[1,1'-Biphenyl]-4-carboxylicacid, ethyl ester supplier

Name
BIPHENYL-3-CARBOXYLIC ACID ETHYL ESTER
EINECS
CAS No. 6301-56-0
Article Data191
CAS DataBase
Density 1.082 g/cm³
Solubility
Melting Point
Formula C₁₅H₁₄O₂
Boiling Point 351.4 °C at 760 mmHg
Molecular Weight 226.275
Flash Point 159.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms 4-Biphenylcarboxylicacid, ethyl ester (6CI,7CI);4-(Ethoxycarbonyl)-1,1'-biphenyl;4-Carbethoxybiphenyl;Ethyl 1,1'-biphenyl-4-carboxylate;Ethyl4-phenylbenzoate;Ethyl biphenyl-4-carboxylate;Ethyl biphenylyl-4-carboxylate;Ethyl p-phenylbenzoate;
PSA 26.30000
LogP 3.53030

Synthetic route

: 5798-75-4
Ethyl 4-bromobenzoate

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With potassium carbonate; Pd(OAc)2 on N,N-diethylaminopropylated alumina In ethanol; water at 20℃; for 4h; Suzuki-Miyaura coupling;	100%
With sodium carbonate; palladium on activated charcoal In ethanol at 20℃; for 3h; Suzuki-Miyaura cross-coupling;	99%
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 6h; Suzuki-Miyaura coupling reaction;	99%

: 5798-75-4
Ethyl 4-bromobenzoate

: 71478-47-2
phenylmanganese(II) chloride

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 0.5h;	99%

: 64-17-5
ethanol

: 201230-82-2
carbon monoxide

: 1591-31-7
4-iodo-biphenyl

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With triethylamine; dichloro bis(acetonitrile) palladium(II) at 70℃; for 24h;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; [(Ph2CH=NOH)PdCl]2 In benzene at 120℃; for 3h;	90%

...Expand

: 98634-20-9
ethyl 4-(tosyloxy)benzoate

: potassium phenyltrifluoborate

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With triethylamine; palladium diacetate In ethanol at 80℃; Suzuki-Miyaura cross-coupling;	99%

: 913621-71-3
[2-(hydroxymethyl)phenyl](diisopropyl)phenylsilane

: 7335-27-5
ethyl 4-chlorobenzoate

A: 913621-73-5
1,1-diisopropyl-1,3-dihydrobenzo[c][1,2]oxasilole

B: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With potassium carbonate; copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); ruphos In tetrahydrofuran; N,N-dimethyl-formamide at 75℃; for 15h; Product distribution / selectivity;	A 95% B 99%
With copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; ruphos In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 15h; Inert atmosphere;	A > 95 %Chromat. B 96%

...Expand

: 125261-30-5
p-(ethoxycarbonyl)phenyl triflate

: potassium phenyltrifluoborate

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; cesium acetate In tetrahydrofuran Stille coupling; Reflux; Inert atmosphere;	99%

: 108-86-1
bromobenzene

: 51934-41-9
4-iodobenzoic acid ethyl ester

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Negishi coupling reaction; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃; Negishi coupling reaction; Inert atmosphere; Stage #3: 4-iodobenzoic acid ethyl ester With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; hexane at 60℃; for 2h; Negishi coupling reaction; Inert atmosphere;	99%
Stage #1: bromobenzene With indium; bathophenanthroline; 3-chloroprop-1-ene; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 100℃; for 23h; Inert atmosphere; Stage #2: 4-iodobenzoic acid ethyl ester With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 80℃; for 21h; Inert atmosphere;	95%

Yield

Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Negishi coupling reaction; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃; Negishi coupling reaction; Inert atmosphere;
Stage #3: 4-iodobenzoic acid ethyl ester With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; hexane at 60℃; for 2h; Negishi coupling reaction; Inert atmosphere;

99%

Stage #1: bromobenzene With indium; bathophenanthroline; 3-chloroprop-1-ene; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 100℃; for 23h; Inert atmosphere;
Stage #2: 4-iodobenzoic acid ethyl ester With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 80℃; for 21h; Inert atmosphere;

95%

: 98634-20-9
ethyl 4-(tosyloxy)benzoate

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); potassium carbonate; triphenylphosphine In toluene at 100℃; for 5h; Suzuki coupling; Inert atmosphere;	99%
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine tetrafluoroborate; potassium carbonate In water; toluene at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;	99%
With potassium phosphate; (NC5H3(N2C7H4(CH2)3CH3)2)NiBr(1+)*Br(1-)=Ni(NC5H3(N2C7H4(CH2)3CH3)2)Br2; triphenylphosphine In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura coupling;	98%
With 1,1'-bis-(diphenylphosphino)ferrocene; (9-phenanthrenyl)Ni(II)(PPh3)2Cl; potassium carbonate In toluene at 110℃; for 20h; Suzuki Coupling; Inert atmosphere;	87%

: 5798-75-4
Ethyl 4-bromobenzoate

: 595-90-4
tetraphenyltin(IV)

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With palladium 10% on activated carbon; lithium chloride In 1-methyl-pyrrolidin-2-one at 90℃; for 24h; Stille coupling;	99%

: 902148-89-4
ethyl 4-(methanesulfonyloxy)benzoate

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine tetrafluoroborate; potassium carbonate In water; toluene at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;	99%
With 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate; sodium carbonate In tert-butyl alcohol at 20 - 120℃; for 18h; Suzuki-Miyaura coupling;	98%
With potassium phosphate; (NC5H3(N2C7H4(CH2)3CH3)2)NiBr(1+)*Br(1-)=Ni(NC5H3(N2C7H4(CH2)3CH3)2)Br2; triphenylphosphine In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura coupling;	91%

: 64-17-5
ethanol

: 619-42-1
4-methoxycarbonylphenyl bromide

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With 2C2H4O2*C40H36N2O2Pd; potassium hydroxide at 50℃; for 1h; Suzuki coupling;	99%

...Expand

: 51934-41-9
4-iodobenzoic acid ethyl ester

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With Pd/C; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;	99%
Stage #1: phenylboronic acid With diethylzinc; lithium chloride In tetrahydrofuran; toluene at 23℃; for 1h; Inert atmosphere; Glovebox; Stage #2: 4-iodobenzoic acid ethyl ester In tetrahydrofuran; toluene at 110℃; for 24h; Inert atmosphere; Glovebox;	95%
With triethylamine In 1,4-dioxane; water at 100℃; for 1h; Suzuki-Miyaura Coupling; Microwave irradiation; Green chemistry;	94%

: ethyl 4-[(fluorosulphonyl)oxy]benzoate

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With palladium diacetate; triethylamine In water at 20℃; for 2h; Suzuki-Miyaura Coupling;	99%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane at 80℃; for 15h; Reagent/catalyst; Suzuki Coupling;	92%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane at 80℃; for 15h; Reagent/catalyst; Inert atmosphere;	40%

: (4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride

: 100-68-5
methyl-phenyl-thioether

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
Stage #1: (4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride With trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5) In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere; Stage #2: methyl-phenyl-thioether In tetrahydrofuran; acetonitrile at 20℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	99%

: 71478-47-2
phenylmanganese(II) chloride

: 125261-30-5
p-(ethoxycarbonyl)phenyl triflate

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
1,2-dimethoxyethane; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 20℃; for 0.0833333h;	98%
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 0.5h;	88%

: 7335-27-5
ethyl 4-chlorobenzoate

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With 2-chloro-1,3-[di-(2,6-diisopropyl)phenyl]-1,3,2-diazaphospholidine; tris-(dibenzylideneacetone)dipalladium(0); cesium fluoride In 1,4-dioxane at 80℃; for 18h; Suzuki-Miyaura cross-coupling; Inert atmosphere;	98%
With potassium carbonate In toluene at 100℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere;	98%
With caesium carbonate In N,N-dimethyl acetamide at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;	94%

: 5798-75-4
Ethyl 4-bromobenzoate

: potassium phenyltrifluoborate

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With choline chloride; palladium diacetate; sodium carbonate; glycerol at 60℃; for 5h; Suzuki-Miyaura Coupling;	98%
With potassium carbonate; triphenylphosphine In methanol at 50℃; for 24h; Suzuki-Miyaura coupling;	85%
With palladium diacetate; potassium carbonate In ethanol; water at 40℃; for 15h; Solvent; Reagent/catalyst; Temperature; Suzuki Coupling; Green chemistry;

: 5798-75-4
Ethyl 4-bromobenzoate

: 23665-09-0
phenylzinc iodide

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; tetrabutylammomium bromide for 4h; Negishi Coupling; Milling;	98%
With lithium chloride In tetrahydrofuran; toluene at 110℃; for 48h; Schlenk technique; Inert atmosphere;	83%

: 64-17-5
ethanol

: 201230-82-2
carbon monoxide

: 92-66-0
4-bromo-1,1'-biphenyl

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With triethylamine at 70℃; under 760.051 Torr; for 3h; Catalytic behavior;	98%

...Expand

: 64-17-5
ethanol

: 92-92-2
biphenyl-4-carboxylic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h; Reagent/catalyst; Solvent; Concentration;	97%
With sulfuric acid
With hydrogenchloride

: 92-66-0
4-bromo-1,1'-biphenyl

: 95-92-1
oxalic acid diethyl ester

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With dmap; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.333333h; Microwave irradiation;	97%

: 120-47-8
Ethyl 4-hydroxybenzoate

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran at 20 - 60℃; for 5h; Inert atmosphere;	96%
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 4h; Inert atmosphere;	96%

: 5798-75-4
Ethyl 4-bromobenzoate

: 100-59-4
phenylmagnesium chloride

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
Stage #1: phenylmagnesium chloride With titanium(IV) tetraethanolate In tetrahydrofuran at 0℃; Stage #2: Ethyl 4-bromobenzoate With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 25℃; for 3h; Further stages.;	95%

: 94-09-7
p-aminoethylbenzoate

: 98-80-6
phenylboronic acid

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
Stage #1: p-aminoethylbenzoate With tert.-butylnitrite; boron trifluoride diethyl etherate In methanol at 0℃; for 0.5h; Schlenk technique; Stage #2: phenylboronic acid In methanol at 0 - 60℃; for 5h; Reagent/catalyst; Solvent; Temperature; Schlenk technique;	95%
Stage #1: p-aminoethylbenzoate With tert.-butylnitrite; acetic acid In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: phenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane In N,N-dimethyl-formamide at 90℃; for 10h; Inert atmosphere;	50%

: 5798-75-4
Ethyl 4-bromobenzoate

: 1078-58-6
diphenylzinc

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With tripiperidino-phosphine; nickel dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 60℃; for 0.5h; Negishi cross-coupling reaction;	95%

: 1126-46-1
Methyl 4-chlorobenzoate

: 98-80-6
phenylboronic acid

A: 720-75-2
methyl 4-phenylbenzoate

B: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; N,N′-bis(2,6-diisopropylphenyl)imidazolylidene hydrochloride; sodium hydroxide; phosphorous acid trimethyl ester In ethanol at 80℃; for 5h; Suzuki Coupling; Inert atmosphere;	A 95% B n/a

...Expand

: 7335-27-5
ethyl 4-chlorobenzoate

: 2-(2-hydroxyprop-2-yl)cyclohexyl(dimethyl)phenylsilane

A: 6301-56-0
ethyl 4-phenylbenzoate

: C11H22OSi

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,2-dimethoxyethane)dichloronickel(II); caesium carbonate; zinc; tricyclohexylphosphine In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 20 - 75℃; for 30h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere; chemoselective reaction;	A 82% B 93%

...Expand

: 106359-54-0
N-hydroxy-[1,1'-biphenyl]-4-carboxamide

: 126-84-1
2,2-diethoxypropane

A: 6301-56-0
ethyl 4-phenylbenzoate

B: 5,5-dimethyl-3-(p-biphenyl)-1,4,2-dioxazole

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 4h;	A n/a B 92%

...Expand

: 591-50-4
iodobenzene

: 131379-16-3
4-(ethoxycarbonyl)phenylzinc iodide

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
With lithium chloride In tetrahydrofuran; toluene at 110℃; for 48h; Schlenk technique; Inert atmosphere;	92%

: 100-68-5
methyl-phenyl-thioether

: 131379-15-2
(4-(ethoxycarbonyl)phenyl)zinc(ll) bromide

: 6301-56-0
ethyl 4-phenylbenzoate

Conditions

Conditions	Yield
Stage #1: (4-(ethoxycarbonyl)phenyl)zinc(ll) bromide With trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5); lithium chloride In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere; Stage #2: methyl-phenyl-thioether In tetrahydrofuran; acetonitrile at 20℃; for 5h; Inert atmosphere;	92%

[1,1'-Biphenyl]-4-carboxylicacid, ethyl ester Specification

This chemical is called [1,1'-Biphenyl]-4-carboxylicacid, ethyl ester, and it can also be named as Ethyl4-phenylbenzoate. With the molecular formula of C₁₅H₁₄O₂, its molecular weight is 226.27. The CAS registry number of this chemical is 6301-56-0, and its systematic name is Ethyl biphenyl-4-carboxylate.

Other characteristics of the [1,1'-Biphenyl]-4-carboxylicacid, ethyl ester can be summarised as followings: (1)ACD/LogP: 4.91 ; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 26.3 Å²; (7)Index of Refraction: 1.556; (8)Molar Refractivity: 67.25 cm³; (9)Molar Volume: 209.1 cm³; (10)Polarizability: 26.66×10^-24cm³; (11)Surface Tension: 39.8 dyne/cm; (12)Density: 1.082 g/cm³; (13)Flash Point: 159.1 °C; (14)Enthalpy of Vaporization: 59.61 kJ/mol; (15)Boiling Point: 351.4 °C at 760 mmHg; (16)Vapour Pressure: 4.12E-05 mmHg at 25°C.

Production method of this chemical: The [1,1'-Biphenyl]-4-carboxylicacid, ethyl ester could be obtained by the reactants of 4-Bromo-benzoic acid ethyl ester and Phenylmanganese chloride. This reaction needs the catalyst of PdCl₂(PPh₃)₂, and the solvents of tetrahydrofuran and 1,2-Dimethoxy-ethane. The yield is 99 %. In addition, this reaction should be taken for30 minutes at the temperature of 0-20 °C.

The [1,1'-Biphenyl]-4-carboxylicacid, ethyl ester could be obtained by the reactants of 4-Bromo-benzoic acid ethyl ester and Phenylmanganese chloride.

Uses of this chemical: The Biphenyl-4-carboxylic acid hydrazide could be obtained by the reactant of [1,1'-Biphenyl]-4-carboxylicacid, ethyl ester. This reaction needs the reagent of NH₂NH₂*H₂O, and the solvent of ethanol. The yield is 85 %. This reaction should be taken for 3 hours at the temperature of 100 °C.

The Biphenyl-4-carboxylic acid hydrazide could be obtained by the reactant of [1,1'-Biphenyl]-4-carboxylicacid, ethyl ester.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(OCC)c2ccc(c1ccccc1)cc2
2.InChI: InChI=1/C15H14O2/c1-2-17-15(16)14-10-8-13(9-11-14)12-6-4-3-5-7-12/h3-11H,2H2,1H3
3.InChIKey: FFQZMOHAQYZTNR-UHFFFAOYAF

Product Name

BIPHENYL-3-CARBOXYLIC ACID ETHYL ESTER

Synthetic route

[1,1'-Biphenyl]-4-carboxylicacid, ethyl ester Specification

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