Ethyl 2-aminobenzoate

An aromatic ester, C9H11NO2, 165.192 g/mol. Boiling point 268 °C at 760 mm Hg, melting point 13 °C, as published.

verified recordOrganic — aromatic ester7 measured properties

Identifiers

Molecular formula: C₉H₁₁NO₂
Molecular weight: 165.192 g/mol
Exact mass: 165.078979 g/mol
IUPAC name: ethyl 2-aminobenzoate
SMILES: CCOC(=O)c1ccccc1N
InChI: InChI=1S/C9H11NO2/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6H,2,10H2,1H3
InChIKey: TWLLPUMZVVGILS-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: 514 °F at 760 mmHg (NTP, 1992)measured · CAMEO Chemicals; 268 °C at 760 mm Hgmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: 55 °F (NTP, 1992)measured · CAMEO Chemicals; 13 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.117 at 68 °F (NTP, 1992) - Denser than water; will sinkmeasured · CAMEO Chemicals; 1.1174 at 20 °C/4 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: Insoluble (NTP, 1992)measured · CAMEO Chemicals; Very soluble in ether, alcoholmeasured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 0.00232 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
LogP: log Kow = 2.57measured · Hazardous Substances Data Bank (HSDB); 2.57measured · Human Metabolome Database (HMDB)
Refractive Index: INDEX OF REFRACTION: 1.5646 @ 20 °C/D; MAX ABSORPTION (ALCOHOL): 225 NM( LOG E= 4.3); 250 NM (LOG E= 3.85); 338 NM (LOG E= 3.7)measured · Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-182; 1.563-1.566measured · reference compound database

Calculated properties

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

Molecular weight: 165.19 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 165.078978594 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 2.6calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 52.3 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 159calculated · 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: 1.4455calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 52.32 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: 3calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 2calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 46.8109 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.2222calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.5326calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon9 atoms · 65.4% by mass
O Oxygen2 atoms · 19.4% by mass
N Nitrogen1 atom · 8.5% by mass
H Hydrogen11 atoms · 6.7% 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: 12
Total atoms, hydrogen included: 23
Rings: 1
Aromatic rings: 1
Stereocentres: 0
Formal charge: 0

Functional groups

Ester
A carbonyl bonded to an oxygen that links to another carbon.
Ether
An oxygen bridging two carbons.
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

No documented reaction with a written procedure and a source involves Ethyl 2-aminobenzoate yet.

Other names for it

The systematic name on this record is ethyl 2-aminobenzoate.

The sources also call it ETHYL ANTHRANILATE, Ethyl o-aminobenzoate, 2-Aminobenzoic acid ethyl ester, Anthranilic acid, ethyl ester, 2-Carboethoxyaniline, o-(Ethoxycarbonyl)aniline, Benzoic acid, o-amino-, ethyl ester, Benzoic acid, 2-amino-, ethyl ester, 2-(Ethoxycarbonyl)aniline, FEMA No. 2421, DTXSID6025272.

Structurally related

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

Where these values came from

reference compound database6877
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.