873-66-5

Basic information

• Product Name: TRANS-BETA-METHYLSTYRENE
• Synonyms: OMEGA-METHYLSTYRENE;PROPENYLBENZENE;TRANS-1-PHENYL-1-PROPENE;TRANS-B-METHYLSTYRENE;TRANS-BETA-METHYLSTYRENE;TRANS-PROPENYLBENZENE;(E)- beta-Methylstyrene;(E)-1-phenylprop-1-ene
• CAS NO: 873-66-5
• Molecular Formula: C₉H₁₀
• Molecular Weight: 118.18
• EINECS: 212-848-0
• Mol File: 873-66-5.mol
• Article Data: 430

Chemical Properties

• Melting Point: -29°C(lit.)
• Boiling Point: 175 °C(lit.)
• Flash Point: 127 °F
• Appearance: Clear colorless to very faintly yellow/Liquid
• Density: 0.911 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.550(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water
• BRN: 1361672
• CAS DataBase Reference: TRANS-BETA-METHYLSTYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-BETA-METHYLSTYRENE(873-66-5)
• EPA Substance Registry System: TRANS-BETA-METHYLSTYRENE(873-66-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 10-37/38-41-43-51/53-65
• Safety Statements: 16-26-36/37/39-61-62
• RIDADR: UN 2618 3/PG 3
• WGK Germany: 2
• RTECS: DA8400500
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 873-66-5(Hazardous Substances Data)

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.]

InChI:InChI=1/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-8H,1H3/b6-2+

Synthetic route

allylbenzene (300-57-2) → 1-propenylbenzene (873-66-5)

Conditions	Yield
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) → 1-propenylbenzene (873-66-5)

Conditions	Yield
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 → 1-propenylbenzene (873-66-5)

Conditions	Yield
With potassium hydride In tetrahydrofuran for 0.5h; Ambient temperature;	100%

(RR,SS)-1-phenyl-1-dimethyl(phenyl)silylprop-2-yl acetate → 1-propenylbenzene (873-66-5)

Conditions	Yield
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 → 1-propenylbenzene (873-66-5)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1h; Ambient temperature;	100%

4-Hydroxy-piperidine-1-carboxylic acid (E)-3-phenyl-allyl ester → 4-HYDROXYPIPERIDINE (5382-16-1) + 1-propenylbenzene (873-66-5)

Conditions	Yield
With phenol In acetonitrile Electrochemical reaction;	A 100% B n/a

methyllithium (917-54-4) + (E)-styrylbromobis(triphenylphosphine)palladium(II) → 1-propenylbenzene (873-66-5)

Conditions	Yield
In diethyl ether; benzene for 17h; Ambient temperature;	98%

Cinnamyl acetate (21040-45-9) → 1-propenylbenzene (873-66-5)

Conditions	Yield
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) + [3-(dimethylamino)propyl]dimethyl aluminium(III) → 1-propenylbenzene (873-66-5)

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 5h;	97%

trans-3-phenylprop-2-enyl chloride (21087-29-6) → 1-propenylbenzene (873-66-5)

Conditions	Yield
With RhCl(PPh3)3; lithium perchlorate In acetonitrile for 17h;	96%

1-phenyl-propan-1-one (93-55-0) → 1-propenylbenzene (873-66-5)

Conditions	Yield
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) → 1-propenylbenzene (873-66-5)

Conditions	Yield
With triethylsilane; Wilkinson's catalyst In benzene for 15h; Heating;	95%

(1,2-dibromopropyl)benzene (1196-45-8, 21087-19-4, 21087-20-7, 127154-65-8) → 1-propenylbenzene (873-66-5)

Conditions	Yield
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-propenylbenzene (873-66-5) + cis-1-phenyl-1-propylene (766-90-5)

Conditions	Yield
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-propenylbenzene (873-66-5) + Propylbenzene (103-65-1)

Conditions	Yield
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) + methylalumoxane → 1-propenylbenzene (873-66-5) + trans-1-phenyl-1-butene (1005-64-7)

Conditions	Yield
[{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) + 1-phenylpropylene oxide (23355-97-7) → 1-propenylbenzene (873-66-5) + 2MoO2(1+)*2S2CN(C2H5)2(1-)=Mo2O4(S2CN(C2H5)2)2

Conditions	Yield
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-propenylbenzene (873-66-5)

Conditions	Yield
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) → 1-propenylbenzene (873-66-5)

Conditions	Yield
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) → 1-propenylbenzene (873-66-5)

Conditions	Yield
With triethylsilane; Wilkinson's catalyst In benzene for 5h; Heating;	90%

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → allylbenzene (300-57-2) + 1-propenylbenzene (873-66-5) + 3-Phenyl-1-propanol (122-97-4) + cis-1-phenyl-1-propylene (766-90-5) + Propylbenzene (103-65-1)

Conditions	Yield
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) + methylmagnesium chloride (676-58-4) → 1-propenylbenzene (873-66-5)

Conditions	Yield
With iron(III)-acetylacetonate In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere; stereoselective reaction;	90%

(E)-3-phenylpropenal (14371-10-9) → allylbenzene (300-57-2) + 1-propenylbenzene (873-66-5)

Conditions	Yield
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) + methylmagnesium chloride (676-58-4) → 1-propenylbenzene (873-66-5)

Conditions	Yield
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) → allylbenzene (300-57-2) + 1-propenylbenzene (873-66-5)

Conditions	Yield
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-propenylbenzene (873-66-5)

Conditions	Yield
With sodium iodide In acetone at 45℃; Reagent/catalyst; Irradiation;	86%

threo-1-diphenylphosphinoyl-1-phenylpropan-2-ol (103786-05-6, 103786-06-7) → 1-propenylbenzene (873-66-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	85.7%

trans-3-phenylprop-2-enyl chloride (21087-29-6) → allylbenzene (300-57-2) + 1-propenylbenzene (873-66-5)

Conditions	Yield
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-propenylbenzene (873-66-5)

Conditions	Yield
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) → Propylbenzene (103-65-1)

Conditions	Yield
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-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
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) → erythro-1,2-dibromo-1-phenylpropane (127154-65-8)

Conditions	Yield
With tetra-N-butylammonium tribromide In 1,2-dichloro-ethane	100%
With lead(IV) acetate; zinc dibromide In chloroform at 20℃; for 0.0833333h;	81%

1-propenylbenzene (873-66-5) → 1-phenylpropylene oxide (23355-97-7)

Conditions	Yield
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) + 4-chloro-benzenesulfenyl chloride (933-01-7) → 1-Chloro-4-((1R,2S)-2-chloro-1-methyl-2-phenyl-ethylsulfanyl)-benzene (22556-38-3, 22556-40-7)

Conditions	Yield
In dichloromethane at -70℃;	100%
With 1,1,2,2-tetrachloroethane Ambient temperature;

1-propenylbenzene (873-66-5) + triphenyl-λ6-sulfanenitrile (191402-10-5) + 1,3-dinitro-5-benzenesulfenylchloride → triphenylsulfonium chloride (4270-70-6) + 1-(3,5-dinitro-phenylsulfanyl)-2-methyl-3-phenyl-aziridine

Conditions	Yield
In dichloromethane at -30℃;	A 100% B 71%

1-propenylbenzene (873-66-5) → (1,2-dibromopropyl)benzene (1196-45-8, 21087-19-4, 21087-20-7, 127154-65-8)

Conditions	Yield
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) + phenylselenium trichloride (42572-42-9) → C15H15Cl3Se (109391-76-6)

Conditions	Yield
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-phenylpropylene oxide (4436-22-0)

Conditions	Yield
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%

1-propenylbenzene (873-66-5) + diiodomethane (75-11-6) → (2-methyl-cyclopropyl)-benzene (4866-54-0, 5070-01-9, 10488-06-9, 29667-47-8, 29667-49-0, 53403-04-6, 57637-49-7, 3145-76-4)

Conditions	Yield
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) → trans-2-methyl-3-phenyloxirane

Conditions	Yield
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) → benzaldehyde (100-52-7)

Conditions	Yield
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) + tris(catecholato)diboron (37737-62-5) → 2,2'-(1-phenylpropane-1,2-diyl)dibenzo[1,3,2]dioxaborole

Conditions	Yield
[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) + 2-benzhydryl-1,3-diphenylpropane-1,3-dione (60999-93-1) → trans,trans-2-methyl-1,3-diphenyl-2,3-dihydro-1H-indene (62677-54-7)

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

1-propenylbenzene (873-66-5) + 5-bromo-4-methoxy-2-methoxymethyloxybenzyl acetate (1153673-79-0) → trans-6-bromo-7-methoxy-3-methyl-2-phenylchroman

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

Conditions	Yield
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) + 3-chlorobenzoate (535-80-8) → (1S, 2R) 2-iodo-1-phenylpropyl 2-chlorobenzoate

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

1-propenylbenzene (873-66-5) → 2-chloro-1-phenylpropan-1-ol (102879-13-0)

Conditions	Yield
With hydrogenchloride; [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.166667h; pH=7; Catalytic behavior;	99%

1-propenylbenzene (873-66-5) + methyl 1-indanone-2-carboxylate (22955-77-7) → 5-(3-methyl-4-phenyl)-4,5-dihydro-2H-spiro[furan-3,2′-indene]-1′,2(3’H)-dione

Conditions	Yield
With iodine; sodium carbonate In water; tert-butyl alcohol at 20℃; for 24h; Inert atmosphere; Irradiation;	99%

1-propenylbenzene (873-66-5) → (1R,2R)-1-phenylpropane-1,2-diol (40421-51-0)

Conditions	Yield
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) + dimethyl(methylthio)sulfonium tetrafluoroborate (5799-67-7) → (R*,S*)-1-phenyl-2-(methylthio)propanamine (81230-67-3)

Conditions	Yield
With ammonia In dichloromethane	98%

1-propenylbenzene (873-66-5) + 2-Iodo-2-cyanopent-4-ynenitrile (130575-06-3) → 2-(2-Iodo-1-methyl-2-phenyl-ethyl)-2-prop-2-ynyl-malononitrile (130575-10-9, 130575-11-0)

Conditions	Yield
In benzene at 80℃;	98%

1-propenylbenzene (873-66-5) + toluene-4-sulfonamide (70-55-3) → N-((1R,2S)-2-bromo-1-phenylpropyl)-4-methylbenzenesulfonamide

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

Upstream product

• 93-54-9 1-Phenyl-1-propanol 
• 144-62-7 oxalic acid 
• 100-42-5 styrene 
• 593-53-3 Methyl fluoride 
• 673-32-5 1-Phenylprop-1-yne 
• 917-64-6 methyl magnesium iodide 
• 7214-56-4 phenyl(styryl)sulfane 
• 7214-53-1 (E)-[2-(phenylsulfanyl)vinyl]benzene 
• 17750-24-2 1-propyl-1,4-dihydronicotinamide 
• 21040-45-9 Cinnamyl acetate 
• 53432-99-8 trans-3-methyl-2-phenyloxetane 
• 591-50-4 iodobenzene 
• 51851-80-0 diethyl 2-propene-1-boronate 
• 29680-62-4 Tris(phenylseleno)borane 

Downstream Products

• 21040-45-9 Cinnamyl acetate 
• 66618-80-2 acetic acid-((1RS,2RS)-2-nitro-1-phenyl-propyl ester) 
• 42790-87-4 1-methyl-4-{[(1E)-1-phenylprop-1-en-2-yl]sulfonyl}benzene 
• 775-24-6 trimethyl(3-phenylpropyl)silane 
• 18027-67-3 1-phenyl-1-(trimethylsilyl)propane 
• 4962-46-3 (±)-erythro-2-bromo-1-phenylpropyl acetate 
• 16622-61-0 1-Fluor-1-chlor-3-methyl-2-phenyl-cyclopropan 
• 16622-61-0 1-Fluor-1-chlor-3-methyl-2-phenyl-cyclopropan 
• 56895-69-3 trans-1,1-dichloro-2-methyl-3-phenylcyclopropane 
• 50987-60-5 2,3,3-Trimethyl-1-phenylbutan 
• 66388-73-6 2,3,5-Trimethyl-4-phenylcyclopentanon 
• 29272-74-0 dimethyl-(5r-methyl-6t-phenyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-amine 
• 29272-72-8 2-ethoxy-5r-methyl-6t-phenyl-5,6-dihydro-4H-[1,3]oxazine 
• 29272-70-6 5r-methyl-6t-phenyl-2-(1-phenyl-propyl)-5,6-dihydro-4H-[1,3]oxazine 

Relevant articles and documents

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

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Ruthenium-Catalyzed E-Selective Partial Hydrogenation of Alkynes under Transfer-Hydrogenation Conditions using Paraformaldehyde as Hydrogen Source

E-alkenes were synthesized with up to 100 % E/Z selectivity via ruthenium-catalyzed partial hydrogenation of different aliphatic and aromatic alkynes under transfer-hydrogenation conditions. Paraformaldehyde as a safe, cheap and easily available solid hydrogen carrier was used for the first time as hydrogen source in the presence of water for transfer-hydrogenation of alkynes. Optimization reactions showed the best results for the commercially available binuclear [Ru(p-cymene)Cl2]2 complex as pre-catalyst in combination with 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP) as ligand (1 : 1 ratio per Ru monomer to ligand). Mechanistic investigations showed that the origin of E-selectivity in this reaction is the fast Z to E isomerization of the formed alkenes. Mild reaction conditions plus the use of cheap, easily available and safe materials as well as simple setup and inexpensive catalyst turn this protocol into a feasible and promising stereo complementary procedure to the well-known Z-selective Lindlar reduction in late-stage syntheses. This procedure can also be used for the production of deuterated alkenes simply using d2-paraformaldehyde and D2O mixtures.

Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle

Iron-catalyzed isomerization of alkenes is reported using an iron(II) β-diketiminate pre-catalyst. The reaction proceeds with a catalytic amount of a hydride source, such as pinacol borane (HBpin) or ammonia borane (H3N?BH3). Reactivity with both allyl arenes and aliphatic alkenes has been studied. The catalytic mechanism was investigated by a variety of means, including deuteration studies, Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy. The data obtained support a pre-catalyst activation step that gives access to an η2-coordinated alkene FeI complex, followed by oxidative addition of the alkene to give an FeIII intermediate, which then undergoes reductive elimination to allow release of the isomerization product.