Cas no 91-48-5 (α-Phenylcinnamic Acid)

α-Phenylcinnamic Acid structure
α-Phenylcinnamic Acid structure
Product Name:α-Phenylcinnamic Acid
CAS No:91-48-5
MF:C15H12O2
MW:224.254584312439
MDL:MFCD00066589
CID:81763
PubChem ID:700620
Update Time:2024-10-26

α-Phenylcinnamic Acid Chemical and Physical Properties

Names and Identifiers

    • alpha-Phenylcinnamic acid
    • a-Phenyl-trans-cinnamic acid, Pract.
    • a-(Phenylmethylene)benzeneacetic acid, Pract.
    • (2E)-2,3-diphenylprop-2-enoic acid
    • 2,3-Diphenylacrylic Acid
    • (2E)-2,3-Diphenylacrylic acid
    • α-Phenylcinnamic Aci
    • α-Phenylcinnamic acid
    • &alpha
    • (E)-2,3-Diphenyl-2-propenoic acid
    • (E)-2,3-Diphenylacrylic acid
    • trans-2,3-Diphenyl-2-propenoic acid
    • trans-2,3-Diphenylacrylic acid
    • trans-2,3-Diphenylpropenoic acid
    • (αE)-α-(Phenylmethylene)benzeneacetic acid (ACI)
    • Acrylic acid, 2,3-diphenyl-, (E)- (8CI)
    • Acrylic acid, 2,3-diphenyl-, trans- (5CI)
    • Benzeneacetic acid, α-(phenylmethylene)-, (E)- (ZCI)
    • (E)-2,3-Diphenylpropenoic acid
    • (E)-α-(Phenylmethylene)benzeneacetic acid
    • (E)-α-Phenylcinnamic acid
    • (E)-α-Stilbenecarboxylic acid
    • trans-α-Phenylcinnamic acid
    • Benzeneacetic acid, .alpha.-(phenylmethylene)-, (E)-
    • Benzeneacetic acid, (E)-
    • 2-Phenylcinnamic acid
    • trans-.alpha.-Phenylcinnamic acid
    • Cinnamic acid, .alpha.-phenyl-
    • cis-alpha-Phenylcinnamic acid
    • (E)-.alpha.-Phenylcinnamic acid
    • NSC-83528
    • (E)-2,3-diphenyl-acrylic acid
    • MFCD00004252
    • .ALPHA.-PHENYLCINNAMIC ACID [MI]
    • (E)-2,3-diphenylprop-2-enoic acid
    • Acrylic acid,3-diphenyl-
    • alpha-Phenylcinnamic acid, (E)-
    • DTXSID00871015
    • AKOS002286967
    • Atropic acid, .beta.-phenyl-
    • Q4734916
    • NSC40614
    • NS00041107
    • (E)-.alpha.-Stilbenecarboxylic acid
    • alpha-Phenylcinnamate
    • alpha-Phenyl-trans-cinnamic acid
    • (Z)-2,3-diphenylacrylic acid
    • CHEMBL1980291
    • .alpha.-Phenylcinnamic acid (cis-form)
    • BDBM50429337
    • EINECS 202-069-4
    • CS-0259613
    • NSC-40614
    • 3368-16-9
    • .alpha.,.beta.-Diphenyl acrylic acid, trans-
    • MLS000737021
    • BBL009868
    • (E)-phenylcinnamic acid
    • alpha-Phenylcinnamic acid, 97%
    • (2E)-2,3-Diphenyl-2-propenoic acid #
    • .alpha.-Phenylcinnamic acid, (E)-
    • Benzeneacetic acid, .alpha.-(phenylmethylene)-
    • 2-Propenoic acid,3-diphenyl-
    • Acrylic acid,3-diphenyl-, (E)-
    • STK298626
    • (e)-alpha-phenylcinnamic acid
    • trans-Stilbene-.alpha.-carboxylic acid
    • 91-48-5
    • .alpha.-Phenylcinnamic acid
    • Acrylic acid, 2,3-diphenyl-, (E)-
    • 0PKH62904B
    • 2,3-diphenylprop-2-enoic acid
    • .alpha.-Phenylcinnamic acid (trans-form)
    • Z56934842
    • NSC 40614
    • .ALPHA.-PHENYLCINNAMIC ACID TRANS-FORM [MI]
    • cis-Stilbene-.alpha.-carboxylic acid
    • D92103
    • EN300-17442
    • ACRYLIC ACID, 2,3-DIPHENYL-, TRANS-
    • NSC83528
    • EN300-7372860
    • 2,3-diphenyl-acrylic acid
    • NSC 83528
    • UNII-0PKH62904B
    • ALBB-025747
    • .alpha.-Stilbenecarboxylic acid
    • STR05165
    • Benzeneacetic acid, alpha-(phenylmethylene)-
    • E-2,3-diphenylpropenoic acid
    • α-Phenylcinnamic Acid
    • MDL： MFCD00066589
    • Inchi： 1S/C15H12O2/c16-15(17)14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-11H,(H,16,17)/b14-11+
    • InChI Key： BIDDLDNGQCUOJQ-SDNWHVSQSA-N
    • SMILES： C(/C1C=CC=CC=1)(\C(=O)O)=C/C1C=CC=CC=1
    • BRN： 1911342

Computed Properties

  • Exact Mass: 224.08400
  • Monoisotopic Mass: 224.084
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 3
  • Complexity: 281
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: 3.5
  • Topological Polar Surface Area: 37.3

Experimental Properties

  • Color/Form: Pale yellow powder
  • Density: 1.198
  • Melting Point: 172.0 to 176.0 deg-C
  • Boiling Point: 325.66°C (rough estimate)
  • Flash Point: 239.8oC
  • Refractive Index: 1.6530 (estimate)
  • Stability/Shelf Life: Stable. Incompatible with strong oxidizing agents.
  • PSA: 37.30000
  • LogP: 3.31180
  • Merck: 7281
  • pka: 4.8 in 60% ethanol

α-Phenylcinnamic Acid Security Information

α-Phenylcinnamic Acid Pricemore >>

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α-Phenylcinnamic Acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Isopropanol ,  Manganese Catalysts: Bathocuproine ,  Dichloro[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylformamide ;  36 h, 60 °C
1.2 Reagents: Hydrochloric acid Solvents: Water
Reference
Ni-Catalyzed Regioselective Hydrocarboxylation of Alkynes with CO2 by Using Simple Alcohols as Proton Sources
Wang, Xueqiang; et al, Journal of the American Chemical Society, 2015, 137(28), 8924-8927

Production Method 2

Reaction Conditions
1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: Palladium diacetate ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Toluene ;  12 h, 80 °C
Reference
Efficient hydrocarboxylation of alkynes based on carbodiimide-regulated in situ CO generation from HCOOH: An alternative indirect utilization of CO2
Xia, Shu-Mei; et al, Chinese Journal of Catalysis, 2022, 43(7), 1642-1651

Production Method 3

Reaction Conditions
1.1 Reagents: Methyl iodide ,  Calcium hydroxide Catalysts: Dicobalt octacarbonyl Solvents: Methanol ,  1,4-Dioxane
Reference
Carbonylation of vinyl halides with carbonylcobalt
Miura, Masahiro; et al, Journal of the Chemical Society, 1989, (1), 73-6

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium tert-butoxide Solvents: Dimethyl sulfoxide ;  5 min, rt
1.2 Reagents: Water
Reference
Elimination vs. substitution in the reaction of 3-stannyl esters and 3-stannyl nitriles with sodium tert-butoxide in DMSO
Chopa, Alicia B.; et al, ARKIVOC (Gainesville, 2003, (10), 382-389

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  25 °C; 45 min, 60 °C; 60 °C → 25 °C
1.2 Reagents: Acetic acid ;  rt; 1 h, rt
1.3 Solvents: Dichloromethane ;  1 h, 25 °C
1.4 25 °C; 10 h, 25 °C
1.5 Reagents: Dichloromethane Solvents: Acetone ;  25 °C
Reference
Stereoselective synthesis of α,β-unsaturated carboxylic acids from alkynes using the Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system
Beesu, Mallesh; et al, Journal of Organometallic Chemistry, 2012, 705, 30-33

Production Method 6

Reaction Conditions
1.1 Reagents: Water Catalysts: Cupric acetate Solvents: Toluene ;  2 - 18 h, 110 °C
1.2 Reagents: Water
Reference
Click amidations, esterifications and one-pot reactions catalyzed by Cu salts and multimetal-organic frameworks (M-MOFs)
Greco, Rossella; et al, Molecular Catalysis, 2022, 522,

Production Method 7

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Ethanol
Reference
Quantitative aspects of radical addition. I. The addition of bromotrichloromethane to cis- and trans-stilbene
Cadogan, J. I. G.; et al, Journal of the Chemical Society, 1962, 4154, 4154-63

Production Method 8

Reaction Conditions
1.1 Reagents: Chlorotrimethylsilane Solvents: Tetrahydrofuran
Reference
New Convenient One-Pot Methods of Conversion of Alkynes to Cyclobutenediones or α,β-Unsaturated Carboxylic Acids Using Novel Reactive Iron Carbonyl Reagents
Periasamy, Mariappan; et al, Journal of Organic Chemistry, 1998, 63(15), 4930-4935

Production Method 9

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Acetic acid ,  Water ;  48 h, 100 °C; 100 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
Reference
Alkyne and Reversible Nitrile Activation: N,N'-Diamidocarbene-Facilitated Synthesis of Cyclopropenes, Cyclopropenones, and Azirines
Moerdyk, Jonathan P.; et al, Journal of the American Chemical Society, 2012, 134(14), 6116-6119

Production Method 10

Reaction Conditions
1.1 Reagents: Dimethyl sulfoxide Catalysts: Cobalt iodide (CoI2) ,  Eosin ;  6 h, 100 °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 11

Reaction Conditions
1.1 Reagents: Diisobutylaluminum hydride Solvents: Heptane ;  24 h, 25 °C
1.2 Reagents: Hydrogen ion Solvents: Water
Reference
Syntheses using alkyne-derived alkenyl- and alkynylaluminum compounds
Zweifel, George; et al, Organic Reactions (Hoboken, 1984, 32,

Production Method 12

Reaction Conditions
1.1 Reagents: 4,5-Bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene-2,7-disulfonic acid Catalysts: Palladium diacetate Solvents: Water ;  5 min
1.2 24 h, 3 bar, 100 °C; 0 °C
Reference
Access to α,β-unsaturated carboxylic acids through water-soluble palladium catalyzed hydroxycarbonylation of alkynes using water as the solvent
Lv, Jinhe; et al, Catalysis Science & Technology, 2021, 11(14), 4708-4713

Production Method 13

Reaction Conditions
1.1 Reagents: Formic acid Catalysts: Triphenylphosphine ,  Palladium diacetate ,  1,4-Bis(diphenylphosphino)butane Solvents: 1,2-Dimethoxyethane
Reference
Palladium-catalyzed hydrocarboxylation of alkynes with formic acid
Zargarian, Davit; et al, Organometallics, 1993, 12(3), 712-24

Production Method 14

Reaction Conditions
1.1 Reagents: Formic-13C acid Catalysts: Palladium diacetate ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Toluene ;  12 h, 80 °C
Reference
Efficient hydrocarboxylation of alkynes based on carbodiimide-regulated in situ CO generation from HCOOH: An alternative indirect utilization of CO2
Xia, Shu-Mei; et al, Chinese Journal of Catalysis, 2022, 43(7), 1642-1651

Production Method 15

Reaction Conditions
1.1 Catalysts: 1,3-Bis(diphenylphosphino)propane ,  Tris(dibenzylideneacetone)dipalladium ,  [1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]chloroc… Solvents: Toluene ;  15 min, rt
1.2 Reagents: Acetic anhydride ;  36 h, 100 °C
Reference
The synergistic copper/ppm Pd-catalyzed hydrocarboxylation of alkynes with formic acid as a CO surrogate as well as a hydrogen source: an alternative indirect utilization of CO2
Xia, Shu-Mei; et al, Green Chemistry, 2021, 23(20), 8089-8095

Production Method 16

Reaction Conditions
1.1 Reagents: Sodium tert-butoxide Solvents: Dimethyl sulfoxide ;  120 min, rt
1.2 Reagents: Water
Reference
Elimination vs. substitution in the reaction of 3-stannyl esters and 3-stannyl nitriles with sodium tert-butoxide in DMSO
Chopa, Alicia B.; et al, ARKIVOC (Gainesville, 2003, (10), 382-389

Production Method 17

Reaction Conditions
1.1 Reagents: Methyl iodide ,  Calcium hydroxide Catalysts: Dicobalt octacarbonyl Solvents: Methanol ,  1,4-Dioxane
Reference
Carbonylation of vinyl halides with carbonylcobalt
Miura, Masahiro; et al, Journal of the Chemical Society, 1989, (1), 73-6

Production Method 18

Reaction Conditions
1.1 Reagents: Bromobenzene ,  Cesium carbonate ,  Water Catalysts: Tri-m-tolylphosphine ,  Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium Solvents: 1,2-Dichloroethane ;  18 h, 130 °C
Reference
Strain-Release-Driven Phosphine and Rhodium Catalysis: Facile Synthesis of Unsymmetrical Tetrasubstituted Alkenes
Zhang, Jing; et al, ACS Catalysis, 2023, 13(15), 10425-10434

Production Method 19

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  25 °C; 0.5 h, 25 °C; 25 °C → 60 °C; 0.5 h, 60 °C; 60 °C → 25 °C
1.2 Reagents: Acetic acid ;  rt; 1 h, rt
1.3 Solvents: Dichloromethane ;  1 h, 25 °C
1.4 25 °C; 10 h, 25 °C
1.5 Reagents: Dichloromethane Solvents: Acetone ;  25 °C
Reference
Stereoselective synthesis of α,β-unsaturated carboxylic acids from alkynes using the Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system
Beesu, Mallesh; et al, Journal of Organometallic Chemistry, 2012, 705, 30-33

Production Method 20

Reaction Conditions
1.1 Reagents: Pyridine Solvents: Acetic anhydride ;  5 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  overnight, acidified, rt
Reference
Synthesis of combretastatin analogs: evaluation of in vitro anticancer activity and molecular docking studies
Kumar, Sunil; et al, Medicinal Chemistry Research, 2012, 21(11), 3720-3729

Production Method 21

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Acetic anhydride ;  24 h, heated
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
Reference
C2-Symmetric Cinchona Alkaloid Derivatives: Versatile Catalysts for the Enantioselective C-C Bond Forming Conjugate Addition of Nucleophiles to Simple α,β-Unsaturated Acyl Pyrazoles
Curran, Simon P.; et al, ChemistrySelect, 2020, 5(48), 15190-15194

Production Method 22

Reaction Conditions
1.1 Reagents: Acetic anhydride ,  Triethylamine ;  24 h, 110 °C
Reference
Synthesis of alpha-pyrones and chromen-2-ones by transition-metal catalyzed annulations of sulfoxonium and iodonium ylides with cis-stilbene acids
John, Stephy Elza; et al, New Journal of Chemistry, 2022, 46(41), 19722-19730

Production Method 23

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane
1.2 Solvents: Tetrahydrofuran
1.3 Reagents: Water
Reference
A simple and efficient route to 2-alkyl-2-alkenoic acids and 2-phenyl-2-alkenoic acids by the Horner synthesis. Application to the stereoselective synthesis of the pheromone manicone
Coutrot, Philippe; et al, Synthesis, 1986, (9), 790-2

Production Method 24

Reaction Conditions
1.1 Reagents: Dimethyl sulfoxide Catalysts: Cobalt iodide (CoI2) ,  Eosin ;  6 h, 100 °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

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Amadis Chemical Company Limited
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(CAS:91-48-5)α-Phenylcinnamic Acid
Order Number:A843947
Stock Status:in Stock
Quantity:25g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 07:01
Price ($):248.0

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Amadis Chemical Company Limited
(CAS:91-48-5)α-Phenylcinnamic Acid
A843947
Purity:99%
Quantity:25g
Price ($):248.0
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