Caffeine (data page)

Chemical properties
Hybrid skeletal structure of the caffeine molecule
Names
	IUPAC names 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione ; 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione; 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
Identifiers
CAS Number	58-08-2 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	17705
ChEBI	CHEBI:27732 ;
ChEMBL	ChEMBL113 ;
ChemSpider	2424 ;
DrugBank	DB00201 ;
EC Number	200-362-1;
Gmelin Reference	103040
IUPHAR/BPS	407;
KEGG	D00528 ;
PubChem CID	2519;
RTECS number	EV6475000;
UNII	3G6A5W338E ;
	InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key: RYYVLZVUVIJVGH-UHFFFAOYSA-N ; InChI=1/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key: RYYVLZVUVIJVGH-UHFFFAOYAW;
	SMILES O=C2N(c1ncn(c1C(=O)N2C)C)C; Cn1cnc2c1c(=O)n(c(=O)n2C)C;
Properties
Chemical formula	C8H10N4O2
Molar mass	194.194 g·mol−1
Appearance	Odorless, white needles or powder
Density	1.23 g/cm3, solid[1]
Melting point	227 to 228 °C (441 to 442 °F; 500 to 501 K) (anhydrous); 234 to 235 °C (453 to 455 °F; 507 to 508 K) (monohydrate)
Boiling point	178 °C (352 °F; 451 K) (sublimation)
Solubility in water	2.17 g/100 mL (25 °C); 18.0 g/100 mL (80 °C); 67.0 g/100 mL (100 °C)
Acidity (pKa)	−0.13–1.22[2]
Dipole moment	3.64 D (calculated)
Thermochemistry[3]
Std enthalpy of; formation (ΔfH⦵298)	α-phase: -345.1±2.3 kJ·mol−1; β-phase: -340.6±2.3 kJ·mol−1
Enthalpy of fusion (ΔfH⦵fus)	21.4±0.6 kJ·mol−1 at 504 K (231 °C; 448 °F)
Enthalpy of vaporization (ΔfHvap)	75.7±0.3 kJ·mol−1 at 504 K (231 °C; 448 °F)
Enthalpy of sublimation (ΔfHsublim)	α-phase: -108.1±1.1 kJ·mol−1; β-phase: -104.2±3.6 kJ·mol−1
Hazards
Safety data sheet	ICSC 0405
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)	2 0 0
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	192 mg/kg (rat, oral)[4]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

This page provides supplementary chemical data on caffeine.

References

Caffeine, International Occupational Safety and Health Information Centre (CIS)
This is the pK_a for protonated caffeine, given as a range of values included in Harry G. Brittain, Richard J. Prankerd (2007). Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of pK_a Values for Pharmaceutical Substances. Academic Press. ISBN 978-0-12-260833-9.
Emel’yanenko, Vladimir N.; Verevkin, Sergey P. (1 December 2008). "Thermodynamic properties of caffeine: Reconciliation of available experimental data". The Journal of Chemical Thermodynamics. 40 (12): 1661–1665. doi:10.1016/j.jct.2008.07.002.
Peters, Josef M. (1967). "Factors Affecting Caffeine Toxicity: A Review of the Literature". The Journal of Clinical Pharmacology and the Journal of New Drugs. 7 (3): 131–141. doi:10.1002/j.1552-4604.1967.tb00034.x. Archived from the original on 2008-06-10. Retrieved 2011-09-25.

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[1] Caffeine, International Occupational Safety and Health Information Centre (CIS)

[pKa-2] This is the pK_a for protonated caffeine, given as a range of values included in Harry G. Brittain, Richard J. Prankerd (2007). Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of pK_a Values for Pharmaceutical Substances. Academic Press. ISBN 978-0-12-260833-9.

[3] Emel’yanenko, Vladimir N.; Verevkin, Sergey P. (1 December 2008). "Thermodynamic properties of caffeine: Reconciliation of available experimental data". The Journal of Chemical Thermodynamics. 40 (12): 1661–1665. doi:10.1016/j.jct.2008.07.002.

[ld50-4] Peters, Josef M. (1967). "Factors Affecting Caffeine Toxicity: A Review of the Literature". The Journal of Clinical Pharmacology and the Journal of New Drugs. 7 (3): 131–141. doi:10.1002/j.1552-4604.1967.tb00034.x. Archived from the original on 2008-06-10. Retrieved 2011-09-25.