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
• Article Data: 19

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

• 885117-56-6 tert-butyl 2-(2,2,2-trifluoroacetamido)benzoate 
• 118-92-3 anthranilic acid 
• 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 
• 610-14-0 2-nitrobenzyl chloride 
• 19165-29-8 N-(trifluoroacetyl)anthranilic acid 
• 134-20-3 2-carbomethoxyaniline 
• 75-65-0 tert-butyl alcohol 
• 55666-41-6 tert-butyl 2-nitrobenzoate 
• 865-48-5 sodium t-butanolate 

Downstream Products

• 232596-54-2 tert-butyl (S)-2-(2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionylamino)-benzoate 
• 1070978-96-9 2,2'-ureylene-di-(tert-butylbenzoate) 
• 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 
• 256477-24-4 tert-butyl 2-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}benzoate 
• 106905-11-7 tert-butyl N-benzyl>anthranilate 
• 101689-29-6 2-(4-Hydroxy-3,6-dioxo-5-undecyl-cyclohexa-1,4-dienylamino)-benzoic acid tert-butyl ester 
• 1207984-12-0 2-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylamino)benzoic acid 
• 845890-39-3 1,1-dimethylethyl 2-{[(3Z)-3-(hydroxyamino)-3-iminopropanoyl]amino}benzoate 
• 1070978-00-5 N-(4-(4-(pyrrolidin-1-yl)butanamido)phenyl)-2-(1,2-dihydro-2,4-dioxoquinazolin-3(4H)-yl)benzamide 
• 1070978-04-9 N-(3-(3-(pyrrolidin-1-yl)propanamido)phenyl)-2-(1,2-dihydro-2,4-dioxoquinazolin-3(4H)-yl)benzamide 

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.

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.

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.