: BBEAQIROQSPTKN-UHFFFAOYAB;
	SMILES c1cc2cccc3c2c4c1cccc4cc3;
Properties
Chemical formula	C16H10
Molar mass	202.256 g·mol−1
Appearance	colorless solid (yellow impurities are often found at trace levels in many samples).
Density	1.271 g/cm3
Melting point	150.62 °C (303.12 °F; 423.77 K)
Boiling point	394 °C (741 °F; 667 K)
Solubility in water	0.049 mg/L (0 °C); 0.139 mg/L (25 °C); 2.31 mg/L (75 °C)
log P	5.08
Band gap	2.02 eV
Magnetic susceptibility (χ)	-147·10−6 cm3/mol
Structure
Crystal structure	Monoclinic
Space group	P21/a
Lattice constant	a = 13.64 Å, b = 9.25 Å, c = 8.47 Å α = 90°, β = 100.28°, γ = 90°
Formula units (Z)	4
Thermochemistry
Heat capacity (C)	229.7 J/(K·mol)
Std molar; entropy (S⦵298)	224.9 J·mol−1·K−1
Std enthalpy of; formation (ΔfH⦵298)	125.5 kJ·mol−1
Enthalpy of fusion (ΔfH⦵fus)	17.36 kJ·mol−1
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	irritant
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H410
Precautionary statements	P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 1 0
Flash point	non-flammable
Related compounds
Related PAHs	benzopyrene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C₁₆H₁₀. This yellow-green solid is the smallest peri-fused PAH (one where the rings are fused through more than one face). Pyrene forms during incomplete combustion of organic compounds.^[10]

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 206. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ ^a ^b ^c Haynes, p. 3.472
^ Haynes, p. 5.162
^ Haynes, p. 5.176
^ Haynes, p. 12.96
^ Haynes, p. 3.579
^ Camerman, A.; Trotter, J. (1965). "The crystal and molecular structure of pyrene". Acta Crystallographica. 18 (4): 636–643. doi:10.1107/S0365110X65001494.
^ Haynes, pp. 5.34, 6.161
^ GHS: PubChem
^ Figueira-Duarte, Teresa M.; Müllen, Klaus (2011). "Pyrene-Based Materials for Organic Electronics". Chemical Reviews. 111 (11): 7260–7314. doi:10.1021/cr100428a. PMID 21740071.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 206. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[crc-2] Haynes, p. 3.472

[3] Haynes, p. 5.162

[4] Haynes, p. 5.176

[5] Haynes, p. 12.96

[6] Haynes, p. 3.579

[7] Camerman, A.; Trotter, J. (1965). "The crystal and molecular structure of pyrene". Acta Crystallographica. 18 (4): 636–643. doi:10.1107/S0365110X65001494.

[8] Haynes, pp. 5.34, 6.161

[9] GHS: PubChem

[10] Figueira-Duarte, Teresa M.; Müllen, Klaus (2011). "Pyrene-Based Materials for Organic Electronics". Chemical Reviews. 111 (11): 7260–7314. doi:10.1021/cr100428a. PMID 21740071.

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Names



Preferred IUPAC name Pyrene^[1]
Other names Benzo[def]phenanthrene
Identifiers
CAS Number	129-00-0^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1307225
ChEBI	CHEBI:39106^Y
ChEMBL	ChEMBL279564^Y
ChemSpider	29153^Y
ECHA InfoCard	100.004.481
Gmelin Reference	84203
KEGG	C14335^Y
PubChem CID	31423
RTECS number	UR2450000
UNII	9E0T7WFW93^Y
CompTox Dashboard (EPA)	DTXSID3024289
InChI InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H^Y Key: BBEAQIROQSPTKN-UHFFFAOYSA-N^Y InChI=1/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H Key: BBEAQIROQSPTKN-UHFFFAOYAB
SMILES c1cc2cccc3c2c4c1cccc4cc3
Properties
Chemical formula	C₁₆H₁₀
Molar mass	202.256 g·mol⁻¹
Appearance	colorless solid (yellow impurities are often found at trace levels in many samples).
Density	1.271 g/cm³^[2]
Melting point	150.62 °C (303.12 °F; 423.77 K)^[2]
Boiling point	394 °C (741 °F; 667 K)^[2]
Solubility in water	0.049 mg/L (0 °C) 0.139 mg/L (25 °C) 2.31 mg/L (75 °C)^[3]
log P	5.08^[4]
Band gap	2.02 eV^[5]
Magnetic susceptibility (χ)	-147·10⁻⁶ cm³/mol^[6]
Structure^[7]
Crystal structure	Monoclinic
Space group	P2₁/a
Lattice constant	a = 13.64 Å, b = 9.25 Å, c = 8.47 Å α = 90°, β = 100.28°, γ = 90°
Formula units (Z)	4
Thermochemistry^[8]
Heat capacity (C)	229.7 J/(K·mol)
Std molar entropy (S^⦵₂₉₈)	224.9 J·mol⁻¹·K⁻¹
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	125.5 kJ·mol⁻¹
Enthalpy of fusion (Δ_fH^⦵_fus)	17.36 kJ·mol⁻¹
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	irritant
GHS labelling:^[9]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H410
Precautionary statements	P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 1 0
Flash point	non-flammable
Related compounds
Related PAHs	benzopyrene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references