Conditions | Yield |
---|---|
With iron(III) chloride; hydrazine hydrate; potassium carbonate; pyrographite In methanol; water at 85℃; for 2h; | 99% |
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; Microwave irradiation; Green chemistry; | 98% |
With trichlorosilane; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 0.833333h; Flow reactor; | 98% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate In ethanol; water at 100℃; for 24h; Reagent/catalyst; Temperature; Solvent; Suzuki Coupling; | 97% |
With tetrabutylammomium bromide; C32H26Cl2N8O4Pd2; potassium carbonate In methanol; water for 0.166667h; Suzuki-Miyaura Coupling; Reflux; | 97% |
With potassium phosphate; 1,3-bis[(methyl-2-methoxy-3-deoxy-4,6-dioxabenzylidene-α-D-altropyranos-3-yl)imidazol-2-ylcarbene]allylpalladium(II) chloride In dodecane; water; toluene at 130℃; for 12h; Reagent/catalyst; Suzuki-Miyaura Coupling; | 95% |
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With hydrogen bromide; Aliquat 336 In octane; water at 130℃; for 12h; Inert atmosphere; | 93% |
2-Chloronicotinoyl chloride
4-Chlorophenylboronic acid
2-Chloronitrobenzene
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
Stage #1: 4-Chlorophenylboronic acid; 2-Chloronitrobenzene With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling; Stage #2: With hydrogenchloride; zinc Stage #3: 2-Chloronicotinoyl chloride | 93% |
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hydroxide In ethanol at 10 - 50℃; Cooling with ice; | 92.6% |
Stage #1: 4'-chlorobiphenyl-2-carboxamide With sodium hydroxide In methanol for 0.5h; Stage #2: With sodium hypochlorite In methanol at 0 - 50℃; for 2.5h; Reagent/catalyst; Solvent; | 88% |
With water; bromine; sodium hydroxide at 0 - 5℃; for 1h; | 6 g |
With sodium hypochlorite at 20℃; for 6h; Hofmann Rearrangement; |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In water; acetone at 65℃; Inert atmosphere; | 92% |
With D-glucose; palladium diacetate; caesium carbonate In water; N,N-dimethyl-formamide at 100℃; for 16h; Suzuki-Miyaura Coupling; Sealed tube; | 88% |
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; | 84% |
(4-chlorphenyl)magnesium bromide
2-Chloroaniline
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); zinc(II) chloride In tetrahydrofuran at 10 - 15℃; for 7h; Inert atmosphere; | 91.6% |
With bis(triphenylphosphine)nickel(II) chloride; zinc(II) chloride In tetrahydrofuran at 10 - 15℃; for 7h; Inert atmosphere; | 91.6% |
4′-chloro-1,1′-biphenyl-2yl-carbonitrile
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
Stage #1: 4′-chloro-1,1′-biphenyl-2yl-carbonitrile With dihydrogen peroxide; sodium hydroxide In ethanol; water Stage #2: With sodium hypochlorite; sodium hydroxide In ethanol; water Hofmann rearrangement; | 82% |
Conditions | Yield |
---|---|
Stage #1: 2-amino-benzeneboronic acid hydrochloride; 1-Chloro-4-iodobenzene With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; triphenylphosphine In ethanol; toluene at 20℃; for 0.0833333h; Stage #2: In ethanol; water; toluene at 120℃; for 2h; Inert atmosphere; Sealed tube; | 75% |
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With Red-Al In toluene at 110℃; | 75% |
Conditions | Yield |
---|---|
Stage #1: para-dichlorobenzene With magnesium; ethylene dibromide; lithium chloride In tetrahydrofuran at 25℃; for 0.5h; Negishi coupling reaction; Stage #2: With zinc(II) chloride In tetrahydrofuran at 25℃; for 0.5h; Negishi coupling reaction; Stage #3: 2-bromoaniline With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 25℃; for 3h; Negishi coupling reaction; | 70% |
4-Chlorophenylboronic acid
2-aminophenylboronic acid
A
3,3'-dinitro-1,1'-biphenyl
B
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With potassium carbonate In water; acetonitrile at 70℃; Schlenk technique; chemoselective reaction; | A 20% B 55% |
4-chlorophenylhydrazine hydrochloride
aniline
A
4-(4-chlorophenyl)aniline
B
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With oxygen; sodium hydroxide In water at 60℃; for 33h; regioselective reaction; | A 9% B 51% |
C6H4ClN2O(1-)*Na(1+)
aniline
A
4-(4-chlorophenyl)aniline
B
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
In water at 70 - 75℃; for 0.5h; Inert atmosphere; | A 8% B 48% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 60℃; for 24h; regioselective reaction; | 48% |
p-chlorobenzenediazonium chloride
aniline
A
4-(4-chlorophenyl)aniline
B
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With sodium hydroxide In water at 75℃; | A 12% B 44% |
aniline
N-4-chlorophenylhydrazine
A
4-(4-chlorophenyl)aniline
B
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With manganese(IV) oxide In acetonitrile at 20℃; Overall yield = 54 %; regioselective reaction; | A 13% B 41% |
chlorobenzene
phenylhydrazine
A
N-(4-chlorophenyl)aniline
B
2-(4-chlorophenyl)aniline
C
2‐(2‐chlorophenyl)aniline
Conditions | Yield |
---|---|
With aluminium trichloride at 20℃; for 3h; | A 25% B 6% C 15% |
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With sodium hypobromide |
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With hydrogenchloride; copper(l) chloride Erhitzen des Reaktionsprodukts mit wss.-aethanol. Salzsaeure; |
N-Phenylhydroxylamine
chlorobenzene
A
N-(4-chlorophenyl)aniline
B
2-(4-chlorophenyl)aniline
C
2‐(2‐chlorophenyl)aniline
D
2′-chlorobiphenyl-4-amine
Conditions | Yield |
---|---|
With PPA; trifluoroacetic acid at 20℃; for 3h; Substitution; decomposition; trifluoroacetylation; Further byproducts. Title compound not separated from byproducts.; | A 42 % Chromat. B 1.8 % Chromat. C 7.5 % Chromat. D 5.6 % Chromat. |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2SO4; aqueous HNO3 / 65 °C 2: Raney nickel / Hydrogenation View Scheme |
di-(p-chlorophenyl)borinic acid
2-bromoaniline
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
Stage #1: di-(p-chlorophenyl)borinic acid With sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Stage #2: With triphenylphosphine In tetrahydrofuran; water at 20℃; for 0.5h; Stage #3: 2-bromoaniline With hydrogenchloride; palladium dichloride In tetrahydrofuran; water at 100℃; under 2625.26 Torr; for 12h; |
Conditions | Yield |
---|---|
With 10% palladium on activated carbon; hydrogen In methanol at 40℃; under 37503.8 Torr; | |
With 10 % platinum on carbon; hydrogen In water; tert-butyl alcohol at 60℃; under 760.051 Torr; |
4-chloro-aniline
A
4-(4-chlorophenyl)aniline
B
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water; acetic acid / 1 h / 0 °C 2: manganese(IV) oxide / acetonitrile / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 0 °C / Inert atmosphere 1.2: 0.08 h / 0 °C / Inert atmosphere 2.1: water / 0.5 h / 70 - 75 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 0 °C / Inert atmosphere 1.2: 0.08 h / 0 °C / Inert atmosphere 2.1: water / 0.5 h / 70 - 75 °C / Inert atmosphere View Scheme |
carbon monoxide
2-iodophenylamine
4-Chlorophenylboronic acid
A
2-amino-4'-chlorobenzophenone
B
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With potassium carbonate at 80℃; under 760.051 Torr; for 12h; Suzuki Coupling; Green chemistry; | A 92 %Chromat. B 7 %Chromat. |
With potassium carbonate at 80℃; under 760.051 Torr; for 12h; Catalytic behavior; Suzuki Coupling; Green chemistry; | A 88 %Chromat. B 10 %Chromat. |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium hydroxide; tetrabutylammomium bromide / water / 0.07 h / 100 °C / Microwave irradiation 2: tetrakis(triphenylphosphine) palladium(0); potassium hydroxide; tetrabutylammomium bromide; copper(l) iodide / water / 0.1 h / 100 °C / Microwave irradiation 3: tin(ll) chloride; hydrogenchloride / water / 0.07 h / 50 °C / Microwave irradiation View Scheme | |
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / acetonitrile / 80 °C / Inert atmosphere 2: tin(II) chloride dihdyrate / ethanol / 5 h / 75 °C View Scheme |
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; methanol; water at 50℃; for 2h; |
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / acetonitrile / 80 °C / Inert atmosphere 2: tin(II) chloride dihdyrate / ethanol / 5 h / 75 °C View Scheme |
S-Phenyl benzenethiosulfonate
tert-butylisonitrile
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With copper(l) iodide In 2-methyltetrahydrofuran at 75℃; for 20h; Microwave irradiation; Molecular sieve; | 99% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In water at 20 - 45℃; for 16h; Reagent/catalyst; | 97% |
In isopropyl alcohol at 40 - 65℃; for 4h; Solvent; Temperature; | 95% |
With potassium carbonate In dichloromethane at 20℃; for 1h; Reagent/catalyst; | 95.04% |
Conditions | Yield |
---|---|
With potassium carbonate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 80℃; | 95% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid In ethanol at 60℃; for 24h; | 91% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; Inert atmosphere; | 90% |
In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique; | |
In tetrahydrofuran at 0 - 20℃; for 2h; |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; | 90% |
4-(trifluoromethyl)pyridine-3-carbonyl chloride
2-(4-chlorophenyl)aniline
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 60℃; | 90% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1-Adamantanecarboxylic acid; acetic acid In tetrahydrofuran at 80℃; for 36h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 65 - 120℃; for 23h; Inert atmosphere; | 89% |
With carbon monoxide; oxygen; potassium carbonate In N,N-dimethyl-formamide at 65 - 120℃; for 28h; |
carbon dioxide
2-(4-chlorophenyl)aniline
8-chlorophenanthridin-6(5H)-one
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium tert-butylate; tris(para-trifluoromethyl)phenyl phosphine In N,N-dimethyl-formamide at 150℃; under 760.051 Torr; for 24h; Sealed tube; Schlenk technique; | 88% |
Stage #1: carbon dioxide; 2-(4-chlorophenyl)aniline With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In 1,2-dichloro-benzene at 20℃; under 760.051 Torr; for 1h; Sealed tube; Stage #2: With methyl trifluoromethanesulfonate In 1,2-dichloro-benzene at 140℃; under 760.051 Torr; for 12h; Sealed tube; Stage #3: With hydrogenchloride; water In 1,2-dichloro-benzene | 48% |
Conditions | Yield |
---|---|
With phosphorus trichloride In acetonitrile at 150℃; for 0.166667h; Microwave irradiation; | 87% |
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h; | 87% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 16h; | 65% |
2-(4-chlorophenyl)aniline
2-diazomalonic acid dibenzyl ester
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid In ethanol at 60℃; for 24h; | 87% |
Conditions | Yield |
---|---|
With m-nitrobenzene boronic acid In toluene at 120℃; for 10h; Temperature; Solvent; Reagent/catalyst; Large scale; | 85.57% |
Conditions | Yield |
---|---|
Stage #1: 2-(4-chlorophenyl)aniline With [(k2-P,N-di(1-adamantyl)-2-morpholinophenylphosphine)Pd(Ph)Cl]; sodium t-butanolate In 1,4-dioxane Inert atmosphere; Glovebox; Stage #2: With ammonia In 1,4-dioxane at 24℃; for 36h; Inert atmosphere; Glovebox; | 83% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; Cooling with ice; | 83% |
2-(4-chlorophenyl)aniline
2-iodo-4’-chlorobiphenyl
Conditions | Yield |
---|---|
Stage #1: 2-(4-chlorophenyl)aniline With hydrogenchloride; sodium nitrite In water at 5℃; for 1.16667h; Stage #2: With potassium iodide In water at 20℃; | 82% |
With sulfuric acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit KI und Kupfer unter Erwaermen; | |
With hydrogenchloride; potassium iodide; sodium nitrite In water at 0 - 20℃; |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 81% |
With pyridine | |
With pyridine In dichloromethane at 20℃; for 16h; Inert atmosphere; |
2-(4-chlorophenyl)aniline
p-toluenesulfonyl chloride
N-Ts-2-(4'-chlorophenyl)aniline
Conditions | Yield |
---|---|
With pyridine at 0 - 25℃; for 1h; | 81% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; mesitylenecarboxylic acid; copper(II) acetate monohydrate In 1,4-dioxane at 80℃; for 48h; Glovebox; Inert atmosphere; | 80% |
2-(4-chlorophenyl)aniline
diphenyl acetylene
(E)-4'-chloro-2'-(1,2-diphenylethenyl)[1,1'-biphenyl]-2-amine
Conditions | Yield |
---|---|
With dichloro(benzene)ruthenium(II) dimer; silver hexafluoroantimonate; acetic acid In 1,4-dioxane at 80℃; for 1h; Inert atmosphere; regioselective reaction; | 78% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; mesitylenecarboxylic acid; copper(II) acetate monohydrate In tetrahydrofuran at 80℃; for 48h; Glovebox; Inert atmosphere; | 78% |
The [1,1'-Biphenyl]-2-amine,4'-chloro-, with its CAS registry number 1204-44-0, has the IUPAC name of 2-(4-chlorophenyl)aniline. With the molecular foumula of C12H10ClN, its formula weight is 203.67.
The characteristics of [1,1'-Biphenyl]-2-amine,4'-chloro- are as follows: (1)ACD/LogP: 3.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.564; (4)ACD/LogD (pH 7.4): 3.566; (5)ACD/BCF (pH 5.5): 300.51; (6)ACD/BCF (pH 7.4): 302.221; (7)ACD/KOC (pH 5.5): 2063.232; (8)ACD/KOC (pH 7.4): 2074.973; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.02 Å2; (13)Index of Refraction: 1.628; (14)Molar Refractivity: 59.976 cm3; (15)Molar Volume: 168.949 cm3; (16)Polarizability: 23.776×10-24cm3; (17)Surface Tension: 46.987 dyne/cm; (18)Density: 1.206 g/cm3; (19)Flash Point: 156.163 °C; (20)Enthalpy of Vaporization: 57.758 kJ/mol; (21)Boiling Point: 334.603 °C at 760 mmHg; (22)Exact Mass: 203.050177; (23)MonoIsotopic Mass: 203.050177; (24)Topological Polar Surface Area: 26; (25)Heavy Atom Count: 14; (26)Complexity: 175; (27)Covalently-Bonded Unit Count: 1.
When you are dealing with this chemical, you should be careful. Being irritating to respiratory system, it may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection and then if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
What's more, the following datas could be converted into the molecular structure:
(1)Canonical SMILES: C1=CC=C(C(=C1)C2=CC=C(C=C2)Cl)N
(2)InChI: InChI=1S/C12H10ClN/c13-10-7-5-9(6-8-10)11-3-1-2-4-12(11)14/h1-8H,14H2
(3)InChIKey: JPBWZIPCMDZOPM-UHFFFAOYSA-N
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