5728-52-9

Basic information

• Product Name: 4-Biphenylacetic acid
• Synonyms: 4-BIPHENYLACETICABID;Biphenyl-4-acetic acid 97%;4-Biphenylacetic acid/Felbinac;4 -BIPHENYLACETIC ACID 99% BP GRADE;4-BIPHENYL ACETIC ACID 98.5%;4-BIPHENYLACETIC ACID(METHOXYMETHYL)-1,1''-BIPHENYL;4-Biphenylacetic acid(methoxymethyl)-1,1'-biphenyl;Napageln
• CAS NO: 5728-52-9
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• EINECS: 227-233-2
• Product Categories: Biphenyl derivatives;Biphenyl & Diphenyl ether;Organic acids;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;TRAXAM
• Mol File: 5728-52-9.mol
• Article Data: 79

Chemical Properties

• Melting Point: 159-160 °C(lit.)
• Boiling Point: 312.08°C (rough estimate)
• Flash Point: 286.6 °C
• Appearance: Beige/Powder
• Density: 1.1035 (rough estimate)
• Vapor Pressure: 8.98E-07mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO: soluble50mg/mL, clear, colorless to yellow
• PKA: 4.29±0.10(Predicted)
• Water Solubility: 39.27mg/L(25 oC)
• Merck: 14,3316
• BRN: 1211592
• CAS DataBase Reference: 4-Biphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Biphenylacetic acid(5728-52-9)
• EPA Substance Registry System: 4-Biphenylacetic acid(5728-52-9)

Safety Data

• Hazard Codes: T,Xn
• Statements: 23/25-36/37/38-25-36/37/38/63-20/21/22
• Safety Statements: 26-36/37/39-45-37/39-28A-26/36/3745/60-20-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DU8229050
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5728-52-9(Hazardous Substances Data)

Usage

Description

Felbinac Is the active metabolite of the non-steroidal antiinflammatory agent, fenbufen. Applied topically as a gel to joints, it is useful in the symptomatic relief of articular inflammation and pain.

Chemical Properties

Off-white powder

Originator

Lederle (USA)

Uses

Different sources of media describe the Uses of 5728-52-9 differently. You can refer to the following data:
1. Anti-inflammatory, analgesic drug.
2. 4-Biphenylacetic acid was used in the synthesis of gastrosparing non-steroidal antiinflammatory drug.

Brand name

Dolinac (Wyeth-Ayerst); Flexfree(Wyeth-Ayerst); Napageln (Wyeth-Ayerst); Target (Wyeth-Ayerst); Traxam (Wyeth-Ayerst).

General Description

4-Biphenylacetic acid is a potential non-steroidal antiinflammatory agent and forms solid inclusion complex with β-cyclodextrin. 4-Biphenylacetic acid on interaction with quinolone antibacterial agents induces functional blockade of the γ-aminobutyric acid receptors.

Safety Profile

Poison by subcutaneous route.Moderately toxic by ingestion and intraperitoneal routes.An experimental teratogen. Other experimentalreproductive effects. When heated to decomposition itemits acrid smoke and fumes.

InChI:InChI=1/C14H12O2/c15-14(16)10-11-6-8-13(9-7-11)12-4-2-1-3-5-12/h1-9H,10H2,(H,15,16)/p-1

Synthetic route

phenylboronic acid (98-80-6) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With sodium carbonate; Pd-complex on fluorous reversed silica gel In water at 80℃; for 16h; Suzuki reaction;	100%
With carbon-doped cobalt; C118H94N4O7P8; palladium diacetate; sodium carbonate In tetrahydrofuran; water at 20 - 60℃; for 14h; Suzuki Coupling; Inert atmosphere;	100%
With palladium diacetate; potassium carbonate In water; toluene at 65℃; for 20h; Solvent; Suzuki-Miyaura Coupling;	100%

methyl 2-(1,1'-biphenyl-4-yl)acetate (59793-29-2) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With methanol; potassium hydroxide for 10h; Reflux;	99%
With water; sodium hydroxide at 70℃; for 4h;	75.5%
With sodium hydroxide In methanol for 4h; Ambient temperature; Yield given;
With water; sodium hydroxide at 20℃; for 3h;	2.56 g

4-biphenylacetonitrile (31603-77-7) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With water; potassium hydroxide In ethylene glycol at 120℃; for 16h;	97.6%
With hydrogenchloride
With water; sodium hydroxide for 4h; Time; Reflux;
With sodium hydroxide In water; butan-1-ol at 100℃; for 8h; Temperature;

sodium tetraphenyl borate (143-66-8) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With sodium carbonate; palladium on activated charcoal In water for 1h; Suzuki reaction; Heating;	96%

4-chlorophenylacetic Acid (1878-66-6) + potassium phenyltrifluoborate → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With choline chloride; palladium diacetate; sodium carbonate; glycerol at 100℃; for 5h; Suzuki-Miyaura Coupling;	95%
With C16H16Cl2N2O4Pd2; tetrabutylammomium bromide; potassium carbonate In water at 100℃; under 749.884 Torr; for 0.25h; Microwave irradiation; Darkness; Inert atmosphere;	86%

4-biphenylylacetic acid ethyl ester (14062-23-8) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
Stage #1: 4-biphenylylacetic acid ethyl ester With potassium hydroxide In water for 0.5h; Reflux; Stage #2: With hydrogenchloride In water	94%
With potassium hydroxide In 1,4-dioxane; water for 18h; Reflux;	76%

2-Chlormethyl-2--<1.3>dioxolan (3418-30-2) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With copper(l) iodide; zinc diacetate at 155℃; for 1.5h;	92.6%

tert-butyl 4-biphenylacetylenyl ether → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With water; triethylamine In toluene at 75℃; for 12h; Inert atmosphere;	92%

2-biphenyl-4-yl-1-morpholin-4-yl-ethanethione (5428-57-9) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With sodium hydroxide for 0.0166667h; microwave irradiation;	90%
With potassium hydroxide 1.) EtOH, reflux; 2.) 100 deg C, 2 h;	79.7%
With sodium hydroxide In methanol; water for 8h; Reflux; Large scale;	78.2%

C14H9O3(1-)*Na(1+) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
Stage #1: C14H9O3(1-)*Na(1+) With hydrazine hydrate; sodium hydroxide In water at 80 - 100℃; for 17h; Stage #2: With hydrogenchloride In water pH=3; Temperature;	87.4%

phenyl trimethylsiloxane (2996-92-1) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With sodium hydroxide; 4,4'-dichlorobenzophenone oxime-derived palladacycle at 120℃; for 1.5h; Hiyama coupling;	84%
With 3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazolium chloride; palladium diacetate; sodium hydroxide In water at 120℃; for 1h; Hiyama Coupling; Microwave irradiation;	81%
With 3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazolium chloride; water; palladium diacetate; sodium hydroxide at 120℃; for 1h; Hiyama coupling; Microwave irradiation;	67%

4-chlorophenylacetic Acid (1878-66-6) + phenylboronic acid (98-80-6) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide; tetra(n-butyl)ammonium hydroxide; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 0.333333h; Suzuki-Miyaura coupling; Microwave irradiation;	82%
Stage #1: 4-chlorophenylacetic Acid; phenylboronic acid With sodium hydroxide In water at 20℃; for 0.0333333h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: With sodium (η3-allyl)(1,3-bis(2,6-diisopropyl-4-sulfonatophenyl)imidazol-2-ylidene)chloridopalladate(II) In water at 60℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;	82.9%
With tetrabutylammomium bromide; potassium carbonate; di-μ-chlorobis[5-hydroxy-2-[1-(hydroxyimino)ethyl]phenyl]palladium(II) dimer In water for 2.5h; Suzuki cross-coupling; Heating;	50 % Chromat.
With phenone oxime-derived palladacycle; tetrabutylammomium bromide; potassium carbonate In water for 2.5h; Suzuki coupling; Heating;	50 % Spectr.

biphenyl-4-methylchloride (1667-11-4) + carbon monoxide (201230-82-2) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
Stage #1: carbon monoxide With C28H22CoN4O6 In butan-1-ol at 60℃; under 760.051 Torr; for 2h; Glovebox; High pressure; Green chemistry; Stage #2: biphenyl-4-methylchloride With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; under 760.051 Torr; for 22h; Glovebox; High pressure; Green chemistry; regioselective reaction;	80%

carbon dioxide (124-38-9) + 1-([1,1'-biphenyl]-4-yl)-N,N,N-trimethylmethanaminium trifluoromethanesulfonate → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium carbonate; caesium carbonate In N,N-dimethyl-formamide at 25 - 30℃; under 760.051 Torr; for 26h; Schlenk technique; Glovebox; Irradiation; Sealed tube;	80%

potassium ethyl xanthogenate (140-89-6) + Biphenyl-4-yl-acetic acid 5-methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indol-3-ylmethyl ester (210578-21-5) → (4-biphenylyl)acetic acid (5728-52-9) + Dithiocarbonic acid O-ethyl ester S-(5-methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indol-3-ylmethyl) ester

Conditions	Yield
With sodium dithionite In tetrahydrofuran; water	A 52% B 78%

4-chlorophenylacetic Acid (1878-66-6) + phenyl trimethylsiloxane (2996-92-1) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With tetrabutyl ammonium fluoride; palladium(II) acetylacetonate; 3,9-bis(2,4-tBu-PhO)tetraoxa-3,9-diphosphaspiro[5.5]undecane In xylene at 80℃; Hiyama coupling;	78%

carbon dioxide (124-38-9) + 4-phenylbenzylidene hydrazine (91954-74-4) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; cesium fluoride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 24h; chemoselective reaction;	77%

iodobenzene (591-50-4) + C8H6KO2(1-)*K(1+) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
In ammonia for 5h; Phenylation; Irradiation;	73%

formic acid (64-18-6) + biphenyl-4-methylchloride (1667-11-4) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 12h; Inert atmosphere;	73%

carbon dioxide (124-38-9) + 2-([1,1'-biphenyl]-4-ylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1202236-78-9) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With potassium ethoxide In 1,4-dioxane at 100℃; for 24h;	70%

carbon dioxide (124-38-9) + 1-([1,1’-biphenyl]-4-yl)-N,N-dimethylmethanamine (127292-60-8) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium carbonate; caesium carbonate; methyl trifluoromethanesulfonate In N,N-dimethyl-formamide at 20℃; for 36h; Irradiation;	63%

carbon dioxide (124-38-9) + biphenyl-4-ylmethyl 2-methoxyacetate (1533458-00-2) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With manganese; dichlorobis(trimethylphosphine)nickel In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 24h; Schlenk technique;	60%

formaldehyd (50-00-0) + biphenyl (92-52-4) + carbon dioxide (124-38-9) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
Stage #1: formaldehyd; biphenyl With hydrogenchloride; phosphoric acid; acetic acid In water at 85℃; for 24h; Stage #2: carbon dioxide With iodine; magnesium In ethyl bromide; diethyl ether at 38℃; for 2.25h; Cooling with ice;	53.24%

para-bromoacetophenone (99-90-1) + phenylboronic acid (98-80-6) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
Stage #1: para-bromoacetophenone; phenylboronic acid With potassium carbonate In tetrahydrofuran for 2h; Inert atmosphere; Stage #2: With morpholine; sulfur for 8h; Reflux;	44.82%

biphenyl-4-methylchloride (1667-11-4) + carbon dioxide (124-38-9) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With samarium; chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; under 760.051 Torr; for 2h; Electrochemical reaction; Cooling with ice;	43%

biphenyl-4-yl-(toluene-4-sulfonyl)-acetic acid ethyl ester (447465-00-1) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
Stage #1: biphenyl-4-yl-(toluene-4-sulfonyl)-acetic acid ethyl ester With magnesium; mercury dichloride In methanol at 20 - 50℃; for 24h; Stage #2: With potassium hydroxide In methanol at 20℃; for 24h; Further stages.;	30%

bromobenzene (108-86-1) + 2-[4-(dihydroxyboranyl)phenyl]acetic acid (90111-58-3) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 100℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere;	18%

4-phenylmandelic acid (450-52-2) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With phosphorus; iodine; acetic acid

(4-biphenylyl)acetic acid (5728-52-9) → biphenyl-4-yl-acetyl chloride (39889-69-5)

Conditions	Yield
With thionyl chloride In benzene at 78 - 80℃; for 2.5h;	100%
With thionyl chloride In N,N-dimethyl-formamide; benzene at 20℃; for 5h;	97%
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 10℃; for 16h; Reflux;	90%

methanol (67-56-1) + (4-biphenylyl)acetic acid (5728-52-9) → methyl 2-(1,1'-biphenyl-4-yl)acetate (59793-29-2)

Conditions	Yield
With TEA; (2-chloro-1-pyridinio)-(Wang resin) triflate In dichloromethane for 0.25h;	100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)pyridinium trifluoromethanesulfonate; triethylamine In dichloromethane at 20℃; for 0.5h;	100%
With thionyl chloride at 0 - 20℃; for 0.5h;	100%

Methyl 3-aminobenzoate (4518-10-9) + (4-biphenylyl)acetic acid (5728-52-9) → 3-(2-biphenyl-4-yl-acetyl-amino)-benzoic acid methyl ester

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%

(4-biphenylyl)acetic acid (5728-52-9) + oxalyl dichloride (79-37-8) → biphenyl-4-yl-acetyl chloride (39889-69-5)

Conditions	Yield
In N-methyl-acetamide; benzene	100%

(4-biphenylyl)acetic acid (5728-52-9) + tetrakis(Nγ-trichloroethoxycarbonyl)polymyxin B (2-10) hydrochloride (1013028-77-7) → 4-biphenylacetyl-tetrakis(Nγ-trichloroethoxycarbonyl)polymyxin B (2-10) (1013028-99-3)

Conditions	Yield
With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 5h; pH=7.8;	100%

(4-biphenylyl)acetic acid (5728-52-9) + dimethyl sulfate (77-78-1) → methyl 2-(1,1'-biphenyl-4-yl)acetate (59793-29-2)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 4h; Cooling with ice;	100%

(4-biphenylyl)acetic acid (5728-52-9) → 2-([1,1'-biphenyl]-4-yl)acetic acid-d2

Conditions	Yield
With water-d2; sodium hydroxide at 120℃; for 12h; Inert atmosphere;	100%

(4-biphenylyl)acetic acid (5728-52-9) + trimethyl orthoformate (149-73-5) → methyl 2-(1,1'-biphenyl-4-yl)acetate (59793-29-2)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 4h; Reflux; Inert atmosphere;	99%
Stage #1: (4-biphenylyl)acetic acid With toluene-4-sulfonic acid In methanol for 1h; Reflux; Stage #2: trimethyl orthoformate In methanol for 2h; Reflux;	99.3%

(4-biphenylyl)acetic acid (5728-52-9) → 2-(biphenyl-4-yl)ethanol (37729-18-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Heating;	99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere;	99%
Stage #1: (4-biphenylyl)acetic acid With sodium tetrahydroborate In tetrahydrofuran at 20 - 30℃; for 0.666667h; Stage #2: With iodine In tetrahydrofuran at 20 - 30℃; for 2h; Product distribution / selectivity;	98.5%

(4-biphenylyl)acetic acid (5728-52-9) + benzyl bromide (100-39-0) → benzyl 2-([1,1'-biphenyl]-4-yl)acetate (111363-79-2)

Conditions	Yield
With potassium carbonate In acetone Heating;	99%

(4-biphenylyl)acetic acid (5728-52-9) + tert-butyl (2,2-difluoro-3-hydroxypropyl)carbamate → C22H25F2NO4

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 16h;	99%

(4-biphenylyl)acetic acid (5728-52-9) + diethylamine (109-89-7) → 2-([1,1'-biphenyl]-4-yl)-N,N-diethylacetamide

Conditions	Yield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	99%

(4-biphenylyl)acetic acid (5728-52-9) + 1,1,1-trichloroethanol (115-20-8) → 2,2,2-trichloroethyl 2-([1,1'-biphenyl]-4-yl)acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 23℃; for 15h; Inert atmosphere;	99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; Inert atmosphere;

(4-biphenylyl)acetic acid (5728-52-9) → methyl 2-(1,1'-biphenyl-4-yl)acetate (59793-29-2)

Conditions	Yield
With hydrogenchloride In methanol; ethyl acetate; Petroleum ether	98%
With sulfuric acid In formic acid for 6h; Reflux;

(4-biphenylyl)acetic acid (5728-52-9) + 3-bromobenzylamine (10269-01-9) → 2-([1,1'-biphenyl]-4-yl)-N-(3-bromobenzyl)acetamide (1572927-05-9)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃;	98%

(4-biphenylyl)acetic acid (5728-52-9) + 2-(N-tert-butoxycarbonylamino)ethanol (26690-80-2) → C21H25NO4

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;	98%

(4-biphenylyl)acetic acid (5728-52-9) + 2-bromo-3-methyl-N-methylaniline → 2-([1,1'-biphenyl]-4-yl)-N-(2-bromo-3-methylphenyl)-N-methylacetamide

Conditions	Yield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In toluene at 90℃; for 14h; Inert atmosphere;	97%

(4-biphenylyl)acetic acid (5728-52-9) + aniline (62-53-3) → 2-([1,1'-biphenyl]-4-yl)-N-phenylacetamide (848175-28-0)

Conditions	Yield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	97%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃;	90%

(4-biphenylyl)acetic acid (5728-52-9) + 4-methoxyphenethylamine hydrochloride (645-58-9) → 2-[(1,1'-biphenyl)-4-yl]-N-(4-methoxyphenethyl)acetamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 25℃;	97%

(4-biphenylyl)acetic acid (5728-52-9) + 2-amino-2-hydroxymethyl-1,3-propanediol (77-86-1) → felbinac trometamol (935886-64-9)

Conditions	Yield
at 50℃; for 0.5h; Product distribution / selectivity;	96%

(4-biphenylyl)acetic acid (5728-52-9) + 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) → 2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-2-(4-(trifluoromethyl)phenyl)acetic acid

Conditions	Yield
With N4,N4,N7,N7-tetramethyl-1,10-phenanthroline-4,7-diamine; iron(II) acetate In tetrahydrofuran at 60℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique; chemoselective reaction;	95%

(4-biphenylyl)acetic acid (5728-52-9) + phenol (108-95-2) → biphenyl-4-ylacetic acid phenyl ester

Conditions	Yield
Stage #1: (4-biphenylyl)acetic acid With phosphoric acid; trifluoroacetic anhydride In acetonitrile at 25℃; for 0.5h; Stage #2: phenol In acetonitrile at 25℃; for 20h;	95%

(4-biphenylyl)acetic acid (5728-52-9) + C16H14BrNO4 (1020672-00-7) → C30H22BrNO4 (1020671-83-3)

Conditions	Yield
With dmap; potassium carbonate; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 80℃; for 6h;	94%

Upstream product

• 450-52-2 4-phenylmandelic acid 
• 63780-50-7 1,1-biphenyl-4-ylacetamide 
• 854827-00-2 acetoxy-biphenyl-4-yl-acetic acid ethyl ester 
• 92-52-4 biphenyl 
• 79-11-8 chloroacetic acid 
• 92-91-1 biphenyl-4-acetaldehyde 
• 4039-92-3 4-phenoxybenzyl chloride 
• 143-33-9 sodium cyanide 
• 31603-77-7 4-biphenylacetonitrile 
• 124-38-9 carbon dioxide 
• 61221-46-3 1-p-biphenylyl-3-chloropropane 
• 5428-57-9 2-biphenyl-4-yl-1-morpholin-4-yl-ethanethione 
• 59793-29-2 methyl 2-(1,1'-biphenyl-4-yl)acetate 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 102595-99-3 2-biphenyl-4-yl-5-phenyl-pent-2-en-4-ynoic acid 
• 39889-69-5 biphenyl-4-yl-acetyl chloride 
• 122361-56-2 cis-1--2--ethylen-carbonsaeure-(1) 
• 103036-02-8 cis-1--2--ethylen-carbonsaeure-(1) 
• 103036-03-9 cis-1,2-Bis--ethylen-carbonsaeure-(1) 
• 15160-54-0 (E)-2-Biphenyl-4-yl-3-(2-bromo-phenyl)-acrylic acid 
• 59793-29-2 methyl 2-(1,1'-biphenyl-4-yl)acetate 
• 141857-33-2 2-Biphenyl-4-yl-3-hydroxy-3-(4-trifluoromethyl-phenyl)-propionic acid 
• 141857-33-2 2-Biphenyl-4-yl-3-hydroxy-3-(4-trifluoromethyl-phenyl)-propionic acid 
• 141857-33-2 2-Biphenyl-4-yl-3-hydroxy-3-(4-trifluoromethyl-phenyl)-propionic acid 
• 141857-33-2 2-Biphenyl-4-yl-3-hydroxy-3-(4-trifluoromethyl-phenyl)-propionic acid 
• 141857-33-2 2-Biphenyl-4-yl-3-hydroxy-3-(4-trifluoromethyl-phenyl)-propionic acid 
• 141857-33-2 2-Biphenyl-4-yl-3-hydroxy-3-(4-trifluoromethyl-phenyl)-propionic acid 
• 105249-66-9 2-Biphenyl-4-yl-N-hydroxy-N-methyl-acetamide 

Relevant articles and documents

Robust, efficient, and recyclable catalysts from the impregnation of preformed dendrimers containing palladium nanoparticles on a magnetic support

The simple impregnation of ?3-Fe2O3(core)/SiO2(shell) magnetic nanoparticles with a dendrimer that contains stabilized Pd nanoparticles is presented as a new method to produce highly efficient heterogeneous catalysts. This technique provides much better stability, recyclability, and activity in C-C cross-coupling reactions and selective oxidation of benzyl alcohol to benzaldehyde in water than unsupported Pd nanoparticles.

Suzuki-Miyaura cross coupling is not an informative reaction to demonstrate the performance of new solvents

The development and study of new solvents has become important due to a proliferation of regulations preventing or limiting the use of many conventional solvents. In this work, the suitability of the Suzuki-Miyaura reaction to demonstrate the usefulness of new solvents was evaluated, including CyreneTM, dimethyl isosorbide, ethyl lactate, 2-methyltetrahydrofuran (2-MeTHF), propylene carbonate, and γ-valerolactone (GVL). It was found that the cross coupling is often unaffected by the choice of solvent, and therefore the Suzuki-Miyaura reaction provides limited information regarding the usefulness of any particular solvent for organic synthesis.

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Cobalt-catalyzed cross-coupling reactions of aryl- And alkylaluminum derivatives with (hetero)aryl and alkyl bromides

A simple cobalt complex, such as Co(phen)Cl2, turned out to be a highly efficient and cheap precatalyst for a host of cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl and alkyl bromides. New C(sp2)-C(sp2) and C(sp2)-C(sp3) bonds were formed in good to excellent yields and with high chemoselectivity, under mild reaction conditions.