454713-47-4

Basic information

• Product Name: tert-butyl (1-bromonaphthalen-2-yl)carbamate
• CAS NO: 454713-47-4
• Molecular Weight: 322.202
• Mol File: 454713-47-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 374.0±25.0 °C(Predicted)
• Density: 1.408±0.06 g/cm3(Predicted)
• CAS DataBase Reference: tert-butyl (1-bromonaphthalen-2-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1-bromonaphthalen-2-yl)carbamate(454713-47-4)
• EPA Substance Registry System: tert-butyl (1-bromonaphthalen-2-yl)carbamate(454713-47-4)

Safety Data

• Hazardous Substances Data: 454713-47-4(Hazardous Substances Data)

Upstream product

• 93-09-4 naphthalene-2-carboxylate 
• 612-52-2 2-naphthylamine hydrochloride 
• 20191-75-7 1-bromo-2-naphthylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 454713-45-2 naphthalen-2-yl-carbamic acid tert-butyl ester 
• 454713-46-3 bis(tert-butyl) 1-bromo-2-naphthyldicarbamate 

Downstream Products

• 454713-41-8 tert-butyl 1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate 
• 7066-24-2 4H-benzo[f]quinazoline-1,3-dione 
• 7066-19-5 benzo[f]quinazolin-1(2H)-one 
• 454713-45-2 naphthalen-2-yl-carbamic acid tert-butyl ester 
• 42414-19-7 N-(naphthalen-2-yl)-3-oxobutanamide 
• 1363479-42-8 (3-(5-(2-morpholinoethoxy)-1H-indole-2-carbonyl)-5-nitro-7-(N-(2-(phosphonooxy)ethyl)sulfamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate trifluoroacetate 
• 1363479-39-3 (E)-(3-(3-(3-methoxyphenyl)acryloyl)-5-nitro-7-(N-(2-(phosphonooxy)ethyl)sulfamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363479-38-2 (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-(N-(2-(phosphonooxy)ethyl)sulfamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate trifluoroacetate 
• 1363479-35-9 (5-nitro-7-(N-(2-(phosphonooxy)ethyl)sulfamoyl)-3-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-methyl phenylmethanesulfonate 
• 1363479-19-9 (7-(N-(2-hydroxyethyl)sulfamoyl)-3-(5-(2-morpholinoethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate trifluoroacetate 
• 1363479-14-4 C₂HF₃O₂*C₃₅H₃₇N₅O₁₀S₂ 
• 1363479-11-1 (7-(N-(2-hydroxyethyl)sulfamoyl)-5-nitro-3-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363481-29-1 (7-(N-(2-((di-tert-butoxyphosphoryl)oxy)ethyl)sulfamoyl)-3-(5-(2-morpholinoethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 

Relevant articles and documents

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.

Substituted benzoquinazolinones. Part 2: Synthesis of amino-, and sulfanyl-derivatives of benzo[f]- and benzo[h]quinazolinones

Amino- and sulfanyl-derivatives of benzoquinazolinones 16a-c, 20a-c and 21a-c were prepared under palladium-catalyzed Buchwald-Hartwig coupling reaction using bromobenzoquinazolinones 15, 19a, 19b and 1-substituted piperazines or mercaptans. The combination of Pd(OAc)2 with XantPhos proved to be the best for these conversions in the presence of KOt-Bu, in 1,4-dioxane as a solvent, at 90-100 °C. The 8-bromobenzo[f]quinazolin-1(2H)-one 15 was synthesized via condensation of the ethyl or tert-butyl 2-amino-8-bromonaphthalene-1-carboxylate 6, 10 with formamide, followed by reaction with 3,4-dimethoxybenzyl bromide. However, the 6-bromobenzo[h]quinazolin-4(3H)-ones 19a, 19b were prepared from ethyl 4-bromo-1-[(tert-butoxycarbonyl)amino]naphthalene-2-carboxylate (17). Biological screening of the potential cytotoxicity of compounds 16a, 20a, 20c on HT29 and HCT116 cell lines, has shown that compound 20a has a significant anticancer activity.

CBI DERIVATIVES SUBJECT TO REDUCTIVE ACTIVATION

A unique class of N-acyl O-amino phenol prodrugs of CBI-TMI and CBI-indole2 were synthesized and shown to be prodrugs, subject to reductive activation by nucleophilic cleavage of a weak N-O bond, effectively releasing the free drug in functional cellular assays for cytotoxic activity approaching or matching the activity of the free drug, yet remain essentially stable to ex vivo DNA alkylation conditions. Most impressively, assessment of the in vivo antitumor activity of a representative O- (acylamino) prodrug, 8, indicate that they approach the potency and exceed the efficacy of the free drug itself (CBI-indole2), indicating that the inactive prodrugs not only effectively release the free drug in vivo, but that they offer additional advantages related to a controlled or targeted release in vivo.