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873-66-5 Usage

Chemical Properties

clear colourless to very faintly yellow liquid

Uses

Trans-β-methylstyrene was used in the epoxidation reaction of an oxidant solution with a solution of dichloromethane, where nickel is used as a catalyst and benzyltributylammonium bromide as a phase-transfer agent.

General Description

The product exhibits potential exothermic hazards at higher temperatures.

Purification Methods

Distil it under N2 from powdered NaOH through a Vigreux column (p 11), and pass it through activated neutral alumina before use [Wong et al. J Am Chem Soc 109 3428 1987]. [Beilstein 5 III 1184, 5 IV 1359.]

Check Digit Verification of cas no

The CAS Registry Mumber 873-66-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 873-66:
(5*8)+(4*7)+(3*3)+(2*6)+(1*6)=95
95 % 10 = 5
So 873-66-5 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+

873-66-5 Well-known Company Product Price

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  • TCI America

  • (M1175)  trans-β-Methylstyrene (stabilized with TBC)  >97.0%(GC)

  • 873-66-5

  • 10mL

  • 1,930.00CNY

  • Detail

873-66-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Trans-1-Phenyl-1-Propene

1.2 Other means of identification

Product number -
Other names Benzene, 1-propenyl-, (E)-

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:873-66-5 SDS

873-66-5Synthetic route

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%
cis-1-phenyl-1-propylene
766-90-5

cis-1-phenyl-1-propylene

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With [(PPh3)3Co(N2)][Li(THF)3] In benzene-d6 at 65℃; for 24h; Kinetics; Temperature; Inert atmosphere; Sealed tube; Darkness;100%
With tri-tert-butyl phosphine; isobutyryl chloride; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 24h; Inert atmosphere;95%
Stage #1: cis-1-phenyl-1-propylene With cobalt(II) chloride; 2,2'-bis(diphenylphosphino)diphenylamine In toluene at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: With sodium triethylborohydride In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; diastereoselective reaction;
92%
(RR,SS)-1-dimethyl(phenyl)silyl-1-phenylpropan-2-ol

(RR,SS)-1-dimethyl(phenyl)silyl-1-phenylpropan-2-ol

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With potassium hydride In tetrahydrofuran for 0.5h; Ambient temperature;100%
(RR,SS)-1-phenyl-1-dimethyl(phenyl)silylprop-2-yl acetate

(RR,SS)-1-phenyl-1-dimethyl(phenyl)silylprop-2-yl acetate

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1h; Ambient temperature;100%
With lithium aluminium tetrahydride; potassium hydride Yield given. Multistep reaction;
(RS,SR)-1-phenyl-1-dimethyl(phenyl)silylprop-2-yl acetate

(RS,SR)-1-phenyl-1-dimethyl(phenyl)silylprop-2-yl acetate

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1h; Ambient temperature;100%
4-Hydroxy-piperidine-1-carboxylic acid (E)-3-phenyl-allyl ester

4-Hydroxy-piperidine-1-carboxylic acid (E)-3-phenyl-allyl ester

A

4-HYDROXYPIPERIDINE
5382-16-1

4-HYDROXYPIPERIDINE

B

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With phenol In acetonitrile Electrochemical reaction;A 100%
B n/a
methyllithium
917-54-4

methyllithium

(E)-styrylbromobis(triphenylphosphine)palladium(II)

(E)-styrylbromobis(triphenylphosphine)palladium(II)

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
In diethyl ether; benzene for 17h; Ambient temperature;98%
Cinnamyl acetate
21040-45-9

Cinnamyl acetate

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With RhCl(PPh3)3; lithium perchlorate In acetonitrile for 17h;97%
With tetraethylammonium tosylate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile Electrochemical reaction, Pb cathode, Pt anode;58%
With iron(III)-acetylacetonate; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere;25%
[(E)-2-bromoethenyl]benzene
588-72-7

[(E)-2-bromoethenyl]benzene

[3-(dimethylamino)propyl]dimethyl aluminium(III)

[3-(dimethylamino)propyl]dimethyl aluminium(III)

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 5h;97%
trans-3-phenylprop-2-enyl chloride
21087-29-6

trans-3-phenylprop-2-enyl chloride

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With RhCl(PPh3)3; lithium perchlorate In acetonitrile for 17h;96%
1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate; hydrogen In toluene at 70℃; under 45603.1 Torr; for 12h; Molecular sieve;96%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium carbonate; bis(pinacol)diborane; bis[2-(diphenylphosphino)phenyl] ether In hexane at 70℃; for 10h; Catalytic behavior; Reagent/catalyst; Solvent; Glovebox; Sealed tube; Inert atmosphere; stereoselective reaction;71%
(E)-3-phenyl-2-propenyl (E)-phenylacrylate
122-69-0, 61019-10-1, 40918-97-6

(E)-3-phenyl-2-propenyl (E)-phenylacrylate

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With triethylsilane; Wilkinson's catalyst In benzene for 15h; Heating;95%
1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With indium In methanol for 7h; Heating;94%
With potassium phosphate buffer; sodium L-ascorbate; di-n-hexyl telluride In chloroform; water at 80℃; for 42h; pH 8.9, other reagents: (p-Me2NC6H4)2Te/glutathione thiol/potassium phosphate buffer, o-Me2NCH2-C6H4-TeC6H5/glutathione thiol/potassium phosphate buffer;87%
With potassium phosphate buffer; sodium L-ascorbate; di-n-hexyl telluride In chloroform; water at 80℃; for 42h; Mechanism; Product distribution; pH 8.9, other vic-dibromides, competition with 1,2-dibromo-2-methyl-1-phenylpropane, reaction rate relative to other vic-dibromides, other reagents: <(p-Me2NC6H4)2Te or o-Me2NCH2C6H4TeC6H5>/glutathione thiol/potassium phosphate buff., other solv.: CDCl3;87%
With 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 130 - 135℃; for 0.05h; microwave irradiation;85%
With di-n-hexyl telluride In chloroform-d1 at 100℃; for 24h;
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

A

1-propenylbenzene
873-66-5

1-propenylbenzene

B

cis-1-phenyl-1-propylene
766-90-5

cis-1-phenyl-1-propylene

Conditions
ConditionsYield
With formic acid; dihydridotetrakis(triphenylphosphine)ruthenium In N,N-dimethyl-formamide at 20℃; for 36h; Inert atmosphere; optical yield given as %de; stereoselective reaction;A n/a
B 94%
With [Ru2(1,2-bis(diphenylphosphino)ethane)3(CO)2Cl4]; hydrogen In toluene at 110℃; under 760.051 Torr; for 10h;A 44%
B 7%
With hydrogen; [C*pRu(η4-CH3CHCHCHCHCO2H)][CF3SO3] In d(4)-methanol at 19.84 - 49.84℃; Title compound not separated from byproducts.;
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

A

1-propenylbenzene
873-66-5

1-propenylbenzene

B

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With C41H38BFeN3P2; hydrogen In tetrahydrofuran at 20 - 90℃; under 7500.75 Torr; for 27h; Inert atmosphere;A 94%
B 11%
With formic acid; para-xylene; 1,3-bis(2,4,6-trimethylphenyl)-3,4,5,6-tetrahydro-pyrimidin-1-ium palladium (divinyltetramethyldisiloxane); triethylamine In acetonitrile at 80℃; for 2h; Catalytic behavior; Inert atmosphere; Schlenk technique; Reflux; chemoselective reaction;
With C42H44ClN4P2Ru(1+)*Cl(1-); potassium tert-butylate; isopropyl alcohol at 80℃; for 72h; Schlenk technique; Inert atmosphere;A n/a
B 77 %Spectr.
With hydrogen; iron(II) acetate; diisobutylaluminium hydride In tetrahydrofuran; toluene at 30℃; under 1500.15 Torr; for 3h; stereoselective reaction;A n/a
B n/a
allylbenzene
300-57-2

allylbenzene

methylalumoxane

methylalumoxane

A

1-propenylbenzene
873-66-5

1-propenylbenzene

B

trans-1-phenyl-1-butene
1005-64-7

trans-1-phenyl-1-butene

Conditions
ConditionsYield
[{N(SiMe3)C(Ph)}2CH][N(SiMe3)C(Ph)NC(Ph)CH(SiMe3)]ZrCl2 Product distribution; Further Variations:; Catalysts;A 93.4%
B 4.15%
bis(diethylcarbamodithioato-S,S')oxomolybdenum
63950-40-3, 25395-92-0

bis(diethylcarbamodithioato-S,S')oxomolybdenum

1-phenylpropylene oxide
23355-97-7

1-phenylpropylene oxide

A

1-propenylbenzene
873-66-5

1-propenylbenzene

B

2MoO2(1+)*2S2CN(C2H5)2(1-)=Mo2O4(S2CN(C2H5)2)2

2MoO2(1+)*2S2CN(C2H5)2(1-)=Mo2O4(S2CN(C2H5)2)2

Conditions
ConditionsYield
In toluene N2 atmosphere, 80°C, 20 h; olefine: GC; pptd. complex: elem. anal.;A 92%
B n/a
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; hydrogen; zinc(II) iodide; zinc In tetrahydrofuran at 25℃; under 760.051 Torr; for 20h; Schlenk technique; stereoselective reaction;91%
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; water; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; for 2.45h; stereoselective reaction;89%
With palladium diacetate; (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane In ethanol; acetonitrile at 145℃; for 36h;81%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With sodium hydride; 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane hydro-chloride In [D3]acetonitrile for 2h;91%
cinnamyl acrylate
128638-89-1

cinnamyl acrylate

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With triethylsilane; Wilkinson's catalyst In benzene for 5h; Heating;90%
(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

A

allylbenzene
300-57-2

allylbenzene

B

1-propenylbenzene
873-66-5

1-propenylbenzene

C

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

3-Phenyl-1-propanol

D

cis-1-phenyl-1-propylene
766-90-5

cis-1-phenyl-1-propylene

E

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid at 25℃; for 4h; Reagent/catalyst; Inert atmosphere; Sealed tube; UV-irradiation;A n/a
B 90%
C n/a
D n/a
E n/a
(E)-β-chlorostyrene
4110-77-4

(E)-β-chlorostyrene

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With iron(III)-acetylacetonate In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere; stereoselective reaction;90%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

A

allylbenzene
300-57-2

allylbenzene

B

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With chloro-trimethyl-silane; 3 A molecular sieve; sodium cyanoborohydride In acetonitrile for 24h; Ambient temperature;A n/a
B 89%
[(E)-2-bromoethenyl]benzene
588-72-7

[(E)-2-bromoethenyl]benzene

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate In tetrahydrofuran at 15 - 20℃; for 0.25h;88%
With 1-methyl-pyrrolidin-2-one; cobalt acetylacetonate In tetrahydrofuran at 15 - 20℃; for 0.25h;82%
Cinnamyl acetate
21040-45-9

Cinnamyl acetate

A

allylbenzene
300-57-2

allylbenzene

B

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With N-propyl-1,4-dihydronicotinamide; lithium perchlorate; RhCl(PPh3)3 In acetonitrile at 70℃; for 17h; var. cat. solv. and addendum;A 0.6 % Chromat.
B 87.3%
With N-propyl-1,4-dihydronicotinamide; lithium perchlorate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 70℃; for 17h; var. cat., solv. and addendum;A 30.8 % Chromat.
B 15.4 % Chromat.
With samarium diiodide; isopropyl alcohol; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(±)-(1-iodopropyl)benzene
4119-41-9

(±)-(1-iodopropyl)benzene

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With sodium iodide In acetone at 45℃; Reagent/catalyst; Irradiation;86%
threo-1-diphenylphosphinoyl-1-phenylpropan-2-ol
103786-05-6, 103786-06-7

threo-1-diphenylphosphinoyl-1-phenylpropan-2-ol

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide85.7%
trans-3-phenylprop-2-enyl chloride
21087-29-6

trans-3-phenylprop-2-enyl chloride

A

allylbenzene
300-57-2

allylbenzene

B

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With Carbowax 400; PdCl2(Ph2PCH2CH2CH2SO3K)2; potassium formate In n-heptane; water at 90℃; Product distribution; other complexes; other polyethers; other allyl and benzyl chlalogenides;A 14.9%
B 85.1%
With chromium chloride; lithium aluminium tetrahydride; isopropyl alcohol In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;
With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; dodecane; toluene at 90℃; for 16h; Reagent/catalyst; Overall yield = 98 %; regioselective reaction;
(1-bromoethyl)benzyl bromide
1196-45-8

(1-bromoethyl)benzyl bromide

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With potassium graphite In benzene for 8h; Product distribution; Ambient temperature; vic-debromination by intercalate, influence of solvent;85%
With tris(2,2'-bipyridyl)ruthenium dichloride; triethylamine In acetonitrile Rate constant; Quantum yield; Mechanism; Irradiation;
1-propenylbenzene
873-66-5

1-propenylbenzene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With hydrogen; sodium triethylborohydride In tetrahydrofuran under 30003 Torr; for 20h; Catalytic behavior; Inert atmosphere;100%
With water; zinc; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane at 90℃; for 20h;99%
With [Fe(nacnac)dippCH2SiMe3]; N-butylamine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 20℃; for 16h; Sealed tube; Schlenk technique; Glovebox; Inert atmosphere;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

1-phenyl-1,2-propandiol
1855-09-0

1-phenyl-1,2-propandiol

Conditions
ConditionsYield
With osmium(VIII) oxide; cinchona alkaloid on mesoporous SBA-15 silica support at 0℃; for 24h;100%
With 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4 In water; acetone; acetonitrile at 20℃;96%
With 4-methylmorpholine N-oxide In water; acetone at 20℃; for 2h; Inert atmosphere;96%
1-propenylbenzene
873-66-5

1-propenylbenzene

erythro-1,2-dibromo-1-phenylpropane
127154-65-8

erythro-1,2-dibromo-1-phenylpropane

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In 1,2-dichloro-ethane100%
With lead(IV) acetate; zinc dibromide In chloroform at 20℃; for 0.0833333h;81%
1-propenylbenzene
873-66-5

1-propenylbenzene

1-phenylpropylene oxide
23355-97-7

1-phenylpropylene oxide

Conditions
ConditionsYield
With Oxone; potassium carbonate; acetic acid; rac-2-F-2,5-(Me)2-5-(2-fluoroisopropyl)-cyclohexanone In 1,2-dimethoxyethane; water at 0℃; for 8h; pH=8.5 - 9;100%
With Oxone; 1-Dodecyl-1-methyl-4-oxopiperidinium trifluoromethanesulfonate In dichloromethane at 0℃; for 24h; pH = 7.5;96%
With phosphate buffer; 3-chloro-benzenecarboperoxoic acid In dichloromethane for 5h;96%
1-propenylbenzene
873-66-5

1-propenylbenzene

4-chloro-benzenesulfenyl chloride
933-01-7

4-chloro-benzenesulfenyl chloride

1-Chloro-4-((1R,2S)-2-chloro-1-methyl-2-phenyl-ethylsulfanyl)-benzene
22556-38-3, 22556-40-7

1-Chloro-4-((1R,2S)-2-chloro-1-methyl-2-phenyl-ethylsulfanyl)-benzene

Conditions
ConditionsYield
In dichloromethane at -70℃;100%
With 1,1,2,2-tetrachloroethane Ambient temperature;
1-propenylbenzene
873-66-5

1-propenylbenzene

triphenyl-λ6-sulfanenitrile
191402-10-5

triphenyl-λ6-sulfanenitrile

1,3-dinitro-5-benzenesulfenylchloride

1,3-dinitro-5-benzenesulfenylchloride

A

triphenylsulfonium chloride
4270-70-6

triphenylsulfonium chloride

1-(3,5-dinitro-phenylsulfanyl)-2-methyl-3-phenyl-aziridine

1-(3,5-dinitro-phenylsulfanyl)-2-methyl-3-phenyl-aziridine

Conditions
ConditionsYield
In dichloromethane at -30℃;A 100%
B 71%
1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With bromine In chloroform at 0 - 20℃; for 2h; Inert atmosphere;99%
With [bis(acetoxy)iodo]benzene; Pyridine hydrobromide In dichloromethane at 20℃; for 6h;80%
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; for 0.5h;78%
1-propenylbenzene
873-66-5

1-propenylbenzene

phenylselenium trichloride
42572-42-9

phenylselenium trichloride

C15H15Cl3Se
109391-76-6

C15H15Cl3Se

Conditions
ConditionsYield
In diethyl ether at 0℃; Mechanism; other unsaturated compounds; also with phenylselenium tribromide;99%
In diethyl ether at 0℃;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

1-phenylpropylene oxide
4436-22-0

1-phenylpropylene oxide

Conditions
ConditionsYield
With [Fe2(μ-O)(H2O)2(BPG2E)](TfO)2*2H2O; dihydrogen peroxide; triethylamine In nitrobenzene; acetonitrile at 25℃; for 5.5h; Inert atmosphere;99%
With copper 1,3,5-benzenetricarboxylate; oxygen; pivalaldehyde In acetonitrile at 40℃; under 760.051 Torr; for 6h;99%
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 4h;99%
Conditions
ConditionsYield
With tetradecafluorohexane; triethylaluminum In hexane at 20℃; for 58h; Darkness;99%
Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane for 0.333333h; cooling;
Stage #2: 1-propenylbenzene In hexane; dichloromethane at 20℃; for 0.5h;
77%
With diethylzinc; trifluoroacetic acid 1.) CH2Cl2, hexane, 20 min; 2.) CH2Cl2, 20 deg C, 30 min; Yield given. Multistep reaction;
With copper(l) chloride; zinc In 1,4-dioxane Simmons-Smith addition; Cyclopropanation; Heating;
1-propenylbenzene
873-66-5

1-propenylbenzene

trans-2-methyl-3-phenyloxirane

trans-2-methyl-3-phenyloxirane

Conditions
ConditionsYield
With dihydrogen peroxide; Ru(2,2':6',2''-terpyridine)(2,6-pyridinedicarboxylate) In tert-Amyl alcohol at 20℃; for 12h; Conversion of starting material;99%
With iron(III) chloride hexahydrate; dihydrogen peroxide; 1-(2,6-diisopropylphenyl)-1H-imidazole In tert-Amyl alcohol at 20℃; chemoselective reaction;94%
Stage #1: 1-propenylbenzene With tris(μ-oxo)di[(1,4,7-trimethyl-1,4,7-triazanonane)manganese(IV)] hexafluorophosphate; scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 0.166667h; Sealed tube;
Stage #2: With dihydrogen peroxide In water; acetonitrile for 0.0833333h; Sealed tube;
77%
1-propenylbenzene
873-66-5

1-propenylbenzene

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium periodate; C53H44As2N2O3Ru In water; ethyl acetate; acetonitrile at 25℃; for 0.5h;99%
With [Fe2(μ-O)(H2O)2(BPG2E)](TfO)2*2H2O; dihydrogen peroxide; oxygen; triethylamine In nitrobenzene; acetonitrile at 25℃; for 5.5h;98%
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 78℃; under 760.051 Torr; for 16h; Green chemistry; chemoselective reaction;96%
1-propenylbenzene
873-66-5

1-propenylbenzene

tris(catecholato)diboron
37737-62-5

tris(catecholato)diboron

2,2'-(1-phenylpropane-1,2-diyl)dibenzo[1,3,2]dioxaborole

2,2'-(1-phenylpropane-1,2-diyl)dibenzo[1,3,2]dioxaborole

Conditions
ConditionsYield
[Rh(Ph2PCH2PPh2)(η6-1,2-C6H4O2BO2C6H4-1,2) In tetrahydrofuran (N2); addn. of alkene to catalyst soln., addn. of B2cat3, stirring at room temp. for 30 h, concn., addn. of hexane;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

2-benzhydryl-1,3-diphenylpropane-1,3-dione
60999-93-1

2-benzhydryl-1,3-diphenylpropane-1,3-dione

trans,trans-2-methyl-1,3-diphenyl-2,3-dihydro-1H-indene
62677-54-7

trans,trans-2-methyl-1,3-diphenyl-2,3-dihydro-1H-indene

Conditions
ConditionsYield
With iron(III) chloride In 1,2-dichloro-ethane at 25 - 50℃; for 3h; Inert atmosphere; stereoselective reaction;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

5-bromo-4-methoxy-2-methoxymethyloxybenzyl acetate
1153673-79-0

5-bromo-4-methoxy-2-methoxymethyloxybenzyl acetate

trans-6-bromo-7-methoxy-3-methyl-2-phenylchroman

trans-6-bromo-7-methoxy-3-methyl-2-phenylchroman

Conditions
ConditionsYield
With platinum(IV) chloride In dichloromethane at 0 - 20℃; Diels-Alder reaction; optical yield given as %de; diastereoselective reaction;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; acrylic acid methyl ester In dichloromethane for 2h; Catalytic behavior; Reagent/catalyst; Reflux;99%
With C34H45Cl2N2ORu Reagent/catalyst;
1-propenylbenzene
873-66-5

1-propenylbenzene

3-chlorobenzoate
535-80-8

3-chlorobenzoate

(1S, 2R) 2-iodo-1-phenylpropyl 2-chlorobenzoate

(1S, 2R) 2-iodo-1-phenylpropyl 2-chlorobenzoate

Conditions
ConditionsYield
With tetrabutylammonium 1,3-bis(3-chlorobenzoyl)dioxiodane In dichloromethane at 25℃; for 12h; Schlenk technique; regioselective reaction;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

2-chloro-1-phenylpropan-1-ol
102879-13-0

2-chloro-1-phenylpropan-1-ol

Conditions
ConditionsYield
With hydrogenchloride; [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.166667h; pH=7; Catalytic behavior;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

methyl 1-indanone-2-carboxylate
22955-77-7

methyl 1-indanone-2-carboxylate

5-(3-methyl-4-phenyl)-4,5-dihydro-2H-spiro[furan-3,2′-indene]-1′,2(3’H)-dione

5-(3-methyl-4-phenyl)-4,5-dihydro-2H-spiro[furan-3,2′-indene]-1′,2(3’H)-dione

Conditions
ConditionsYield
With iodine; sodium carbonate In water; tert-butyl alcohol at 20℃; for 24h; Inert atmosphere; Irradiation;99%
1-propenylbenzene
873-66-5

1-propenylbenzene

(1R,2R)-1-phenylpropane-1,2-diol
40421-51-0

(1R,2R)-1-phenylpropane-1,2-diol

Conditions
ConditionsYield
With potassium dioxotetrahydroxoosmate(VI); iodine; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 0℃; for 27h; electrolysis; further cond.: chemical method;98.6%
With potassium osmate(VI); potassium carbonate; potassium hexacyanoferrate(III); molecular sieve; 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 0 - 20℃; for 18h;98%
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;97%
1-propenylbenzene
873-66-5

1-propenylbenzene

dimethyl(methylthio)sulfonium tetrafluoroborate
5799-67-7

dimethyl(methylthio)sulfonium tetrafluoroborate

(R*,S*)-1-phenyl-2-(methylthio)propanamine
81230-67-3

(R*,S*)-1-phenyl-2-(methylthio)propanamine

Conditions
ConditionsYield
With ammonia In dichloromethane98%
1-propenylbenzene
873-66-5

1-propenylbenzene

2-Iodo-2-cyanopent-4-ynenitrile
130575-06-3

2-Iodo-2-cyanopent-4-ynenitrile

2-(2-Iodo-1-methyl-2-phenyl-ethyl)-2-prop-2-ynyl-malononitrile
130575-10-9, 130575-11-0

2-(2-Iodo-1-methyl-2-phenyl-ethyl)-2-prop-2-ynyl-malononitrile

Conditions
ConditionsYield
In benzene at 80℃;98%
1-propenylbenzene
873-66-5

1-propenylbenzene

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-((1R,2S)-2-bromo-1-phenylpropyl)-4-methylbenzenesulfonamide

N-((1R,2S)-2-bromo-1-phenylpropyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With N-Bromosuccinimide; vanadia In dichloromethane at 25℃; for 3h;98%

873-66-5Relevant articles and documents

A highly substitutable palladium(II) complex stabilized by the smallest steric N-heterocyclic carbene, IMe (IMe = 1,3- dimethylimidazole-2-ylidene)

Lee, Eunsung,Bae, Dae Young,Yandulov, Dmitry V.

, p. 1745 - 1746 (2016)

-

Okamoto et al.

, p. 197,198 (1968)

Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism

Kim, Daniel,Pillon, Guy,Diprimio, Daniel J.,Holland, Patrick L.

supporting information, p. 3070 - 3074 (2021/03/08)

Double-bond transposition in alkenes (isomerization) offers opportunities for the synthesis of bioactive molecules, but requires high selectivity to avoid mixtures of products. Generation of Z-alkenes, which are present in many natural products and pharmaceuticals, is particularly challenging because it is usually less thermodynamically favorable than generation of the E isomers. We report a β-dialdiminate-supported, high-spin cobalt(I) complex that can convert terminal alkenes, including previously recalcitrant allylbenzenes, to Z-2-alkenes with unprecedentedly high regioselectivity and stereoselectivity. Deuterium labeling studies indicate that the catalyst operates through a π-allyl mechanism, which is different from the alkyl mechanism that is followed by other Z-selective catalysts. Computations indicate that the triplet cobalt(I) alkene complex undergoes a spin state change from the resting-state triplet to a singlet in the lowest-energy C-H activation transition state, which leads to the Z product. This suggests that this change in spin state enables the catalyst to differentiate the stereodefining barriers in this system, and more generally that spin-state changes may offer a route toward novel stereocontrol methods for first-row transition metals.

A donor-acceptor complex enables the synthesis of: E -olefins from alcohols, amines and carboxylic acids

Chen, Kun-Quan,Shen, Jie,Wang, Zhi-Xiang,Chen, Xiang-Yu

, p. 6684 - 6690 (2021/05/31)

Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability concerns in organic synthesis. Metallaphotoredox-catalyzed defunctionalizations were reported to achieve such transformations under mild conditions. However, all these valuable strategies require a transition metal catalyst, a ligand or an expensive photocatalyst, with the challenges of controlling the region- and stereoselectivities remaining. Herein, we present a fundamentally distinct strategy enabled by electron donor-acceptor (EDA) complexes, for the selective synthesis of olefins from these simple and easily available starting materials. The conversions took place via photoactivation of the EDA complexes of the activated substrates with alkali salts, followed by hydrogen atom elimination from in situ generated alkyl radicals. This method is operationally simple and straightforward and free of photocatalysts and transition-metals, and shows high regio- and stereoselectivities.

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