3-Aminobenzoic acid

3-Aminobenzoic acid^[1]^[2]
Skeletal formula	Ball-and-stick model
Names
	Preferred IUPAC name 3-Aminobenzoic acid
	Other names meta-Aminobenzoic acid; m-Aminobenzoic acid; MABA; 3-Carboxyaniline; m-Carboxyaniline
Identifiers
CAS Number	99-05-8 ;
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:42682 ;
ChEMBL	ChEMBL307782 ;
ChemSpider	7141 ;
DrugBank	DB02054 ;
ECHA InfoCard	100.002.477
EC Number	202-724-4
PubChem CID	7419 ;
UNII	G2X3B3O37U ;
	InChI InChI=1S/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10) Key: XFDUHJPVQKIXHO-UHFFFAOYSA-N ; InChI=1/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10) Key: XFDUHJPVQKIXHO-UHFFFAOYAM;
	SMILES O=C(O)c1cc(N)ccc1;
Properties
Chemical formula	C7H7NO2
Molar mass	137.13598
Appearance	White solid
Density	1.51 g/cm3
Melting point	178 to 80 °C (352 to 176 °F; 451 to 353 K)
Acidity (pKa)	3.07 (carboxyl; H2O); 4.79 (amino; H2O) [3] ;
Hazards
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H302, H315, H319, H335
GHS precautionary statements	P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
	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

Last updated March 05, 2019

3-Aminobenzoic acid (also known as meta-aminobenzoic acid or MABA) is an organic compound with the molecular formula H₂NC₆H₄CO₂H. MABA is a white solid, although commercial samples are often colored. It is only slightly soluble in water. It is soluble in acetone, boiling water, hot alcohol, hot chloroform and ether. It consists of a benzene ring substituted with an amino group and a carboxylic acid.

Organic compound Chemical compound that contains carbon (except for a several compounds traditionally classified as inorganic compounds)

In chemistry, an organic compound is generally any chemical compound that contains carbon. Due to carbon's ability to catenate, millions of organic compounds are known. Study of the properties and synthesis of organic compounds is the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds, along with a handful of other exceptions, are not classified as organic compounds and are considered inorganic. No consensus exists among chemists on precisely which carbon-containing compounds are excluded, making the definition of an organic compound elusive. Although organic compounds make up only a small percentage of the Earth's crust, they are of central importance because all known life is based on organic compounds. Most synthetically produced organic compounds are ultimately derived from petrochemicals consisting mainly of hydrocarbons.

In organic chemistry, amines (, UK also ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; see Category:Amines for a list of amines. Inorganic derivatives of ammonia are also called amines, such as chloramine (NClH₂); see Category:Inorganic amines.

Carboxylic acid oxoacid having the structure RC(=O)OH, used as a suffix in systematic name formation to denote the –C(=O)OH group including its carbon atom

A carboxylic acid is an organic compound that contains a carboxyl group. The general formula of a carboxylic acid is R–COOH, with R referring to the rest of the molecule. Carboxylic acids occur widely and include the amino acids and acetic acid.

Related Research Articles

A hydroxy or hydroxyl group is the entity with the formula OH. It contains oxygen bonded to hydrogen. In organic chemistry, alcohol and carboxylic acids contain hydroxy groups. The anion [OH⁻], called hydroxide, consists of a hydroxyl group.

In chemistry, a salt is an ionic compound that can be formed by the neutralization reaction of an acid and a base. Salts are composed of related numbers of cations and anions so that the product is electrically neutral. These component ions can be inorganic, such as chloride (Cl⁻), or organic, such as acetate ; and can be monatomic, such as fluoride (F⁻), or polyatomic, such as sulfate.

Lead(II) sulfate (PbSO₄) is a white solid, which appears white in microcrystalline form. It is also known as fast white, milk white, sulfuric acid lead salt or anglesite.

Cerium(IV) sulfate a yellow to yellow/orange solid cerium salt

Cerium(IV) sulfate, also called ceric sulfate, is an inorganic compound. It exists as the anhydrous salt Ce(SO₄)₂ as well as a few hydrated forms: Ce(SO₄)₂(H₂O)_x, with x equal to 4, 8, or 12. These salts are yellow to yellow/orange solids that are moderately soluble in water and dilute acids. Its neutral solutions slowly decompose, depositing the light yellow oxide CeO₂. Solutions of ceric sulfate have a strong yellow color. The tetrahydrate loses water when heated to 180-200 °C.

Pterin is a heterocyclic compound composed of a pteridine ring system, with a "keto group" and an amino group on positions 4 and 2 respectively. It is structurally related to the parent bicyclic heterocycle called pteridine. Pterins, as a group, are compounds related to pterin with additional substituents. Pterin itself is of no biological significance.

Iron(II) acetate is a coordination complex with formula Fe(C₂H₃O₂)₂. It is a white solid, although impure samples can be slightly colored. A light green tetrahydrate is also known, which is highly soluble in water.

Silver sulfate (Ag₂SO₄) is an ionic compound of silver used in silver plating and as a non-staining substitute to silver nitrate. This sulfate is stable under ordinary conditions of use and storage, though it darkens upon exposure to air or light. It is minimally soluble in water.

Sodium iodate (NaIO₃) is the sodium salt of iodic acid. Sodium iodate is an oxidizing agent, and as such it can cause fires upon contact with combustible materials or reducing agents.

Picolinic acid is an organic compound with the formula C₅H₄N(CO₂H). It is a derivative of pyridine with a carboxylic acid substituent at the 2-position. It is an isomer of nicotinic acid, which has the carboxyl side chain at the 3-position. It is a white solid that is soluble in water.

3-Nitrobenzoic acid is an organic compound with the formula C₆H₄(NO₂)CO₂H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alternative name of m-Nitrobenzoic acid. This compound can be useful as it is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.

The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone.

Camptothecin (CPT) is a topoisomerase inhibitor. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark and stem of Camptotheca acuminata, a tree native to China used as a cancer treatment in Traditional Chinese Medicine. CPT showed remarkable anticancer activity in preliminary clinical trials. However, it has low solubility, so synthetic and medicinal chemists have developed numerous syntheses of camptothecin and various derivatives to increase the benefits of the chemical, with good results. Two CPT analogues have been approved and are used in cancer chemotherapy today, topotecan and irinotecan.

Norleucine (abbreviated as Nle) is an amino acid with the formula CH₃(CH₂)₃CH(NH₂)CO₂H. A systematic name for this compound is 2-aminohexanoic acid. The compound is an isomer of the more common amino acid leucine. Like most other α-amino acids, norleucine is chiral. It is a white, water-soluble solid.

Thiosalicylic acid is an organosulfur compound containing carboxyl and sulfhydryl functional groups. Its molecular formula is C₆H₄(SH)(CO₂H). it is a yellow solid that is slightly soluble in water, ethanol and diethyl ether, and alkanes, but more soluble in DMSO.

Antimony sulfate, Sb₂(SO₄)₃, is a hygroscopic material is formed by reacting antimony or its compounds with hot sulfuric acid. It is used in doping of semiconductors and in the production of explosives and fireworks.

Metanilic acid is an isomer of sulfanilic acid with molecular formula C^₆H^₇NO^₃S and molecular weight 173.18968 g/mol. It is a white powder that is slightly soluble in water.

References

↑ m-Carboxyaniline - Compound Summary, PubChem.
↑ 3-aminobenzoic acid, Medical Subject Headings database.
↑ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89. ISBN 978-1498754286.

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[1] -Carboxyaniline - Compound Summary, PubChem.

[2] 3-aminobenzoic acid, Medical Subject Headings database.

[CRC97-3] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89. ISBN 978-1498754286.

3-Aminobenzoic acid

See also

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References