Production Method 1

54879-20-8

888214-21-9

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Dimethyl sulfoxide ,  Water ;  2 h, 50 °C; cooled
1.2 Reagents: Sodium nitrite ;  1 h, cooled
1.3 Reagents: Sodium iodide ;  1 h, rt
1.4 Reagents: Sodium bisulfite Solvents: Water ;  rt

Reference

Design, Synthesis, and Evaluation of o-(Biphenyl-3-ylmethoxy)nitrophenyl Derivatives as PD-1/PD-L1 Inhibitors with Potent Anticancer Efficacy In Vivo

OuYang, Yiqiang; Gao, Jian; Zhao, Lei; Lu, Junfeng; Zhong, Haiqing; et al, Journal of Medicinal Chemistry, 2021, 64(11), 7646-7666

Production Method 2

54879-20-8

888214-21-9

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  0 °C; 20 min, 0 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  0 °C; 60 min, 0 °C
1.3 Reagents: Sodium bicarbonate ,  Sodium thiosulfate Solvents: Water ;  0 °C

Reference

Gold(I)-Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes

Ikeuchi, Takaya; Inuki, Shinsuke ; Oishi, Shinya ; Ohno, Hiroaki, Angewandte Chemie, 2019, 58(23), 7792-7796

Production Method 3

54879-20-8

888214-21-9

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Acetonitrile ;  0 °C; 5 min, 0 °C
1.2 Reagents: NanO 2 ;  0 °C; 20 min, 0 °C
1.3 Reagents: Potassium iodide Catalysts: Cuprous iodide ;  0 °C; 4 h, rt
1.4 Reagents: Sodium thiosulfate ;  rt

Reference

Molecular hybridization used to design and synthesize neo-tanshinlactone derivatives as PD-1/PD-L1 inhibitors

Zhang, Menghan; Liu, Jianmin; Wang, Yue; Wang, Ping; Morris-Natschke, Susan; et al, Bioorganic & Medicinal Chemistry, 2022, 54,

Production Method 4

54879-20-8

888214-21-9

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  30 min, 0 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  3 h, 60 °C
1.3 Reagents: Sodium thiosulfate Solvents: Water

Reference

Enantioselective Synthesis of 6/5-Spirosilafluorenes by Asymmetric Ring Expansion of 4/5-Spirosilafluorenes with Alkynes

Chen, Hua; Zhang, Haixia; Du, Huimin; Kuang, Yuzhong; Pang, Qinjiao; et al, Organic Letters, 2023, 25(9), 1558-1563

Production Method 5

54879-20-8

888214-21-9

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  0 °C
1.2 Reagents: Sodium nitrate Solvents: Water ;  30 min, 0 °C; 1 h, 0 °C
1.3 Reagents: Potassium iodide Solvents: Water ;  1 h, rt
1.4 Reagents: Sodium thiosulfate Solvents: Water ;  rt

Reference

Di-bromo-Based Small-Molecule Inhibitors of the PD-1/PD-L1 Immune Checkpoint

Konieczny, Magdalena ; Musielak, Bogdan ; Kocik, Justyna ; Skalniak, Lukasz ; Sala, Dominik ; et al, Journal of Medicinal Chemistry, 2020, 63(19), 11271-11285

Production Method 6

888214-21-9

Reaction Conditions

1.1 Reagents: Silica ,  Bromine Solvents: Chloroform ;  rt
1.2 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  10 °C
1.3 Reagents: Potassium iodide ;  10 °C; 10 °C → 80 °C

Reference

Synthesis of 1-(2-ethynyl-6-methylphenyl)- and 1-(2-ethynyl-6-methoxyphenyl)-naphthalene and their cyclization

Storch, Jan; Cermak, Jan; Karban, Jindrich, Tetrahedron Letters, 2007, 48(38), 6814-6816

Production Method 7

625-95-6

888214-21-9

202865-85-8

858841-53-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Methylium, triphenyl-, tetrafluoroborate(1-) (1:1) Solvents: Acetonitrile ,  Dichloromethane ;  rt
1.2 Reagents: Water

Reference

Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C-H functionalization.

Ni, Shengjun; El Remaily, Mahmoud Abd El Aleem Ali Ali; Franzen, Johan, Advanced Synthesis & Catalysis, 2018, 360(21), 4197-4204

2-Bromo-1-iodo-3-methylbenzene Raw materials

• 3-Iodotoluene
• 2-Bromo-3-methylaniline

2-Bromo-1-iodo-3-methylbenzene Preparation Products

• 2-Bromo-5-iodotoluene (202865-85-8)
• 2-Bromo-1-iodo-3-methylbenzene (888214-21-9)
• 1-Bromo-2-iodo-4-methylbenzene (858841-53-9)

• 1. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 2. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389
• 3. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
• 4. Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe?
  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161
• 5. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789

• 26670-89-3(2-Bromo-4-iodotoluene)
• 68920-65-0(2-Bromo-5-iodo-1,3-dimethylbenzene)
• 175278-10-1(3,5-Dibromo-4-iodotoluene)
• 68920-03-6(2-Bromo-5-iodo-1,3-dimethylbenzene)
• 689260-53-5(2-Bromo-5-iodo-1,3-dimethylbenzene)
• 202865-85-8(2-Bromo-5-iodotoluene)
• 71838-98-7(2-Bromo-1-iodo-4-methylbenzene)
• 71838-95-4(2-Bromo-1-iodo-4-methylbenzene)
• 858841-53-9(1-Bromo-2-iodo-4-methylbenzene)
• 71838-16-9(3-Bromo-4-iodotoluene)