Theobromine

An aromatic compound, C7H8N4O2, 180.167 g/mol. Boiling point Sublimes 290-295 °C, melting point 357 °C, as published.

verified recordOrganic — aromatic compound5 measured properties

Identifiers

Molecular formula: C₇H₈N₄O₂
Molecular weight: 180.167 g/mol
Exact mass: 180.064725 g/mol
IUPAC name: 3,7-dimethylpurine-2,6-dione
SMILES: Cn1cnc2c1c(=O)[nH]c(=O)n2C
InChI: InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: Sublimes at 554-563 °F (NTP, 1992)measured · CAMEO Chemicals; Sublimes 290-295 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: 675 °F (NTP, 1992)measured · CAMEO Chemicals; 357 °Cmeasured · DrugBank
Density: 1.522 g/cu cm at 20 °C; relative density: 1.522 at 20 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: less than 1 mg/mL at 64 °F (NTP, 1992)measured · CAMEO Chemicals; 330 mg/L (at 25 °C)measured · DrugBank
LogP: -0.78measured · DrugBank; log Kow = -0.78measured · Hazardous Substances Data Bank (HSDB)

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 180.16 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 180.06472551 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: -0.8calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 67.2 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 267calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 1calculated · reference compound database
H-bond acceptors: 3calculated · reference compound database
logP: -1.0397calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 72.68 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 1calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 5calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 46.5757 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.2857calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.5625calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon7 atoms · 46.7% by mass
N Nitrogen4 atoms · 31.1% by mass
O Oxygen2 atoms · 17.8% by mass
H Hydrogen8 atoms · 4.5% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 13
Total atoms, hydrogen included: 21
Rings: 2
Aromatic rings: 2
Stereocentres: 0
Formal charge: 0

Functional groups

Aromatic ring
A flat six-membered ring with delocalised electrons.
Aromatic ring (five-membered)
A flat five-membered ring with delocalised electrons, such as furan, thiophene or pyrrole.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Theobromine yet.

Other names for it

The systematic name on this record is 3,7-dimethylpurine-2,6-dione.

The sources also call it 3,7-Dimethylxanthine, Diurobromine, Theosalvose, Santheose, Teobromin, Theostene, 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione, Thesal, 3,7-dimethylpurine-2,6-dione, Xantheose, FEMA No. 3591.

Structurally related

Nothing structurally close to Theobromine has a page here yet.

Where these values came from

reference compound database5429
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.