Production Method 1

833-81-8

Reaction Conditions

1.1 Solvents: Tetrahydrofuran

Reference

Triflones (CF3SO2C). Survey of reactivity and synthetic utility

Hendrickson, James B.; et al, Journal of the American Chemical Society, 1974, 96(7), 2275-6

Production Method 2

5342-87-0

833-81-8

Reaction Conditions

1.1 Catalysts: Iodine Solvents: Dichloromethane ;  20 h, 25 °C

Reference

Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions

Jereb, Marjan; et al, Acta Chimica Slovenica, 2017, 64(4), 747-762

Production Method 3

5342-87-0

833-81-8

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Acetic acid ;  heated

Reference

Friedel-Crafts alkylation of benzene with 1,2-diphenyl-2-propanol, 1-chloro-2,3-diphenylpropane, and 2-methyl-1-phenyl-2-butanol

Khalaf, Ali A.; et al, Journal of the Indian Chemical Society, 2010, 87(5), 595-600

Production Method 4

5342-87-0

833-81-8

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Acetic acid ,  Water ;  0 °C; 0 °C → rt; 10 min, rt
1.2 Reagents: Sodium carbonate Solvents: Water ;  neutralized, rt

Reference

Thermally Induced Carbohydroxylation of Styrenes with Aryldiazonium Salts

Kindt, Stephanie; et al, Angewandte Chemie, 2016, 55(30), 8744-8747

Production Method 5

98-80-6

673-32-5

833-81-8

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium ,  Benzoic acid, 3,3′,3′′-phosphinidynetris-, lithium salt (1:3) Solvents: Toluene ,  Water ;  2.5 h, 100 °C

Reference

Efficient synthesis of trisubstituted alkenes in an aqueous-organic system using a versatile and recyclable Rh/m-TPPTC catalyst

Genin, Emilie; et al, Tetrahedron Letters, 2004, 45(21), 4157-4161

Production Method 6

948-97-0

833-81-8

Reaction Conditions

1.1 Catalysts: Sodium triethylborohydride ,  (SP-5-41)-[2-[[Bis(1,1-dimethylethyl)phosphino-κP]methyl]-6-[(4S)-4-(1,1-dimethy… Solvents: Pentane ,  Tetrahydrofuran ;  8 h, rt
1.2 Reagents: Oxygen ;  rt

Reference

Iron Catalyzed Isomerization of α-Alkyl Styrenes to Access Trisubstituted Alkenes

Xu, Songgen; et al, Chinese Journal of Chemistry, 2021, 39(3), 585-589

Production Method 7

591-50-4

833-81-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: 2456428-19-4 Solvents: Polyethylene glycol ;  2 h, 130 °C

Reference

Promising new catalytic properties of a Co (II)-carboxamide complex and its derived Co3O4 nanoparticles for the Mizoroki-Heck and the Epoxidation reactions

Kiani, Mahsa ; et al, Applied Organometallic Chemistry, 2020, 34(11),

Production Method 8

833-81-8

Reaction Conditions

1.1 Catalysts: Palladium diacetate ,  6A,6B,6C,6D,6E,6F,6G-Heptakis[(aminoiminomethyl)amino]-6A,6B,6C,6D,6E,6F,6G-hept… Solvents: Dimethylformamide ,  Water ;  15 min, rt
1.2 Reagents: Potassium carbonate ;  30 min, rt
1.3 16 h, 80 °C

Reference

The Aminocyclodextrin/Pd(OAc)2 Complex as an Efficient Catalyst for the Mizoroki-Heck Cross-Coupling Reaction

Kanagaraj, Kuppusamy; et al, Chemistry - A European Journal, 2013, 19(43), 14425-14431

Production Method 9

14447-41-7

333-27-7

833-81-8

Reaction Conditions

1.1 Reagents: sec-Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  94 s, -50 °C
1.2 10 min, -50 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis-trans Isomerization in Flow

Lee, Hyune-Jea; et al, Organic Letters, 2021, 23(8), 2904-2910

Production Method 10

591-50-4

673-32-5

833-81-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Catalysts: Tetrabutylammonium fluoride ,  Bathocuproine ,  Nickel bromide Solvents: Dimethylformamide ;  12 h, rt

Reference

Highly stereoselective synthesis of trans-alkenes via electrochemical Ni-catalyzed hydroarylation of alkynes with aryl iodides

Zhang, Haoxiang; et al, Organic & Biomolecular Chemistry, 2023, 21(25), 5189-5193

Production Method 11

98-80-6

873-66-5

833-81-8

Reaction Conditions

1.1 Reagents: Propionic acid ,  Potassium fluoride Catalysts: Tempo ,  Palladium diacetate ;  1 h, rt

Reference

1,2,3-Trisubstituted Indanes by Highly Diastereoselective Palladium-Catalyzed Oxyarylation of Indenes with Arylboronic Acids and Nitroxides

Kirchberg, Sylvia; et al, Angewandte Chemie, 2010, 49(38), 6877-6880

Production Method 12

98-86-2

2959-74-2

833-81-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Toluene

Reference

Allylic and benzylic carbanions substituted by heteroatoms

Biellmann, Jean-Francois; et al, Organic Reactions (Hoboken, 1982, 27,

Production Method 13

62673-31-8

98-86-2

833-81-8

Reaction Conditions

1.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  10 min, 60 °C
1.2 Solvents: Tetrahydrofuran ;  rt; rt → -28 °C
1.3 Reagents: Chlorotrimethylsilane Solvents: Tetrahydrofuran ;  -28 °C; -28 °C → rt; 8 h, rt
1.4 Reagents: Ammonium chloride Solvents: Diethyl ether ,  Water ;  10 min

Reference

Palladium-catalyzed stereoselective synthesis of (E)-stilbenes via organozinc reagents and carbonyl compounds

Wang, Jin-Xian; et al, Advanced Synthesis & Catalysis, 2006, 348, 1262-1270

Production Method 14

833-81-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: 2456428-19-4 Solvents: Polyethylene glycol ;  2 h, 130 °C

Reference

Promising new catalytic properties of a Co (II)-carboxamide complex and its derived Co3O4 nanoparticles for the Mizoroki-Heck and the Epoxidation reactions

Kiani, Mahsa ; et al, Applied Organometallic Chemistry, 2020, 34(11),

Production Method 15

98-80-6

673-32-5

833-81-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium chloride ,  N,N-Bis(1-methylethyl)-P,P-diphenylphosphinous amide Solvents: Tetrahydrofuran ;  30 min, rt; rt → 65 °C; 24 h, 65 °C

Reference

Palladium-catalyzed hydroarylation of alkynes with arylboronic acids

Xu, Xiaoling; et al, Tetrahedron, 2010, 66(13), 2433-2438

Production Method 16

98-80-6

673-32-5

833-81-8

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium ,  Benzoic acid, 3,3′,3′′-phosphinidynetris-, lithium salt (1:3) Solvents: Toluene ,  Water ;  rt; 2.5 h, 100 °C; 100 °C → rt

Reference

Rh-catalyzed addition of boronic acids to alkynes for the synthesis of trisubstituted alkenes in a biphasic system - Mechanistic study and recycling of the Rh/m-TPPTC catalyst

Genin, Emilie; et al, Journal of Organometallic Chemistry, 2004, 689(23), 3820-3830

Production Method 17

948-97-0

833-81-8

Reaction Conditions

1.1 Catalysts: Tetrabutylammonium acetate Solvents: Tetrabutylammonium bromide ;  120 °C

Reference

Pd Nanoparticle Catalyzed Heck Arylation of 1,1-Disubstituted Alkenes in Ionic Liquids. Study on Factors Affecting the Regioselectivity of the Coupling Process

Calo, Vincenzo; et al, Organometallics, 2003, 22(21), 4193-4197

Production Method 18

591-50-4

833-81-8

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Palladium (nanoparticles) ,  Copper (nanoparticles) Solvents: Dimethylformamide ;  18 h, 100 °C

Reference

Preparation of monometallic (Pd, Ag) and bimetallic (Pd/Ag, Pd/Ni, Pd/Cu) nanoparticles via reversed micelles and their use in the Heck reaction

Heshmatpour, Felora; et al, Tetrahedron, 2012, 68(14), 3001-3011

Production Method 19

591-50-4

833-81-8

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Triallyl cyanurate (reaction products with SBA-15 supported mercaptopropyltrimethoxysilane…) Solvents: Dimethylformamide ;  6 h, 120 °C

Reference

Carbon-carbon bond forming reactions: Application of covalently anchored 2,4,6-triallyloxy-1,3,5-triazine (TAT) Pd(II) complex over modified surface of SBA-15 to Heck, Suzuki, Sonogashira and Hiyama cross coupling reactions

Singh, Chandani; et al, Catalysis Communications, 2015, 69, 11-15

Production Method 20

833-81-8

Reaction Conditions

1.1 Reagents: Sodium acetate Catalysts: Palladium (wool-supported) Solvents: Water ,  Polyethylene glycol ;  80 °C

Reference

Biopolymer-metal complex wool-Pd as a highly active heterogeneous catalyst for Heck reaction in aqueous media

Wu, Shang; et al, Tetrahedron, 2011, 67(1), 250-256

Production Method 21

833-81-8

Reaction Conditions

1.1 Reagents: Norbornene ,  Pinacolborane Catalysts: Tetrakis(trimethylphosphine)iron Solvents: Hexane ;  18 h, 50 °C
1.2 Reagents: Potassium carbonate Catalysts: Palladium diacetate ,  Tri-tert-butylphosphonium tetrafluoroborate Solvents: 1,4-Dioxane ,  Water ;  5 h, 100 °C

Reference

Iron-Catalyzed E-Selective Dehydrogenative Borylation of Vinylarenes with Pinacolborane

Wang, Chao; et al, ACS Catalysis, 2016, 6(11), 7585-7589

Production Method 22

833-81-8

Reaction Conditions

1.1 Reagents: Zinc ,  Titanium tetrachloride Solvents: Pyridine

Reference

Convenient method for the preparation of styrene derivatives by the use of titanium(IV) chloride and zinc

Song, Suk-Zu; et al, Chemistry Letters, 1974, (10), 1161-2

Production Method 23

948-99-2

833-81-8

Reaction Conditions

1.1 Catalysts: Bis(tri-tert-butylphosphine)palladium Solvents: Tetrahydrofuran ;  3 h, 50 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Pd-catalyzed selective tandem arylation-alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

Shi, Ji-cheng; et al, Journal of Organometallic Chemistry, 2003, 687(2), 518-524

Production Method 24

2629-47-2

873-66-5

833-81-8

Reaction Conditions

1.1 Catalysts: Palladium diacetate Solvents: Acetonitrile
1.2 Reagents: Sodium chloride Solvents: Water

Reference

Palladium(II)-catalyzed phenylation of unsaturated compounds using phenylantimony chlorides under air

Matoba, Kazutaka; et al, Journal of Organometallic Chemistry, 1999, 574(1), 3-10

Production Method 25

1804967-87-0

833-81-8

Reaction Conditions

1.1 Catalysts: Lithium bromide ,  Palladium chloride Solvents: N-Methyl-2-pyrrolidone ;  15 h, 160 °C

Reference

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Meng, Guangrong; et al, Angewandte Chemie, 2015, 54(48), 14518-14522

Production Method 26

10182-84-0

833-81-8

Reaction Conditions

1.1 Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  60 s, rt → 130 °C; 60 s, 130 °C

Reference

Microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts

Li, Jian; et al, Letters in Organic Chemistry, 2013, 10(1), 42-46

Production Method 27

676-58-4

41796-38-7

833-81-8

Reaction Conditions

1.1 Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Tetrahydrofuran ;  12 h, rt
1.2 Reagents: Water ;  rt

Reference

An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

Yang, Zhaozhen; et al, Organic & Biomolecular Chemistry, 2013, 11(13), 2175-2185

Production Method 28

591-50-4

673-32-5

833-81-8

Reaction Conditions

1.1 Reagents: Ethanol ,  Sodium hydroxide ,  Bis(pinacolato)diborane Catalysts: Sodium methoxide ,  Copper ,  Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  2 h, 60 °C
1.2 2 - 6 h, 60 °C

Reference

(E)-Alkene Synthesis via Nano-Copper/Homogeneous Palladium Co-Catalysis and Selectivity Amplification

Liu, Shiwen; et al, Asian Journal of Organic Chemistry, 2017, 6(5), 507-511

Production Method 29

98-80-6

873-66-5

833-81-8

Reaction Conditions

1.1 Reagents: Sodium carbonate ,  Oxygen Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  rt → 50 °C; 3 h, 50 °C

Reference

Oxygen-Promoted Pd(II) Catalysis for the Coupling of Organoboron Compounds and Olefins

Jung, Young Chun; et al, Organic Letters, 2003, 5(13), 2231-2234

Production Method 30

637-50-3

833-81-8

Reaction Conditions

1.1 Catalysts: Palladium diacetate ,  6A,6B,6C,6D,6E,6F,6G-Heptakis[(aminoiminomethyl)amino]-6A,6B,6C,6D,6E,6F,6G-hept… Solvents: Dimethylformamide ,  Water ;  15 min, rt
1.2 Reagents: Potassium carbonate ;  30 min, rt
1.3 11 h, 80 °C

Reference

The Aminocyclodextrin/Pd(OAc)2 Complex as an Efficient Catalyst for the Mizoroki-Heck Cross-Coupling Reaction

Kanagaraj, Kuppusamy; et al, Chemistry - A European Journal, 2013, 19(43), 14425-14431

Production Method 31

98-86-2

2959-74-2

833-81-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Benzene

Reference

Synthetic applications of phosphoryl-stabilized anions

Wadsworth, William S. Jr., Organic Reactions (Hoboken, 1977, 25,

Production Method 32

676-58-4

41796-39-8

833-81-8

Reaction Conditions

1.1 Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Tetrahydrofuran ;  12 h, rt
1.2 Reagents: Water ;  rt

Reference

An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

Yang, Zhaozhen; et al, Organic & Biomolecular Chemistry, 2013, 11(13), 2175-2185

Production Method 33

62673-31-8

98-86-2

833-81-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: 1,4-Dioxane ;  cooled
1.2 5 min, 0 °C
1.3 Solvents: 1,4-Dioxane ;  5 min; 8 h, 80 °C

Reference

Lewis Acid Promoted Carbon-Carbon Double-Bond Formation via Organozinc Reagents and Carbonyl Compounds

Peng, Zhi-Yong; et al, Journal of Organic Chemistry, 2009, 74(17), 6855-6858

trans-alpha-methylstilbene Raw materials

• Phenylboronic acid
• Iodobenzene
• Benzeneethanol, a-methyl-a-phenyl-
• β-Methylstyrene (Mixture of Cis-Trans isomers)
• Benzylzinc bromide, 0.50 M in THF
• Methylmagnesium Chloride (3M in THF)
• Stibine,chlorodiphenyl-
• Benzene,1,1'-(1-methylene-1,2-ethanediyl)bis-
• 1,1'-[(Z)-1-chloroethene-1,2-diyl]dibenzene
• Benzene, 1,1'-[1-(ethylthio)-1,2-ethenediyl]bis-, (Z)- (9CI)
• 2,6-Piperidinedione, 1-benzoyl-
• Benzene, 1,1'-[(1E)-1-bromo-1,2-ethenediyl]bis-
• trans-b-Methylstyrene (Stabilized with 3,5-di-tert-butylcatechol)
• Methyl trifluoromethanesulfonate
• 1-Phenyl-1-propyne
• Acetophenone
• 1,2-Diphenylethenylsulfanylbenzene
• Iodonium, diphenyl-
• Benzyldiphenylphosphine oxide

trans-alpha-methylstilbene Preparation Products

• trans-alpha-methylstilbene (833-81-8)

• 1. An ionic liquid loaded magnetically confined polymeric mesoporous adsorbent for extraction of parabens from environmental and cosmetic samples?
  Masrudin Md Yusoff,Muggundha Raoov,Noorfatimah Yahaya,Noorashikin Md Salleh RSC Adv., 2017,7, 35832-35844
• 2. Acenaphthenic hopanoids, a novel series of aromatised
  Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre Albrecht Chem. Commun., 2001, 1976-1977
• 3. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
  Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin Fan J. Mater. Chem. B, 2019,7, 3088-3099
• 4. Aggregation-induced emission leading to two distinct emissive species in the solid-state structure of high-dipole organic chromophores?
  Felix Witte,Philipp Rietsch,Nithiya Nirmalananthan-Budau,Florian Weigert,Jan P. G?tze,Ute Resch-Genger,Siegfried Eigler,Beate Paulus Phys. Chem. Chem. Phys., 2021,23, 17521-17529
• 5. An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform?
  Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao You Analyst, 2015,140, 1827-1831

Professional Introduction to trans-alpha-Methylstilbene (CAS No. 833-81-8)

trans-alpha-Methylstilbene, with the chemical formula C??H?? and CAS number 833-81-8, is a naturally occurring stilbene derivative that has garnered significant attention in the field of chemobiology and pharmaceutical research. This compound, a trans-isomer of alpha-methylstilbene, belongs to the larger class of stilbenes, which are known for their diverse biological activities. Stilbenes are polyphenolic compounds that are synthesized by plants as part of their defense mechanisms against environmental stressors. Among these, trans-alpha-methylstilbene has emerged as a compound of interest due to its potential therapeutic applications and mechanistic insights into cellular processes.

The structural uniqueness of trans-alpha-methylstilbene lies in its double bond configuration, which influences its interactions with biological targets. The presence of a methyl group at the alpha position relative to the stilbene core modifies its electronic properties, making it a valuable candidate for studying structure-activity relationships (SARs) in drug design. This compound exhibits notable bioactivity, particularly in the context of antioxidant and anti-inflammatory responses, which have been extensively explored in preclinical studies.

Recent advancements in metabolomics and lipidomics have highlighted the role of trans-alpha-methylstilbene in modulating lipid profiles and enhancing cellular redox balance. Studies have demonstrated that this compound can interact with enzymes involved in cholesterol synthesis and metabolism, suggesting its potential utility in managing hyperlipidemia and related cardiovascular disorders. Additionally, trans-alpha-methylstilbene has shown promise in inhibiting inflammatory pathways by modulating cytokine production and reducing oxidative stress markers.

In vitro and in vivo studies have further elucidated the mechanisms by which trans-alpha-methylstilbene exerts its biological effects. For instance, research indicates that this compound can activate nuclear factor erythroid 2–related factor 2 (Nrf2), a transcription factor critical for antioxidant response. By upregulating genes involved in glutathione synthesis, trans-alpha-methylstilbene enhances cellular protection against oxidative damage. Moreover, its ability to modulate microRNA expression has opened new avenues for exploring its role in gene regulation and disease intervention.

The pharmacokinetic profile of trans-alpha-methylstilbene has also been a subject of interest. Unlike some other stilbenes that undergo rapid metabolism, CAS No. 833-81-8 exhibits a longer half-life, allowing for sustained biological activity. This characteristic makes it an attractive candidate for therapeutic applications where prolonged exposure to bioactive molecules is desirable. Furthermore, studies suggest that oral administration of trans-alpha-methylstilbene leads to bioavailability comparable to other stilbenes found in dietary supplements, such as resveratrol.

The potential therapeutic applications of trans-alpha-methylstilbene extend beyond antioxidant and anti-inflammatory effects. Emerging research has explored its role in neuroprotection, where it has been shown to mitigate neuroinflammatory responses associated with conditions like Alzheimer's disease and Parkinson's disease. The compound's ability to cross the blood-brain barrier has further intrigued researchers, as it suggests potential for treating central nervous system disorders without significant permeability issues.

In conclusion, CAS No. 833-81-8, or more accurately referred to as trans-alpha-methylstilbene, represents a promising natural product with multifaceted biological activities. Its structural features contribute to its unique pharmacological profile, making it an invaluable tool for studying disease mechanisms and developing novel therapeutic strategies. As research continues to uncover new insights into the bioactivity of this compound, it is poised to play an increasingly significant role in chemobiology and pharmaceutical innovation.

• 779-51-1(Benzene,1,1'-(1-methyl-1,2-ethenediyl)bis-)
• 782-06-9(Benzene,1,1'-[(1E)-1,2-dimethyl-1,2-ethenediyl]bis-)
• 2082-61-3((but-2-en-2-yl)benzene)
• 93872-36-7(Benzene, 1,1'-(1,2-dimethyl-1,2-ethenediyl)bis[4-methyl-)
• 782-05-8(Benzene, 1,1'-(1,2-dimethyl-1,2-ethenediyl)bis-, (Z)-)
• 88951-73-9(2-Butenylidene, 3-phenyl-)
• 919789-88-1(Benzene, 1-methyl-4-(1-methyl-2-phenyl-1-propen-1-yl)-)
• 917762-09-5(Benzene, 1,4-bis[2-phenyl-1,2-bis[4-(2-phenylethenyl)phenyl]ethenyl]-)
• 1017-22-7(Benzene,1,1'-[(1Z)-1-methyl-1,2-ethenediyl]bis-)
• 60623-85-0(Benzene, 1-methyl-4-(2-phenyl-1-propenyl)-)