isatoic anhydride

anthranilic acid, N-carboxy-, cyclic anhydride

CAS: 118-48-9 C8 H5 N O3 MW: 163.13245000

Identification

Nameisatoic anhydride
IUPAC1H-3,1-benzoxazine-2,4-dione
CAS Number118-48-9
EINECS204-255-0
FDA UNIIR8TFA74Y4U
Molecular FormulaC8 H5 N O3
Molecular Weight163.13245000
MDL NumberMFCD00006700
Nikkaji NumberJ5.526C
Beilstein0136786

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Flash Point 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w) 0.978 (est)
Soluble in water, 401.9 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorypharmaceuticals / chemical synthisis
Recommendation for isatoic anhydride usage levels up tonot for fragrance use.
Recommendation for isatoic anhydride flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

anthranilic acid N-carboxylic acid anhydride anthranilic acid, N-carboxy-, cyclic anhydride 1H- benzo[d][1,3]oxazine-2,4-dione benzoic acid, 2-(carboxyamino)-, cyclic anhydride 1H-3,1- benzoxazine-2,4-dione 1H-3,1- benzoxazine-2,4-quinone 2H-3,1- benzoxazine-2,4(1H)-dione 4H-3,1- benzoxazine-2,4(1H)-dione isatoic acid anhydride isatoicanhydride PubMed: Efficient [Formula: see text]-catalyzed synthesis of novel and diverse 2,3-dihydroquinazolin-4(1[Formula: see text])-ones. PubMed: Efficient synthesis of 2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-ones catalyzed by dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation. PubMed: Inorganic-organic hybrid silica based tin complex as a novel, highly efficient and recyclable heterogeneous catalyst for the one-pot preparation of spirooxindoles in water. PubMed: One-pot synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion. PubMed: Biotin-conjugated N-methylisatoic anhydride: a chemical tool for nucleic acid separation by selective 2'-hydroxyl acylation of RNA. PubMed: Synthesis and biological evaluation of 2-aminobenzamide derivatives as antimicrobial agents: opening/closing pharmacophore site. PubMed: N,N'-(Propane-1,3-di-yl)bis-(2-amino-benzamide). PubMed: The folding of the hepatitis C virus internal ribosome entry site depends on the 3'-end of the viral genome. PubMed: Palladium-catalyzed regioselective carbonylation of C-H bonds of N-alkyl anilines for synthesis of isatoic anhydrides. PubMed: A highly efficient green synthesis of N-alkyl 2-[(2-oxo-2-aryl ethyl) amino] benzamide derivatives from reaction of isatoic anhydride, primary amines and 2-bromoacethophenone. PubMed: Synthesis and cytotoxicity testing of new amido-substituted triazolopyrrolo[2,1-c][1,4]benzodiazepine (PBDT) derivatives. PubMed: Hydrolase-like properties of a cofactor-independent dioxygenase. PubMed: A new cascade reaction: concurrent construction of six and five membered rings leading to novel fused quinazolinones. PubMed: Palladium-catalyzed decarboxylative coupling of isatoic anhydrides with arylboronic acids. PubMed: 1,3-Dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: formation of novel benzodiazepinones. PubMed: Synthesis of 2,3-dihydroquinazolin-4(1H)-ones by three-component coupling of isatoic anhydride, amines, and aldehydes catalyzed by magnetic Fe(3)O(4) nanoparticles in water. PubMed: Glycosylation, sugar hydrazones, and antimicrobial evaluation of some 6-substituted-1,2,4-triazines. PubMed: Cytotoxicity and reversal of multidrug resistance by tryptanthrin-derived indoloquinazolines. PubMed: Reactions of ortho-lithiophenyl (-hetaryl) isocyanides with carbonyl compounds: rearrangements of 2-metalated 4H-3,1-benzoxazines. PubMed: Time-resolved RNA SHAPE chemistry. PubMed: Novel and efficient one-pot tandem synthesis of 2-styryl-substituted 4(3H)-quinazolinones. PubMed: Synthesis, NMR and crystallographic studies of 2-substituted dihydroquinazolinones derived from (S)-phenylethylamine. PubMed: 96-well plate-to-plate gravity fluorous solid-phase extraction (F-SPE) for solution-phase library purification. PubMed: Automated liquid-liquid extraction workstation for library synthesis and its use in the parallel and chromatography-free synthesis of 2-alkyl-3-alkyl-4-(3H)-quinazolinones. PubMed: Hydrogen-bonding in 2-aminobenzoyl-alpha-chymotrypsin formed by acylation of the enzyme with isatoic anhydride: IR and mass spectroscopic studies. PubMed: Practical synthesis of potential endothelin receptor antagonists of 1,4-benzodiazepine-2,5-dione derivatives bearing substituents at the C3-, N1- and N4-positions. PubMed: Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic comparison. PubMed: Plate-to-plate fluorous solid-phase extraction for solution-phase parallel synthesis. PubMed: A direct, continuous, sensitive assay for protein disulphide-isomerase based on fluorescence self-quenching. PubMed: The energetics of isomeric benzoxazine diones: isatoic anhydride revisited. PubMed: Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation. PubMed: Synthesis and pharmacological activity of 1,4-benzodiazepine derivatives. PubMed: An efficient, convenient synthesis of novel medium-sized 13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione macrolides as anticipated antineoplastic agents. PubMed: Stereoselective Synthesis of Tilivalline(1). PubMed: Structures of native and complexed complement factor D: implications of the atypical His57 conformation and self-inhibitory loop in the regulation of specific serine protease activity. PubMed: Aminoacyl-tRNA analogues; synthesis, purification and properties of 3'-anthraniloyl oligoribonucleotides. PubMed: Structure-activity relationships of a series of substituted benzamides: potent D2/5-HT2 antagonists and 5-HT1a agonists as neuroleptic agents. PubMed: Preliminary synthetic studies of methyllycaconitine, a potent nicotinic acetylcholine receptor antagonist: rapid syntheses of AE-bicyclic analogues. PubMed: Further search for small molecular inactivants capable of eliciting respiratory mucosal immunogenicity by modifying Sendai virus core RNA. PubMed: Rates of thrombin acylation and deacylation upon reaction with low molecular weight acylating agents, carbamylating agents and carbonylating agents. PubMed: [Polycyclic azines with heteroatoms in the 1- and 3-position. 40. Synthesis of heterocyclic immunomodulators. 3. Synthesis of n-1 substituted 3-(2-mercaptoethyl)quinazoline-2,4-(1H,3H)-diones from bis(2-(2-aminobenzoylamino)ethyl)disulfane and testing of immunostimulant activity]. PubMed: The kinetics of non-stoichiometric bursts of beta-lactam hydrolysis catalysed by class C beta-lactamases. PubMed: Fluorescence properties of o-aminobenzoyl-labeled proteins. PubMed: tRNA fluorescent labeling at 3' end inducing an aminoacyl-tRNA-like behavior. PubMed: Inactivation of arginine esterase E-I of Bitis gabonica venom by irreversible inhibitors including a water-soluble carbodiimide, a chloromethyl ketone and isatoic anhydride. PubMed: Biosynthesis and modulation of endothelin from bovine pulmonary arterial endothelial cells. PubMed: Antihypertensive activity of 2[(2-hydroxyphenyl)amino]-4(3H)-quinazolinone. PubMed: Substituted isatoic anhydrides: selective inactivators of trypsin-like serine proteases. PubMed: Assessment of antiprotease activity of some carbamate derivatives. PubMed: New ribose-modified fluorescent analogs of adenine and guanine nucleotides available as substrates for various enzymes. PubMed: Suicide enzyme inactivators. PubMed: New fluorescent analogs of cAMP and cGMP available as substrates for cyclic nucleotide phosphodiesterase. PubMed: Nicafenine, a new analgesic. I. Synthesis and physicochemical properties. PubMed: Aromatic amines condensed with aminothiazoles, directly and with isatoic anhydride, for schistosomiasis treatment I. PubMed: Antifertility effects of isatoic anhydride and derivatives.