64113-91-3

Basic information

• Product Name: tert-Butyl 2-aminobenzoate
• Synonyms: TERT-BUTYL ANTHRANILATE;TERT-BUTYL 2-AMINOBENZOATE;H-2-Abz-OtBu(Tert-butyl 2-AMinobenzoate);tert-Butyl 2-aminobenzoate >=97.0%
• CAS NO: 64113-91-3
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• EINECS: 231-816-7
• Mol File: 64113-91-3.mol

Chemical Properties

• Boiling Point: 284.1 °C at 760 mmHg
• Flash Point: 142.6 °C
• Appearance: nigger-brown liquid
• Density: 1.06 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00138mmHg at 25°C
• Refractive Index: n20/D 1.540
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 2.17±0.10(Predicted)
• BRN: 2936796
• CAS DataBase Reference: tert-Butyl 2-aminobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl 2-aminobenzoate(64113-91-3)
• EPA Substance Registry System: tert-Butyl 2-aminobenzoate(64113-91-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-43
• Safety Statements: 26-36-36/37
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 64113-91-3(Hazardous Substances Data)

Usage

Uses

tert-Butyl 2-Aminobenzoate is a useful reagent for preparing alkylamino quinazolinones.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 447, 1978 DOI: 10.1021/jo00397a015

InChI:InChI=1/C11H15NO2/c1-2-3-8-14-11(13)9-6-4-5-7-10(9)12/h4-7H,2-3,8,12H2,1H3

Upstream product

• 55666-41-6 tert-butyl 2-nitrobenzoate 
• 134-20-3 2-carbomethoxyaniline 
• 75-65-0 tert-butyl alcohol 
• 19165-29-8 N-(trifluoroacetyl)anthranilic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 774-65-2 benzoic acid tert-butyl ester 
• 552-16-9 ortho-nitrobenzoic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 75-91-2 tert.-butylhydroperoxide 
• 529-23-7 o-aminobenzaldehyde 
• 2835-06-5 phenylglycin 
• 118-92-3 anthranilic acid 
• 885117-56-6 tert-butyl 2-(2,2,2-trifluoroacetamido)benzoate 
• 865-48-5 sodium t-butanolate 

Downstream Products

• 101689-29-6 2-(4-Hydroxy-3,6-dioxo-5-undecyl-cyclohexa-1,4-dienylamino)-benzoic acid tert-butyl ester 
• 668261-27-6 tert-butyl 2-amino5-iodobenzoate 
• 1207984-13-1 tert-butyl 2-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylamino)benzoate 
• 1331753-56-0 tert-butyl 2-((2-chloro-4-methoxyphenyl)amino)benzoate 
• 1452776-80-5 tert-butyl 2-(3-(4-methylbenzenesulfonyl)thioureido)benzoate 
• 1452849-69-2 (Z)-tert-butyl 2-((4-methylbenzenesulfonamido)(methylsulfanyl)-methyleneamino)benzoate 
• 1452849-70-5 (Z)-2-((4-methylbenzenesulfonamido)(methylsulfanyl)-methyleneamino)benzoic acid 
• 1452776-81-6 3-(4-methylbenzenesulfonyl)-2-(methylsulfanyl)quinazolin-4(3H)-one 
• 890091-28-8 tert-butyl 2-isothiocyanatobenzoate 
• 845890-39-3 1,1-dimethylethyl 2-{[(3Z)-3-(hydroxyamino)-3-iminopropanoyl]amino}benzoate 
• 256478-16-7 tert-butyl 2-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}benzoate 
• 256477-24-4 tert-butyl 2-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}benzoate 
• 88072-01-9 2-(3-Bromo-propionylamino)-benzoic acid tert-butyl ester 
• 106880-81-3 benzyl <<<(tert-butoxycarbonyl)phenyl>carbamoyl>methyl>carbamate 

Relevant articles and documents

Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration

Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.

Regioselective sulfonylation and N- to O-sulfonyl migration of quinazolin-4(3H)-ones and analogous thienopyrimidin-4(3H)-ones

The sulfonylation of quinazolin-4(3H)-ones and related tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones with mesyl, tosyl, and p-cyanobenzenesulfonyl chloride was studied. A hydrogen substituent at 2-position directed the sulfonyl group to the N-3 position, while alkylsulfanyl or amino substituents led to sulfonylation of the carbonyl oxygen. The latter effect was attributed to steric influence and the positive mesomeric effect of the 2-substituent. An access to N-sulfonylated 2-substituted regioisomers was established. An unexpected 1,3-sulfonyl migration was observed and further analyzed. This process occurred as an intramolecular N- to O-shift as verified by kinetic and crossover experiments.

One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction-heterocyclization of 2-nitroacylbenzenes under neutral conditions

Classically, 2,1-benzisoxazoles (anthranils) are prepared from 2-nitroacylbenzenes by a reductive heterocyclization reaction with Sn or SnCl2 concentrated HCl. Acid sensitive functionalities are expected to be incompatible with these conditions; milder approaches to the synthesis of 2,1-benzisoxazoles would be welcomed. We demonstrate that SnCl 2·2H2O in a 1:1 mixture of EtOAc/MeOH is capable of mediating the tandem reduction-heterocyclization of a variety of 2-nitroacylbenzenes to their corresponding 2,1-benzisoxazoles in good to excellent yields under essentially neutral conditions. Importantly, several commonly used acid-labile protecting groups, including Boc carbamate, tert-butyl ether, and tert-butyl ester, proved orthogonal to these reaction conditions.

Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity

A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.

Rational design of substituted diarylureas: A scaffold for binding to G-quadruplex motifs

The design and synthesis of a series of urea-based nonpolycyclic aromatic ligands with alkylaminoanilino side chains as telomeric and genomic G-quadruplex DNA interacting agents are described. Their interactions with quadruplexes have been examined by means of fluorescent resonance energy transfer melting, circular dichroism, and surface plasmon resonance-based assays. These validate the design concept for such urea-based ligands and also show that they have significant selectivity over duplex DNA, as well as for particular G-quadruplexes. The ligand-quadruplex complexes were investigated by computational molecular modeling, providing further information on structure-activity relationships. Preliminary biological studies using short-term cell growth inhibition assays show that some of the ligands have cancer cell selectivity, although they appear to have low potency for intracellular telomeric G-quadruplex structures, suggesting that their cellular targets may be other, possibly oncogene-related quadruplexes.

UREYLENE DERIVATIVES

The invention concerns compounds of Formula (I) or a salt, solvate or pro-drug thereof. The compounds may be used in therapy, particularly anti-cancer therapy.

Preparation of novel antibacterial agents. Replacement of the central aromatic ring with heterocycles

Discovery of novel antibacterial agents is a significant challenge. We have recently reported on our discovery of novel antibacterial agents in which we have rapidly optimized potency utilizing a parallel chemistry approach. These advanced leads suffer from high affinity for human serum albumin (HSA). In an effort to decrease the affinity for HSA we have prepared a series of heterocyclic analogs, which retained antibacterial activity and demonstrated reduced affinity for HSA.

Selective urokinase-type plasminogen activator inhibitors. 4. 1-(7-Sulfonamidoisoquinolinyl)guanidines

1-Isoquinolinylguanidines were previously disclosed as potent and selective inhibitors of urokinase-type plasminogen activator (uPA). Further investigation of this template has revealed that incorporation of a 7-sulfonamide group furnishes a new series of potent and highly selective uPA inhibitors. Potency and selectivity can be achieved with sulfonamides derived from a variety of amines and is further enhanced by the incorporation of sulfonamides derived from amino acids. The binding mode of these 1-isoquinolinylguanidines has been investigated by X-ray cocrystallization studies. uPA inhibitor 26 was selected for further evaluation based on its excellent enzyme potency (Ki 10 nM) and selectivity profile (4000-fold versus tPA and 2700-fold versus plasmin). In vitro, compound 26 is able to inhibit exogenous uPA in human chronic wound fluid (IC50 = 0.89 μM). In vivo, in a porcine acute excisional wound model, following topical delivery, compound 26 is able to penetrate into pig wounds and inhibit exogenous uPA activity with no adverse effect on wound healing parameters. On the basis of this profile, compound 26 (UK-371,804) was selected as a candidate for further preclinical evaluation for the treatment of chronic dermal ulcers.

Selective removal of the N-(tert-butoxycarbonyl) protecting group using H-β zeolite

A simple and efficient protocol for the selective removal of Boc group from nitrogen atom in conjugation with an aromatic system employing H-β zeolite is described.

ANTIBACTERIAL BENZOIC ACID DERIVATIVES

The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.