Conditions | Yield |
---|---|
With caesium carbonate; hydroquinone; palladium diacetate In N,N-dimethyl acetamide at 75℃; for 2h; Ullmann coupling; | 99% |
With dipotassium hydrogenphosphate; digold(I)bis(diphenylphosphinomethane)dichloride; triethylamine In methanol; acetonitrile at 20℃; for 16h; Inert atmosphere; UV-irradiation; | 91% |
With Palladacycle; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 12h; | 76% |
Conditions | Yield |
---|---|
With (1E,2E)-N1,N2-bis(2,6-dimethylphenyl)ethane-1,2-diimine; nickel dibromide; zinc In tetrahydrofuran at 70℃; for 10h; Inert atmosphere; | 99% |
With Ni(acetylacetate)2; 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene In toluene at 80℃; for 18h; | 96% |
With sodium hydroxide; triethylammonium formate; zinc In methanol for 3h; Heating; | 95% |
methyl 4-(methanesulfonyloxy)benzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With tetraethylammonium iodide; zinc; bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 67℃; for 10h; | 99% |
bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc In tetrahydrofuran 1.) r.t., 5 min, 2.) 67 deg C, 10 h; Yield given; |
methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
Methyl 4-chlorobenzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With palladium diacetate; cesium fluoride; CyJohnPhos In 1,4-dioxane at 25℃; Inert atmosphere; | 99% |
With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Sealed tube; | 97% |
With cesium fluoride; palladium diacetate; CyJohnPhos In 1,4-dioxane at 25℃; for 18h; Product distribution / selectivity; | 96% |
With potassium phosphate; (1,2-bis(diphenylphosphino)ethane)nickel(II) chloride; 1,2-bis-(diphenylphosphino)ethane In 1,4-dioxane at 110℃; for 18h; Suzuki-Miyaura cross-coupling; Inert atmosphere; | 67% |
methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
4-methoxycarbonylphenyl bromide
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Sealed tube; | 99% |
With potassium phosphate; (1,2-bis(diphenylphosphino)ethane)nickel(II) chloride; 1,2-bis-(diphenylphosphino)ethane In 1,4-dioxane at 110℃; for 18h; Suzuki-Miyaura cross-coupling; Inert atmosphere; | 79% |
methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
methyl 4-(methanesulfonyloxy)benzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 4h; Inert atmosphere; | 99% |
With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 1.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Sealed tube; | 97% |
With potassium phosphate; trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine In tetrahydrofuran at 25℃; for 12h; Suzuki coupling; Inert atmosphere; | 95% |
With bis(1,5-cyclooctadiene)nickel (0); cesium fluoride; tricyclohexylphosphine In toluene at 120℃; for 24h; | 20% |
methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
methyl 4-iodobenzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Sealed tube; | 98% |
4-methoxycarbonylphenyl bromide
4-methoxycarbonylphenylboronic acid
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 80℃; for 10h; Catalytic behavior; Suzuki Coupling; | 97.3% |
4-methoxycarbonylphenylboronic acid
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With C54H74Cl2N4O2Pd2 In ethanol at 22℃; for 6h; | 97% |
With Cu2(ophen)2 In N,N-dimethyl-formamide at 20℃; for 20h; | 95% |
With palladium diacetate at 20℃; for 0.5h; | 93% |
Conditions | Yield |
---|---|
Stage #1: 4,4'-diphenic acid With thionyl chloride Reflux; Stage #2: methanol at 0℃; | 95% |
With phosphorus pentachloride | |
Stage #1: 4,4'-diphenic acid With thionyl chloride Reflux; Stage #2: methanol at 0℃; | |
With sulfuric acid Reflux; |
4,4'-diphenic acid
methyl iodide
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 70℃; for 24h; Sealed tube; | 95% |
methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
methyl 4-(tosyloxy)benzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium phosphate; bis (1,5-cyclopentadiene)nickel (0); tricyclohexylphosphine In tetrahydrofuran at 25℃; for 8h; Inert atmosphere; | 93% |
With potassium phosphate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In tetrahydrofuran at 20 - 25℃; for 8 - 12h; Product distribution / selectivity; | 93% |
methanol
(4,4'-dimethyl-1,1'-biphenyl)
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With carbon tetrabromide; oxygen for 48h; Irradiation; | 93% |
With 2,3-dicarboxyanthraquinone; oxygen for 48h; Irradiation; | 87% |
With hydrogenchloride; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate at 20℃; under 760.051 Torr; for 30h; Schlenk technique; Irradiation; Green chemistry; | 76% |
4-methoxycarbonylphenyl bromide
A
4,4'-biphenyldicarboxylic acid dimethyl ester
B
methyl 4-benzylbenzoate
Conditions | Yield |
---|---|
With (1,2-dimethoxyethane)dichloronickel(II); lithium perchlorate; potassium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; Catalytic behavior; Solvent; Reagent/catalyst; Electrochemical reaction; Inert atmosphere; Glovebox; | A 5% B 93% |
methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
methyl 4-((N, N-dimethylsulfamoyl)oxy)benzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium phosphate; trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine In tetrahydrofuran at 25℃; for 18h; Suzuki coupling; Inert atmosphere; | 91% |
With bis(1,5-cyclooctadiene)nickel (0); cesium fluoride; tricyclohexylphosphine In toluene at 120℃; for 24h; | 38% |
4-iodoanisol
2-bromobenzoic acid methyl ester
A
benzoic acid methyl ester
B
2,2'-Dimethoxybiphenyl
C
4,4'-biphenyldicarboxylic acid dimethyl ester
D
2'-methoxy-biphenyl-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With pyridine; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; Electrolysis; iron rod as anode; stainless steel grid as cathode; | A n/a B n/a C n/a D 90% |
[(E)-2-bromoethenyl]benzene
methyl 4-iodobenzoate
A
4,4'-biphenyldicarboxylic acid dimethyl ester
B
(E)-methyl 4-styrylbenzoate
Conditions | Yield |
---|---|
With C26H31IN2NiO2; zinc for 1.2h; | A 10% B 90% |
Methyl 4-chlorobenzoate
2-bromoanisole
A
4,4'-biphenyldicarboxylic acid dimethyl ester
B
methyl 2’-methoxy-[1,1'-biphenyl]-4-carboxylate
Conditions | Yield |
---|---|
With manganese; cobalt (II) bromide; triphenylphosphine; trifluoroacetic acid In pyridine; N,N-dimethyl-formamide at 50℃; | A 3 %Chromat. B 89% |
diazomethane
methyl 4-iodobenzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
Stage #1: methyl 4-iodobenzoate; C8H8BO4Pol With palladium diacetate; potassium carbonate In water; acetonitrile at 100℃; for 5h; Wang resin; Suzuki-Miyaura Coupling; Sealed tube; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 0.833333h; Wang resin; Stage #3: diazomethane | 89% |
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With di-tert-butyl peroxide; palladium diacetate In acetonitrile at 60℃; for 12h; | 88% |
methyl 4-(tosyloxy)benzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(acetylacetonato)palladium(II); zinc In tetrahydrofuran at 25℃; for 6h; | 87% |
bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc In tetrahydrofuran 1.) r.t., 5 min, 2.) 67 deg C, 10 h; Yield given; |
methyl coumalate
methyl 4-vinylbenzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
palladium on activated charcoal In m-xylene at 140℃; for 12h; | 86% |
Methyl 4-(((4-fluorophenyl)sulfonyl)oxy)benzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc In tetrahydrofuran 1.) r.t., 5 min, 2.) 67 deg C, 5 h; | 85% |
Conditions | Yield |
---|---|
With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In dimethyl sulfoxide at 70℃; for 1h; | 85% |
methanol
4-iodobenzoic acid
4-carboxyphenylboronic acid
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium cyanide at 20℃; for 24h; | 85% |
Conditions | Yield |
---|---|
With manganese; 3-chloroprop-1-ene; trifluoroacetic acid; cobalt(II) bromide In pyridine; acetonitrile at 50℃; for 1.5h; | 84% |
With bis(triphenylphosphine)nickel(II) chloride; tetra-(n-butyl)ammonium iodide; zinc |
1-bromo-4-methoxy-benzene
Methyl 4-chlorobenzoate
A
4,4'-biphenyldicarboxylic acid dimethyl ester
B
methyl 4-(4'-methoxyphenyl)benzoate
Conditions | Yield |
---|---|
With manganese; cobalt (II) bromide; triphenylphosphine; trifluoroacetic acid In pyridine; N,N-dimethyl-formamide at 50℃; | A 6 %Chromat. B 84% |
Methyl 4-((phenylsulfonyl)oxy)benzoate
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc In tetrahydrofuran 1.) r.t, 5 min, 2.) 67 deg C, 5 h; | 83% |
2-bromobenzoic acid methyl ester
Ethyl 4-bromobenzoate
A
benzoic acid methyl ester
B
diethyl biphenyl-4,4'-dicarboxylate
C
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With pyridine; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; Electrolysis; iron rod as anode; stainless steel grid as cathode; | A n/a B n/a C n/a D 82% |
bromostyrene
methyl 4-iodobenzoate
A
4,4'-biphenyldicarboxylic acid dimethyl ester
B
(E)-methyl 4-styrylbenzoate
C
1,4-diphenyl-1,3-butadiene
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In tetrahydrofuran at 0 - 20℃; for 12h; Reagent/catalyst; Schlenk technique; Sealed tube; Inert atmosphere; | A 8% B 82% C 20% |
With bis(1,5-cyclooctadiene)nickel (0); 4,4'-di-tert-butyl-2,2'-bipyridine; lithium chloride; magnesium chloride; zinc In tetrahydrofuran at 0 - 20℃; for 12h; Time; Temperature; Reagent/catalyst; Schlenk technique; Sealed tube; Inert atmosphere; | A 14% B 81% C 16% |
4,4'-biphenyldicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In acetic acid under 2844.3 Torr; for 0.5h; | 100% |
With rhodium(III) oxide; palladium 10% on activated carbon; hydrogen; acetic acid In water at 250℃; under 15201 - 45603.1 Torr; for 16h; | 96% |
4,4'-biphenyldicarboxylic acid dimethyl ester
dibenzothiophene-5,5′-dioxide-3,7-dicarboxylic acid
Conditions | Yield |
---|---|
With chlorosulfonic acid at 130 - 155℃; for 3h; | 99% |
With chlorosulfonic acid at 150℃; for 3h; | 95% |
With chlorosulfonic acid at 140℃; for 3h; | 0.862 g |
4,4'-biphenyldicarboxylic acid dimethyl ester
dimethyl 2,2’-dinitro-[1,1’-biphenyl]-4,4’-dicarboxylate
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 20℃; for 11h; | 98.3% |
Stage #1: 4,4'-biphenyldicarboxylic acid dimethyl ester With sulfuric acid at 20℃; for 0.166667h; Stage #2: With nitric acid at 20℃; for 4.33333h; Cooling with ice; | 90% |
Stage #1: 4,4'-biphenyldicarboxylic acid dimethyl ester With sulfuric acid at 20℃; for 0.166667h; Stage #2: With nitric acid at 20℃; for 4.33333h; | 90% |
4,4'-biphenyldicarboxylic acid dimethyl ester
dimethyl 2-nitro-[1,1’-biphenyl]-4,4’-dicarboxylate
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 5℃; Cooling with ice; | 97% |
With sulfuric acid; nitric acid at 0 - 20℃; for 24h; | 93% |
With sulfuric acid; nitric acid at -20 - 0℃; for 0.5h; | 89% |
4,4'-biphenyldicarboxylic acid dimethyl ester
water
4,4'-bis(hydroxymethyl)biphenyl
Conditions | Yield |
---|---|
With LiAlH4 In tetrahydrofuran; ethanol; acetone | 96.6% |
Conditions | Yield |
---|---|
With LiAlH4 In tetrahydrofuran; tetrahydrofuran-water; acetone | 96.6% |
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Reflux; | 90% |
With lithium aluminium tetrahydride at 75℃; for 12h; | 90% |
Conditions | Yield |
---|---|
With sulfuric acid In water; acetic acid at 120℃; for 24h; Reflux; | 96.6% |
With sodium hydroxide In tetrahydrofuran; water at 80℃; for 48h; Reflux; | 88% |
4,4'-biphenyldicarboxylic acid dimethyl ester
2-amino-[1,1′-biphenyl]-4,4′-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; water for 16h; Reflux; | 95% |
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 0.25 h / 0 - 5 °C 2: tin; hydrogenchloride / water / 2 h / Reflux 3: potassium hydroxide; water / tetrahydrofuran / Reflux View Scheme |
4,4'-biphenyldicarboxylic acid dimethyl ester
1,1′-Biphenyl-4,4′-dicarbohydrazide
Conditions | Yield |
---|---|
With hydrazine hydrate at 70℃; for 24h; | 94% |
With hydrazine hydrate at 100℃; for 24h; | 92.6% |
With hydrazine hydrate In methanol; water for 12h; | 80% |
Conditions | Yield |
---|---|
With boric acid In pyridine; diphenylether at 160 - 250℃; for 13h; | 92.4% |
4,4'-biphenyldicarboxylic acid dimethyl ester
2-amino-4-phenylphenol
C38H24N2O2
Conditions | Yield |
---|---|
With boric acid In pyridine; diphenylether at 160 - 260℃; for 15h; | 89.7% |
Biphenyl dimethyl dicarboxylate (DDB) is a hepatoprotectant, which is used as an adjuvant agent in a treatment for chronic hepatitis. Amantadine is an antiviral agent, which is utilized primarily in the treatment of influenza, but also, occasionally in the treatment of hepatitis.With the CAS NO. 792-74-5, it is also called as Dimethyl 4,4'-biphenyldicarboxylate; (1,1'-Biphenyl)-4,4'-dicarboxylic acid, dimethyl ester; 4,4'-Biphenyldicarboxylic acid, dimethyl ester; EINECS 212-341-4; HSDB 5754; (1,1'-Biphenyl)-4,4'-dicarboxylic acid, dimethyl ester; Dimethyl (1,1'-biphenyl)-4,4'-dicarboxylate.
Physical properties about Biphenyl dimethyl dicarboxylate are: (1)ACD/LogP: 4.251; (2)ACD/LogD (pH 5.5): 4.25; (3)ACD/LogD (pH 7.4): 4.25; (4)ACD/BCF (pH 5.5): 1001.10; (5)ACD/BCF (pH 7.4): 1001.10; (6)ACD/KOC (pH 5.5): 4890.38; (7)ACD/KOC (pH 7.4): 4890.38; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.559; (11)Molar Refractivity: 74.391 cm3; (12)Molar Volume: 230.504 cm3; (13)Polarizability: 29.491 10-24cm3; (14)Surface Tension: 43.0200004577637 dyne/cm; (15)Density: 1.173 g/cm3; (16)Flash Point: 204.666 °C; (17)Enthalpy of Vaporization: 65.883 kJ/mol; (18)Boiling Point: 407.01 °C at 760 mmHg
You can still convert the following datas into molecular structure:
(1)InChI=1S/C16H14O4/c1-19-15(17)13-7-3-11(4-8-13)12-5-9-14(10-6-12)16(18)20-2/h3-10H,1-2H3;
(2)InChIKey=BKRIRZXWWALTPU-UHFFFAOYSA-N;
(3)Smilesc1(c2ccc(cc2)C(=O)OC)ccc(cc1)C(=O)OC;
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