phenylboronic acid
2-(4-bromophenyl)-acetic acid
(4-biphenylyl)acetic acid
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
(4-biphenylyl)acetic acid
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
(4-biphenylyl)acetic acid
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
2-(4-bromophenyl)-acetic acid
(4-biphenylyl)acetic acid
Conditions | Yield |
---|---|
With sodium carbonate; palladium on activated charcoal In water for 1h; Suzuki reaction; Heating; | 96% |
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
(4-biphenylyl)acetic acid
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% |
Conditions | Yield |
---|---|
With copper(l) iodide; zinc diacetate at 155℃; for 1.5h; | 92.6% |
(4-biphenylyl)acetic acid
Conditions | Yield |
---|---|
With water; triethylamine In toluene at 75℃; for 12h; Inert atmosphere; | 92% |
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% |
(4-biphenylyl)acetic acid
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
2-(4-bromophenyl)-acetic acid
(4-biphenylyl)acetic acid
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% |
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. |
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% |
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
Biphenyl-4-yl-acetic acid 5-methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indol-3-ylmethyl ester
A
(4-biphenylyl)acetic acid
Conditions | Yield |
---|---|
With sodium dithionite In tetrahydrofuran; water | A 52% B 78% |
4-chlorophenylacetic Acid
phenyl trimethylsiloxane
(4-biphenylyl)acetic acid
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
4-phenylbenzylidene hydrazine
(4-biphenylyl)acetic acid
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% |
Conditions | Yield |
---|---|
In ammonia for 5h; Phenylation; Irradiation; | 73% |
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
2-([1,1'-biphenyl]-4-ylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
(4-biphenylyl)acetic acid
Conditions | Yield |
---|---|
With potassium ethoxide In 1,4-dioxane at 100℃; for 24h; | 70% |
carbon dioxide
1-([1,1’-biphenyl]-4-yl)-N,N-dimethylmethanamine
(4-biphenylyl)acetic acid
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
biphenyl-4-ylmethyl 2-methoxyacetate
(4-biphenylyl)acetic acid
Conditions | Yield |
---|---|
With manganese; dichlorobis(trimethylphosphine)nickel In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 24h; Schlenk technique; | 60% |
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% |
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% |
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
(4-biphenylyl)acetic acid
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
2-[4-(dihydroxyboranyl)phenyl]acetic acid
(4-biphenylyl)acetic acid
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% |
Conditions | Yield |
---|---|
With phosphorus; iodine; acetic acid |
(4-biphenylyl)acetic acid
biphenyl-4-yl-acetyl chloride
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
(4-biphenylyl)acetic acid
methyl 2-(1,1'-biphenyl-4-yl)acetate
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% |
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
oxalyl dichloride
biphenyl-4-yl-acetyl chloride
Conditions | Yield |
---|---|
In N-methyl-acetamide; benzene | 100% |
(4-biphenylyl)acetic acid
tetrakis(Nγ-trichloroethoxycarbonyl)polymyxin B (2-10) hydrochloride
4-biphenylacetyl-tetrakis(Nγ-trichloroethoxycarbonyl)polymyxin B (2-10)
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
dimethyl sulfate
methyl 2-(1,1'-biphenyl-4-yl)acetate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 4h; Cooling with ice; | 100% |
(4-biphenylyl)acetic acid
Conditions | Yield |
---|---|
With water-d2; sodium hydroxide at 120℃; for 12h; Inert atmosphere; | 100% |
(4-biphenylyl)acetic acid
trimethyl orthoformate
methyl 2-(1,1'-biphenyl-4-yl)acetate
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
2-(biphenyl-4-yl)ethanol
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
benzyl bromide
benzyl 2-([1,1'-biphenyl]-4-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h; | 99% |
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
methyl 2-(1,1'-biphenyl-4-yl)acetate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; ethyl acetate; Petroleum ether | 98% |
With sulfuric acid In formic acid for 6h; Reflux; |
(4-biphenylyl)acetic acid
3-bromobenzylamine
2-([1,1'-biphenyl]-4-yl)-N-(3-bromobenzyl)acetamide
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% |
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
Conditions | Yield |
---|---|
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In toluene at 90℃; for 14h; Inert atmosphere; | 97% |
(4-biphenylyl)acetic acid
aniline
2-([1,1'-biphenyl]-4-yl)-N-phenylacetamide
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% |
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 25℃; | 97% |
(4-biphenylyl)acetic acid
2-amino-2-hydroxymethyl-1,3-propanediol
felbinac trometamol
Conditions | Yield |
---|---|
at 50℃; for 0.5h; Product distribution / selectivity; | 96% |
(4-biphenylyl)acetic acid
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
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% |
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% |
Conditions | Yield |
---|---|
With dmap; potassium carbonate; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 80℃; for 6h; | 94% |
Name :4-Biphenylacetic acid
Synonyms :BIPHENYL-4-ACETIC ACID;FELBINAC;CI 83544;4-PHENYLPHENYLACETIC ACID;4-CARBOXYMETHYLBIPHENYL;4-BIPHENYLACETIC ACID;[1,1'-BIPHENYL]-4-ACETIC ACID;P-BIPHENYLACETIC ACID
Molecular Structure :
Molecular Formula :C14H12O2
Molecular Weight :212.25
CAS Registry Number :5728-52-9
Melting point :156-160 oC
EINECS :227-233-2
The compound 4-biphenylacetic acid is known and its preparation described in the literature, F. Blicke, et al., J. Am. Chem. Soc., 65, 1725 (1943). U.S. Pat. No. 3,784,704 also discloses the preparation of 4-biphenylacetic acid, and its usein producing long lasting amelioration of pain in warm-blooded animals. French Pat. No. 7,166M, patented Feb. 23, 1970, reports that 4-biphenylacetic acid possesses anti-inflammatory, antipyretic and analgesic activity.
1. | orl-rat LD50:410 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. | ||
2. | ipr-rat LD50:495 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. | ||
3. | scu-rat LD50:148 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. | ||
4. | orl-mus LD50:675 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. | ||
5. | ipr-mus LD50:508 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. | ||
6. | scu-mus LD50:730 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. | ||
7. | scu-dog LD50:320 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. | ||
8. | scu-rbt LD50:1280 mg/kg | KSRNAM Kiso to Rinsho. Clinical Report. 20 (1986),2107. |
Poison by subcutaneous route. Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes.
T: Toxic
R25 :Toxic if swallowed.
R36/37/38 : Irritating to eyes, respiratory system and skin.
S26 :In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28 :After contact with skin, wash immediately with plenty of soap-suds.
S36/37 : Wear suitable protective clothing and gloves.
S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
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