Cas no 88241-65-0 ((2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid)

(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid structure
88241-65-0 structure
Product Name:(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid
CAS No:88241-65-0
MF:C15H12O2
MW:224.254584312439
MDL:MFCD00014010
CID:709304
PubChem ID:5842785
Update Time:2024-10-26

(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Propenoic acid,3-[1,1'-biphenyl]-4-yl-, (2E)-
    • 7Α-METHYL-3,3-DIMETHOXY-5(10)-ESTRENE-17-ONE
    • trans-p-Phenylcinnamic Acid
    • (E)-4-Phenylcinnamic acid
    • trans-3-(4-Phenylphenyl)-2-propenoic acid
    • (2E)-3-[1,1′-Biphenyl]-4-yl-2-propenoic acid (ACI)
    • 2-Propenoic acid, 3-[1,1′-biphenyl]-4-yl-, (E)- (ZCI)
    • (E)-3-([1,1′-Biphenyl]-4-yl)acrylic acid
    • trans-4-Phenylcinnamic acid
    • 4-Phenylcinnamic acid
    • (2E)-3-biphenyl-4-ylacrylic acid
    • EN300-833098
    • (e)-3-(biphenyl-4-yl)acrylic acid
    • 2-propenoic acid, 3-[1,1'-biphenyl]-4-yl-, (2E)-
    • (2E)-3-{[1,1'-BIPHENYL]-4-YL}PROP-2-ENOIC ACID
    • 3-([1,1'-Biphenyl]-4-yl)acrylic acid
    • NS00051791
    • MFCD00014010
    • JS-042C
    • CHEMBL3621534
    • BDBM50124584
    • p-Phenylcinnamic acid
    • AH-034/04876017
    • F2147-0938
    • J-501863
    • 88241-65-0
    • CS-0156434
    • 13026-23-8
    • (E)-3-(4-phenylphenyl)prop-2-enoic acid
    • AKOS000263551
    • ALBB-010269
    • SCHEMBL165794
    • EN300-152469
    • (E)-3-([1,1'-biphenyl]-4-yl)acrylic acid
    • (2E)-3-(4-phenylphenyl)prop-2-enoic acid
    • 3-[1,1'-biphenyl]-4-ylacrylic acid
    • 3-[1,1'-Biphenyl]-4-yl-2-propenoic acid, AldrichCPR
    • (2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid
    • MDL： MFCD00014010
    • Inchi： 1S/C15H12O2/c16-15(17)11-8-12-6-9-14(10-7-12)13-4-2-1-3-5-13/h1-11H,(H,16,17)/b11-8+
    • InChI Key： DMJDEZUEYXVYNO-DHZHZOJOSA-N
    • SMILES： C(/C1C=CC(C2C=CC=CC=2)=CC=1)=C\C(=O)O

Computed Properties

  • Exact Mass: 224.083729621g/mol
  • Monoisotopic Mass: 224.083729621g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 3
  • Complexity: 24.8
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 0.2
  • Topological Polar Surface Area: 37.3?2

Experimental Properties

  • Color/Form: Not determined
  • Density: 1.178±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 226.4-228.7 oC
  • Boiling Point: 412.912 °C at 760 mmHg
  • Flash Point: 308.021 °C
  • Solubility: Almost insoluble (0.061 g/l) (25 o C),
  • Solubility: Dissolved in Dimethylformamide

(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid Security Information

  • WGK Germany：3
  • Hazard Category Code： 36/37/38-20/21/22
  • Safety Instruction： 22-24/25
  • FLUKA BRAND F CODES：8
  • Hazardous Material Identification： Xn

(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid Pricemore >>

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(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Titanium tetrachloride Solvents: Dichloromethane ;  20 min, rt
1.2 Reagents: Triethylamine ;  10 min, rt; 3 - 4 h, rt
Reference
TiCl4-mediated olefination of aldehydes with acetic acid and alkyl acetates. A stereoselective approach to (E)-α,β-unsaturated carboxylic acids and esters
Augustine, John Kallikat; et al, Tetrahedron Letters, 2014, 55(24), 3503-3506

Production Method 2

Reaction Conditions
1.1 Reagents: Piperidine Solvents: Pyridine ;  24 h, 80 - 90 °C
Reference
Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives as novel anticancer agents
Qian, Yong; et al, Bioorganic & Medicinal Chemistry, 2010, 18(14), 4991-4996

Production Method 3

Reaction Conditions
1.1 Reagents: Lithium tert-butoxide ,  Bis(pinacolato)diborane Catalysts: Cuprous iodide ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Dimethylacetamide ;  24 h, 60 °C; 60 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
Reference
Stereoselective defluorinative carboxylation of gem-difluoroalkenes with carbon dioxide
Xie, Shi-Liang; et al, Organic Chemistry Frontiers, 2019, 6(21), 3678-3682

Production Method 4

Reaction Conditions
1.1 Catalysts: β-Cyclodextrin ,  Phenylalanine ammonia-lyase Solvents: Water ;  40 h, pH 8.8, 30 °C
1.2 Solvents: Methanol ;  30 °C
Reference
Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky L- and D-Arylalanines
Filip, Alina; et al, ChemCatChem, 2018, 10(12), 2627-2633

Production Method 5

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ,  Water ;  7 h, reflux
2.1 Catalysts: β-Cyclodextrin ,  Phenylalanine ammonia-lyase Solvents: Water ;  40 h, pH 8.8, 30 °C
2.2 Solvents: Methanol ;  30 °C
Reference
Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky L- and D-Arylalanines
Filip, Alina; et al, ChemCatChem, 2018, 10(12), 2627-2633

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  30 min, rt
1.2 Solvents: Dimethylformamide ;  0 °C; 3 h, rt; 4 h, 60 °C
2.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  4 - 6 h, reflux
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, -10 °C
2.3 Solvents: Toluene ;  16 - 24 h, reflux
3.1 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ,  Water ;  7 h, reflux
4.1 Catalysts: β-Cyclodextrin ,  Phenylalanine ammonia-lyase Solvents: Water ;  40 h, pH 8.8, 30 °C
4.2 Solvents: Methanol ;  30 °C
Reference
Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky L- and D-Arylalanines
Filip, Alina; et al, ChemCatChem, 2018, 10(12), 2627-2633

Production Method 7

Reaction Conditions
1.1 Catalysts: Piperidine Solvents: Pyridine ;  2 h, reflux
Reference
Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus
Giancotti, Gilda; et al, European Journal of Medicinal Chemistry, 2018, 149, 56-68

Production Method 8

Reaction Conditions
1.1 Catalysts: Piperidine Solvents: Pyridine ;  24 h, 80 - 90 °C
Reference
Synthesis, molecular modeling and biological evaluation of β-ketoacyl-acyl carrier protein synthase III (FabH) as novel antibacterial agents
Zhang, Hong-Jia; et al, Bioorganic & Medicinal Chemistry, 2011, 19(15), 4513-4519

Production Method 9

Reaction Conditions
1.1 Reagents: Hydrogen peroxide ,  Sodium chlorite
Reference
Traceless sulfone linker cleavage triggered by ozonolysis: solid-phase synthesis of diverse α-β-unsaturated carbonyl compounds
Chang, Yi-Fan; et al, Tetrahedron Letters, 2008, 49(3), 543-547

Production Method 10

Reaction Conditions
1.1 Reagents: Tetrabutylammonium tetrafluoroborate Solvents: Dimethylformamide ;  8 h, 1 atm, 35 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified
Reference
Stereoselective electrochemical carboxylation of α,β-unsaturated sulfones
Yang, Zi-Xin; et al, Chinese Chemical Letters, 2023, 34(6),

Production Method 11

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C
1.2 1 - 3 h, rt
1.3 Reagents: Acetic acid ,  Water ;  rt
1.4 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  6 - 24 h, rt
1.5 Reagents: Hydrochloric acid Solvents: Water ;  pH 1 - 2, rt
Reference
Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
Zhao, Bin; et al, Organic & Biomolecular Chemistry, 2021, 19(3), 568-573

Production Method 12

Reaction Conditions
1.1 Reagents: Potassium methoxide Catalysts: Cuprous chloride Solvents: Dimethylacetamide ;  24 h, 1 atm, 70 °C
1.2 Reagents: Hydrochloric acid Solvents: Water
Reference
Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO2 Catalyzed by Cuprous Halide
Hong, Junting; et al, European Journal of Organic Chemistry, 2020, 2020(19), 2813-2818

Production Method 13

Reaction Conditions
1.1 Reagents: Dimethyl sulfoxide Catalysts: Cobalt iodide (CoI2) ,  Eosin ;  15 h, 50 °C
Reference
Carboxylation of styrenes with CBr4 and DMSO via cooperative photoredox and cobalt catalysis
Song, Cai-xia; et al, RSC Advances, 2017, 7(19), 11233-11243

Production Method 14

Reaction Conditions
1.1 Solvents: Dimethylformamide ,  Tetrahydrofuran ;  60 °C
1.2 Reagents: Potassium carbonate ,  Sodium benzenesulfinate (resin-bound) Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,2-Dimethoxyethane ,  Water ;  90 °C
1.3 Reagents: Dimethyl sulfoxide ,  Butyllithium ;  5 min, rt
1.4 Solvents: Tetrahydrofuran ;  30 min, rt
1.5 Solvents: Tetrahydrofuran ;  rt
1.6 Reagents: Ozone Solvents: Dichloromethane ;  5 min, 0 °C
1.7 Reagents: Sodium methoxide Solvents: Methanol ,  Dichloromethane ;  3 h, rt
2.1 Reagents: Hydrogen peroxide ,  Sodium chlorite
Reference
Traceless sulfone linker cleavage triggered by ozonolysis: solid-phase synthesis of diverse α-β-unsaturated carbonyl compounds
Chang, Yi-Fan; et al, Tetrahedron Letters, 2008, 49(3), 543-547

Production Method 15

Reaction Conditions
1.1 Solvents: Dimethylformamide ,  Tetrahydrofuran ;  60 °C
1.2 Reagents: Potassium carbonate ,  Sodium benzenesulfinate (resin-bound) Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,2-Dimethoxyethane ,  Water ;  90 °C
1.3 Reagents: Dimethyl sulfoxide ,  Butyllithium ;  5 min, rt
1.4 Solvents: Tetrahydrofuran ;  30 min, rt
1.5 Solvents: Tetrahydrofuran ;  rt
1.6 Reagents: Ozone Solvents: Dichloromethane ;  5 min, 0 °C
1.7 Reagents: Sodium methoxide Solvents: Methanol ,  Dichloromethane ;  3 h, rt
2.1 Reagents: Hydrogen peroxide ,  Sodium chlorite
Reference
Traceless sulfone linker cleavage triggered by ozonolysis: solid-phase synthesis of diverse α-β-unsaturated carbonyl compounds
Chang, Yi-Fan; et al, Tetrahedron Letters, 2008, 49(3), 543-547

Production Method 16

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ;  10 h, 75 °C
2.1 Reagents: Dimethyl sulfoxide Catalysts: Cobalt iodide (CoI2) ,  Eosin ;  15 h, 50 °C
Reference
Carboxylation of styrenes with CBr4 and DMSO via cooperative photoredox and cobalt catalysis
Song, Cai-xia; et al, RSC Advances, 2017, 7(19), 11233-11243

Production Method 17

Reaction Conditions
1.1 Reagents: Sodium acetate ,  Iodine Solvents: Acetonitrile ;  3 h, reflux; reflux → rt
1.2 Reagents: Sodium thiosulfate Solvents: Water
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized
2.1 Reagents: Tetrabutylammonium tetrafluoroborate Solvents: Dimethylformamide ;  8 h, 1 atm, 35 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified
Reference
Stereoselective electrochemical carboxylation of α,β-unsaturated sulfones
Yang, Zi-Xin; et al, Chinese Chemical Letters, 2023, 34(6),

Production Method 18

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  4 - 6 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, -10 °C
1.3 Solvents: Toluene ;  16 - 24 h, reflux
2.1 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ,  Water ;  7 h, reflux
3.1 Catalysts: β-Cyclodextrin ,  Phenylalanine ammonia-lyase Solvents: Water ;  40 h, pH 8.8, 30 °C
3.2 Solvents: Methanol ;  30 °C
Reference
Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky L- and D-Arylalanines
Filip, Alina; et al, ChemCatChem, 2018, 10(12), 2627-2633

Production Method 19

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide ,  Triphenylphosphine Solvents: Dichloromethane ;  30 min, rt
2.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  30 min, rt
2.2 Solvents: Dimethylformamide ;  0 °C; 3 h, rt; 4 h, 60 °C
3.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  4 - 6 h, reflux
3.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, -10 °C
3.3 Solvents: Toluene ;  16 - 24 h, reflux
4.1 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ,  Water ;  7 h, reflux
5.1 Catalysts: β-Cyclodextrin ,  Phenylalanine ammonia-lyase Solvents: Water ;  40 h, pH 8.8, 30 °C
5.2 Solvents: Methanol ;  30 °C
Reference
Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky L- and D-Arylalanines
Filip, Alina; et al, ChemCatChem, 2018, 10(12), 2627-2633

Production Method 20

Reaction Conditions
1.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2 - 3, rt
2.1 Reagents: N-Bromosuccinimide ,  Triphenylphosphine Solvents: Dichloromethane ;  30 min, rt
3.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  30 min, rt
3.2 Solvents: Dimethylformamide ;  0 °C; 3 h, rt; 4 h, 60 °C
4.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  4 - 6 h, reflux
4.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, -10 °C
4.3 Solvents: Toluene ;  16 - 24 h, reflux
5.1 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ,  Water ;  7 h, reflux
6.1 Catalysts: β-Cyclodextrin ,  Phenylalanine ammonia-lyase Solvents: Water ;  40 h, pH 8.8, 30 °C
6.2 Solvents: Methanol ;  30 °C
Reference
Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky L- and D-Arylalanines
Filip, Alina; et al, ChemCatChem, 2018, 10(12), 2627-2633

(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid Raw materials

(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid Preparation Products

(2E)-3-{1,1'-biphenyl-4-yl}prop-2-enoic acid Related Literature

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