5668-93-9

Basic information

• Product Name: 3-ETHYLBIPHENYL
• Synonyms: 3-ETHYLBIPHENYL;1,1'-Biphenyl, 3-ethyl-;1-ethyl-3-phenylbenzene;3-ethyl-1,1’-biphenyl;biphenyl,3-ethyl-;m-ethylbiphenyl;3-ETHYLBIPHENYL EP
• CAS NO: 5668-93-9
• Molecular Formula: C₁₄H₁₄
• Molecular Weight: 182.26
• Mol File: 5668-93-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: -27 °C
• Boiling Point: 284 °C
• Flash Point: 125.3°C
• Appearance: /
• Density: 1.00
• Vapor Pressure: 0.00539mmHg at 25°C
• Refractive Index: 1.5910 to 1.5950
• CAS DataBase Reference: 3-ETHYLBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHYLBIPHENYL(5668-93-9)
• EPA Substance Registry System: 3-ETHYLBIPHENYL(5668-93-9)

Safety Data

• Hazardous Substances Data: 5668-93-9(Hazardous Substances Data)

Usage

General Description

3-Ethylbiphenyl is an organic chemical compound classified as a biphenyl, featuring two phenyl rings connected by a single carbon bridge. It carries one ethyl group attached to one of the carbon atoms on the phenyl ring. The chemical formula for this odorless, colorless compound is C14H14. It is commonly used in research and development and in the production of certain types of polymers. As with most chemicals, proper care should be given when handling 3-Ethylbiphenyl to avoid possible health hazards, especially as the compound can be harmful if swallowed, inhaled, or comes into contact with the skin.

InChI:InChI=1/C14H14/c1-2-12-7-6-10-14(11-12)13-8-4-3-5-9-13/h3-11H,2H2,1H3

Synthetic route

3-methoxybiphenyl (2113-56-6) + triethylaluminum (97-93-8) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
Stage #1: 3-methoxybiphenyl With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In di-isopropyl ether; toluene at 20℃; for 0.0833333h; Glovebox; Inert atmosphere; Stage #2: triethylaluminum In di-isopropyl ether; toluene at 120℃; for 72h; Glovebox; Inert atmosphere;	95%

3-(methoxymethyl)-1,1'-biphenyl (1016160-90-9) + methylmagnesium bromide (75-16-1) → 3-ethyl-1,1'-biphenyl (5668-93-9)

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;	91%

potassium phenyltrifluoborate + 3-ethylphenyl trifluoromethanesulfonate (263908-61-8) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With acetone; trifluoroacetic acid In water at 15℃; UV-irradiation; Inert atmosphere;	64%

ethyl bromide (74-96-4) + biphenyl (92-52-4) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With aluminium trichloride

biphenyl (92-52-4) + ethene (74-85-1) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With aluminium trichloride

biphenyl (92-52-4) + chloroethane (75-00-3) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With aluminium trichloride

diethyl ether (60-29-7) + 3-ethylcyclohex-2-en-1-one (17299-34-2) + phenylmagnesium bromide → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
Kochen des nach der Hydrolyso erhaltenen Reaktionsprodukts mit Palladium/Kohle;

3-ethylcyclohex-2-en-1-one (17299-34-2) + phenylmagnesium bromide → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With diethyl ether Kochen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit Palladium-Kohle;

(RS)-1-([1,1'-biphenyl]-3-yl)ethanol (58114-12-8) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With copper chromite at 200℃; under 102971 Torr; Hydrogenolyse;

phenylium (17333-73-2) + ethylbenzene (100-41-4) → 3-ethyl-1,1'-biphenyl (5668-93-9) + 2-ethyl-1,1'-biphenyl (1812-51-7) + 4-ethylbiphenyl (5707-44-8)

Conditions	Yield
Product distribution; Rate constant; with totally tritiated phenyl cation, gas and liquid phases at r.t., solid phase at temp. of liquid N2;	A 26 % Chromat. B 36 % Chromat. C 38 % Chromat.

4-ethylbiphenyl (5707-44-8) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With aluminium trichloride; ethylbenzene; benzene at 89.9℃; for 6h; Thermodynamic data; Equilibrium constant; var. temp., time, ΔrHm0, ΔrSm0;

ethylbenzene (100-41-4) + benzene (71-43-2) → biphenyl (92-52-4) + 3-ethyl-1,1'-biphenyl (5668-93-9) + 2-ethyl-1,1'-biphenyl (1812-51-7) + 4-ethylbiphenyl (5707-44-8) + 4,4'-diethylbiphenyl (13049-40-6) + 3,4’-diethyl-1,1’-biphenyl (13049-39-3)

Conditions	Yield
With palladium diacetate; thallium(III) trifluoroacetate at 60 - 70℃; Product distribution; selectivity in the oxidative coupling; partial rate factors;

3-ethyl-1-phenyl-cyclohexene → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With aluminum oxide; chromium(III) oxide at 475℃;

5-ethyl-1-phenyl-cyclohexene → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
With aluminum oxide; chromium(III) oxide at 475℃;

(RS)-1-([1,1'-biphenyl]-3-yl)ethanol (58114-12-8) + hydrogen + copper oxide-chromium oxide → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
at 200℃; under 102971 Torr;

[(1,1'-biphenyl)-3-yl]magnesium bromide (103068-18-4) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: copper chromite / 200 °C / 102971 Torr / Hydrogenolyse View Scheme

ethylbenzene (100-41-4) + Diphenyliodonium triflate (66003-76-7) → 3-ethyl-1,1'-biphenyl (5668-93-9) + 2-ethyl-1,1'-biphenyl (1812-51-7) + 4-ethylbiphenyl (5707-44-8)

Conditions	Yield
With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); trifluoroacetic acid at 100℃; for 24h; Overall yield = 72 %; Overall yield = 32.8 mg;

3-ethylphenol (620-17-7) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: trifluoroacetic acid; acetone / water / 15 °C / UV-irradiation; Inert atmosphere View Scheme

phenylboronic acid (98-80-6) → 3-ethyl-1,1'-biphenyl (5668-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 0.5 h / 0 - 20 °C 2: trifluoroacetic acid; acetone / water / 15 °C / UV-irradiation; Inert atmosphere View Scheme

3-ethyl-1,1'-biphenyl (5668-93-9) + aqueous KMnO4-solution → biphenyl-carboxylic acid-(3)

3-ethyl-1,1'-biphenyl (5668-93-9) + chromic acid → m-phenyl-benzoic acid

Upstream product

• 74-96-4 ethyl bromide 
• 92-52-4 biphenyl 
• 17333-73-2 phenylium 
• 100-41-4 ethylbenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 98-80-6 phenylboronic acid 
• 263908-61-8 3-ethylphenyl trifluoromethanesulfonate 
• 620-17-7 3-ethylphenol 
• 2113-56-6 3-methoxybiphenyl 
• 97-93-8 triethylaluminum 
• 1016160-90-9 3-(methoxymethyl)-1,1'-biphenyl 
• 75-16-1 methylmagnesium bromide 
• 103068-18-4 [(1,1'-biphenyl)-3-yl]magnesium bromide 
• 58114-12-8 (RS)-1-([1,1'-biphenyl]-3-yl)ethanol 

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