2-Aminopyridine

An aromatic amine, C5H6N2, 94.117 g/mol. Boiling point 210.6 °C, melting point 58.1 °C, as published. Appears in 1 documented reaction.

verified recordOrganic — aromatic amine7 measured properties1 documented reactions

Identifiers

Molecular formula: C₅H₆N₂
Molecular weight: 94.117 g/mol
Exact mass: 94.053098 g/mol
IUPAC name: pyridin-2-amine
SMILES: Nc1ccccn1
InChI: InChI=1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
InChIKey: ICSNLGPSRYBMBD-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: 399 to 410 °F at 760 mmHg (NTP, 1992)measured · CAMEO Chemicals; 210.6 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: 138 to 140 °F (NTP, 1992)measured · CAMEO Chemicals; 58.1 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.065 @ 20 °C/4 °Cmeasured · Hazardous Substances Data Bank (HSDB); 1.07 @25 °Cmeasured · PAC Chemical Database, U.S. Department of Energy
Solubility: 10 to 50 mg/mL at 66 °F (NTP, 1992)measured · CAMEO Chemicals; Soluble in alcohol, benzene, ether, and hot petrol ethermeasured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 0.8 mmHg at 77 °F (NIOSH, 2024)measured · CAMEO Chemicals; 0.09 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
LogP: log Kow= 0.48measured · Hazardous Substances Data Bank (HSDB); 0.49measured · ILO-WHO International Chemical Safety Cards (ICSCs)
Flash Point: 198 °F (NTP, 1992)measured · CAMEO Chemicals; 198 ° Fmeasured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

Calculated properties

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

Molecular weight: 94.11 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 94.0530982 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 0.5calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 38.9 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 54calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 1calculated · reference compound database
H-bond acceptors: 2calculated · reference compound database
logP: 0.6638calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 38.91 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: 2calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 28.6494 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.5127calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon5 atoms · 63.8% by mass
N Nitrogen2 atoms · 29.8% by mass
H Hydrogen6 atoms · 6.4% 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: 7
Total atoms, hydrogen included: 13
Rings: 1
Aromatic rings: 1
Stereocentres: 0
Formal charge: 0

Functional groups

Primary aromatic amine
An –NH2 group attached directly to an aromatic ring, as in aniline. Much less basic than an alkyl amine, because the lone pair is delocalised into the ring.
Aromatic ring
A flat six-membered ring with delocalised electrons.

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

1 documented reaction involves 2-Aminopyridine, each with a written procedure and a source, and all of them are buchwald–hartwig amination. A few are shown.

Buchwald–Hartwig amination

Buchwald–Hartwig amination · as a reactant

A recorded experiment with its conditions, its yield where one was published, and a link to the source.

All 1 buchwald–hartwig amination records

Other names for it

The systematic name on this record is pyridin-2-amine.

The sources also call it pyridin-2-amine, 2-Pyridinamine, 2-Pyridylamine, o-Aminopyridine, Pyridine, 2-amino-, Amino-2 pyridine, 1,2-Dihydro-2-iminopyridine, alpha-Pyridinamine, alpha-Pyridylamine, alpha-Aminopyridine, DTXSID0024505.

Structurally related

Nothing structurally close to 2-Aminopyridine has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as 2-Aminopyridine. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

(R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)-

C₃₂H₆₂FeP₂, 564.641 g/mol.

1,1'-Carbonyldiimidazole

used as a reactant

C₇H₆N₄O, 162.152 g/mol.

1,2-dihydro-4-hydroxy-1-phenyl-N-(2-pyridyl)-3-quinolinecarboxamide

formed as a product

C₂₁H₁₇N₃O₂, 343.386 g/mol.

1,2-Dichloroethane

used as a reactant

C₂H₄Cl₂, 98.96 g/mol.

Where these values came from

reference compound database10439
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.