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300-57-2

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300-57-2 Usage

Description

Allylbenzene is a colorless, flammable liquid with chemical properties that make it incompatible with strong oxidizing agents. It is commonly used in organic synthesis due to its reactive nature, and upon decomposition, it releases carbon monoxide and carbon dioxide.

Uses

Used in Organic Synthesis:
Allylbenzene is used as a key intermediate in the production of various chemicals and materials. Its reactivity and compatibility with different chemical processes make it a valuable component in the synthesis of pharmaceuticals, fragrances, and other specialty chemicals.
Used in Pharmaceutical Industry:
Allylbenzene is used as a building block for the synthesis of certain pharmaceutical compounds. Its ability to react with other molecules allows for the creation of new drugs with specific therapeutic properties.
Used in Fragrance Industry:
In the fragrance industry, allylbenzene is used as a component in the creation of various scent compounds. Its chemical structure contributes to the overall aroma profile of the final product.
Used in Specialty Chemicals:
Allylbenzene is also utilized in the production of specialty chemicals, such as additives for the plastics and coatings industries. Its versatility in chemical reactions enables the development of unique products with specific properties tailored to various applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 7777, 1973 DOI: 10.1021/ja00804a039

Health Hazard

Exposures to allylbenzene cause irritation to the skin, eyes, and respiratory system. It causes harmful effects if inhaled or swallowed and causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.

storage

Allylbenzene should be kept stored in a cool, dry, well-ventilated area with adequate ventilation during use.

Precautions

Workers while handling allylbenzene should not breathe dust or vapor, or ingest the chemical substance. Allylbenzene should only be used in a chemical fume hood and sources of ignition should be avoided. Workers should wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA protection regulations.

Check Digit Verification of cas no

The CAS Registry Mumber 300-57-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 0 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 300-57:
(5*3)+(4*0)+(3*0)+(2*5)+(1*7)=32
32 % 10 = 2
So 300-57-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-8H,1H3/b6-2+

300-57-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A12965)  Allylbenzene, 98%   

  • 300-57-2

  • 25g

  • 618.0CNY

  • Detail
  • Alfa Aesar

  • (A12965)  Allylbenzene, 98%   

  • 300-57-2

  • 100g

  • 2177.0CNY

  • Detail

300-57-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name prop-2-enylbenzene

1.2 Other means of identification

Product number -
Other names 2-Propenylbenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:300-57-2 SDS

300-57-2Synthetic route

Allyl acetate
591-87-7

Allyl acetate

trimethyl(phenyl)stannane
934-56-5

trimethyl(phenyl)stannane

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In N,N,N,N,N,N-hexamethylphosphoric triamide for 6h;100%
With [Pd(triphenylphosphine)(allyl)(chloride)] In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 5h;96 % Chromat.
allyl bromide
106-95-6

allyl bromide

phenyltriethoxytitanium
95576-66-2

phenyltriethoxytitanium

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; diethyl ether at 25℃; for 3h;100%
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

phenyltriethoxytitanium
95576-66-2

phenyltriethoxytitanium

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; diethyl ether at 25℃; for 1.5h;100%
phenylzinc chloride
28557-00-8

phenylzinc chloride

allyl bromide
106-95-6

allyl bromide

A

allylbenzene
300-57-2

allylbenzene

B

biphenyl
92-52-4

biphenyl

C

zinc dibromide

zinc dibromide

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 3.5 h);A 100%
B 0%
C n/a
bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 3 h);A 55%
B 40%
C n/a
Allyl acetate
591-87-7

Allyl acetate

phenylzinc chloride
28557-00-8

phenylzinc chloride

A

allylbenzene
300-57-2

allylbenzene

B

biphenyl
92-52-4

biphenyl

C

zinc diacetate
557-34-6

zinc diacetate

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 5 h);A 100%
B 0%
C n/a
C14H15NSe
1224431-84-8

C14H15NSe

cyclohexene
110-83-8

cyclohexene

A

allylbenzene
300-57-2

allylbenzene

B

cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform-d1 at 20℃;A 100%
B 100%
1-iodo-3-phenylpropan
4119-41-9

1-iodo-3-phenylpropan

A

allylbenzene
300-57-2

allylbenzene

B

1,6-diphenylhexane
1087-49-6

1,6-diphenylhexane

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Electrochemical reaction; Inert atmosphere;A 1%
B 99%
bromobenzene
108-86-1

bromobenzene

allyl bromide
106-95-6

allyl bromide

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
Stage #1: bromobenzene With iodine; magnesium In diethyl ether Inert atmosphere; Reflux;
Stage #2: allyl bromide In diethyl ether at 0 - 20℃; for 2.08333h; Inert atmosphere;
99%
Stage #1: bromobenzene With magnesium In tetrahydrofuran
Stage #2: allyl bromide In tetrahydrofuran
Stage #3: With ammonium chloride In water
With magnesium In tetrahydrofuran at 20℃;
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 20℃;
Stage #2: allyl bromide In tetrahydrofuran for 1h;
propargyl benzene
10147-11-2

propargyl benzene

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With hydrogen In toluene at 20℃; under 38002.6 Torr; for 12h; Autoclave; chemoselective reaction;99%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 3h;96%
With hydrogen In acetonitrile at 120℃; under 22502.3 Torr; for 15h; Autoclave; Sealed tube;72%
Allyl acetate
591-87-7

Allyl acetate

diphenylmagnesium
555-54-4

diphenylmagnesium

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
Cu(acac)2-PPh3 In tetrahydrofuran at 40℃; for 4h;98%
Cu(acac)2-PPh3 In tetrahydrofuran at 40℃; for 4h; Product distribution; effects of solvent, catalyst and catalyst activator; further solvents, further catalysts;
Allyl acetate
591-87-7

Allyl acetate

diphenylmagnesium
555-54-4

diphenylmagnesium

A

allylbenzene
300-57-2

allylbenzene

B

1,1-diphenylethanol
599-67-7

1,1-diphenylethanol

Conditions
ConditionsYield
With copper acetylacetonate; triphenylphosphine In tetrahydrofuran at 40℃; for 4h;A 98%
B n/a
With copper acetylacetonate; triphenylphosphine In tetrahydrofuran at 40℃; for 4h; Product distribution; effect of catalysts, activator ligands, solvents on yield; effect of variation of ester residue in the allyl ester partner; reactions between further dialkyl- and diarylmagnesiums and allyl esters;A 98%
B n/a
allyl bromide
106-95-6

allyl bromide

phenylboronic acid
98-80-6

phenylboronic acid

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With 2C2H3O2(1-)*Pd(2+)*3Na(1+)*C18H12O9PS3(3-); potassium tert-butylate; glycerol at 100℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;98%
With potassium tert-butylate; (1,3-di(2,4,6-(CH3)3-C6H2)-imidazol-2-ylidene)Pd(OAc)2 In isopropyl alcohol at 20℃; for 2h; Suzuki-Miyaura coupling;93%
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 110℃; for 15h; Suzuki-Miyaura coupling; Inert atmosphere;90%
allyl phenyl ether
1746-13-0

allyl phenyl ether

phenylzinc chloride
28557-00-8

phenylzinc chloride

A

allylbenzene
300-57-2

allylbenzene

B

biphenyl
92-52-4

biphenyl

C

zinc phenate

zinc phenate

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 8 h);A 98%
B 0%
C n/a
Cinnamyl bromide
4392-24-9

Cinnamyl bromide

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With C11H22P(1+)*Br(1-); lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; dodecane; toluene at 90℃; for 16h; Reagent/catalyst; regioselective reaction;96%
With hydrogenchloride; indium 1.) DMF, 1 h, RT, 2.) 1 min; Yield given. Multistep reaction;
2-(tosyloxy)dodecane
102736-19-6

2-(tosyloxy)dodecane

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With Pd(P(t-Bu)2Me)2; potassium tert-butylate; N-cyclohexyl-cyclohexanamine In 1,4-dioxane at 80℃; for 8h; Inert atmosphere;96%
trimethyl(phenyl)stannane
934-56-5

trimethyl(phenyl)stannane

allyl bromide
106-95-6

allyl bromide

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 70℃;95%
With bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 70℃; for 3h;95%
carbon monoxide
201230-82-2

carbon monoxide

(2E)-3-phenylprop-2-en-1-yl formate
23510-72-7

(2E)-3-phenylprop-2-en-1-yl formate

A

allylbenzene
300-57-2

allylbenzene

B

1-phenylpropene
637-50-3

1-phenylpropene

C

trans-styrylacetic acid
2243-53-0, 59744-46-6, 1914-58-5

trans-styrylacetic acid

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In toluene at 60℃; under 45600 Torr; for 15h;A 1%
B 1%
C 95%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In toluene under 15200 Torr; for 96h; Product distribution; Ambient temperature; other reagents, other solvents, var. temp., pressure, time;
CH2=CH-CH2-OR'', PhCCMgR'

CH2=CH-CH2-OR'', PhCCMgR'

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
Cu(acac)2-PPh3 In tetrahydrofuran95%
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

phenylboronic acid
98-80-6

phenylboronic acid

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With 2C2H3O2(1-)*Pd(2+)*3Na(1+)*C18H12O9PS3(3-); potassium tert-butylate; glycerol at 100℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;95%
With potassium tert-butylate; (1,3-di(2,4,6-(CH3)3-C6H2)-imidazol-2-ylidene)Pd(OAc)2 In isopropyl alcohol at 20℃; for 0.5h; Suzuki-Miyaura coupling;72%
With potassium tert-butylate In isopropyl alcohol at 50℃; for 12h; Inert atmosphere;71%
With potassium hydroxide; phenone oxime-derived palladacycle; tetrabutylammomium bromide In water; acetone at 20℃; for 2h; Suzuki coupling;69%
With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate In acetonitrile at 80℃; for 18h; Temperature; chemoselective reaction;21 %Spectr.
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

benzyl bromide
100-39-0

benzyl bromide

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 20℃; for 14h; Kumada-Corriu reaction; Inert atmosphere;95%
Stage #1: vinyl magnesium bromide With indium(III) chloride In tetrahydrofuran
Stage #2: benzyl bromide With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Heating;
82%
trimethyl(phenyl)stannane
934-56-5

trimethyl(phenyl)stannane

allyl bromide
106-95-6

allyl bromide

A

allylbenzene
300-57-2

allylbenzene

B

trimethyltin bromide
1066-44-0

trimethyltin bromide

Conditions
ConditionsYield
With ((π-C3H5)PdCl)2 In N,N-dimethyl-formamide 70°C;A 95%
B n/a
C14H15NSe
1224431-84-8

C14H15NSe

A

allylbenzene
300-57-2

allylbenzene

B

PySeOH
428876-71-5

PySeOH

Conditions
ConditionsYield
Stage #1: C14H15NSe With Dess-Martin periodane In dichloromethane at 20℃;
Stage #2: With water; sodium carbonate at 20℃;
A 95%
B n/a
benzyl bromide
100-39-0

benzyl bromide

trivinyl indium
75076-64-1

trivinyl indium

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 1h; Heating;94%
phenylaluminium dichloride
3530-39-0

phenylaluminium dichloride

allyl bromide
106-95-6

allyl bromide

A

allylbenzene
300-57-2

allylbenzene

B

biphenyl
92-52-4

biphenyl

C

aluminium bromide
7727-15-3

aluminium bromide

Conditions
ConditionsYield
bis(η3-allyl-μ-chloropalladium(II)) In diethyl ether Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 8 h);A 94%
B <1
C n/a
tetrakis(triphenylphosphine) palladium(0) In diethyl ether Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 20 h);A <1
B <1
C n/a
3-benzyl propionaldehyde
18328-11-5

3-benzyl propionaldehyde

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃; for 3h; Time;94%
With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃; for 3h;94%
With methoxy(cyclooctadiene)rhodium(I) dimer; 3-Methoxybenzoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 40 - 80℃; chemoselective reaction;90 %Spectr.
bromobenzene
108-86-1

bromobenzene

C10H20AlNO

C10H20AlNO

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 60℃; for 12h;93%
3-Cinnamyloxy-methoxy-benzol
4646-99-5

3-Cinnamyloxy-methoxy-benzol

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere;93%
1,2-epoxy-3-phenylpropane
4436-24-2

1,2-epoxy-3-phenylpropane

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; under 4500.45 Torr; for 25h; Glovebox; chemoselective reaction;92%
With bis(acetylacetonate)nickel(II); diethylzinc In 1,2-dimethoxyethane; hexane at 80℃; for 48h; Inert atmosphere;88%
With carbon monoxide In water at 27℃; under 760.051 Torr; for 24h; chemoselective reaction;69%
(allylsulfonyl)benzene
16212-05-8

(allylsulfonyl)benzene

phenylmagnesium bromide

phenylmagnesium bromide

allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With copper acetylacetonate; triphenylphosphine In tetrahydrofuran at 60℃; for 4h; further reagents and solvents;92%
allylbenzene
300-57-2

allylbenzene

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With tetramethyldialuminoxane; [Zr(NPhPPh2)4] In tetrahydrofuran-d8 at 20℃; for 0.25h; Isomerization;100%
With tetramethyldialuminoxane; [{N(SiMe3)C(Ph)}2CH]2TiCl2 In (2)H8-toluene at 25℃; for 1h; Kinetics; Further Variations:; Catalysts;99.5%
With C44H58Cl2N4Pd In isopropyl alcohol at 70℃; for 3h; optical yield given as %de; diastereoselective reaction;98%
allylbenzene
300-57-2

allylbenzene

1-phenylpropene
637-50-3

1-phenylpropene

Conditions
ConditionsYield
With potassium hydroxide In 1,2-dimethoxyethane at 40℃; for 0.5h;100%
With potassium hydroxide In butan-1-ol for 3h; Heating;100%
With bis(1,5-cyclooctadiene)nickel(0); [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In toluene at 130℃; for 1h; Reagent/catalyst; Temperature; Time;99%
allylbenzene
300-57-2

allylbenzene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With Pt-Sn-citrate; hydrogen In methanol at 50℃; under 3800 Torr; for 3h; var. temperatures; var. pressures;100%
With Pt-Sn-citrate; hydrogen In methanol at 50℃; under 3800 Torr; for 3h;100%
With C49H60BF2IrN5(1+)*C32H12BF24(1-); hydrogen In 1,2-dichloro-ethane at 20℃; for 0.166667h; Reagent/catalyst; Schlenk technique;100%
allylbenzene
300-57-2

allylbenzene

1-(2,3-dichloropropyl)benzene
67168-93-8

1-(2,3-dichloropropyl)benzene

Conditions
ConditionsYield
With tetraethylammonium trichloride In dichloromethane100%
With Phenylselenyl chloride; tetrabutyl-ammonium chloride; chlorine In tetrachloromethane; acetonitrile for 0.666667h; Heating;94%
With hydrogenchloride; potassium permanganate In acetonitrile69%
allylbenzene
300-57-2

allylbenzene

Conditions
ConditionsYield
With water; 4-methylmorpholine N-oxide; osmium; Cu-Al-hydrotalcite In toluene at 60℃; for 11h;100%
With potassium osmate; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 20℃; for 24h;91%
With water; oxygen; palladium diacetate; sodium carbonate at 100℃; under 6080.41 Torr; for 24h; Autoclave;82%
allylbenzene
300-57-2

allylbenzene

trichloro(2-chloro-3-phenylpropyl)-λ4-tellane

trichloro(2-chloro-3-phenylpropyl)-λ4-tellane

Conditions
ConditionsYield
With tellurium tetrachloride In tetrachloromethane at 0 - 25℃; for 9h; regioselective reaction;100%
With tellurium tetrachloride In tetrachloromethane for 1h; Ambient temperature;70%
allylbenzene
300-57-2

allylbenzene

cis-1,4-bis(acetyloxy)but-2-ene
25260-60-0

cis-1,4-bis(acetyloxy)but-2-ene

(E/Z)-4-phenyl-2-buten-1-yl acetate
83540-71-0, 36215-15-3

(E/Z)-4-phenyl-2-buten-1-yl acetate

Conditions
ConditionsYield
With [Ru(dmf)3(1,3-dimesitylimidazolin-2-ylidene)(=CH-2-(2-PrO)-C6H4)][(BF4)2] In toluene at 100℃; for 1h;100%
Cl2Ru(SIMes)(2-(isopropyl)oxy-5-nitrobenzylidene) In toluene at 70℃; for 18h; Product distribution; Further Variations:; Catalysts; reaction time;68%
With C70H113Cl2N3O4Ru In neat (no solvent) at 40℃; for 16h; Cross Metathesis; Inert atmosphere;57%
allylbenzene
300-57-2

allylbenzene

phenylacetaldehyde
122-78-1

phenylacetaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 75℃; for 6h;100%
With sodium periodate; C31H29Br2N3Ru*CH2Cl2 In water; ethyl acetate; acetonitrile at 25℃; for 0.5h; Inert atmosphere; Schlenk technique;96%
Stage #1: allylbenzene With sodium periodate; C22H23N7Ru(2+)*F6P(1-)*CF3O3S(1-) In water; acetone at 20℃; for 2h;
Stage #2: With sodium sulfite In dichloromethane; water for 0.166667h; Catalytic behavior; Reagent/catalyst;
65%
allylbenzene
300-57-2

allylbenzene

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(E)-2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

(E)-2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

Conditions
ConditionsYield
silver hexafluoroantimonate; (S)-SEGPHOS-PdCl2 In dichloromethane at 20℃; for 0.5h; Ene reaction;100%
With silver hexafluoroantimonate; (R)-(2,2'-bis(diphenylphosphanyl)biphenyl)dichloroplatinum(II) In dichloromethane at -20℃; for 1h;83%
allylbenzene
300-57-2

allylbenzene

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

Conditions
ConditionsYield
With silver hexafluoroantimonate; chiral SEGPHOS-Pd(II) In dichloromethane at 20℃; for 0.5h; Friedel-Crafts reaction;100%
allylbenzene
300-57-2

allylbenzene

N-methylaniline
100-61-8

N-methylaniline

N-(2-Methyl-3-phenylpropyl)-anilin
96594-31-9

N-(2-Methyl-3-phenylpropyl)-anilin

Conditions
ConditionsYield
With 3-Methyl-1H-pyridin-2-one; dimethyl-amine; tantalum (V)-pentakis-dimethylamide In toluene at 110℃; for 16h; Glovebox; Inert atmosphere;100%
With (N-[2,6-diisopropylphenyl]pivalamidate)tetrakis(dimethylamido)tantalum In (2)H8-toluene at 130℃; for 19h; Inert atmosphere;85%
Stage #1: allylbenzene With N,N'-bis(2,6-dicyclopentyl-4-methoxyphenyl)formamidine; tetrabenzyl titanium at 20℃; for 0.333333h; Glovebox; Inert atmosphere;
Stage #2: N-methylaniline at 155℃; for 0.1h; Sealed tube;
85%
Ta[N(CH3)2]5 at 160 - 165℃; for 41h;77%
allylbenzene
300-57-2

allylbenzene

(S)-(2,3-epoxypropyl)benzene
91420-74-5

(S)-(2,3-epoxypropyl)benzene

Conditions
ConditionsYield
With whole E. coli cells expressing monooxygenase from Herbaspirillum huttiense HhMO and NADH-dependent flavin oxidoreductase PsStyB In aq. phosphate buffer; octane at 37℃; pH=6; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; Solvent; pH-value; Concentration; Green chemistry; Enzymatic reaction; enantioselective reaction;100%
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C
2: [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); water; acetic acid / tetrahydrofuran / 20 h / Cooling with ice
View Scheme
With FAD; 1-Benzyl-1,4-dihydronicotinamide; styrene monooxygenase In aq. buffer at 30℃; for 1h; pH=7; enantioselective reaction;n/a
With D-glucose; recombinant Marinobacterium litorale styrene monooxygenase expressed as a fused protein in Escherichia coli BL21(DE3) In aq. phosphate buffer; deuteromethanol for 9h; pH=8; Enzymatic reaction; enantioselective reaction;26 mg
allylbenzene
300-57-2

allylbenzene

methyl dimethyl 2-(trifluoromethyl)propanedioate
5838-00-6

methyl dimethyl 2-(trifluoromethyl)propanedioate

(E)-dimethyl 2-cinnamyl-2-(trifluoromethyl)malonate
1440140-61-3

(E)-dimethyl 2-cinnamyl-2-(trifluoromethyl)malonate

Conditions
ConditionsYield
With 2,6-dimethoxy-p-quinone; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 20℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique;100%
methanol
67-56-1

methanol

allylbenzene
300-57-2

allylbenzene

tribromo(2-methoxy-3-phenylpropyl)-λ4-tellane

tribromo(2-methoxy-3-phenylpropyl)-λ4-tellane

Conditions
ConditionsYield
With tellurium(IV) tetrabromide at 20 - 60℃; for 6h; regioselective reaction;100%
methanol
67-56-1

methanol

allylbenzene
300-57-2

allylbenzene

trichloro(2-methoxy-3-phenylpropyl)-λ4-tellane

trichloro(2-methoxy-3-phenylpropyl)-λ4-tellane

Conditions
ConditionsYield
With tellurium tetrachloride In dichloromethane at 20 - 25℃; for 20h; regioselective reaction;100%
allylbenzene
300-57-2

allylbenzene

pyridin-2-yl sulfenyl chloride
59089-57-5

pyridin-2-yl sulfenyl chloride

2-(phenylmethyl)-2H,3H-thiazolo[3,2-]pyridine-4-ium chloride

2-(phenylmethyl)-2H,3H-thiazolo[3,2-]pyridine-4-ium chloride

Conditions
ConditionsYield
Stage #1: pyridin-2-yl sulfenyl chloride With bromine In dichloromethane at 20℃; for 0.5h;
Stage #2: allylbenzene In dichloromethane at 20℃; for 60h; regioselective reaction;
100%
allylbenzene
300-57-2

allylbenzene

1-(2,3-dideuteropropyl)benzene
118297-06-6

1-(2,3-dideuteropropyl)benzene

Conditions
ConditionsYield
With deuterium; Wilkinson's catalyst In toluene99.4%
allylbenzene
300-57-2

allylbenzene

1,2-epoxy-3-phenylpropane
4436-24-2

1,2-epoxy-3-phenylpropane

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Cooling with ice; Inert atmosphere;99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h; Inert atmosphere;99%
With NH-pyrazole; water; dihydrogen peroxide; methyltrioxorhenium(VII) In various solvent(s) for 21h; Ambient temperature;97%
allylbenzene
300-57-2

allylbenzene

(2,3-dibromopropyl)benzene
1586-98-7

(2,3-dibromopropyl)benzene

Conditions
ConditionsYield
With tetrapropylammonium nonabromide In dichloromethane at 0 - 23℃; for 0.0166667h; Reagent/catalyst; Inert atmosphere;99%
With acetic acid; lithium bromide Ambient temperature;98%
With aluminum (III) chloride; ammonium metavanadate; tetrabutylammomium bromide; oxygen In 1,2-dimethoxyethane at 50℃; for 18h;95%
allylbenzene
300-57-2

allylbenzene

bis(methoxycarbonyl)(phenyliodinio)methanide
145838-86-4

bis(methoxycarbonyl)(phenyliodinio)methanide

dimethyl 2-(phenylmethyl)cyclopropane-1,1-dicarboxylate
3709-22-6

dimethyl 2-(phenylmethyl)cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
dirhodium tetraacetate at 120℃; for 0.0166667h;99%
With dirhodium tetraacetate In dichloromethane at 25℃; for 3h;53%
allylbenzene
300-57-2

allylbenzene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

(E)-5-phenyl-3-penten-2-one
42762-51-6

(E)-5-phenyl-3-penten-2-one

Conditions
ConditionsYield
[1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium In dichloromethane for 12h; Heating;99%
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane Reflux; Inert atmosphere;81%
allylbenzene
300-57-2

allylbenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl (E)-4-phenyl-2-butenoate
63158-17-8, 73845-39-3, 34541-75-8

methyl (E)-4-phenyl-2-butenoate

Conditions
ConditionsYield
[1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium In dichloromethane for 12h; Heating;99%
With RuCl2(CHPh)(IMes)2; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; for 4h; Cross Metathesis; Inert atmosphere; Sealed tube; Irradiation;60%
With RuCl2(CHPh)(IMes)2; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; for 4h; Alkene (Olefin) Metathesis; Inert atmosphere; Irradiation; Sealed tube;60%
With RuCl2(CHPh)(IMes)2; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; for 4h; Irradiation; Sealed tube; Inert atmosphere;60%
allylbenzene
300-57-2

allylbenzene

dithiocarbonic acid S-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl] ester O-ethyl ester

dithiocarbonic acid S-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl] ester O-ethyl ester

S-(5-(2,4-difluorophenyl)-5-oxo-1-phenylpentan-2-yl) O-ethyl carbonodithioate
1246016-64-7

S-(5-(2,4-difluorophenyl)-5-oxo-1-phenylpentan-2-yl) O-ethyl carbonodithioate

Conditions
ConditionsYield
With dilauryl peroxide In cyclohexane Inert atmosphere; Reflux;99%

300-57-2Relevant articles and documents

Ring-opening 1,3-arylboration of arylcyclopropanes mediated by BCl3

Arisawa, Mitsuhiro,Kuboki, Yuichi,Murai, Kenichi

, p. 37797 - 37799 (2020)

Herein, we report a ring-opening 1,3-arylboration of aryl cyclopropanes using BCl3 in the presence of arene nucleophiles. Formal 1,3-oxy arylation and 1,3-amino arylation of the arylcyclopropane via one-pot derivatization of the installed boron group were also achieved.

Boosting catalyst activity in cis -selective semi-reduction of internal alkynes by tailoring the assembly of all-metal aromatic tri-palladium complexes

Monfredini, Anna,Santacroce, Veronica,Deyris, Pierre-Alexandre,Maggi, Raimondo,Bigi, Franca,Maestri, Giovanni,Malacria, Max

, p. 15786 - 15790 (2016)

Highly symmetric [Pd3]+ clusters that present delocalized metal-metal bonds can catalyse the selective semi-reduction of internal alkynes to cis-alkenes. Studies on factors governing the formation of all-metal aromatics enabled the design of an optimised catalytic system that delivers cis-alkenes with almost complete selectivity on a gram scale with very low catalyst loadings (0.03 mol%).

Gold nanoparticles-graphene hybrids as active catalysts for Suzuki reaction

Li, Yang,Fan, Xiaobin,Qi, Junjie,Ji, Junyi,Wang, Shulan,Zhang, Guoliang,Zhang, Fengbao

, p. 1413 - 1418 (2010)

Graphene was successfully modified with gold nanoparticles in a facile route by reducing chloroauric acid in the presence of sodium dodecyl sulfate, which is used as both a surfactant and reducing agent. The gold nanoparticles-graphene hybrids were characterized by high-resolution transmission electron microscopy, atomic force microscopy, X-ray photoelectron spectroscopy, Raman spectroscopy, X-ray diffraction and energy X-ray spectroscopy. We demonstrate for the first time that the gold nanoparticles-graphene hybrids can act as efficient catalysts for the Suzuki reaction in water under aerobic conditions. The catalytic activity of gold nanoparticles-graphene hybrids was influenced by the size of the gold nanoparticles.

Merging Pd0/PdII Redox and PdII/PdII Non-redox Catalytic Cycles for the Allylarylation of Electron-Deficient Alkenes

Semba, Kazuhiko,Ohta, Naoki,Paulus, Fritz,Ohata, Masaki,Nakao, Yoshiaki

, p. 5035 - 5040 (2021)

An allylarylation of electron-deficient alkenes with aryl boronates and allylic carbonates has been developed. This method allows access to a wide variety of carbon skeletons from readily available starting materials. Mechanistic studies indicate that this reaction is enabled by a cooperative catalysis based on merging Pd0/PdII redox and PdII/PdII non-redox catalytic cycles.

Synthesis, Properties, and Catalytic Application of a Triptycene-Type Borate-Phosphine Ligand

Konishi, Shota,Iwai, Tomohiro,Sawamura, Masaya

, p. 1876 - 1883 (2018)

A borate-containing caged triarylphosphine L-X (X = Na or NBu4), featuring a 9-phospha-10-boratriptycene framework, was synthesized and characterized by NMR spectroscopy and X-ray diffraction analysis. The NMR coupling constant of the corresponding phosphine selenide indicated a higher electron-donating property of the borate-phosphine L compared to that of the 9-phospha-10-silatriptycene derivative (Ph-TRIP). The coordination property of L-X to [PdCl(η3-allyl)]2 was dependent on the countercation, giving a neutral Pd complex [PdCl(η3-allyl)(L-NBu4)] from L-NBu4 in CH2Cl2 or a zwitterionic Pd complex [Pd(η3-allyl)(MeCN)(L)] from L-Na in MeCN/CH2Cl2. Utility of L-X as a ligand for metal catalysis was demonstrated in the Pd-catalyzed Suzuki-Miyaura cross-coupling of aryl chlorides.

Vol'pin et al.

, p. 849 (1971)

-

Frey,H.M.,Midcalfe,J.

, p. 2529 - 2531 (1970)

-

Designed electron-deficient gold nanoparticles for a room-temperature Csp3-Csp3coupling reaction

Yu, Qiu-Ying,Su, Hui,Zhai, Guang-Yao,Zhang, Shi-Nan,Sun, Lu-Han,Chen, Jie-Sheng,Li, Xin-Hao

supporting information, p. 741 - 744 (2021/02/06)

Stille cross-coupling reactions catalysed by an ideal catalyst combining the high activity of homogeneous catalysts and the reusability of heterogeneous catalysts are of great interest for C-C bond formation, which is a widely used reaction in fine chemistry. Despite great effort to increase the utilization ratio of surface metal atoms, the activity of heterogeneous catalysts under mild conditions remains unsatisfactory. Herein, we design a proof-of-concept strategy to trigger the room-temperature activity of heterogeneous Au catalysts by decreasing the electron density at the interface of a rationally designed Schottky heterojunction of Au metals and boron-doped carbons. The electron-deficient Au nanoparticles formed as a result of the rectifying contact with boron-doped carbons facilitate the autocleavage of C-Br bonds for highly efficient C-C coupling reactions of alkylbromides and allylstannanes with a TOF value of 5199 h-1 at room temperature, surpassing that of the state-of-the-art homogeneous catalyst. This journal is

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Geng, Jiao,Hu, Xingbang,Liu, Qiang,Wu, Youting,Yang, Liu,Yao, Chenfei

, p. 3685 - 3690 (2021/05/31)

Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.

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