100-41-4

Basic information

• Product Name: Ethylbenzene
• Synonyms: EB;Ethylbenzol;NSC 406903;Phenylethane;a-Methyltoluene
• CAS NO: 100-41-4
• Molecular Formula: C₈H₁₀
• Molecular Weight: 106.165
• EINECS: 202-849-4
• Mol File: 100-41-4.mol
• Article Data: 1946

Chemical Properties

• Melting Point: -94℃
• Boiling Point: 136.248 °C at 760 mmHg
• Flash Point: 25.941 °C
• Appearance: colourless liquid
• Density: 0.865 g/cm³
• Vapor Pressure: 9.21mmHg at 25°C
• Refractive Index: 1.497
• Water Solubility: 0.0206 g/100 mL
• CAS DataBase Reference: Ethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylbenzene(100-41-4)
• EPA Substance Registry System: Ethylbenzene(100-41-4)

Safety Data

• Hazard Codes: F:Flammable;;
• Statements: R11:; R20:
• Safety Statements: S16:; S24/25:; S29:
• RIDADR: 1175
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 100-41-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H10/c1-2-8-6-4-3-5-7-8/h3-7H,2H2,1H3

Synthetic route

styrene (292638-84-7) → ethylbenzene (100-41-4)

Conditions	Yield
With hydrogen; p In methanol for 0.316667h; other substrates;	100%
With polymeric thiol; hydrogen; palladium on activated charcoal for 1h; Product distribution; var. catalysts, further thiol; poisoning effect of thiols;	100%
With hydrogen; Pd-1percent Ho In neat (no solvent) at 90℃; for 0.00583333h; Product distribution; selective hydrogenation; variation of temperature and contact time;	100%

4-ethenylcyclohexene (100-40-3) → ethylbenzene (100-41-4)

Conditions	Yield
With n-butyllithium; potassium 2-methylbutan-2-olate Mechanism; 1) r.t., 17 h, 2) reflux, 7 h; further reagent: D2O;	100%
at 400℃; Leiten ueber Chrom(III)-oxyd;
at 300 - 320℃; Leiten ueber Nickel-Aluminiumoxyd;

1-Phenylethanol (98-85-1, 13323-81-4) → ethylbenzene (100-41-4)

Conditions	Yield
With formic acid; ammonium formate; 5%-palladium/activated carbon In ethanol; water at 80℃; Product distribution / selectivity;	100%
With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction;	99%
With hydrogen; palladium diacetate; sodium dioctyl sulfosuccinate In tetrahydrofuran at 25℃; under 760.051 Torr; for 24h;	99%

phenylacetylene (536-74-3) → ethylbenzene (100-41-4)

Conditions	Yield
With hydrogen; palladium on C60 In methanol under 760 Torr; for 0.216667h; Ambient temperature; other substrates: cyclohexene, hex-1-ene, other catalysts: palladium on activated charcoal, C60, other reaction time;	100%
silver tetrafluoroborate; (Ph2PCH2PPh2CHC(O)Ph)>I In dichloromethane at 65℃; for 18h; Pressure (range begins): 120 ;	100%
With hydrogen; N,N′-bis(salicylidene)-ethylenediamino‑palladium In methanol for 0.85h;	100%

acetophenone (98-86-2) → ethylbenzene (100-41-4)

Conditions	Yield
With hydrogen at 80℃; under 37503.8 Torr; for 0.5h; Autoclave; chemoselective reaction;	100%
With hydrogen In ethanol at 39.84℃; under 760.051 Torr; for 5h;	100%
With Pd/C; hydrogen In chloroform at 20℃; under 760.051 Torr; for 8h; Catalytic behavior;	100%

styrene (292638-84-7) + hydrogen (1333-74-0) → ethylbenzene (100-41-4)

Conditions	Yield
With C52H46ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 16h; Reagent/catalyst; Time;	100%
With [Ir(6-Neo)(COD)Cl] In ethanol under 3750.38 Torr; for 1h; Solvent;	100 %Spectr.
at 80℃; under 30003 Torr; for 24h; Reagent/catalyst;

hydrogen (1333-74-0) → ethylbenzene (100-41-4)

Conditions	Yield
With C61H98ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 14h;	100%

styrene (292638-84-7) + Dimethylphenylsilane (766-77-8) → ethylbenzene (100-41-4) + dimethyl(phenyl)(2-phenylethenyl)silane (128756-74-1)

Conditions	Yield
With C11H14FeO4Si2 In toluene at 50℃; for 24h; Kinetics; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique;	A n/a B 100%

ethyl acetate (141-78-6) + benzene (71-43-2) → ethylbenzene (100-41-4)

Conditions	Yield
With hydrogen at 240 - 400℃; under 15001.5 Torr; Reagent/catalyst; Temperature;	99.5%

ethene (74-85-1) + benzene (71-43-2) → ethylbenzene (100-41-4)

Conditions	Yield
Product distribution; Heating; synthesis by chemorectification;	99%
mesoporous ZSM-5 Si/Al=120 at 310 - 370℃; under 1875.19 - 3750.38 Torr; Product distribution / selectivity;	75%
boron trifluoride at 180℃; under 22501.8 Torr; Product distribution; other temperatures, other volumetric rates;	59.9%

benzyl bromide (100-39-0) + [3-(dimethylamino)propyl]dimethyl aluminium(III) → ethylbenzene (100-41-4)

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 3h;	99%

styrene (292638-84-7) + nitrobenzene (98-95-3) → ethylbenzene (100-41-4) + aniline (62-53-3)

Conditions	Yield
With hydrogen; 5% rhodium-on-charcoal; tris(acetylacetonato)cobalt In tetrahydrofuran at 20℃; for 16h;	A 99% B 89%
With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 16h;	A 98% B 80%
With hydrogen; 5% rhodium-on-charcoal In tetrahydrofuran at 20℃; for 16h; Product distribution / selectivity;	A 93% B 31%
With hydrogen at 110℃; under 4560.31 Torr; for 24h; Autoclave; chemoselective reaction;

benzyl methyl ether (538-86-3) + methylmagnesium bromide (75-16-1) → ethylbenzene (100-41-4)

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide In diethyl ether; toluene at 80℃; for 10h;	99%

dihydrocinnamonitrile (645-59-0) → ethylbenzene (100-41-4)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triisopropyl phosphite; chlorotriisopropylsilane In ethyl-cyclohexane at 160℃; for 15h; Inert atmosphere;	99%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triisopropyl phosphite; chlorotriisopropylsilane In ethylcyclohexane at 160℃; for 15h; Inert atmosphere;	99 %Chromat.
With bis(acetylacetonate)nickel(II); 1,1,3,3-Tetramethyldisiloxane; trimethylaluminum; tricyclohexylphosphine In toluene at 130℃; for 24h; Inert atmosphere;	67 %Chromat.
With bis(1,5-cyclooctadiene)nickel (0); hydrogen; trimethylaluminum; tricyclohexylphosphine In toluene at 130℃; under 750.075 Torr; for 24h; Schlenk technique;	79 %Chromat.
With lithium borohydride; C30H21F6N2NiO2P In tetrahydrofuran at 70℃; for 3h; Schlenk technique; Inert atmosphere;	7 %Chromat.

styrene (292638-84-7) + benzaldehyde (100-52-7) → ethylbenzene (100-41-4) + benzyl alcohol (100-51-6)

Conditions	Yield
With 3% Au/meso-CeO2; potassium formate In water at 25℃; chemoselective reaction;	A 7% B 99%
With gold supported on mesoporous ceria; hydrogen In isopropyl alcohol at 100℃; under 7500.75 Torr; for 1h;
With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex; C32H63CoNP2Si; hydrogen In tetrahydrofuran at 25℃; under 760.051 Torr; for 24h;	A 16 %Chromat. B 99 %Chromat.
With hydrogen In isopropyl alcohol at 130℃; under 11400.8 Torr; for 5h; Reagent/catalyst;

2-phenoxy-1-phenylethanol (4249-72-3) → ethylbenzene (100-41-4) + phenol (108-95-2)

Conditions	Yield
With formic acid In water at 120℃; for 3h; Green chemistry;	A 98% B 99%
With Cu/Al2O3; hydrogen In ethyl acetate at 150℃; under 18751.9 Torr; for 21h; Inert atmosphere; Autoclave;	A 19.1% B 21.7%
With nickel-molybdenum sulfide; hydrogen; potassium hydroxide In methanol at 180℃; under 7500.75 Torr; for 1h;	A 46 %Chromat. B 54 %Chromat.

2-phenethoxybenzene (40515-89-7) → ethyl-cyclohexane (1678-91-7) + ethylbenzene (100-41-4) + cyclohexanol (108-93-0)

Conditions	Yield
With hydrogen; lanthanum(lll) triflate In isopropyl alcohol at 120℃; for 2h;	A 33% B 66% C 99%
With hydrogen In n-heptane at 160℃; under 750.075 Torr; for 6h; Catalytic behavior; Temperature;	A 8 %Chromat. B 92 %Chromat. C 100 %Chromat.
With isopropyl alcohol at 170℃; under 7500.75 Torr; Inert atmosphere; Autoclave;

(1-chloroethyl)benzene (672-65-1) → ethylbenzene (100-41-4)

Conditions	Yield
With phosphonic Acid; iodine In benzene at 100℃; for 36h; Inert atmosphere;	98%
With sodium tetrahydroborate; cetyltributylphosphonium bromide In water; toluene at 80℃; for 3h; Product distribution;	85%
With sodium tetrahydroborate; water In methanol at 20℃; for 0.5h;	81%

(C5(CH3)5)Fe(CO)2(CH2CH2(C6H5)) + trimethylstannane (1631-73-8) → (C5(CH3)5)Fe(H)(CO)(Sn(CH3)3)2 + 3-Phenyl-1-propanol (122-97-4) + ethylbenzene (100-41-4)

Conditions	Yield
In benzene-d6 under Ar; 90°C, 6 h;	A 98% B 63% C 4%

phenylacetylene (536-74-3) → styrene (292638-84-7) + ethylbenzene (100-41-4)

Conditions	Yield
With hydrogen In hexane at 30℃; under 760.051 Torr; for 6h;	A 97% B 3%
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;	A 95% B n/a
With hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 0.5h;	A 9% B 91%

3-Phenyl-propionic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester (124552-52-9) → ethylbenzene (100-41-4)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 3h; Heating; decarboxylation was investigated;	97%

1-phenylethyl acetate (93-92-5, 50373-55-2) → ethylbenzene (100-41-4)

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen In neat (no solvent) at 25℃; under 750.075 Torr; for 18h; Time;	97%
With triethylsilane; indium tribromide In chloroform at 60℃; for 1h; Inert atmosphere;	76%
With pyrrolidine; samarium diiodide; water In tetrahydrofuran; decane at 20℃;	73 %Chromat.

2-phenethoxybenzene (40515-89-7) → ethylbenzene (100-41-4) + cyclohexanol (108-93-0) + phenol (108-95-2)

Conditions	Yield
With Ni0.85Rh0.15; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst;	A 96% B 27% C 59%
With Ni0.85Ru0.15; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst;	A 76% B 69% C 26%
With 57 wt. % Ni/SiO2 In water at 120℃; under 4500.45 Torr; for 1.5h; Activation energy; Catalytic behavior; Temperature; Pressure; Autoclave;

(1-bromoethyl)benzne (585-71-7, 38661-81-3) → ethylbenzene (100-41-4)

Conditions	Yield
With phosphonic Acid; iodine In 1,2-dichloro-ethane at 120℃; for 36h; Inert atmosphere;	95%
With zinc-modified cyanoborohydride In diethyl ether for 3h; Ambient temperature;	91%
With zinc(II) tetrahydroborate In diethyl ether for 1h; Ambient temperature;	91%

(η5-C5H5)Fe(CO)2CH2CH2C6H5 + trimethylstannane (1631-73-8) → (C5H5)Fe(H)(CO)(Sn(CH3)3)2 + ethylbenzene (100-41-4)

Conditions	Yield
In benzene-d6 Irradiation (UV/VIS); under Ar; room temp., 7 h; not isolated; NMR;	A 95% B 86%

CF3O3S(1-)*C17H19N2OS(1+) (847778-96-5) + methyllithium (917-54-4) → ethylbenzene (100-41-4)

Conditions	Yield
With 1,2-dimethoxy-4-methylbenzene In tetrahydrofuran at 60℃; for 0.0833333h;	95%

styrene (292638-84-7) + 1,1-Diphenylethylene (530-48-3) → 1,1'-ethylidenebis-benzene (612-00-0) + ethylbenzene (100-41-4)

Conditions	Yield
With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen at 20℃; under 1500.15 Torr; for 3h;	A 18% B 95%

C16H18O (1480731-83-6) → ethylbenzene (100-41-4)

Conditions	Yield
With palladium on activated charcoal In 1,4-dioxane at 160℃; for 8h; Thermodynamic data;	95%

acetophenone (98-86-2) → ethylbenzene (100-41-4) + 1-Phenylethanol (98-85-1, 13323-81-4)

Conditions	Yield
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 5h;	A 6% B 94%
With carbon dioxide; 5%-palladium/activated carbon; hydrogen In water at 49.84℃; under 15001.5 Torr; for 13h; Autoclave; Green chemistry;	A 93% B 7%
With hydrogen In ethanol at 39.84℃; under 760.051 Torr; for 4h;	A 92% B 8%

ethylbenzene (100-41-4) → ethyl-cyclohexane (1678-91-7)

Conditions	Yield
With hydrogen at 150℃; under 2280.15 Torr; for 0.166667h; Kinetics; Reagent/catalyst; Temperature;	100%
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 120℃; under 37503.8 Torr; for 18h;	89%
With octylated silica; hydrogen; sodium 4-dodecylbenzenesulfonate; {[(CH3)(C8H17)3N](+)[RhCl4](-)} at 80℃; under 10343 Torr; for 24h;	63%

ethylbenzene (100-41-4) → 1-Phenylethanol (98-85-1, 13323-81-4)

Conditions	Yield
With cerium(IV) triflate; water In acetonitrile at 20℃; for 20h;	100%
With C20H26B10Cl2FeN6; dihydrogen peroxide In methanol at 20℃; for 6h;	91%
With perchloric acid; C13H30N4*Fe(3+)*CF3O3S(1-)*C2H2F3O(1-)*C6H5IO In 2,2,2-trifluoroethanol; acetone at -40℃; for 0.166667h; Kinetics; Inert atmosphere; Schlenk technique; Further stages;	39%

ethylbenzene (100-41-4) → (1-bromoethyl)benzne (585-71-7, 38661-81-3)

Conditions	Yield
With manganese(IV) oxide; bromine In dichloromethane at 20℃; for 0.166667h;	100%
With bromine In tetrachloromethane Solvent;	100%
With carbon tetrabromide; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dichloromethane at 20℃; for 36h; Solvent; Reagent/catalyst; Schlenk technique; Inert atmosphere; Irradiation;	99%

ethylbenzene (100-41-4) → acetophenone (98-86-2)

Conditions	Yield
With potassium permanganate; iron(III) chloride In acetone at -78 - 20℃; for 16h;	100%
With potassium bromate; cerium(IV) oxide In 1,4-dioxane; water; acetic acid at 95℃; for 1h;	100%
With cerium(IV) triflate; water In acetonitrile at 20℃; for 19.5h;	99.7%

ethylbenzene (100-41-4) + 10-methylacridinium perchlorate (26456-05-3) → 9-(1-phenyl-1-ethyl)-10-methyl-9,10-dihydroacridine

Conditions	Yield
In water; acetonitrile Irradiation;	100%
In acetonitrile at 24.9℃; Rate constant; Quantum yield; Irradiation; also in MeOH;

ethylbenzene (100-41-4) + 2,2,2-trichloroethyl sulfamate (69226-51-3) → 2,2,2-trichloroethyl (1-phenylethyl)sulfamate

Conditions	Yield
With [bis(acetoxy)iodo]benzene; C32H44ClN4O4Rh2*3CH2Cl2 at 20℃; for 3h; Inert atmosphere;	100%
With [bis(acetoxy)iodo]benzene; bis[rhodium(α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid)]; sodium hydrogencarbonate	90%
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene In water at 4℃; for 24h;	86%

ethylbenzene (100-41-4) → 4-Ethylphenol (123-07-9) + 1-Phenylethanol (98-85-1, 13323-81-4) + 2-phenylethanol (60-12-8)

Conditions	Yield
With rabbit liver microsomal cytochrome P-450 In water at 25℃; for 12h;	A 0.13% B 99.8% C 0.08%

chloro(pentamethylcyclopentadienyl)ruthenium(II) tetramer (126821-58-7) + ethylbenzene (100-41-4) → [(η5-pentamethylcyclopentadienyl)Ru(η6-ethylbenzene)]Cl (942477-60-3)

Conditions	Yield
In water other Radiation; (N2); using Schlenk techniques; combining of ethylbenzene (8 equiv.), ((C5Me5)RuCl)4 (1 equiv.) and H2O in glass microwave reaction vessel with stir bar; sealing; microwave irradn. at 50 W (ca. 130°C for 10 min); evapn. of solvent under reduced pressure, extn., trituration with hexane; drying;	99%
In tetrahydrofuran; water other Radiation; (N2); using Schlenk techniques; combining of ethylbenzene (1 equiv.), ((C5Me5)RuCl)4 (1 equiv.), H2O and THF (2:1); microwave irradn. for 15 minat 130°C; cooling to room temp., removal of solvent under reduced pressure, trituration with toluene; drying;	99%
In water Sonication; (N2); using Schlenk techniques; combining of benzene (8 equiv.), ((C5Me5)RuCl)4 (1 equiv.) and H2O in Schlenk tube with stir bar; sealing; heating in oil bath (ca. 115.degre.C) with intermittent sonication for 1-3 ds; cooling to ca. 25°C; evapn. of solvent under reduced pressure, extn./trituration with toluene; drying;

ethylbenzene (100-41-4) + 5-bromo-2-chloro-benzoyl chloride (21900-52-7) → (5-bromo-2-chlorophenyl)(4-ethylphenyl)methanone (879545-43-4)

Conditions	Yield
Stage #1: ethylbenzene; 5-bromo-2-chloro-benzoyl chloride With aluminum (III) chloride at 10℃; for 0.5h; Stage #2: With sodium hydroxide In water at 15 - 20℃; for 5h;	99%
Stage #1: ethylbenzene; 5-bromo-2-chloro-benzoyl chloride With aluminum (III) chloride In chloroform at 5℃; Friedel Crafts acylation; Cooling; Stage #2: With water In chloroform Cooling with ice;

N-tert-butoxycarbonyl-L-leucine (13139-15-6) + ethylbenzene (100-41-4) → 1-phenylethyl N-(tert-butoxycarbonyl)-L-leucinate (1375009-11-2)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 8h;	99%

ethylbenzene (100-41-4) + 1-naphthalenecarboxylic acid (86-55-5) → 1-phenylethyl 1-naphthoate (1375008-87-9)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 3h;	99%

ethylbenzene (100-41-4) + p-Toluic acid (99-94-5) → 1-phenylethyl 4-methylbenzoate (212261-14-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 8h;	99%
With di-tert-butyl peroxide; C11H23N2(1+)*Br4Fe(1-) at 110℃; for 16h;	84%

ethylbenzene (100-41-4) + para-chlorobenzoic acid (74-11-3) → 1-phenylethyl 4-chlorobenzoate (111021-11-5)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 8h;	99%
With di-tert-butyl peroxide; C11H23N2(1+)*Br4Fe(1-) at 110℃; for 24h;	88%

ethylbenzene (100-41-4) + ortho-chlorobenzoic acid (118-91-2) → 1-phenylethyl 2-chlorobenzoate (111021-09-1)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 8h;	99%

Upstream product

• 64742-89-8 PETROLEUM ETHER 
• 112926-00-8 Silica gel 
• 1330-20-7 Xylene 
• 25340-17-4 Diethylbenzene 
• 61790-53-2 Celite 

Downstream Products

• 56781-71-9 4-(2-Methoxyethyl)Phenol 
• 3844-45-9 Erioglaucine disodium salt 
• 153435-63-3 2-(Tributylstannyl)pyrimidine 
• 123-07-9 4-Ethylphenol 
• 100-19-6 4-Nitroacetophenone 
• 105-05-5 1,4-DIETHYLBENZENE 
• 614-39-1 Procainamide hydrochloride 
• 108-67-8 Mesitylene 
• 30339-32-3 α-phenyl-2-p-tolylethylamine 
• 61069-78-1 Sisthsne 
• 18773-95-0 2-Acetylbenzimidazole 
• 49763-66-8 4-N-OCTYLBENZALDEHYDE 
• 98-85-1 DL-1-Phenethylalcohol 
• 619-64-7 4-Ethylbenzoic acid 
• 112410-23-8 Tebufenozide 
• 96-83-3 Iopanoic acid 
• 6245-59-6 sodium 3-[[4-(benzoylethylamino)-2-methylphenyl]azo]-4-hydroxynaphthalene-1-sulphonate 
• 602267-60-7 1-(2-ISOCYANO-ETHYL)-4-METHYL-PIPERAZINE 
• 84-51-5 2-Ethyl anthraquinone 

Recommend Products

• 100-42-5  styrene 
• 108-88-3  toluene 
• 71-43-2  benzene 
• 75-21-8  oxirane 
• 100-41-4  ethylbenzene 
• 64353-29-3  4-ethylphenylethylamine 
• 151-56-4  ethyleneimine 
• 103-45-7  acetic acid phenethyl ester 
• 123-91-1  1,4-dioxane 
• 67-56-1  methanol 
• 2243-35-8  2-acetoxyacetophenone 
• 64-19-7  acetic acid 
• 5467-53-8  γ-(p-ethylphenyl)butyric acid 
• 96-48-0  4-butanolide 

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