2,5-Diphenyloxazole supplier

Name
2,5-Diphenyloxazole
EINECS 202-181-3
CAS No. 92-71-7
Article Data135
CAS DataBase
Density 1.128 g/cm³
Solubility NEGLEGIBLE
Melting Point 72-74 °C(lit.)
Formula C₁₅H₁₁NO
Boiling Point 359.998 °C
Molecular Weight 221.258
Flash Point 162.302 °C
Transport Information
Appearance light beige solid
Safety 24/25-36/37-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,5-Diphenyl-1,3-oxazole;DPO (scintillator);NSC 24856;NSC 49168;Tritosol;PPO;PPO(scintillator);
PSA 26.03000
LogP 4.00860

Synthetic route

: 18735-78-9
2,5-diphenyloxazole-4-carboxylic acid

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; for 24h;	100%

: C17H15NO3

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In diethyl ether; dichloromethane at -78 - 20℃; for 0.25h;	100%

: 1006-68-4
5-phenyloxazole

: 5123-13-7
5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With oxygen; copper(l) chloride; sodium t-butanolate In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 0.333333h;	98%

: 4190-14-1
N-(2-oxo-2-phenylethyl)benzamide

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With sulfuric acid at 30 - 100℃; Temperature; Large scale;	96.7%
With Burgess Reagent In tetrahydrofuran for 0.333333h; Cyclization; Robinson-Gabriel reaction; microwave irradiation;	93%
With sulfuric acid; acetic anhydride at 90℃;	88%

: 536-74-3
phenylacetylene

: 582-61-6
benzoyl azide

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With [(tris(3,5-dimethylpyrazolylmethyl)amine)Cu]PF6 at 40℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	95%

: N-bromo-2-benzoyl-3-phenylaziridine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
In 1,4-dioxane Reflux;	95%

: 1006-68-4
5-phenyloxazole

: 65-85-0
benzoic acid

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;	95%

: trans-phenyl(3-phenylaziridin-2-yl)methanone

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With N-Bromosuccinimide In 1,4-dioxane for 1h; Solvent; Reagent/catalyst; Temperature; Reflux;	93%

: 20662-88-8
2-phenyloxazole

: 591-50-4
iodobenzene

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With triphenylphosphine; silver carbonate; [Pd((diphenylphosphanyl)ferrocene)Cl2]*CH2Cl2 In water at 60℃; for 24h;	92%
With triphenylphosphine; silver carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dichloromethane; water at 60℃; for 24h;	92%
With caesium carbonate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 140℃; for 17h; Phenylation;	79%

: 20662-88-8
2-phenyloxazole

: 108-86-1
bromobenzene

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With potassium carbonate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 140℃; for 17h; Phenylation;	90%

: 7570-84-5, 51659-21-3, 65309-87-7, 74280-88-9
trans-2-phenyl-3-benzoylaziridine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With iodine; dicyclohexyl-carbodiimide In acetonitrile Reagent/catalyst; Solvent; Time; Reflux;	90%

: 98-86-2
acetophenone

: 2835-06-5
phenylglycin

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With iodine; 4-aminobenzene sulfonic acid In dimethyl sulfoxide at 100℃; for 5h; Reagent/catalyst; Solvent;	90%

: 1006-68-4
5-phenyloxazole

: 108-86-1
bromobenzene

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium tert-butoxide In 1,4-dioxane at 120℃; for 2h; Inert atmosphere; regioselective reaction;	89%
With copper(l) iodide; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 150℃; for 0.25h; microwave irradiation;	81%

: 70-11-1
α-bromoacetophenone

: 100-46-9
benzylamine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With potassium phosphate; tris(2,2'-bipyridyl)ruthenium dichloride; Bromotrichloromethane In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube; Irradiation;	88%
With iodine; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Time; Solvent; Reagent/catalyst;	82%
With carbon dioxide; DBN; eosin y In dimethyl sulfoxide at 20℃; for 20h; Reagent/catalyst; Solvent; Schlenk technique; Irradiation;	76%
With tert.-butylhydroperoxide; iodine; caesium carbonate In tetrahydrofuran; water at 60℃; for 12h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	74%

: 292638-84-7
styrene

: 622-79-7
benzyl azide

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With copper(I) bromide In chlorobenzene at 80℃; for 17h;	88%
With oxygen; copper(l) chloride In toluene at 80℃; for 8h; Reagent/catalyst; Solvent;	82%

: 2-benzoyl-4-phenylisoxazol-5(2H)-one

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In 1,4-dioxane at 20℃; for 3h; Catalytic behavior; Solvent; Inert atmosphere; Irradiation;	88%

: 72997-93-4
1-benzyl-2-benzoyl-3-phenylaziridine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With N-Bromosuccinimide In 1,4-dioxane for 0.5h; Reagent/catalyst; Reflux;	87%

: trans-2-benzoyl-3-phenyl-1-phthalimidoaziridine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
In toluene at 160℃; for 2h;	86%

: 1006-68-4
5-phenyloxazole

: 2996-92-1
phenyl trimethylsiloxane

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With [2,2]bipyridinyl; copper (II)-fluoride; nickel(II) bromide 2-methoxyethyl ether complex; cesium fluoride In N,N-dimethyl acetamide at 150℃; Inert atmosphere;	86%

: 94-41-7
benzalacetophenone

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; ammonium acetate at 20℃; for 5h; Reagent/catalyst; Temperature;	86%

: Benzoic acid (Z)-2-azido-1-phenyl-vinyl ester

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
In cyclohexane at 90℃; for 24h;	84%

: 78007-47-3
trans-N-styryl-benzamide

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; 3-pyridinecarboxylic acid ethyl ester; tetrabutylammomium bromide; copper(ll) bromide In acetonitrile at 20℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere;	84%
With trimethylsilyl trifluoromethanesulfonate; bis-[(trifluoroacetoxy)iodo]benzene In diethyl ether; dichloromethane at -78 - 0℃; Solvent; Reagent/catalyst; Temperature;	75%
With 1-methyl-1H-imidazole; copper dichloride In 1,4-dioxane at 140℃; for 20h; Sealed tube;	74 %Spectr.

: 4636-16-2
iodoacetophenone

: 100-46-9
benzylamine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With iodine In dimethyl sulfoxide at 100℃;	84%

: 536-74-3
phenylacetylene

: 932-90-1
Benzaldoxime

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
Stage #1: Benzaldoxime With trifluorormethanesulfonic acid; silica gel In toluene at 50℃; for 0.5h; Stage #2: phenylacetylene In toluene at 70℃; for 3.5h; Stage #3: With copper(II) choride dihydrate; lithium chloride hydrate; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; propan-1-ol; toluene at 60℃; under 9750.98 Torr; for 4h; Reagent/catalyst;	84%

: 1006-68-4
5-phenyloxazole

: 591-50-4
iodobenzene

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With copper(l) iodide; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 160℃; for 2h; Inert atmosphere;	83%
With lithium tert-butoxide In diethyl ether at 30℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;	76%
With copper(l) iodide; dimethylaminoacetic acid; lithium tert-butoxide In diethyl ether at 25 - 27℃; for 16h; Inert atmosphere; Sealed tube; Irradiation;	74%

: 122-78-1
phenylacetaldehyde

: 100-46-9
benzylamine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With pyridine; oxygen; potassium carbonate; copper(I) bromide In toluene at 20 - 80℃; under 760.051 Torr; for 16.1667h; Reagent/catalyst; Solvent; Schlenk technique;	82%

: 292638-84-7
styrene

: 100-46-9
benzylamine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; iodine In dimethyl sulfoxide at 80℃;	81%

: 1006-68-4
5-phenyloxazole

: 80-17-1
benzenesufonyl hydrazide

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With copper diacetate; palladium diacetate; triphenylphosphine In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;	81%

: 1006-68-4
5-phenyloxazole

: 108-90-7
chlorobenzene

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With PdCl2(C3H3N2(CH3))(C3H2N2(C6H3(C3H7)2)2); lithium tert-butoxide In toluene at 130℃; for 18h; Inert atmosphere;	81%

: 1074-12-0
phenylglyoxal hydrate

: 100-46-9
benzylamine

: 92-71-7
2,5-diphenyloxazole

Conditions

Conditions	Yield
With silver carbonate In 1,4-dioxane at 50℃; for 12h;	78%
With pyridine; oxygen; potassium carbonate; lithium bromide; copper(ll) bromide In toluene at 110℃; for 11h;	74%
With tert.-butylhydroperoxide; iodine In dimethyl sulfoxide at 80℃;

: 92-71-7
2,5-diphenyloxazole

: (R)-2,5-diphenyloxazoline

Conditions

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene; hydrogen In toluene at 80℃; under 38002.6 Torr; for 24h; Autoclave; optical yield given as %ee; enantioselective reaction;	97%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); C48H44Fe2P2; hydrogen; N,N,N',N'-tetramethylguanidine In 2-methyl-propan-1-ol at 80℃; for 4h; enantioselective reaction;	97%

: 92-71-7
2,5-diphenyloxazole

: 106-38-7
para-bromotoluene

: 26107-35-7
2,5-diphenyl-4-(p-tolyl)oxazole

Conditions

Conditions	Yield
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	96%

: 92-71-7
2,5-diphenyloxazole

A: 128600-19-1
4,5-Dimethoxy-2,5-diphenyl-2-oxazoline

B: 126193-96-2
N-benzoyl-1,2,2-trimethoxy-2-phenylethyl amine

Conditions

Conditions	Yield
With bromine; potassium carbonate In methanol 1.) -78 deg C, 1 h; 2.) -15 - -5 deg C, 5 h; Yields of byproduct given;	A 95.5% B n/a

: 92-71-7
2,5-diphenyloxazole

: 126193-96-2
N-benzoyl-1,2,2-trimethoxy-2-phenylethyl amine

Conditions

Conditions	Yield
With bromine; potassium carbonate In methanol 1.) -78 deg C, 1 h; 2.) -15 deg C, 3 d;	95.5%
Multi-step reaction with 2 steps 1: 95.5 percent / K2CO3, Br2 / methanol / 1.) -78 deg C, 1 h; 2.) -15 - -5 deg C, 5 h 2: Br2, K2CO3 / methanol / 48 h / -10 °C View Scheme

: 92-71-7
2,5-diphenyloxazole

: 7007-08-1
4-bromo-2,5-diphenyloxazole

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 80℃; for 1h; Inert atmosphere;	85%
With 2,2,6,6-tetramethyl-piperidine; bromine; sec.-butyllithium 1a) THF, dry ice bath, 0.5 h, b) ice cooling; Yield given. Multistep reaction;

: 92-71-7
2,5-diphenyloxazole

: 189278-27-1
2-bromo-6-(trifluoromethyl)pyridine

: 2,5-diphenyl-4-(6-(trifluoromethyl)pyridin-2-yl)oxazole

Conditions

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Schlenk technique;	85%

: 92-71-7
2,5-diphenyloxazole

: C15H27NO

Conditions

Conditions	Yield
With dichloro(μ-chloro)(μ-hydrido)bis(η-p-cymene)diruthenium(II); hydrogen In 1,4-dioxane at 90℃; under 37503.8 Torr; for 40h;	85%

2,5-Diphenyloxazole Consensus Reports

Reported in EPA TSCA Inventory.

2,5-Diphenyloxazole Specification

The 2,5-Diphenyloxazole, with the CAS registry number 92-71-7, is also known as Oxazole, 2,5-diphenyl-. It belongs to the product categories of Isoxazoles, Oxadiazoles, Oxazoles; Oxazole & Isoxazole. Its EINECS registry number is 202-181-3. This chemical's molecular formula is C₁₅H₁₁NO and molecular weight is 221.25. What's more, both its IUPAC name and systematic name are the same which is called 2,5-Diphenyl-1,3-oxazole. It should be stored in a cool and sealed place.

Physical properties about 2,5-Diphenyloxazole are: (1)ACD/LogP: 4.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.68; (4)ACD/LogD (pH 7.4): 4.68; (5)ACD/BCF (pH 5.5): 2120.62; (6)ACD/BCF (pH 7.4): 2120.64; (7)ACD/KOC (pH 5.5): 8369.09; (8)ACD/KOC (pH 7.4): 8369.15; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.03 Å²; (13)Index of Refraction: 1.586; (14)Molar Refractivity: 65.828 cm³; (15)Molar Volume: 196.021 cm³; (16)Polarizability: 26.096×10^-24 cm³; (17)Surface Tension: 43.05 dyne/cm; (18)Density: 1.129 g/cm³; (19)Flash Point: 162.302 °C; (20)Enthalpy of Vaporization: 58.18 kJ/mol; (21)Boiling Point: 359.998 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of 2,5-Diphenyloxazole: this chemical can be prepared by 2-Benzoylamino-1-phenyl-ethanone. This reaction needs reagent Burgess reagent and solvent tetrahydrofuran. The reaction time is 20 min. The yield is 93 %.

2,5-Diphenyloxazole can be prepared by 2-Benzoylamino-1-phenyl-ethanone.

Uses of 2,5-Diphenyloxazole: (1) it is used as an organic scintillator; (2) it is used to produce other chemicals. For example, it can react with [1,2]oxathiolane 2,2-dioxide to get 3-(2,5-diphenyloxazolio-3)propanesulfonate. The reaction occurs with reagent 1,2-dichloro-benzene at temperature of 170 °C for 30 min. The yield is 70 %.

2,5-Diphenyloxazole can react with [1,2]oxathiolane 2,2-dioxide to get 3-(2,5-diphenyloxazolio-3)propanesulfonate.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing and gloves. And you must avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: n1cc(oc1c2ccccc2)c3ccccc3
(2) InChI: InChI=1S/C15H11NO/c1-3-7-12(8-4-1)14-11-16-15(17-14)13-9-5-2-6-10-13/h1-11H
(3) InChIKey: CNRNYORZJGVOSY-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	750mg/kg (750mg/kg)		National Technical Information Service. Vol. AD277-689,

Product Name

2,5-Diphenyloxazole

Synthetic route

2,5-Diphenyloxazole Consensus Reports

2,5-Diphenyloxazole Specification

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