Production Method 1

6630-33-7

2605-67-6

92991-89-4

Reaction Conditions

1.1 Solvents: Dichloromethane ;  overnight, rt

Reference

Preparation of 6,7-dihydro-4h-pyrazolo[1,5-a]pyrazine indole-2-carboxamides active against the hepatitis B virus (HBV)

, World Intellectual Property Organization, , ,

Production Method 2

92991-89-4

Reaction Conditions

1.1 Reagents: Methanesulfonic acid ,  tert-Butyl nitrite Catalysts: Palladium diacetate Solvents: Methanol ,  Dimethylformamide ;  167 min, 25 °C
1.2 Reagents: Triethylamine Solvents: Ethyl acetate

Reference

Multicomponent, flow diazotization/Mizoroki-Heck coupling protocol. Dispelling myths about working with diazonium salts

Nalivela, Kumara S.; Tilley, Michael; McGuire, Michael A.; Organ, Michael G., Chemistry - A European Journal, 2014, 20(22), 6603-6607

Production Method 3

583-55-1

92991-89-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Palladium (supported on sulfur-terminated gallium arsenide plate) Solvents: Acetonitrile ;  12 h, 100 °C; 100 °C → rt

Reference

Development of a method for preparing a highly reactive and stable, recyclable and environmentally benign organopalladium catalyst supported on sulfur-terminated gallium arsenide(001): a three-component catalyst, {Pd}-S-GaAs(001), and its properties

Arisawa, Mitsuhiro; Hamada, Masahiro; Takamiya, Ikuko; Shimoda, Masahiko; Tsukamoto, Shiro; et al, Advanced Synthesis & Catalysis, 2006, 348(9), 1063-1070

Production Method 4

6630-33-7

2605-67-6

92991-89-4

Reaction Conditions

1.1 Solvents: Dichloromethane ;  12 h, rt

Reference

Preparation method of fluconazole aniline metabolite

, China, , ,

Production Method 5

867-13-0

6630-33-7

92991-89-4

Reaction Conditions

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

Reference

Highly diastereoselective radical cyclisations of chiral sulfinimines

Rochette, Elise M.; Lewis, William; Dossetter, Al G.; Stockman, Robert A., Chemical Communications (Cambridge, 2013, 49(82), 9395-9397

Production Method 6

583-55-1

6213-88-3

92991-89-4

Reaction Conditions

1.1 Reagents: Zinc Solvents: Tetrahydrofuran
1.2 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Tetrahydrofuran

Reference

o-Bromophenylzinc compound: a readily available and efficient synthetic equivalent of o-phenylene 1-anion 2-cation

Okano, Masateru; Amano, Masayuki; Takagi, Kentaro, Tetrahedron Letters, 1998, 39(19), 3001-3004

Production Method 7

14874-70-5

17333-81-2

92991-89-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Palladium diacetate ,  (3aR,7aR)-Octahydro-1,3-bis(2-methylphenyl)-2H-benzimidazole-2-thione Solvents: Methanol ;  4 h, rt

Reference

Synthesis of a Novel C2-Symmetric Thiourea and Its Application in the Pd-Catalyzed Cross-Coupling Reactions with Arenediazonium Salts under Aerobic Conditions

Dai, Mingji; Liang, Bo; Wang, Cuihua; Chen, Jiahua; Yang, Zhen, Organic Letters, 2004, 6(2), 221-224

Production Method 8

16695-14-0

6630-33-7

92991-89-4

Reaction Conditions

1.1 Reagents: Pyridine Catalysts: Piperidine ;  2 - 6 h, reflux; rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 7, rt

Reference

Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer

Larionova, Natalia A.; Ondozabal, Jun Miyatake ; Cambeiro, Xacobe C., Advanced Synthesis & Catalysis, 2021, 363(2), 558-564

Production Method 9

16695-14-0

6630-33-7

92991-89-4

Reaction Conditions

1.1 Catalysts: Piperidine Solvents: Pyridine ;  2 - 6 h, reflux; reflux → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 7

Reference

Efficient reduction of electron-deficient alkenes enabled by a photoinduced hydrogen atom transfer

Larionova, Natalia A.; Ondozabal, Jun Miyatake; Cambeiro, Xacobe C., ChemRxiv, 2020, 1, 1-5

Production Method 10

583-55-1

92991-89-4

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Catalysts: Palladium (dibenzylideneacetone-containing complexes with diphenylhosphine-functionalized chloromethylated polystyrene) Solvents: Dimethylformamide ,  Toluene ,  Water ;  20 h, 100 °C; 100 °C → rt

Reference

Mizoroki-Heck reactions of methyl acrylate in presence of a palladated rasta resin

Derible, Antoine; Becht, Jean-Michel; Le Drian, Claude, Tetrahedron Letters, 2013, 54(32), 4207-4209

Production Method 11

583-55-1

92991-89-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Palladium (polystyrene-supported) Solvents: Dimethylformamide ,  Toluene ,  Water ;  20 h, 100 °C

Reference

Reusable polystyrene-supported Pd catalyst for Mizoroki-Heck reactions with extremely low amounts of supported Pd

Diebold, Carine; Schweizer, Stephane; Becht, Jean-Michel; Le Drian, Claude, Organic & Biomolecular Chemistry, 2010, 8(21), 4834-4836

Production Method 12

583-55-1

92991-89-4

Reaction Conditions

1.1 Catalysts: Benzenemethanamine, N,N-dibutyl-4-ethenyl-, polymer with ethenylbenzene and (4-e… (palladium complexes) Solvents: Dimethylformamide ;  20 h, 100 °C

Reference

A bifunctional palladated rasta resin for Mizoroki-Heck reactions

Derible, Antoine; Yang, Yun-Chin; Toy, Patrick H.; Becht, Jean-Michel; Drian, Claude Le, Tetrahedron Letters, 2014, 55(31), 4331-4333

Production Method 13

583-55-1

92991-89-4

Reaction Conditions

1.1 Reagents: Monopotassium phosphate Catalysts: Palladium Solvents: Ethanol ,  Water ;  1.5 h, 80 °C

Reference

Remarkably facile Heck reactions in aqueous two-phase system catalyzed by reusable Pd/C under ligand-free conditions

Yuan, Yan-Qin; Guo, Sheng-Rong, Synthetic Communications, 2012, 42(7), 1059-1069

Production Method 14

6630-33-7

2605-67-6

92991-89-4

Reaction Conditions

1.1 Solvents: Dichloromethane ;  12 h, rt

Reference

Comprehensive evaluation of chiral penflufen metabolite (penflufen-3-hydroxy-butyl): Identification, synthesis, enantioseparation, toxicity and enantioselective metabolism

Di, Shanshan; Liu, Ruiquan; Liu, Zhenzhen; Xu, Hao; Zhao, Huiyu; et al, Ecotoxicology and Environmental Safety, 2023, 251,

Production Method 15

7345-79-1

92991-89-4

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ;  rt; rt → 70 °C; 3.5 h, 70 °C
1.2 Reagents: Water ;  0 °C

Reference

Preparation of arylcyclopropylamine compounds useful for the treatment of breast cancer

, United States, , ,

Production Method 16

7345-79-1

92991-89-4

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ;  rt; rt → 70 °C; 3.5 h, 70 °C → reflux

Reference

Preparation of arylcyclopropylamine derivatives for use as antiparkinsonian agents

, United States, , ,

Production Method 17

14874-70-5

17333-81-2

92991-89-4

Reaction Conditions

1.1 Catalysts: Palladium (charcoal-supported) Solvents: Methanol ;  12 h, 25 °C

Reference

Heck cross-coupling of aryldiazonium tetrafluoroborate with acrylates catalyzed by palladium on charcoal

Felpin, Francois-Xavier; Fouquet, Eric; Zakri, Cecile, Advanced Synthesis & Catalysis, 2008, 350(16), 2559-2565

Production Method 18

583-55-1

92991-89-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Palladium (diarylphosphinopolystyrene-supported) ,  Chlorobis(3-methylphenyl)phosphine (reaction products with Merrifield resin, palladium complex) Solvents: Acetonitrile ;  20 h, 80 °C

Reference

Development of efficient and reusable diarylphosphinopolystyrene-supported palladium catalysts for C-C bond forming cross-coupling reactions

Schweizer, Stephane; Becht, Jean-Michel; Le Drian, Claude, Advanced Synthesis & Catalysis, 2007, 349(7), 1150-1158

Production Method 19

583-55-1

92991-89-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide ;  2 h, 50 °C

Reference

Pd-catalyzed one-pot sequential unsymmetrical cross-coupling reactions of aryl/heteroaryl 1,2-dihalides

Danodia, Abhinandan K.; Saunthwal, Rakesh K.; Patel, Monika; Tiwari, Rakesh K.; Verma, Akhilesh K., Organic & Biomolecular Chemistry, 2016, 14(27), 6487-6496

Production Method 20

16695-14-0

6630-33-7

92991-89-4

Reaction Conditions

1.1 Catalysts: Piperidine Solvents: Pyridine ;  2 - 6 h, reflux; reflux → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 7, rt

Reference

A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines

Larionova, Natalia A. ; Ondozabal, Jun Miyatake; Smith, Emily G.; Cambeiro, Xacobe C., Organic Letters, 2021, 23(14), 5383-5388

methyl (2E)-3-(2-bromophenyl)prop-2-enoate Raw materials

• Triethyl phosphonoacetate
• 3-Methoxy-3-oxopropanoic acid
• Borate(1-),tetrafluoro-
• 2-Bromobenzenediazonium
• 2-Bromobenzaldehyde
• (Carbomethoxymethylene)triphenylphosphorane
• 2-Bromocinnamic acid
• 2-Bromoiodobenzene
• methyl (2E)-3-iodoprop-2-enoate

methyl (2E)-3-(2-bromophenyl)prop-2-enoate Preparation Products

• methyl (2E)-3-(2-bromophenyl)prop-2-enoate (92991-89-4)

• 1. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 2. Dissociative dynamics of O2 on Ag(110)?
  Ivor Lon?ari? Phys. Chem. Chem. Phys., 2015,17, 9436-9445
• 3. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 4. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 5. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990

• 79432-87-4((E)-Methyl 3-(3-bromophenyl)acrylate)
• 84878-00-2(2-Propenoic acid, 3-(4-bromophenyl)-, methyl ester, (2Z)-)
• 102540-15-8((E)-Methyl 3-(2-bromophenyl)acrylate)
• 3650-77-9(3-Bromocinnamic Acid Methyl Ester)
• 99134-25-5((E)-ethyl3-(2-bromophenyl)acrylate)
• 7345-79-1(2-Bromocinnamic acid)
• 7499-56-1(2-Bromocinnamic acid)
• 3650-78-0(Methyl 3-(4-bromophenyl)acrylate)
• 24393-53-1(Ethyl 3-(4-Bromophenyl)acrylate)
• 71205-17-9(Methyl 3-(4-bromophenyl)acrylate)