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103-26-4

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103-26-4 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 103-26-4 differently. You can refer to the following data:
1. Methyl cinnamate appears as white to slightly yellow crystals with a cherry and balsamic aroma. Melting point 34 ℃. The boiling point is 260°C, and the refractive index (nD20) is 1.5670. Relative density (d435) 1.0700. Soluble in alcohol, ether, glycerin, propylene glycol, most non-volatile oils and mineral oils, insoluble in water.Natural products are contained in basil oil (up to 52%), galangal oil and bay leaf oil.
2. Methyl cinnamate has a fruity, balsamic odor similar to strawberry and a corresponding sweet taste.

Preparative Methods

It is obtained by esterification of cinnamic acid with methanol. The mixture of cinnamic acid, methanol and sulfuric acid (or hydrochloric acid) was heated to reflux for 5 h, and the excess amount of methanol was added. Cool and spate the acid layer, washed with water and 10% sodium carbonate solution, and then washed with water to neutral. The crude product was subjected to recrystallization or vacuum distillation [collection of 132-134 ° C (2.0 kPa) fraction] to give methyl cinnamate with a yield of about 70%.

Description

Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98 %) with a 2 - 6 % fresh weight yield in the leaf and twigs. Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry. It is known to attract males of various orchid bees, such as Aglae caerulea. Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida.

Occurrence

Reported found in the oil from rhizomes of Alpinia malaccensis, in the oil from leaves of Ocimum canum Sims.; in the oil of Narcissus jonquilla L.; in the oil from rhizomes of Gastrochilus panduratum Ridl.; two isomers (cis- and trans-) exist in natural. Also reported found in cranberry, guava, pineapple, strawberry fruit and jam, cinnamon leaf, Camembert cheeses, cocoa, avocado, plum, prune, cloudberry, starfruit, plum brandy, rhubarb, beli (Aegle marmelos Correa), loquat and Bourbon vanilla.

Uses

Different sources of media describe the Uses of 103-26-4 differently. You can refer to the following data:
1. Methyl cinnamate is used as a fragrance ingredient in cosmetics and household products.
2. Methyl cinnamate was used to inhibit monophenolase and diphenolase activity of mushroom tyrosinase and it also has antimicrobial ability. It is mainly is used in the flavor and perfume industries. It is known to attract males of various orchid bees, such as Aglae caerulea.

Preparation

Methyl cinnamate is synthesized by esterification of cinnamic acid with methanol using HCl as catalyst, or by adding HCl to a boiling solution of cinnamyl nitrile in methanol.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 1133, 1974 DOI: 10.1021/ja00811a029Tetrahedron Letters, 29, p. 6119, 1988 DOI: 10.1016/S0040-4039(00)82281-9

General Description

Methyl cinnamate is an important flavoring agent and fragrance ingredient. It is one of the main aroma components of basil oil, Japanese and Korean matsutake mushrooms.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 103-26-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 3 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 103-26:
(5*1)+(4*0)+(3*3)+(2*2)+(1*6)=24
24 % 10 = 4
So 103-26-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+

103-26-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0360)  Methyl Cinnamate  >99.0%(GC)

  • 103-26-4

  • 25g

  • 135.00CNY

  • Detail
  • TCI America

  • (C0360)  Methyl Cinnamate  >99.0%(GC)

  • 103-26-4

  • 500g

  • 730.00CNY

  • Detail
  • Alfa Aesar

  • (A15975)  Methyl cinnamate, predominantly trans, 99%   

  • 103-26-4

  • 100g

  • 194.0CNY

  • Detail
  • Alfa Aesar

  • (A15975)  Methyl cinnamate, predominantly trans, 99%   

  • 103-26-4

  • 500g

  • 776.0CNY

  • Detail
  • Alfa Aesar

  • (A15975)  Methyl cinnamate, predominantly trans, 99%   

  • 103-26-4

  • 2500g

  • 3486.0CNY

  • Detail

103-26-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl cinnamate

1.2 Other means of identification

Product number -
Other names METHYL TRANS-CINNAMATE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103-26-4 SDS

103-26-4Synthetic route

methanol
67-56-1

methanol

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With sulfuric acid at 65℃; for 16h;100%
With sulfuric acid100%
With ammonium cerium(IV) nitrate at 20℃; for 240h;99%
iodobenzene
591-50-4

iodobenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
ς4,λ5-phosphinine palladium In 1-methyl-pyrrolidin-2-one at 100℃; for 120h; Heck reaction;100%
With palladium diacetate; 15-crown-15 tagged triarylphoshine; triethylamine In tetrahydrofuran for 8h; Heck reaction; Heating;100%
With triethylamine; polymer(fiber)-supported palladium In 1,4-dioxane at 100℃; for 1h; Heck reaction;100%
(2R,3R)-3-Hydroxy-3-phenyl-2-trimethylsilanyl-propionic acid methyl ester

(2R,3R)-3-Hydroxy-3-phenyl-2-trimethylsilanyl-propionic acid methyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane for 1h;100%
benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With palladium(II) acetate In water at 20℃; for 0.5h; Green chemistry; stereoselective reaction;100%
With 1-(2-hydroxyethyl)-3-methylimidazolium prolinate; palladium diacetate In neat (no solvent) at 20℃; for 0.5h; Heck Reaction; Green chemistry;99%
With Pd/Al2O3 In methanol at 25℃;96%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

phenylacetylene
536-74-3

phenylacetylene

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; toluene-4-sulfonic acid; 1,4-di(diphenylphosphino)-butane In acetonitrile at 110℃; under 5171.62 Torr; for 1h; Autoclave; regioselective reaction;100%
With triiron dodecarbonyl; triethylamine In tetrahydrofuran at 90℃; under 1034.32 Torr; for 0.333333h; Inert atmosphere; Microwave irradiation; regioselective reaction;57%
With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene; bis(dibenzylideneacetone)-palladium(0) In dichloromethane at 20℃; for 14h; regioselective reaction;11%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

methanol
67-56-1

methanol

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
Stage #1: methanol With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: (E)-3-phenylpropenal With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
99%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; Amberlyst 15 at 20℃; for 20h; Product distribution / selectivity;98%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; acetic acid In toluene for 6h; Product distribution / selectivity; Heating / reflux;98%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

phenylboronic acid
98-80-6

phenylboronic acid

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With palladium diacetate; acetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetic acid at 90℃; for 27h; Heck reaction;99%
With potassium fluoride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bis(acetylacetonato)palladium(II); propionic acid at 20℃; for 2h; Oxidative Heck reaction; Inert atmosphere; diastereoselective reaction;96%
SiO2-Rh(0) In water; toluene at 100℃; for 10h; Heck-type reaction;90%
methanol
67-56-1

methanol

Cinnamic acid
621-82-9

Cinnamic acid

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride at 20℃; for 2h; Esterification;99%
methanol
67-56-1

methanol

3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one
109299-93-6

3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With [t-Bu2SnCl(OH)]2 In toluene for 24h; Heating;99%
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 25℃; for 12h; Sealed tube; Inert atmosphere; Green chemistry; chemoselective reaction;85%
methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

benzyl alcohol
100-51-6

benzyl alcohol

A

methyl (2Z)-3-phenylprop-2-enoate
19713-73-6

methyl (2Z)-3-phenylprop-2-enoate

B

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
Stage #1: benzyl alcohol With Celite; pyridinium chlorochromate In dichloromethane at 20℃; for 3h;
Stage #2: methyl (triphenylphosphoranylidene)acetate In dichloromethane at 20℃; for 24h; Wittig olefination;
A n/a
B 99%
With oxygen In N,N-dimethyl-formamide at 80℃; for 18h; Reagent/catalyst; Solvent; Temperature; Time; Wittig Olefination; Overall yield = 49 %;A n/a
B n/a
phenyldiazonium silica sulfate

phenyldiazonium silica sulfate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With 1-(2-hydroxyethyl)-3-methylimidazolium prolinate; palladium diacetate In neat (no solvent) at 20℃; for 0.5h; silica; Heck Reaction; Green chemistry;99%
methanol
67-56-1

methanol

C24H19NO3

C24H19NO3

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With trimethylphosphane In dichloromethane; toluene at 20℃; for 1.5h; Solvent;99%
methanol
67-56-1

methanol

C24H19NO3

C24H19NO3

A

5,5-diphenyl-oxazolidin-2-one
52481-82-0

5,5-diphenyl-oxazolidin-2-one

B

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With trimethylphosphane In toluene at 20℃; for 3h; Reagent/catalyst; Solvent;A 99%
B 88%
methyl β-phenyl-β-methoxy-propionate
16510-80-8, 42332-80-9, 3461-35-6

methyl β-phenyl-β-methoxy-propionate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With sodium chloride; sulfuric acid; sodium methylate; sodium hydrogencarbonate; benzaldehyde In acetic acid methyl ester; water; ethyl acetate; toluene98.1%
With hydrogenchloride; sodium chloride; sulfuric acid; sodium methylate; benzaldehyde In methanol; acetic acid methyl ester; toluene
With trifluorormethanesulfonic acid In toluene at 75℃; for 40h; Inert atmosphere;n/a
methyl (2Z)-3-phenylprop-2-enoate
19713-73-6

methyl (2Z)-3-phenylprop-2-enoate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; triethylamine; palladium diacetate In dichloromethane for 8h; Heating;98%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Heating;96%
diphenyldisulfane In tetrahydrofuran for 7h; Heating;93%
rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate
21770-48-9, 52742-03-7, 52777-73-8, 113569-01-0, 113626-43-0

rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With zinc In acetic acid for 0.0166667h; microwave irradiation;98%
With dimethyl sulfoxide at 75℃; for 2h;97%
With 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 130 - 135℃; for 0.0333333h; microwave irradiation;95%
methanol
67-56-1

methanol

ethyl cinnamate
4192-77-2

ethyl cinnamate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide98%
With Merrifield resin-supported N3=P(MeNCH2CH2)3N at 23 - 25℃; for 3h; Inert atmosphere;94%
acrylonitrile; triphenylphosphine at 25℃; for 24h;60 % Chromat.
bromobenzene
108-86-1

bromobenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With polystyrene-supported palladacycle catalyst; sodium acetate In N,N-dimethyl acetamide at 130℃; for 48h; Heck reaction;98%
With sodium acetate; polystyrene-supported palladacycle In N,N-dimethyl acetamide at 130℃; for 48h; Heck reaction;97%
With triethylamine In N,N-dimethyl-formamide at 120℃; for 6h; Heck Reaction;95%
Methyl erythro-2,3-dibromo-3-phenylpropanoate
52777-73-8

Methyl erythro-2,3-dibromo-3-phenylpropanoate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With sodium sulfide; cetyltributylphosphonium bromide In toluene at 25℃; for 0.0833333h;97%
With N,N-dimethyl-formamide at 155 - 160℃; for 1h;93%
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at -10℃; for 3.25h;80%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

phenylacetylene
536-74-3

phenylacetylene

A

2-phenyl-acrylic acid methyl ester
1865-29-8

2-phenyl-acrylic acid methyl ester

B

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With palladium diacetate; toluene-4-sulfonic acid; 2-(diphenylphosphino)pyridine at 60℃; under 41253.3 - 45003.6 Torr;A 97%
B n/a
With bis-triphenylphosphine-palladium(II) chloride; toluene-4-sulfonic acid; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 110℃; under 5171.62 Torr; for 1h; Autoclave; regioselective reaction;A 90%
B 10%
With palladium diacetate; toluene-4-sulfonic acid; 1,4-di(diphenylphosphino)-butane In acetonitrile at 110℃; under 5171.62 Torr; for 1h; Autoclave; regioselective reaction;A 11%
B 89%
dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

benzaldehyde
100-52-7

benzaldehyde

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With chromium dichloride In tetrahydrofuran at 20℃; for 12h;97%
With manganese In tetrahydrofuran for 3h; Heating;72%
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction;72%
With chloro-trimethyl-silane; zinc In tetrahydrofuran at 50℃; for 3h;70%
methanol
67-56-1

methanol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With perchloric acid; sodium percarbonate; vanadia for 0.3h; Heating;97%
With Bromotrichloromethane; C14H18N3(1+)*ClO4(1-); rhodamine 6G; potassium carbonate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Irradiation;79%
With perchloric acid; dihydrogen peroxide; vanadia In water for 2h; oxidative esterification; Heating;95 % Chromat.
methanol
67-56-1

methanol

{3-(3-phenylprop-2-enoyloxy)propyl}trimethylammonium bistrifluoromethanesulfonimidate
827027-68-9

{3-(3-phenylprop-2-enoyloxy)propyl}trimethylammonium bistrifluoromethanesulfonimidate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With hydrogenchloride In water for 3h; Heck reaction; Inert atmosphere; Reflux;97%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

methyl iodide
74-88-4

methyl iodide

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.75h; Esterification;96%
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h;81%
In N,N-dimethyl-formamide Inert atmosphere;
(OC)5Cr=C(OMe)[(E)-CHCHPh]

(OC)5Cr=C(OMe)[(E)-CHCHPh]

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With pyridine N-oxide In dichloromethane at 23℃; for 0.333333h;96%
methanol
67-56-1

methanol

iron pentacarbonyl
13463-40-6, 71564-23-3

iron pentacarbonyl

phenylacetylene
536-74-3

phenylacetylene

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100℃; for 0.5h; regioselective reaction;96%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With potassium bromide In N,N-dimethyl-formamide at 130℃; for 12h; Schlenk technique;96%
C17H12F5NO2

C17H12F5NO2

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With tetrakis(acetonitrile)palladium bistriflate; (S)-4-methyl-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole; sodium carbonate; silver carbonate In 1,2-dichloro-ethane at 130℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Heck Reaction; Sealed tube; Inert atmosphere;96%
methyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-3-phenylpropionate
138964-16-6, 138964-17-7

methyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-3-phenylpropionate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Ambient temperature;95%
3-phenyl-2-selena<2.2.1>bicyclohept-5-ene
273919-21-4

3-phenyl-2-selena<2.2.1>bicyclohept-5-ene

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

Methyl cinnamate
103-26-4

Methyl cinnamate

Conditions
ConditionsYield
In toluene for 38h; Heating;95%
Methyl cinnamate
103-26-4

Methyl cinnamate

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

Conditions
ConditionsYield
With hydrogen; palladium In ethyl acetate at 25℃; under 760.051 Torr; for 1h;100%
With hydrogen; polymer incarcerated platinum In tetrahydrofuran at 20℃; for 1h; atmospheric pressure;100%
With hydrogen; palladium in polystyrene In tetrahydrofuran at 25℃; under 760.051 Torr; for 1h;100%
Methyl cinnamate
103-26-4

Methyl cinnamate

methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate
124649-67-8

methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate

Conditions
ConditionsYield
With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; chiral triazine catalyst In water; tert-butyl alcohol at 0℃; for 14h;100%
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4 In water; tert-butyl alcohol at 20℃; for 12h;96%
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; tetraethylammonium acetate; dihydrogen peroxide; polyaniline-supported Os-Re In tert-butyl alcohol at 0℃; Sharpless asymmetric dihydroxylation;94%
Methyl cinnamate
103-26-4

Methyl cinnamate

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate
122743-18-4

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate

Conditions
ConditionsYield
With 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 20℃; for 10h;100%
With AD-mix-α99%
With osmium(VIII) oxide; dihydroquinidine 9-O-(4-chlorobenzoate); potassium hexacyanoferrate(III)92%
1-octadecanol
112-92-5

1-octadecanol

Methyl cinnamate
103-26-4

Methyl cinnamate

octadecyl (2E)-3-phenylprop-2-enoate
61415-12-1

octadecyl (2E)-3-phenylprop-2-enoate

Conditions
ConditionsYield
Stage #1: 1-octadecanol; Methyl cinnamate In xylene for 0.5h; Heating;
Stage #2: With TiO(acac)2 In xylene for 14h; Heating;
100%
methanol
67-56-1

methanol

Methyl cinnamate
103-26-4

Methyl cinnamate

methyl (±)-anti-2-iodo-3-methoxy-3-phenylpropanoate
93643-71-1, 131846-31-6, 133379-84-7

methyl (±)-anti-2-iodo-3-methoxy-3-phenylpropanoate

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; iodine at 50℃; for 15h;99%
With iodine; silver nitrate for 6h; Ambient temperature;78%
With iodine; silver nitrate
Yield given. Multistep reaction;
Methyl cinnamate
103-26-4

Methyl cinnamate

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
93102-05-7

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

(3SR,4SR)methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate
87813-03-4

(3SR,4SR)methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0℃;99%
trifluoroacetic acid In dichloromethane for 3h; Ambient temperature;87%
With trifluoroacetic acid In dichloromethane
Methyl cinnamate
103-26-4

Methyl cinnamate

methyl (2Z)-3-phenylprop-2-enoate
19713-73-6

methyl (2Z)-3-phenylprop-2-enoate

Conditions
ConditionsYield
With 1,3,6,8-tetraphenylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile at 30℃; for 24h; Reagent/catalyst; Concentration; Wavelength; Inert atmosphere; UV-irradiation;99%
boron trifluoride diethyl etherate In dichloromethane for 3h; Irradiation;85%
In cyclohexane Irradiation;64%
Methyl cinnamate
103-26-4

Methyl cinnamate

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

Conditions
ConditionsYield
With C17H16BrMnNO3P; potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 6h; Autoclave; chemoselective reaction;99%
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh)3(CO); hydrogen In tetrahydrofuran at 120℃; under 37503.8 Torr; for 18h; Inert atmosphere; Autoclave;87%
With lithium aluminium tetrahydride In tetrahydrofuran for 0.166667h; Ambient temperature;100 % Chromat.
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh3)(CO); hydrogen In tetrahydrofuran at 120℃; under 38002.6 Torr; for 18h; Autoclave; Industrial scale;
Methyl cinnamate
103-26-4

Methyl cinnamate

rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate
21770-48-9, 52742-03-7, 52777-73-8, 113569-01-0, 113626-43-0

rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide In tetrachloromethane at 20℃; for 2h; Bromination;99%
With Oxone; ammonium bromide In water; acetonitrile for 12h; Reflux; stereoselective reaction;97%
With Selectfluor; potassium bromide In water; acetonitrile for 2h;89%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Methyl cinnamate
103-26-4

Methyl cinnamate

tert-butyl cinnamate
14990-09-1

tert-butyl cinnamate

Conditions
ConditionsYield
With sodium 4-tert-butylphenolate; sodium t-butanolate In tetrahydrofuran under 40 - 50 Torr; for 6h;99%
With potassium tert-butylate In tetrahydrofuran Ambient temperature;96%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

Methyl cinnamate
103-26-4

Methyl cinnamate

methyl 3-(4-methylphenyl)-3-phenylpropionate
23426-02-0

methyl 3-(4-methylphenyl)-3-phenylpropionate

Conditions
ConditionsYield
chloro(1,5-cyclooctadiene)rhodium(I) dimer In water at 90℃; for 6h;99%
With potassium hydroxide; [Rh(OH)(cod)]2 In 1,2-dimethoxyethane at 0℃; for 6h;97%
With chlorobis(ethylene)rhodium(I) dimer; C47H55O7P; potassium hydroxide In 1,4-dioxane; water at 20℃; for 24h; Inert atmosphere;73%
N-aminophthalamide
1875-48-5

N-aminophthalamide

Methyl cinnamate
103-26-4

Methyl cinnamate

(2S,3R)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-aziridine-2-carboxylic acid methyl ester

(2S,3R)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-aziridine-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; potassium carbonate In dichloromethane at 20℃; for 12h;99%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

acetic anhydride
108-24-7

acetic anhydride

Methyl cinnamate
103-26-4

Methyl cinnamate

acetic acid
64-19-7

acetic acid

α,β-bis(acetyloxy)benzenepropanoic acid methyl ester

α,β-bis(acetyloxy)benzenepropanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: [bis(acetoxy)iodo]benzene; Methyl cinnamate; acetic acid With boron trifluoride diethyl etherate In water at 20℃; for 8h;
Stage #2: acetic anhydride In water at 20℃; optical yield given as %de; diastereoselective reaction;
99%
2-(furan-3-yl)acetic acid
123617-80-1

2-(furan-3-yl)acetic acid

Methyl cinnamate
103-26-4

Methyl cinnamate

(2S,3R)-2-(furan-3-yl)-5-methoxy-5-oxo-3-phenylpentanoic acid

(2S,3R)-2-(furan-3-yl)-5-methoxy-5-oxo-3-phenylpentanoic acid

Conditions
ConditionsYield
Stage #1: 2-(furan-3-yl)acetic acid With n-butyllithium; N1,N3-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine In tetrahydrofuran; hexane at -90 - 0℃; for 0.583333h; Michael Addition; Inert atmosphere;
Stage #2: Methyl cinnamate In tetrahydrofuran; hexane at -90℃; for 0.5h; Michael Addition; Inert atmosphere; enantioselective reaction;
99%
(p-hydroxyphenyl)boronic acid
71597-85-8

(p-hydroxyphenyl)boronic acid

Methyl cinnamate
103-26-4

Methyl cinnamate

methyl (R)-3-(4-hydroxyphenyl)-3-phenylpropanoate

methyl (R)-3-(4-hydroxyphenyl)-3-phenylpropanoate

Conditions
ConditionsYield
With C50H56Cl2O4Rh2 In ethanol at 60℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry; enantioselective reaction;99%

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Evaluation of larvicidal activity and ecotoxicity of linalool, Methyl cinnamate (cas 103-26-4) and Methyl cinnamate (cas 103-26-4)/linalool in combination against Aedes aegypti08/11/2019

The frequent use of synthetic pesticides to control Aedes aegypti population can lead to environmental and/or human contamination and the emergence of resistant insects. Linalool and methyl cinnamate are presented as an alternative to the synthetic pesticides, since they can exhibit larvicidal, ...detailed

103-26-4Relevant articles and documents

Palladium nanoparticles on β-cyclodextrin functionalised graphene nanosheets: A supramolecular based heterogeneous catalyst for C-C coupling reactions under green reaction conditions

Putta, Chandrababu,Sharavath, Vittal,Sarkar, Suprabhat,Ghosh, Sutapa

, p. 6652 - 6660 (2015)

The use of functional properties of native cyclodextrins in palladium nanoparticle-β-cyclodextrin-graphene nanosheet (Pd@CD-GNS) catalyzed carbon-carbon (C-C) coupling reactions have been investigated under green reaction conditions. The supramolecular catalyst was prepared by deposition of Pd nanoparticles (Pd NPs) on CD-GNS using ethanol as the greener solvent and in situ reducing agent. The catalyst was characterised by FTIR, XRD, RAMAN, UV-Vis spectroscopy, TEM, SAED, XPS and ICP-AES. The catalytic activity of these catalysts is investigated in C-C coupling reactions such as Suzuki-Miyaura and Heck-Mizoroki reactions of aryl bromides and aryl chlorides containing functional groups under green reaction conditions i.e. in water, under phosphine free and aerobic conditions. This catalyst afforded excellent selectivities for the products in good to excellent yields under low Pd loadings (0.2-0.05 mol%), while ensuring the recovery and reusability of the catalysts. The reused catalyst was characterized by FTIR, TEM, XPS and ICP-AES. The CD supramolecular mediators loaded on GNS act as stabilising agents for the Pd NPs. The excellent catalytic activity of this system was attributed to the presence of CDs, excellent dispersibility in water, hydrophobic nature of the GNS support for the accumulation of organic substrates in water, "Breslow effect", the presence of PTC to overcome the mass transfer limitation onto the surface of GNS and formation of ternary CD/substrate/additive complexes on the Pd-GNS surface.

Chalcone and cinnamate synthesis via one-pot enol silane formation-Mukaiyama aldol reactions of ketones and acetate esters

Downey, C. Wade,Glist, Hadleigh M.,Takashima, Anna,Bottum, Samuel R.,Dixon, Grant J.

, p. 3080 - 3083 (2018)

Aryl alkyl ketones, acetate esters, and acetamides undergo facile one-pot enol silane formation, Mukaiyama aldol addition, and dehydrosilyloxylation in the presence of an amine base and excess trimethylsilyl trifluoromethanesulfonate. The chalcone and cinnamate products are generally recovered in high yield. The relative stoichiometry of the trimethylsilyl trifluoromethanesulfonate and amine base reagents determines whether the reaction yields the β-silyloxy carbonyl product or the α,β-unsaturated carbonyl.

Simultaneous immobilization of a matrix containing palladium and phase transfer catalyst on silica nanoparticles: Application as a recoverable catalyst for the Heck reaction in neat water

Hajipour, Abdol R.,Azizi, Ghobad

, p. 20704 - 20708 (2014)

Simultaneous covalent anchoring of a phosphonium-palladium complex/phase transfer catalyst matrix on the surface of silica nanoparticles and the application of the resulting catalyst in the Heck reaction of a variety of different haloarenes in neat aqueous media is described. This journal is the Partner Organisations 2014.

Highly active Pd(II) cyclometallated imine catalysts for the Heck reaction

Ohff, Manuela,Ohff, Andreas,Milstein, David

, p. 357 - 358 (1999)

The new cyclopalladated, phosphine-free imine complexes 1-3 are exceptional catalysts for the Heck arylation, leading to more than a million turnovers in some cases; the catalysts are very thermally and air stable and are recovered unchanged after the catalysis.

Magnetic dendritic polymer nanocomposites as supports for palladium: A highly efficient and reusable catalyst for Mizoroki-Heck and Suzuki-Miyaura coupling reactions

Ma, Rong,Yang, Pengbo,Bian, Fengling

, p. 4748 - 4756 (2018)

A novel catalyst Fe3O4@SiO2-Dendrimer-Pd based on palladium immobilized on magnetic dendritic polymer nanocomposites was successfully synthesized and characterized by FT-IR, EA, XRD, TEM, EDX, VSM and XPS. This nanocatalyst showed excellent catalytic activity for solvent-free Mizoroki-Heck reaction and Suzuki-Miyaura reaction in EtOH/H2O at a palladium loading of only 0.009 mol%. Moreover, the Fe3O4@SiO2-Dendrimer-Pd catalyst could be conveniently recovered by an external magnet and used consecutively five times with excellent yields. The remarkable catalytic performances and convenient magnetic separability of the Fe3O4@SiO2-Dendrimer-Pd catalyst make it promising for practical application.

Sulfilimine palladacycles: Stable and efficient catalysts for carbon-carbon coupling reactions

Thakur, Vinay V.,Ramesh Kumar,Sudalai

, p. 2915 - 2918 (2004)

A new family of sulfilimine-based palladacycles (1-4) has been synthesized in high yields from easily accessible starting materials and is found to exhibit high catalytic activities for carbon-carbon bond-formation in Suzuki, Heck, Sonogashira and Ullmann-type reactions, affording coupled products in excellent yields.

Cellulose supported Pd(II) complex catalyzed carbon-carbon bonds formation

Sarkar, Shaheen M.,Rashid,Karim, Kaykobad Md. Rezaul,Mustapha, Siti Noor Hidayah,Lian, Yuen Mei,Zamri, Normaiza,Khan, Md. Maksudur Rahman,O'Reilly, Emmet J.,Rahman, Md. Lutfor

, p. 2856 - 2861 (2019)

Corn-cobs are an agro-industrial waste and composed of cellulose mostly. In this study cellulose was isolated from the waste corn-cobs and modified to polymeric hydroxamic acid palladium complex 1 and characterized by using a variety of spectroscopic methods such as field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The complex 1 exhibited high catalytic activity towards Suzuki and Heck coupling reactions of activated and deactivated aryl halides to give the respective coupling products with high yield. Moreover, the complex 1 was recovered and recycled five times with no considerable loss of catalytic overall performance.

Catalysis of the Heck-type reaction of alkenes with arylboronic acids by silica-supported rhodium: An efficient phosphine-free reusable catalytic protocol

Trivedi, Rajiv,Roy, Sarabindu,Roy, Moumita,Sreedhar,Kantam, M. Lakshmi

, p. 1575 - 1578 (2007)

A 3-aminopropyl-functionalized silica-supported rhodium(0) catalyst (SiO2-Rh0) was prepared and employed in the Heck-type coupling of arylboronic acids and alkenes, affording good-to-excellent yields of substituted alkenes; the catalyst was recovered by filtration and reused for several cycles. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

A convenient synthesis of 2-(6-methoxy-2-naphthyl)propenoic acid (a naproxen precursor)

Scrivanti,Matteoli

, p. 9015 - 9018 (1995)

The title compound has been synthesised via the quantitative hydrocabonylation of the corresponding 1-alkyne in the presence of a palladium catalyst. The reaction proceeds at best under 30 bar of CO, but for the purposes of a laboratory scale synthesis it can be carried out successfully even at atmospheric pressure.

PALLADIUM-CATALYZED OXIDATIVE COUPLING OF AROMATIC COMPOUNDS WITH OLEFINS USING t-BUTYL PERBENZOATE AS A HYDROGEN ACCEPTER

Tsuji, Jiro,Nagashima, Hideo

, p. 2699 - 2702 (1984)

Benzene and furans undergo oxidative coupling with olefins with an aid of t-butyl perbenzoate and a catalytic amount of Pd salts.The perbenzoate acts as a hydrogen accepter.In the absence of olefins, Pd catalyzed benzoxylation of aromatic compounds takes place.

Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature

Wang, Shi-Meng,Song, Hai-Xia,Wang, Xiao-Yan,Liu, Nan,Qin, Hua-Li,Zhang, Cheng-Pan

, p. 11893 - 11896 (2016)

The first Pd-catalyzed Mizoroki-Heck-type reaction of [Ph2SRfn][OTf] with alkenes is described. The reaction of [Ph2SRfn][OTf] (Rfn = CF3, CH2CF3) with alkenes in the presence of 10 mol% Pd[P(t-Bu)3]2 and TsOH at room temperature provided the corresponding phenylation products in good to high yields. The bases that benefit the traditional Mizoroki-Heck reactions severely inhibited the transformation with [Ph2SRfn][OTf], whereas acids significantly improved the reaction. This protocol supplies a new class of cross-coupling partners for Mizoroki-Heck-type reactions and gains important insights into the reactivity of phenylsulfonium salts either with or without fluorine-containing alkyl groups as the promising phenylation reagents in organic synthesis.

A click strategy for the immobilization of palladium nanoparticles onto silica: Efficient and recyclable catalysts for carbon-carbon bond formation under mild reaction conditions

Hajipour, Abdol R.,Abolfathi, Parisa,Mohammadsaleh, Fatemeh

, p. 78080 - 78089 (2016)

An interesting silica-supported nano-palladium catalyst was successfully prepared through "click" reaction of azide-functionalized silica with methylpropargylimidazolium bromide followed by immobilization of palladium nanoparticles (NPs), in which the click-triazole as an important functional entity acts as both a stable linker and a good chelator. The palladium-NPs are stabilized by synergistic effect of coordination and electrostatic interactions. The as-prepared nanocatalyst was well characterized and found to be highly efficient in Heck and Suzuki-Miyaura coupling in terms of activity and recyclability in aqueous ethanol under phosphine-free and low Pd loading (0.1 mol%) conditions.

In-situ-generated palladium nanoparticles in novel ionic liquid: an efficient catalytic system for Heck–Matsuda coupling

Gaikwad,Undale,Patil,Pore,Korade,Kamble

, p. 4445 - 4458 (2017)

Abstract: A green, convenient, ecological and recyclable method comprising dual functionalized, task-specific, ionic liquid (IL)-triggered, in situ-generated Pd nanoparticles (NPs) and their catalytic application for Heck–Matsuda coupling of olefins is described. Both arenediazonium tetrafluoroborate and silica sulphate salts are coupled with olefins under ligand-free and aerobic conditions at ambient temperature furnishing excellent yields of products. The Ionic liquid used acts as a reducing as well as stabilizing agent for in situ-generated Pd NPs. The formed NPs were characterized by transmission electron microscopy (TEM) analysis, having a size below 50?nm, and exhibited high catalytic activity. The catalytic system can be reused for eight times effectively without any significant loss of activity. The method was found to be highly stereo-specific, giving exclusively the ‘E’ isomer.

Sodium 2-(2-pyridin-3-ylethylamino)sulfonate: an efficient ligand and base for palladium-catalyzed Heck reaction in aqueous media

Pawar, Shivaji S.,Dekhane, Deepak V.,Shingare, Murlidhar S.,Thore, Shivaji N.

, p. 4252 - 4255 (2008)

The first successful Pd(OAc)2, N-donor ligand and base mediated Heck coupling reaction of aryl halides and alkenes in water is described. The corresponding Heck products were obtained in good to excellent yields.

A dithizone-functionalized polystyrene resin-supported Pd(II) complex as an effective catalyst for Suzuki, Heck, and copper-free Sonogashira reactions under aerobic conditions in water

Bakherad, Mohammad,Jajarmi, Saeideh

, p. 152 - 159 (2013)

A novel polystyrene-supported palladium(II) dithizone complex is found to be a highly active catalyst for the Suzuki, Heck, and Sonogashira reactions of aryl halides in water. By this protocol, aryl halides, coupled with phenyl boronic acid (Suzuki reaction), alkenes (Heck reaction) or terminal alkyne (Sonogashira reaction), smoothly affords the corresponding cross-coupling products in good to excellent yields. Furthermore, the catalyst shows good thermal stability and recyclability. The catalyst was recycled for the Suzuki, Heck, and Sonogashira reactions for five runs without appreciable loss of its catalytic activity and negligible metal leaching.

Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions

Ishida, Takumi,Nishihara, Yasushi,Wang, Xiu,Wang, Zhenhua

, p. 7526 - 7533 (2020)

Acyl fluorides are subjected to methoxylation with tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) to afford the corresponding methyl esters in good to excellent yields. This transformation is featured by C(sp2)-OMe bond cleavage under metal-free conditions. Unprecedented utilization of TMPP as a methoxylating agent realized the installation of an OMe group into the desired products.

Fluorapatite-supported palladium catalyst for Suzuki and Heck coupling reactions of haloarenes

Kantam, M. Lakshmi,Kumar, K. B. Shiva,Srinivas,Sreedhar

, p. 1141 - 1149 (2007)

A fluorapatite-supported palladium catalyst (PdFAP) was synthesized by treatment of fluorapatite (prepared by incorporating the basic species fluoride ion into apatite in situ by co-precipitation) with bis(benzonitrile) palladium(II) chloride in acetone. The catalyst displayed high catalytic activity for Suzuki coupling of aryl iodides and bromides with boronic acids at room temperature and chloroarenes at 130°C in the presence of tetrabutylammonium bromide to give biaryls in excellent yields. Heck olefination of chloroarenes was also successfully carried out by this catalyst. PdFAP was recovered quantitatively by simple filtration and reused with consistent activity. PdFAP was well characterized by XRD, FTIR, XPS, ICP-AES, CO 2 TPD and CHN elemental analysis.

Pd complex of an NNN pincer ligand supported on γ-Fe2O3@SiO2 magnetic nanoparticles: A new catalyst for Heck, Suzuki and Sonogashira coupling reactions

Sobhani, Sara,Zeraatkar, Zohre,Zarifi, Farzaneh

, p. 7076 - 7085 (2015)

In this study, a Pd complex of bis(imino)pyridine as an NNN pincer ligand supported on γ-Fe2O3@SiO2 magnetic nanoparticles (Pd-BIP-γ-Fe2O3@SiO2) was synthesized and characterized by SEM, TEM, FT-IR, TGA, ICP, XRD, XPS, VSM and elemental analysis. The synthesized catalyst was used successfully as a new air- and moisture-stable phosphine-free Pd catalyst for Heck, Suzuki and Sonogashira coupling reactions of aryl iodides, bromides and chlorides with alkyl acrylates, styrene, phenylboronic acid and phenylacetylene. The true heterogeneous magnetically-recyclable catalyst can be separated easily using a magnetic bar and reused ten times without any drastic loss of its catalytic activity.

Arylation and Alkylation of Olefins by Arylamines or Hydrazines via Carbon-Nitrogen Bond Cleavage in the Presence of Palladium(II) Salts

Akiyama, Fumitaka,Miyazaki, Hiroshi,Kaneda, Kiyotomi,Teranishi, Shiichiro,Fujiwara, Yuzo,et al.

, p. 2359 - 2361 (1980)

Arylamines (ArNH2) have been found to function as arylating agents by way of C-N bond cleavage to give aryl-substituted olefins when treated with palladium salts and acetic acid.The reactivity of various amines and olefins has been investigated.Hydrazines such as phenylhydrazine and methylhydrazine are also able to act as arylating and alkylating agents, respectively.The addition of tert-butyl nitrite greatly increases the yields.

Palladium-catalysed cross-coupling reactions in supercritical carbon dioxide

Early,Gordon,Carroll,Holmes,Shute,McConvey

, p. 1966 - 1967 (2001)

Heck and Suzuki reactions proceed in good yield in supercritical carbon dioxide in the presence of palladium acetate and tri-tert-butylphosphine with both free and polymer-tethered substrates.

Manganese phthalocyanine immobilized on silica gel: Efficient and recyclable catalyst for single-step oxidative esterification of aldehydes with alcohols

Sharma,Gulati, Shikha

, p. 291 - 303 (2012)

The functionalization of silica gel was carried out using 3-aminopropyltriethoxysilane as a reactive surface modifier followed by covalent grafting of novel tetrakis-(2-methoxy-4-formylphenoxy)phthalocyaninato manganese(III) acetate complex. The resulting inorganic-organic hybrid material was found to be a highly selective and recyclable catalyst for the single-step synthesis of esters. The catalyst was characterized by elemental analysis (CHN), diffuse reflectance UV-visible, 13C CPMAS and 29Si CPMAS NMR spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), BET surface area analysis, energy dispersive X-ray fluorescence (ED-XRF), Fourier-transform infrared (FT-IR) and atomic absorption spectroscopy (AAS) techniques, which demonstrates the covalent grafting of the complex onto functionalized silica gel. The catalytic performance of the novel inorganic-organic hybrid catalyst was evaluated in the direct oxidative esterification of aldehydes with alcohols, at ambient temperature, using hydrogen peroxide as an environment friendly oxidant. The hybrid catalyst presented up to 100% of substrate conversion with high turn-over numbers (TONs), up to 100% of selectivity toward the ester product, and can be recovered and reused for multiple cycles without appreciable loss in its catalytic activity.

Poly(hydroxamic acid) palladium catalyst for heck reactions and its application in the synthesis of Ozagrel

Sarkar, Shaheen M.,Rahman, Md. Lutfor,Chong, Kwok Feng,Yusoff, Mashitah Mohd

, p. 103 - 110 (2017)

Bio-waste corn-cob cellulose supported poly(hydroxamic acid) palladium complex was synthesized and it is characterized using some different techniques such as FTIR, FESEM, HRTEM, EDX, XPS, UV–vis, TGA and ICP-AES analyses. The cellulose supported heterogeneous palladium complex showed high stability and catalytic activity toward Mizoroki-Heck reaction of aryl/heteroaryl halides and arenediazonium tetrafluoroborate with a variety of olefins to give the corresponding coupling products in up to 97% yield. The palladium complex was also applied to the synthesis of Ozagrel a thromboxane A2-synthetase inhibitor with excellent yield. The complex was separated from the reaction mixture by simple filtration and repeatedly used up to seven times without significant loss of its catalytic performance.

Thiophene Methanimine–Palladium Schiff Base Complex Anchored on Magnetic Nanoparticles: A Novel, Highly Efficient and Recoverable Nanocatalyst for Cross-Coupling Reactions in Mild and Aqueous Media: Γ-Fe2O3/AEPH2-TC-Pd Catalyzed Suzuki–Miyaura and Heck–Mizoroki Reactions

Jahanshahi, Roya,Akhlaghinia, Batool

, p. 2640 - 2655 (2017)

Abstract: In this study, a novel thiophene methanimine–palladium Schiff base complex anchored on decorated γ-Fe2O3 with 2-aminoethyl dihydrogen phosphate (γ-Fe2O3/AEPH2-TC-Pd) was synthesized as a new magnetically separable nanocatalyst. Characterization of the new designed nanocatalyst was performed successfully using different techniques such as FT-IR, XRD, XPS, TEM, TGA, VSM, ICP and elemental analysis. This nanocatalyst presented a superb catalytic activity for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions. The most important features of the prepared catalytic system which makes the current protocol more beneficial from both industrial and environmental viewpoints are its ease of recovery and reusability up to nine cycles without appreciable loss of the catalytic performance, as well as accomplishing the reactions under mild conditions in aqueous media which is a great challenge in some cross-coupling reactions. Graphical Abstract: [Figure not available: see fulltext.].

Aminophosphine Palladium(0) Complex Supported on ZrO2 Nanoparticles (ZrO2@AEPH2-PPh2-Pd(0)) as an Efficient Heterogeneous Catalyst for Suzuki–Miyaura and Heck–Mizoroki Reactions in Green Media

Razavi, Nasrin,Akhlaghinia, Batool,Jahanshahi, Roya

, p. 360 - 373 (2017)

Abstract: A new aminophosphine palladium(0) complex supported on ZrO2nanoparticles (ZrO2@AEPH2-PPh2-Pd(0)) was successfully synthesized and characterized using FT-IR, XRD, XPS, SEM, TEM, EDS, TGA and ICP techniques. Characterization results revealed that the synthesized catalyst had tetragonal and monoclinic structure with spherical morphology. The prepared nanocatalyst was showed excellent reactivity in the Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions. Moreover, this nanocatalyst can be easily recovered and reused for at least six cycles without deterioration in catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis and crystal structures of a series of (μ-thiophenolato)(μ-pyrazolato-N,N′) double bridged dipalladium(II) complexes and their application in Mizoroki-Heck reaction as highly efficient catalysts

Khadir, Narjes,Tavakoli, Ghazal,Assoud, Abdeljalil,Bagherzadeh, Mojtaba,Boghaei, Davar M.

, p. 107 - 117 (2016)

Three new binucleating S-protected ligand precursors, 2-(N,N-dimethylthiocarbamato)-5-methylisophthalaldehyde di-2′-hydroxy 5′-methylanil (1b), 2-(N,N-dimethylthiocarbamato)-5-tert-butylisophthalaldehyde di-2′-hydroxyanil (2a) and 2-(N,N-dimethylthiocarbamato)-5-tert-butylisophthalaldehyde di-2′-hydroxy 5′-methylanil (2b), have been synthesized. The reaction of these ligand precursors with PdCl2 in the presence of pyrazole under Pd-mediated S-C cleavage yielded a series of binuclear palladium(II) complexes of general formula [LPd2(pz)], where pz is the exogenous bridging pyrazolyl ligand and L3- represents a series of pentadentate thiophenol-based bridging ligands originated from their corresponding ligand precursors. All the compounds were characterized by elemental analysis, IR, 1H NMR and UV-Vis spectroscopies. The binuclear μ-thiophenolato-μ-pyrazolato palladium(II) complexes have also been characterized by single crystal X-ray diffraction analysis. Crystal structure analyses of the complexes show that two PdII centers are located in distorted square-planar environments, arranged in binuclear units with PdPd distance of 3.57 ?. The catalytic activity of these new binuclear palladium complexes was studied in Mizoroki-Heck C-C coupling reaction of methyl- and n-butyl acrylate with various types of aryl iodides and bromides. All reactions were completed for very short times with very excellent yield. Reactions were stereoselective and only trans isomers were obtained in each case.

A Straightforward, Purification-Free Procedure for the Synthesis of Ando and Still-Gennari Type Phosphonates

Janicki, Ignacy,Kie?basiński, Piotr

, p. 378 - 382 (2021/10/21)

Z-Selective Still-Gennari and Ando modifications of the typically E-selective Horner-Wadsworth-Emmons reaction are highly valuable synthetic tools in organic chemistry. These procedures are based on application of bis(2,2,2-trifluoroethyl) phosphonates or diaryl phosphonates, respectively, for the olefination of carbonyl groups. In our research, we present an improved, straightforward, purificationfree procedure for the synthesis of these reagents. The key step of our procedure is the reaction of phosphonic dichlorides with the appropriate sodium alkoxides, which results in 52-97% isolated yields of the desired products on a gram scale. The whole three-step process is performed in one pot. Most importantly, the product is obtained in over 95% purity after simple extraction, avoiding column chromatography and distillation. Moreover, we present the synthesis of a novel Still-Gennari type reagent, bis(1,1,1,3,3,3-hexafluoroisopropyl) phosphonates, which may exhibit improved Z-selectivity in Still-Gennari olefinations.

Synthesis of α-diazoesters from α-hydrazonoesters: Utilization of α-hydrazonoesters and α-diazoesters for convenient interconversion

Yasui, Eiko,Ishimine, Kanako,Nitanai, Sohta,Hatakeyama, Nanami,Nagumo, Shinji

, (2022/04/07)

We have developed a novel method to synthesize α-diazoesters from α-hydrazonoesters with a catalytic amount of Cu(OAc)2 in acetonitrile. When the reaction was carried out under an argon atmosphere, the reaction stopped halfway, suggesting that this reaction required oxygen to reoxidize the catalyst. Since hydrazonoesters can be obtained by reduction of α-diazoesters with P(n-Bu)3 in diisopropyl ether, these 2 compounds are mutually interconvertible with ease. Whereas α-diazoesters are unstable and unsuitable for storage, hydrazonoesters are more stable, especially crystalline hydrazonoesters. Thus, hydrazonoesters, which are suitable for long-term storage, could be conveniently used as precursors for α-diazoesters.

Synthesis of novel 1-phenyl-benzopyrrolizidin-3-one derivatives and evaluation of their cytoneuroprotective effects against NMDA-induced injury in PC12 cells

Cao, Jiafu,Li, Qiji,Liao, Xiu,Wang, Enhua,Wang, Li,Yang, Juan,Yang, Lishou,Yang, Qian,Yang, Xiaosheng,Yang, Yan

supporting information, (2022/02/23)

A range of novel 1-phenyl-benzopyrrolizidin-3-one derivatives were synthesized and evaluated for neuroprotective effects against N-methyl-?-aspartate (NMDA)-induced injury in PC12 cells. Interestingly, derivatives that 1-phenyl moiety bearing electron-donating group, especially benzyloxy, and the trans-forms exhibited better protective activity against NMDA-induced neurotoxicity. Compound 11 m demonstrated the best neuroprotective potency and shown a dose-dependent prevention. The increased intracellular calcium (Ca2+) influx caused by NMDA in PC12 cells was reversed in the case of compound 11 m pretreatment at 15 μM. These results suggested that the synthesized 1-phenyl-benzopyrrolizidin-3-one derivatives exerted neuroprotective effect on NMDA-induced excitotoxicity in PC12 cells associated with inhibition of Ca2+ overload and can be further optimized for the development of neuroprotective agents.

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