Production Method 1

24424-99-5

78839-75-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran

Reference

Pyrrole, Imidazolone and Imidazolidinone Chemistry for the Synthesis of Heterocyclic Natural Products

Cantos-Llopart, Carme, 2003, , ,

Production Method 2

24424-99-5

78839-75-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  24 h, reflux

Reference

Rhodium-Catalyzed Tandem Conjugate Addition-Mannich Cyclization Reaction: Straightforward Access to Fully Substituted Tetrahydroquinolines

Youn, So Won; Song, Ju-Hyun; Jung, Dai-Il, Journal of Organic Chemistry, 2008, 73(14), 5658-5661

Production Method 3

24424-99-5

78839-75-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  reflux

Reference

Inhibition studies with rationally designed inhibitors of the human low molecular weight protein tyrosine phosphatase

Zabell, Adam P. R.; Corden, Steven; Helquist, Paul; Stauffacher, Cynthia V.; Wiest, Olaf, Bioorganic & Medicinal Chemistry, 2004, 12(8), 1867-1880

Production Method 4

24424-99-5

78839-75-5

Reaction Conditions

1.1 Catalysts: Iron oxide (Fe2O3) Solvents: Water ;  70 min, 30 - 35 °C

Reference

Nano-γ-Fe2O3: efficient, reusable and green catalyst for N-tert-butoxycarbonylation of amines in water

Medisetti, Venkataramana; Parimi, Umadevi; Anagani, Ramesh Babu; Satyanarayana, K. V. V. V., Green and Sustainable Chemistry, 2014, 4(2), 95-101

Production Method 5

24424-99-5

78839-75-5

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: 1,4-Dioxane ,  Water ;  6 h, reflux
1.2 Reagents: Water

Reference

A Sequential Transition Metal and Organocatalytic Approach to the Enantioselective Synthesis of C2-Spiroindoline Systems

Sah, Pooja; Gond, Aakash Kumar; Saini, Gaurav; Kapur, Manmohan, Organic Letters, 2023, 25(51), 9170-9175

Production Method 6

24424-99-5

78839-75-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  30 min, 0 °C
1.2 Catalysts: 4-(Dimethylamino)pyridine ;  0 °C
1.3 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  0 °C

Reference

Arene dearomatization via radical hydroarylation

Flynn, Autumn R.; McDaniel, Kelly A.; Hughes, Meredith E.; Vogt, David B.; Jui, Nathan T., ChemRxiv, 2019, 1, 1-9

Production Method 7

3422-01-3

78839-75-5

Reaction Conditions

1.1 Reagents: tert-Butyllithium Solvents: Pentane ,  Tetrahydrofuran ;  -75 °C; 3 h, -50 °C; -75 °C
1.2 Reagents: Carbon tetrabromide Solvents: Tetrahydrofuran ;  -75 °C; > 1 min, -75 °C

Reference

Nucleus- and side-chain fluorinated 3-substituted indoles by a suitable combination of organometallic and radical chemistry

Bellezza, Francesca; Cipiciani, Antonio; Ruzziconi, Renzo; Spizzichino, Sara, Journal of Fluorine Chemistry, 2008, 129(2), 97-107

Production Method 8

24424-99-5

78839-75-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  1 h, reflux; reflux → rt; 30 min, 0 °C; overnight, reflux; reflux → rt

Reference

Axial Chirality Control During Suzuki-Miyaura Cross-Coupling Reactions: The tert-Butylsulfinyl Group as an Efficient Chiral Auxiliary

Colobert, Francoise; Valdivia, Victoria; Choppin, Sabine; Leroux, Frederic R.; Fernandez, Inmaculada; et al, Organic Letters, 2009, 11(22), 5130-5133

Production Method 9

78839-75-5

Reaction Conditions

1.1 Reagents: Cesium carbonate Solvents: Acetonitrile ;  1 h, 100 °C
1.2 Reagents: Ethyl acetate

Reference

Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates

Li, Peihe; Ma, Nuannuan; Wang, Zheng; Dai, Qipu ; Hu, Changwen, Journal of Organic Chemistry, 2018, 83(15), 8233-8240

Production Method 10

24424-99-5

78839-75-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  3 d, reflux

Reference

Aryl radical cyclization with alkyne followed by tandem carboxylation in methyl 4-tert-butylbenzoate-mediated electrochemical reduction of 2-(2-propynyloxy)bromobenzenes in the presence of carbon dioxide

Katayama, Asahi; Senboku, Hisanori; Hara, Shoji, Tetrahedron, 2016, 72(31), 4626-4636

Production Method 11

24424-99-5

78839-75-5

Reaction Conditions

1.1 Catalysts: Sulfamic acid ;  15 min, rt

Reference

Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst

Upadhyaya, Dharita J.; Barge, Alessandro; Stefania, Rachele; Cravotto, Giancarlo, Tetrahedron Letters, 2007, 48(47), 8318-8322

Production Method 12

24424-99-5

78839-75-5

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: 1,4-Dioxane ,  Water ;  6 h, reflux; cooled
1.2 Reagents: Water

Reference

A sequential transition metal and organocatalytic approach to the enantioselective synthesis of C2-spiroindoline systems

Sah, Pooja; Gond, Aakash Kumar; Saini, Gaurav; Kapur, Manmohan, ChemRxiv, 2023, 1, 1-11

Production Method 13

24424-99-5

78839-75-5

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: 1,4-Dioxane ,  Water ;  6 h, 80 °C; 80 °C → rt
1.2 Reagents: Water ;  rt

Reference

Domino Pd0-Catalyzed C(sp3)-H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates

Rocaboy, Ronan; Dailler, David; Zellweger, Florian; Neuburger, Markus; Salome, Christophe; et al, Angewandte Chemie, 2018, 57(37), 12131-12135

Production Method 14

24424-99-5

78839-75-5

Reaction Conditions

1.1 Catalysts: 4-(Dimethylamino)pyridine Solvents: Tetrahydrofuran ;  16 h, reflux; cooled
1.2 Reagents: Potassium carbonate Solvents: Methanol ;  3 h, reflux

Reference

Probing cytochrome P450 (CYP) bioactivation with chloromethylindoline bioprecursors derived from the duocarmycin family of compounds

Ortuzar, Natalia; Karu, Kersti; Presa, Daniela ; Morais, Goreti R.; Sheldrake, Helen M. ; et al, Bioorganic & Medicinal Chemistry, 2021, 40,

Production Method 15

24424-99-5

78839-75-5

Reaction Conditions

1.1 Catalysts: 4-(Dimethylamino)pyridine Solvents: Tetrahydrofuran ;  24 h, reflux

Reference

Indole synthesis by controlled carbolithiation of o-aminostyrenes

Kessler, Albane; Coleman, Claire M.; Charoenying, Patchanee; O'Shea, Donal F., Journal of Organic Chemistry, 2004, 69(23), 7836-7846

Production Method 16

24424-99-5

78839-75-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  30 min, 0 °C
1.2 Catalysts: 4-(Dimethylamino)pyridine ;  0 °C; 0 °C
1.3 Solvents: Water
1.4 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  0 °C
1.5 Solvents: Water ;  basified

Reference

Hydroarylation of Arenes via Reductive Radical-Polar Crossover

Flynn, Autumn R.; McDaniel, Kelly A.; Hughes, Meredith E.; Vogt, David B.; Jui, Nathan T., Journal of the American Chemical Society, 2020, 142(20), 9163-9168

Production Method 17

24424-99-5

78839-75-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  1 h, rt → reflux; reflux → rt
1.2 0.5 h, rt
1.3 Reagents: Sodium hydride ;  14 h, rt → reflux; reflux → rt
1.4 Reagents: Water

Reference

Ruthenium Amide Complexes - Synthesis and Catalytic Activity in Olefin Metathesis and in Ring-Opening Polymerisation

Gawin, Anna; Pump, Eva ; Slugovc, Christian ; Kajetanowicz, Anna ; Grela, Karol, European Journal of Inorganic Chemistry, 2018, 2018(16), 1766-1774

Production Method 18

24424-99-5

78839-75-5

Reaction Conditions

1.1 Catalysts: 4-(Dimethylamino)pyridine Solvents: Tetrahydrofuran ;  24 h, reflux

Reference

One stone three birds: regiodivergent access to amino-substituted benzophospholes and their structure-property relationships

Zhu, Jiahao; Wang, Lili; Duan, Zheng, ChemRxiv, 2022, 1, 1-10

N-Boc 2-Bromoaniline Raw materials

• Di-tert-butyl dicarbonate
• N-(tert-Butoxycarbonyl)aniline

N-Boc 2-Bromoaniline Preparation Products

• N-Boc 2-Bromoaniline (78839-75-5)

• 1. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
  Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034
• 2. An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode
  Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. Killard Analyst, 2008,133, 391-399
• 3. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 4. An integrated cathode and solid electrolyte via in situ polymerization with significantly reduced interface resistance?
  Jialiang Yuan,Ran Dong,Yuan Li,Yang Liu,Zhuo Zheng,Yuxia Liu,Yan Sun,Benhe Zhong,Zhenguo Wu,Xiaodong Guo Chem. Commun., 2021,57, 13004-13007
• 5. An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S?
  Rongning Liang,Tanji Yin,Ruiqing Yao,Wei Qin RSC Adv., 2016,6, 73308-73312

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylcarbamic acid esters
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

• 104919-70-2(Ethyl N-(2-bromophenyl)carbamate)
• 548771-40-0(tert-butyl N-(2-bromo-4-hydroxyphenyl)carbamate)
• 496874-88-5(Imidodicarbonic acid, (2-bromophenyl)-, 1,1-dimethylethyl methyl ester (9CI))
• 25216-74-4(tert-Butyl N-(3-Bromophenyl)carbamate)
• 954238-73-4((2-AMINO-3-BROMO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER)
• 885270-70-2(2-Amino-4-Boc-Amino-Phenylbromide)
• 1187926-96-0(tert-Butyl (2-bromo-4,5-dimethylphenyl)carbamate)
• 131818-17-2(tert-Butyl 4-Bromophenylcarbamate)
• 364607-53-4(N-BOC 2-Bromo-4-methylaniline)
• 885270-68-8((5-Amino-2-Bromo-Phenyl)-Carbamic Acid Tert-Butyl Ester Aldrichcpr)