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92-92-2 Usage

Chemical Properties

white to light yellow crystal powder

Uses

Biphenyl-4-carboxylic acid is employed in the synthesis, characterization of europium, terbium complexes.

Synthesis Reference(s)

Synthetic Communications, 25, p. 3695, 1995 DOI: 10.1080/00397919508015507

Purification Methods

Crystallise the acid from *C6H6/pet ether or aqueous EtOH. [Beilstein 9 IV 2479.]

Check Digit Verification of cas no

The CAS Registry Mumber 92-92-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 2 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 92-92:
(4*9)+(3*2)+(2*9)+(1*2)=62
62 % 10 = 2
So 92-92-2 is a valid CAS Registry Number.
InChI:InChI=1/C13H10O2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,(H,14,15)/p-1

92-92-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A12438)  Biphenyl-4-carboxylic acid, 98%   

  • 92-92-2

  • 25g

  • 405.0CNY

  • Detail
  • Alfa Aesar

  • (A12438)  Biphenyl-4-carboxylic acid, 98%   

  • 92-92-2

  • 100g

  • 951.0CNY

  • Detail
  • Alfa Aesar

  • (A12438)  Biphenyl-4-carboxylic acid, 98%   

  • 92-92-2

  • 500g

  • 3194.0CNY

  • Detail

92-92-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Biphenylcarboxylic acid

1.2 Other means of identification

Product number -
Other names RARECHEM AL BO 0062

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:92-92-2 SDS

92-92-2Synthetic route

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium phosphate monohydrate; 4,4'-di-tBu-2,2'-dipyridylpalladium(II) dichloride In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling;100%
With potassium carbonate; palladium dichloride In water at 20 - 90℃; Suzuki coupling; Inert atmosphere;99%
With potassium carbonate In water at 90℃; for 0.25h; Suzuki reaction; Inert atmosphere;99%
C21H16N2O4

C21H16N2O4

A

phenylacetonitrile
140-29-4

phenylacetonitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 100%
B 94%
C22H18N2O5

C22H18N2O5

A

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 94%
B 100%
C22H18N2O5
183657-71-8

C22H18N2O5

A

2-methoxy-benzeneacetonitrile
7035-03-2

2-methoxy-benzeneacetonitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 100%
B 95%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate; Pd-complex on fluorous reversed silica gel In water at 80℃; for 16h; Suzuki reaction;100%
With potassium carbonate; carbapalladacycle complex*periodic mesoporous organosilica for 24h; Suzuki coupling; Heating;100%
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 3.5h; Suzuki-Miyaura coupling reaction;100%
carbon dioxide
124-38-9

carbon dioxide

4-biphenylylmagnesium bromide
3315-91-1

4-biphenylylmagnesium bromide

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 4-biphenylylmagnesium bromide In tetrahydrofuran at 20℃; under 3000.3 Torr; gas-liquid flow reactor assembly;
Stage #2: With polymer-supported sulfonic acid In tetrahydrofuran
100%
para-bromoacetophenone
99-90-1

para-bromoacetophenone

phenylboronic acid
98-80-6

phenylboronic acid

immobilized 4-bromobenzoic acid

immobilized 4-bromobenzoic acid

A

biphenyl-4-acetaldehyde
92-91-1

biphenyl-4-acetaldehyde

B

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

C

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: para-bromoacetophenone; phenylboronic acid; immobilized 4-bromobenzoic acid With potassium carbonate In water; N,N-dimethyl-formamide
Stage #2: With potassium hydroxide In ethanol; water
A 100%
B 19%
C 81%
biphenyl-4-yl methanol
3597-91-9

biphenyl-4-yl methanol

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With silica-supported Jones reagent In dichloromethane for 0.035h;99.5%
With diethylene glycol dimethyl ether at 70℃; for 0.583333h; Sonication;96%
With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide In methanol at 20℃; for 6h; In air;89%
methyl 4-phenylbenzoate
720-75-2

methyl 4-phenylbenzoate

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran at 0 - 20℃; for 3h;99%
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 20h;99%
With water In methanol at 30 - 50℃; Rate constant; Thermodynamic data; Kinetics; ΔH(excit), ΔS(excit), log A;
para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 80℃; for 2h; Suzuki Coupling; Green chemistry;99%
With glucosamine-based dicyclohexylarylphosphine; sodium carbonate; palladium diacetate In ethanol; water; toluene at 80℃; Suzuki-Miyaura cross coupling reaction;97%
With sodium hydroxide; polyaniline-supported palladium In water at 80℃; for 4h; Suzuki coupling;97%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

tetraphenyltin(IV)
595-90-4

tetraphenyltin(IV)

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With dmap; palladium dichloride for 0.333333h; Stille Cross Coupling; Microwave irradiation;99%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

tetraphenyltin(IV)
595-90-4

tetraphenyltin(IV)

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With dmap; palladium dichloride for 0.25h; Stille Cross Coupling; Microwave irradiation;99%
4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With oxovanadium(IV) sulfate; hydrogen bromide; oxygen; acetic acid In water at 100℃; under 750.075 Torr; for 20h;98%
With oxygen; Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry;92%
With carbon tetrabromide; oxygen; triphenylphosphine In ethyl acetate for 10h; fluorescent irradiation;90%
C25H18N2O4

C25H18N2O4

A

naphthalen-1-ylacetonitrile
132-75-2

naphthalen-1-ylacetonitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 98%
B 95%
C139H116O19

C139H116O19

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; methanol for 3h; Heating;98%
Methyl 4-chlorobenzoate
1126-46-1

Methyl 4-chlorobenzoate

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 24h; Suzuki Coupling;98%
C20H20N2O4

C20H20N2O4

A

2-cyclopentylacetonitrile
5732-87-6

2-cyclopentylacetonitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 75%
B 97%
C29H21N3O4

C29H21N3O4

A

2-(1-phenyl-1H-indol-3-yl)acetonitrile

2-(1-phenyl-1H-indol-3-yl)acetonitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 86%
B 97%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate at 100℃; for 0.583333h; Suzuki-Miyaura Coupling; Sealed tube;97%
With potassium carbonate for 1.5h; Suzuki-Miyaura Coupling;96%
With potassium carbonate at 100℃; for 2h; Catalytic behavior;95%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

potassium phenyltrifluoborate

potassium phenyltrifluoborate

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In water at 80℃; for 2h; Suzuki-Miyaura Coupling;97%
With palladium diacetate; potassium carbonate In water at 65℃; for 2h; Suzuki-Miyaura cross-coupling;96%
With potassium carbonate; palladium diacetate In methanol for 2h; Suzuki reaction; Heating;96%
With {2,6-bis[(di-1-piperidinylphosphino)amino]phenyl}palladium(II) chloride; potassium carbonate In 1,4-dioxane; water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura reaction;59%
With Na2[Pd(BuHSS)]; caesium carbonate In water at 80℃; for 1h; Suzuki-Miyaura Coupling; Sealed tube;
C181H148O25

C181H148O25

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; methanol for 3h; Heating;97%
carbon dioxide
124-38-9

carbon dioxide

2-([1,1'-biphenyl]-4-yl)-5,5-dimethyl-1,3,2-dioxaborinane
5123-05-7

2-([1,1'-biphenyl]-4-yl)-5,5-dimethyl-1,3,2-dioxaborinane

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;97%
With (1,3-bis(2,6-diisopropyl-4-(morpholinomethyl)phenyl)imidazolidin-2-ylidene)copper(I) bromide; potassium tert-butylate In tetrahydrofuran under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;91%
Stage #1: carbon dioxide; 2-([1,1'-biphenyl]-4-yl)-5,5-dimethyl-1,3,2-dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In 1,4-dioxane at 100℃; under 15201 Torr; for 8h; Inert atmosphere; Autoclave;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;
80%
N-methoxy-3-((triisopropylsilyl)ethynyl)-[1,1'-biphenyl]-4-carboxamide
173171-19-2

N-methoxy-3-((triisopropylsilyl)ethynyl)-[1,1'-biphenyl]-4-carboxamide

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With tert.-butylnitrite; water at 29℃; for 0.583333h;97%
carbon dioxide
124-38-9

carbon dioxide

[1,1’-biphenyl]-4-yl sulfurofluoridate
51451-35-5

[1,1’-biphenyl]-4-yl sulfurofluoridate

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;97%
biphenyl-4-acetaldehyde
92-91-1

biphenyl-4-acetaldehyde

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; acetic acid at 120℃; for 12h; Inert atmosphere; Schlenk technique;96%
With Iron(III) nitrate nonahydrate; iodine; oxygen; dimethyl sulfoxide at 130℃; under 750.075 Torr; for 12h; Sealed tube; Green chemistry;81%
With Iron(III) nitrate nonahydrate; iodine; oxygen In dimethyl sulfoxide at 130℃; for 12h; Sealed tube;81%
C21H22N2O4
183657-81-0

C21H22N2O4

A

2-cyclohexylacetonitrile
4435-14-7

2-cyclohexylacetonitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 93%
B 96%
C22H18N2O4
183657-67-2

C22H18N2O4

A

2-tolylmethylnitrile
22364-68-7

2-tolylmethylnitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 94%
B 96%
C23H18N2O5

C23H18N2O5

A

4-oxo-4-phenylbutanenitrile
5343-98-6

4-oxo-4-phenylbutanenitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 96%
B 96%
(cyclohexyl)(difluoro)(phenyl)silane
350792-91-5

(cyclohexyl)(difluoro)(phenyl)silane

Wang-resin-CH2O-(p-C6H4)-CH2OC(O)(p-C6H4)-I

Wang-resin-CH2O-(p-C6H4)-CH2OC(O)(p-C6H4)-I

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran at 80℃; for 48h; Condensation;96%
(cyclohexyl)(difluoro)(phenyl)silane
350792-91-5

(cyclohexyl)(difluoro)(phenyl)silane

Wang resin-tethered 4-iodobenzoic acid

Wang resin-tethered 4-iodobenzoic acid

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; for 48h;96%
methanol
67-56-1

methanol

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

methyl 4-phenylbenzoate
720-75-2

methyl 4-phenylbenzoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1h;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 1h;100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;98%
biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

biphenyl-4-yl methanol
3597-91-9

biphenyl-4-yl methanol

Conditions
ConditionsYield
100%
Stage #1: biphenyl-4-carboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; for 4h; Cooling with ice; Inert atmosphere;
Stage #2: With water In tetrahydrofuran; diethyl ether for 16h;
99%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;89%
biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

4-biphenyl-carboxylic acid chloride
14002-51-8

4-biphenyl-carboxylic acid chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide Heating / reflux;100%
With thionyl chloride; N,N-dimethyl-formamide at 85℃; for 16h; Industrial scale;100%
Stage #1: biphenyl-4-carboxylic acid With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333h;
Stage #2: With oxalyl dichloride In dichloromethane at 20℃; for 12h;
100%
biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

α,α-dideuterio-p-phenylbenzyl alcohol
86130-03-2

α,α-dideuterio-p-phenylbenzyl alcohol

Conditions
ConditionsYield
With lithium aluminium deuteride In diethyl ether at 0 - 20℃; for 2h;100%
With lithium aluminium deuteride In diethyl ether for 30h; Heating;53%
With lithium aluminium deuteride In diethyl ether for 1h; Heating;
With lithium aluminium deuteride In diethyl ether at 0 - 20℃;
(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-styryl)-hexahydro-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-styryl)-hexahydro-cyclopenta[b]furan-2-one

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-((E)-styryl)-hexahydro-cyclopenta[b]furan-5-yl ester

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-((E)-styryl)-hexahydro-cyclopenta[b]furan-5-yl ester

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 18h;100%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃;100%
(3aR,4R,5R,6aS)-4-((E)-2-Biphenyl-4-yl-vinyl)-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-4-((E)-2-Biphenyl-4-yl-vinyl)-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-2-biphenyl-4-yl-vinyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-2-biphenyl-4-yl-vinyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃;100%
(3S,4S,5R,6S)-1-N-benzyloxycarbonyl-3-aminomethyl-4,5-O-isopropylidene-6-methyl-hexahydropyridazine-4,5-diol
1239670-92-8

(3S,4S,5R,6S)-1-N-benzyloxycarbonyl-3-aminomethyl-4,5-O-isopropylidene-6-methyl-hexahydropyridazine-4,5-diol

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

(3S,4S,5R,6S)-1-N-benzyloxycarbonyl-3-(p-phenylbenzoylaminomethyl)-4,5-O-isopropylidene-6-methyl-hexahydropyridazine-4,5-diol
1239670-94-0

(3S,4S,5R,6S)-1-N-benzyloxycarbonyl-3-(p-phenylbenzoylaminomethyl)-4,5-O-isopropylidene-6-methyl-hexahydropyridazine-4,5-diol

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;100%
D-threoninol
44520-55-0

D-threoninol

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

C17H19NO3
1260145-29-6

C17H19NO3

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 72h;100%
methylamine
74-89-5

methylamine

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

methyl 4-phenylbenzoate
720-75-2

methyl 4-phenylbenzoate

Conditions
ConditionsYield
With propane-1,3-diyl dinitrite In tetrahydrofuran at 90℃; under 12929 Torr; for 0.166667h; Reagent/catalyst; Time; Flow reactor;100%
With 1,3-(2,2-dimethyl)propanedinitrite In tetrahydrofuran; tert-butyl alcohol at 80℃; for 6h;
(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

(±)-1-phenylethyl [1,1'-biphenyl]-4-carboxylate

(±)-1-phenylethyl [1,1'-biphenyl]-4-carboxylate

Conditions
ConditionsYield
With propane-1,3-diyl dinitrite In 2-methyltetrahydrofuran at 86℃; under 12929 Torr; for 0.333333h; Flow reactor;100%
aniline
62-53-3

aniline

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

N-phenyl-[1,1'-biphenyl]-4-carboxamide
112561-32-7

N-phenyl-[1,1'-biphenyl]-4-carboxamide

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;89%
With trimethylaluminum In toluene at 90℃; for 1h;85%
With tetrachloromethane; cross-linked polymer (containing 2.00 mmol of phosphine/g) In 1,2-dichloro-ethane for 3h; Heating;73%
allyl alcohol
107-18-6

allyl alcohol

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

allyl biphenyl-4-carboxylate
115694-59-2

allyl biphenyl-4-carboxylate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1h;99%
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 1h;99%
With N-(methylpolystyrene)-4-(methylamino)pyridine; TEA; (2-chloro-1-pyridinio)-(Wang resin) triflate In dichloromethane for 1h;92%
2,2'-azobis(isobutyronitrile)
78-67-1

2,2'-azobis(isobutyronitrile)

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

N-(2-cyanopropan-2-yl)-N-isobutyrylbiphenyl-4-carboxamide

N-(2-cyanopropan-2-yl)-N-isobutyrylbiphenyl-4-carboxamide

Conditions
ConditionsYield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;99%
dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate

dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

fluoromethyl [1,1'-biphenyl]-4-carboxylate

fluoromethyl [1,1'-biphenyl]-4-carboxylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 40℃; for 8h; Reagent/catalyst; Solvent; Temperature; Time; Schlenk technique; Inert atmosphere;99%
D2-monofluoromethyl-phenyl bis(carbomethoxy) methylide

D2-monofluoromethyl-phenyl bis(carbomethoxy) methylide

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

fluoromethyl-D2 [1,1'-biphenyl]-4-carboxylate

fluoromethyl-D2 [1,1'-biphenyl]-4-carboxylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 40℃; for 8h; Schlenk technique; Inert atmosphere;99%
diethylamine
109-89-7

diethylamine

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

N,N-diethyl-[1,1'-biphenyl]-4-carboxamide

N,N-diethyl-[1,1'-biphenyl]-4-carboxamide

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;99%
[(3aR,4S,6R,6aR)-4-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]-(4-chlorophenyl)methanol

[(3aR,4S,6R,6aR)-4-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]-(4-chlorophenyl)methanol

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

C44H45ClO5Si

C44H45ClO5Si

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; for 2h;98.4%
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; for 2h;98.4%
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; for 2h;98.4%

92-92-2Relevant articles and documents

A bimetallic complex containing a cyclopentadienyl-annulated imidazol-2-ylidene

Arduengo III, Anthony J.,Tapu, Daniela,Marshall, William J.

, p. 16400 - 16401 (2005)

A bimetallic carbene complex architecture that incorporates a cyclopentadienyl-annulated imidazol-2-ylidene moiety is characterized. The ligand architecture enables direct electronic interaction between the π- and σ-bonded metals. A preliminary example of aqueous Suzuki coupling employing a metallocene-fused imidazol-2-ylidene-derived catalyst is described. Copyright

Peptide template effects for the synthesis and catalytic application of Pd nanoparticle networks

Jakhmola, Anshuman,Bhandari, Rohit,Pacardo, Dennis B.,Knecht, Marc R.

, p. 1522 - 1531 (2010)

Translation of nanomaterials from spherical to other shapes has demonstrated property and activity enhancement for applications ranging from optics to catalysis. Unfortunately, synthetic techniques for the controlled production of shaped nanomaterials, which can employ harsh conditions, remains challenging. In contrast, the fabrication of nanostructures using peptides has achieved the generation of functionally active materials using bio-conditions; however, these methods are typically limited to spherical materials. By merging these techniques, the biomimetic/ambient production of functional, shaped nanostructures may be achieved. Here we present the fabrication of non-spherical Pd nanostructures prepared using a peptide template. By controlling the Pd: peptide ratio, the production of at least three different Pd morphologies is possible: nanoparticles, short linear nanoribbons, and nanoparticle networks. Furthermore, all of the materials are active for Stille C-coupling catalysis using aqueous and room temperature conditions at low Pd concentrations. The results suggest that both the zerovalent Pd materials and the ligand surface structure modulate the reactivity, which may be exploitable for optimal functionality. The Royal Society of Chemistry 2010.

Morton,Massengale,Richardson

, p. 126,128 (1940)

Photosensitizing properties of 2,4-dichlorobenzoic acid and chlorinated biphenyl carboxylic acids, potentially key components of chromophoric dissolved organic matter

Boreen, Anne L.,McNeill, Kristopher

, p. 4113 - 4115 (2005)

2,4-Dichlorobenzoic acid and a suite of models of chlorinated biphenyl carboxylic acids were found to be efficient sensitizers of the reactive oxygen species singlet oxygen (1O2). The Royal Society of Chemistry 2005.

G-/C-rich oligonucleotides stabilized pd nanocatalysts for the Suzuki coupling reaction under mild conditions

Li, Wei,Fu, Yingming,Fu, Yan,Wang, Xian,Zhang, Jinli

, p. 578 - 586 (2013)

Pd nanoparticles with narrow size distributions between 1.3 and 3.3 nm are prepared using G-/C-rich oligonucleotide as the template. These DNA-Pd nanoparticles efficiently catalyze the Suzuki coupling reaction and exhibit highly catalytic activities under mild conditions, which are greatly dependent upon the particle size of Pd nanoparticles besides the DNA sequence. For the coupling reaction of iodobenzene and phenylboronic acid at 60 C in the presence of KOH, it can be achieved high TOF value of 2646 mol biphenyl (mol Pd × h)-1 over AG22-Pd and 3640 mol biphenyl (mol Pd × h) -1 over CT22-Pd. Under the optimal experimental conditions, the yield of 100 % in biphenyl is obtained with only 0.0055 mol% AG22-Pd at 60 C for 1 h in the solvent of EtOH/H2O (1:2) using Na2CO3 or K2CO3 as the base. It is illustrated that G-/C-rich oligonucleotides are promising templates to modulate easily the morphology of Pd nanoparticles in aqueous solution with high catalytic activity.

Rapid and amenable Suzuki coupling reaction in water using microwave and conventional heating

Leadbeater, Nicholas E.,Marco, Maria

, p. 888 - 892 (2003)

It is possible to prepare biaryls in good yield very rapidy (5-10 min) on small (1 mmol) and larger (10-20 mmol) scales from aryl halides and phenylboronic acid using water as a solvent and palladium acetate as catalyst. The reaction can be performed equally well using microwave and conventional heating, showing that using these conditions probably no nonthermal microwave effects are associated with the impressive speed of the reaction.

Langmuir-Blodgett films of cyclopalladated ferrocenylimine: preparation, characterization, and application in Suzuki coupling reaction

Mu, Bing,Li, Tiesheng,Li, Chenghuan,Liu, Pingping,Shang, Wei,Wu, Yangjie

, p. 2599 - 2604 (2009)

Langmuir monolayer and Langmuir-Blodgett (LB) films of cyclopalladated ferrocenylimine 1 were prepared and characterized. The surface pressure (π)-area (A) isotherm of complex 1 indicated the formation of highly condensed monolayer on the subphase. Ultraviolet-visible (UV-vis) and Fourier transform infrared (FTIR) spectroscopy showed that complex 1 monolayer was transferred successfully onto solid supports. Atomic force microscopy (AFM) image suggested that LB films transferred on the solid substrate were well-ordered, homogeneous. Cyclic voltammograms of LB films deposited on glassy carbon electrodes showed quasi-reversible oxidation/reduction waves of ferrocene moiety. From the average thickness of monolayer, the hydrocarbon chain could be fairly directed perpendicular to the substrates. Finally, LB films of complex 1 presented a largely improved catalytic efficiency for Suzuki reaction with respect to its cast films and homogeneous reactions under the same conditions. The results might have an implication on the catalytic mechanism of this reaction.

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun

supporting information, p. 2020 - 2024 (2022/03/31)

A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling

Liu, Chengwei,Ji, Chong-Lei,Zhou, Tongliang,Hong, Xin,Szostak, Michal

supporting information, p. 10690 - 10699 (2021/04/09)

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.

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