2-(4-Biphenylyl)-5-phenyl-1,3,4-oxadiazole supplier

Name
2-(4-BIPHENYLYL)-5-PHENYL-1,3,4-OXADIAZOLE
EINECS 212-712-0
CAS No. 852-38-0
Article Data9
CAS DataBase
Density 1.172 g/cm³
Solubility Soluble in toluene and xylene, insoluble in water
Melting Point 167-169 °C
Formula C₂₀H₁₄N₂O
Boiling Point 480.7 °C at 760 mmHg
Molecular Weight 298.344
Flash Point 240.7 °C
Transport Information
Appearance white fine crystalline powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,3,4-Oxadiazole,2-(4-biphenylyl)-5-phenyl- (6CI,8CI);2-(4-Biphenyl)-5-phenyl-1,3,4-oxadiazole;2-(4-Biphenylyl)-5-phenyl-1,3,4-oxadiazole;2-(p-Biphenyl)-5-phenyl-1,3,4-oxadiazole;2-Phenyl-5-(4-biphenylyl)-1,3,4-oxadiazole;2-Phenyl-5-(4'-biphenylyl)-1,3,4-oxadiazole;2-Phenyl-5-p-biphenylyl-1,3,4-oxadiazole;2-p-Biphenylyl-5-phenyl-1,3,4-oxadiazole;5-(4'-Biphenylyl)-2-phenyl-1,3,4-oxadiazole;5-p-Biphenylyl-2-phenyl-1,3,4-oxadiazole;NSC 24858;PBD;Phenyl-2-p-biphenylyl-5-oxadiazole-1,3,4;
PSA 38.92000
LogP 5.07060

Synthetic route

: 613-94-5
benzoic acid hydrazide

: 92-92-2
biphenyl-4-carboxylic acid

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
With PS-PPh3; trichloroacetonitrile In acetonitrile at 150℃; for 0.333333h; microwave irradiation;	85%

: 412956-37-7
C20H16N2O

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Stage #1: C20H16N2O With iodine; potassium carbonate In dimethyl sulfoxide at 20℃; Green chemistry; Stage #2: With dihydrogen peroxide In water; dimethyl sulfoxide at 20℃; for 7h; Green chemistry;	85%
With sodium hypochlorite In water; tert-butyl alcohol at 0 - 20℃;	225 mg

: 18622-23-6
4-phenylbenzohydrazide

: 591-50-4
iodobenzene

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; sodium acetate In N,N-dimethyl-formamide at 130℃; for 3h; Inert atmosphere;	74%

...Expand

: 86268-09-9
Biphenyl-4-carboxylic acid [1-phenyl-meth-(E)-ylidene]-hydrazide

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
With lead dioxide In acetic acid at 90 - 100℃; for 0.5h;	65%

: 100989-00-2
DC-S337

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
With trichlorophosphate
With trichlorophosphate for 10h; Reflux;

: C17H16O4

: 613-94-5
benzoic acid hydrazide

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multistep reaction;

: 92-92-2
biphenyl-4-carboxylic acid

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-methylimidazole / CH2Cl2; toluene / 0.5 h / 0 - 20 °C View Scheme

: 613-94-5
benzoic acid hydrazide

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: POCl3 View Scheme

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

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: POCl3 View Scheme

: 720-75-2
methyl 4-phenylbenzoate

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine 2: pyridine / Heating 3: trichlorophosphate / 10 h / Reflux View Scheme

: 18622-23-6
4-phenylbenzohydrazide

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / Heating 2: trichlorophosphate / 10 h / Reflux View Scheme

: 613-94-5
benzoic acid hydrazide

: 3218-36-8
4-Phenylbenzaldehyde

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tert-butyl alcohol / Reflux 2: sodium hypochlorite / tert-butyl alcohol; water / 0 - 20 °C View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 136180-46-6
4-(5-phenyl-1,3,4-oxadiazole-2-yl)-biphenyl-4'-yl sulfonic acid

Conditions

Conditions	Yield
With chlorosulfonic acid In dichloromethane for 2h; Heating;	96%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 92-92-2
biphenyl-4-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen iodide In acetic acid for 15h; Heating;	90%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 75-36-5
acetyl chloride

: 128860-87-7
2-(4'-acetylbiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane for 5h; Heating;	80%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 136180-49-9
2-(2',4',5'-tribromobiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
With bromine; iron In carbon disulfide for 4h; Heating;	79%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 598-21-0
2-Bromoacetyl bromide

: 128860-88-8
2-(4'-bromoacetylbiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane for 3h; Heating;	68%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 136180-43-3
2-(4'-nitrobiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
With sulfuric acid; nitric acid In dichloromethane for 2h; Ambient temperature;	65%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 136180-48-8
2-(4'-bromobiphenyl-4'-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid at 60℃; for 4h;	63%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 1-fluoro-4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditetrafluoroborate

: 5158-46-3
methylzinc chloride

A: 2-(4'-methyl-[1,1'-biphenyl]-4-yl)-5-(p-tolyl)-1,3,4-oxadiazole

B: 2-(4'-methyl-[1,1'-biphenyl]-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
Stage #1: 2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole; 1-fluoro-4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditetrafluoroborate With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; C20H28N4O2Pd(2+)*2BF4(1-) In acetonitrile at 23℃; for 24h; Sealed tube; Stage #2: methylzinc chloride With 1-methyl-pyrrolidin-2-one; bis(tricyclohexylphosphine)nickel(II) dichloride; tert-butylammonium hexafluorophosphate(V) In tetrahydrofuran at 50℃; for 20h; Negishi Coupling; Sealed tube;	A 5% B 54%

Yield

Stage #1: 2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole; 1-fluoro-4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditetrafluoroborate With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; C20H28N4O2Pd(2+)*2BF4(1-) In acetonitrile at 23℃; for 24h; Sealed tube;
Stage #2: methylzinc chloride With 1-methyl-pyrrolidin-2-one; bis(tricyclohexylphosphine)nickel(II) dichloride; tert-butylammonium hexafluorophosphate(V) In tetrahydrofuran at 50℃; for 20h; Negishi Coupling; Sealed tube;

A 5%
B 54%

...Expand

: 53587-10-3
hippuryl chloride

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 154532-11-3
4'-<(benzoylaminomethyl)carbonyl>-4-(5-phenyl-1,3,4-oxadiazol-2-yl)biphenyl

Conditions

Conditions	Yield
With aluminium trichloride In carbon disulfide 1) 1 h, room temperature; 2) reflux, 5.5 h;	47%

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

CH3COX: CH3COX

: 128860-87-7
2-(4'-acetylbiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 132584-97-5
2-(4'-cyanobiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 64 percent / Lawesson reagent / xylene / 3 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 132584-91-9
2-(4'-carboxybiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: sodium hypobromite View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 132584-94-2
2-(4'-aminocarbonylbiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 132584-98-6
2-(4'-aminothiocarbonylbiphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 2-Phenyl-5-[4'-(4-phenyl-thiazol-2-yl)-biphenyl-4-yl]-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 62 percent / dioxane / 7.5 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 2-Phenyl-5-[4'-(4-p-tolyl-thiazol-2-yl)-biphenyl-4-yl]-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 41 percent / dioxane / 7 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 2-{4'-[4-(4-Bromo-phenyl)-thiazol-2-yl]-biphenyl-4-yl}-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 28 percent / dioxane / 5 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 2-[4'-(4-Naphthalen-2-yl-thiazol-2-yl)-biphenyl-4-yl]-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 33 percent / dioxane / 7 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 2-[4'-(4-Naphthalen-1-yl-thiazol-2-yl)-biphenyl-4-yl]-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 30 percent / dioxane / 4.5 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 2-{4'-[4-(4-Methoxy-phenyl)-thiazol-2-yl]-biphenyl-4-yl}-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 42 percent / dioxane / 4 h / Heating View Scheme

: 852-38-0
2-biphenyl-4-yl-5-phenyl-[1,3,4]oxadiazole

: 2-[4'-(4-Biphenyl-4-yl-thiazol-2-yl)-biphenyl-4-yl]-5-phenyl-[1,3,4]oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: sodium hypobromite 3: 1.) carbonyldiimidazole, 2.) NH3 / 1.) CH2Cl2, 0.5 h, reflux, 2.) 45 min 4: 76 percent / Lawesson reagent / benzene / 2 h / Heating 5: 26 percent / dioxane / 9 h / Heating View Scheme

2-(4-Biphenylyl)-5-phenyl-1,3,4-oxadiazole Specification

The 2-(4-Biphenylyl)-5-phenyl-1,3,4-oxadiazole is an organic compound with the formula C₂₀H₁₄N₂O. The IUPAC name of this chemical is 2-phenyl-5-(4-phenylphenyl)-1,3,4-oxadiazole. With the CAS registry number 852-38-0 and EINECS 212-712-0, it is also named as 1,3,4-Oxadiazole, 2-(1,1'-biphenyl)-4-yl-5-phenyl-. The product's category is Biphenyl Derivatives. It is white fine crystalline powder which is soluble in toluene and xylene, insoluble in water. When using it, people should not breathe dust and avoid contact with skin and eyes. Additionally, this chemical should be sealed in the container and stored at the temperature of 2-8 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 6.34; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.34; (4)ACD/LogD (pH 7.4): 6.34; (5)ACD/BCF (pH 5.5): 38447.32; (6)ACD/BCF (pH 7.4): 38447.32; (7)ACD/KOC (pH 5.5): 66593.3; (8)ACD/KOC (pH 7.4): 66593.3; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.612; (13)Molar Refractivity: 88.51 cm³; (14)Molar Volume: 254.5 cm³; (15)Polarizability: 35.08×10^-24 cm³; (16)Surface Tension: 47.9 dyne/cm; (17)Enthalpy of Vaporization: 71.68 kJ/mol; (18)Vapour Pressure: 6.2E-09 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 298.110613; (21)MonoIsotopic Mass: 298.110613; (22)Topological Polar Surface Area: 38.9; (23)Heavy Atom Count: 23; (24)Complexity: 355.

Uses of 2-(4-Biphenylyl)-5-phenyl-1,3,4-oxadiazole: It can react with acetyl chloride to get 1-[4'-(5-phenyl-[1,3,4]oxadiazol-2-yl)-biphenyl-4-yl]-ethanone. This reaction needs reagent AlCl₃ and solvent CH₂Cl₂ by heating. The reaction time is 5 hours. The yield is 80%.

People can use the following data to convert to the molecule structure.
1. SMILES:n1nc(oc1c2ccccc2)c4ccc(c3ccccc3)cc4
2. InChI:InChI=1/C20H14N2O/c1-3-7-15(8-4-1)16-11-13-18(14-12-16)20-22-21-19(23-20)17-9-5-2-6-10-17/h1-14H
3. InChIKey:WMAXWOOEPJQXEB-UHFFFAOYAA

Product Name

2-(4-BIPHENYLYL)-5-PHENYL-1,3,4-OXADIAZOLE

Synthetic route

2-(4-Biphenylyl)-5-phenyl-1,3,4-oxadiazole Specification

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