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556998

Sigma-Aldrich

Phthalamic acid

97%

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About This Item

Linear Formula:
H2NC(O)C6H4CO2H
CAS Number:
Molecular Weight:
165.15
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

mp

140-143 °C (lit.)

SMILES string

NC(=O)c1ccccc1C(O)=O

InChI

1S/C8H7NO3/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H2,9,10)(H,11,12)

InChI key

CYMRPDYINXWJFU-UHFFFAOYSA-N

General description

Phthalamic acid can be synthesized from the reaction between ammonia and phthalic anhydride by a modified Auger′s method. Kinetic studies of the intramolecular carboxylic-group assisted hydrolysis of amide bond of phthalamic acid provided the value of pseudo-first order rate constant (kobs) as 5.1×10-5sec-1 at pH 1.3-1.8 and 35°C. It undergoes hydrolysis about 105 times faster than benzamide.

Application

Phthalamic acid may be used to synthesize anthranilic acid via reaction with sodium hypochlorite.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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?General acid-base catalysis in the intramolecular hydrolysis of phthalamic acid1?
Bender L M
Journal of the American Chemical Society, 79(5), 1258-1259 (1957)
CCXXXVII.?The preparation of phthalamic acids and their conversion into anthranilic acids.
Chapman E and Stephen E.
Journal of the Chemical Society, 127, 1791-1797 (1925)
Mireille Canal-Raffin et al.
Particle and fibre toxicology, 4, 8-8 (2007-09-22)
Pesticides, in particular folpet, have been found in rural and urban air in France in the past few years. Folpet is a contact fungicide and has been widely used for the past 50 years in vineyards in France. Slightly water-soluble
The hydrolysis and cyclization of some phthalamic acid derivatives.
J Brown et al.
Journal of the American Chemical Society, 88(19), 4468-4474 (1966-10-05)
Yoshiyuki Ogino et al.
Chirality, 29(6), 282-293 (2017-04-20)
Enantiomeric thalidomide undergoes various kinds of biotransformations including chiral inversion, hydrolysis, and enzymatic oxidation, which results in several metabolites, thereby adding to the complexity in the understanding of the nature of thalidomide. To decipher this complexity, we analyzed the multidimensional

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