[ CAS No. 5565-72-0 ]

Name: 5565-72-0|2-(3-Nitrophenyl)-1,3,4-oxadiazole|98%
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SKU: A283912
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Quality Control of [ 5565-72-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 5565-72-0 ]

CAS No. :	5565-72-0	MDL No. :	MFCD00085145
Formula :	C₈H₅N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NSIRBOSXFXTYQL-UHFFFAOYSA-N
M.W :	191.14 g/mol	Pubchem ID :	2739389
Synonyms :

Safety of [ 5565-72-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5565-72-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 5565-72-0 ]

[ 5565-72-0 ] Synthesis Path-Downstream 1~22

1
[ 103274-29-9 ]
[ 5565-72-0 ]

Reference： [1]Runti et al. [Annali di Chimica, 1959, vol. 49, p. 1649,1656, 1663]

2
[ 5565-72-0 ]
[ 35219-13-7 ]
[ 5378-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol for 1h; Ambient temperature;

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

3
[ 122-51-0 ]
[ 618-94-0 ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sulfuric acid; silica gel at 20℃;
78.9%	at 100℃; for 3h;	4.A Step A: 2-(3-nitrophenyl)-1,3,4-oxadiazole 2-(3-nitrophenyl)-l,3,4-oxadiazole. A mixture of 3-nitrobenzohydrazide (1.8 g, 10 mmol), triethoxymethane (5 mL) and 0.1 mL CH(OEt)3 was stirred at 100 °C for 3 hr. The mixture was concentrated to small volume and cooled down to give a colorless crystal. The solid was collected by filtration and dried under vacuum to afford the desired compound (1.5 g, 78.9% yield). MS: 192.2 (M+l)+.
	In xylene for 6.7h; Heating;

4.A Step A: Step A: 2-(3-nitrophenyl)-1,3,4-oxadiazole A mixture of 3-nitrobenzohydrazide (1.8 g, 10 mmol), triethoxymethane (5 mL) and 0.1 mL CH(OEt)3 was stirred at 100° C. for 3 hr. The mixture was concentrated to small volume and cooled down to give a colorless crystal. The solid was collected by filtration and dried under vacuum to afford the desired compound (1.5 g, 78.9% yield). MS: 192.2 (M+1)+.

Reference： [1]Dabiri, Minoo; Salehi, Peyman; Baghbanzadeh, Mostafa; Zolfigol, Mohammad Ali; Bahramnejad, Mahboobeh [Synthetic Communications, 2007, vol. 37, # 7, p. 1201 - 1209]
[2]Current Patent Assignee: SERVIER MONDE - WO2013/107405, 2013, A1 Location in patent: Page/Page column 65
[3]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]
[4]Maillard,J. et al. [Bulletin de la Societe Chimique de France, 1966, p. 376 - 381]
[5]Current Patent Assignee: SERVIER MONDE - US2015/87600, 2015, A1 Location in patent: Page/Page column

4
[ 138267-85-3 ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In benzene for 0.0833333h; Ambient temperature;
85%	With Chloroacetic anhydride In toluene for 0.5h;

Reference： [1]Hussein, Ahmad Q.; El-Abadelah, Mustafa M.; Nazer, Musa Z.; Awadallah, Adel M. [Heterocycles, 1994, vol. 38, # 5, p. 981 - 990]
[2]El-Abadelah, M. M.; Nazer, M. Z.; Hussein, A. Q.; Awadallah, A. M.; Rademacher, P.; Woydt, M. [Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1229 - 1234]

Yield	Reaction Conditions	Operation in experiment
	Hydrazid, RC(OEt)3;
	entspr. Benzhydrazid, RC(OEt)3;

6
[ 618-94-0 ]
[ 149-73-5 ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With Al3+-K10 montmorillonite clay; In neat (no solvent); at 55℃; for 0.25h;Microwave irradiation;	General procedure: A 5 mL microwave vial was charged with acidhydrazide (100 mg, 1 eq), trimethyl orthoester (2 eq) and Al3+-K10 clay (75 mg). The resulting mixture was kept under microwave irradiation maintaining the temperature at 55 C for 15 min (Microwave irradiations were performed on CEM-discover model No. 908010). The reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with ethyl acetate stirred well, filtered, washed well with ethyl acetate. Filtrate was evaporated under reduced pressure to obtain highly pure product. In some cases, products were purified by column chromatography using 60-120 mesh silica with 20-100 % ethyl acetate in pet ether as eluting solvents. The catalyst recovered by filtration was reused for another 5 more times.

Reference： [1]Monatshefte fur Chemie,2007,vol. 138,p. 1253 - 1255
[2]Tetrahedron Letters,2014,vol. 55,p. 3678 - 3682

7
[ 126175-90-4 ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / 0.33 h / Heating 2: 85 percent / chloroacetic anhydride / toluene / 0.5 h

Reference： [1]El-Abadelah, M. M.; Nazer, M. Z.; Hussein, A. Q.; Awadallah, A. M.; Rademacher, P.; Woydt, M. [Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1229 - 1234]

8
[ 618-94-0 ]
[ 5565-72-0 ]

Reference： [1]Runti et al. [Annali di Chimica, 1959, vol. 49, p. 1649,1656, 1663]

9
[ 5565-72-0 ]
[ 6336-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C 3: aq. NaOH / Heating

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

10
[ 5565-72-0 ]
[ 96432-49-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C 3: aq. NaOH / Heating

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

11
[ 5565-72-0 ]
[ 92150-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: benzene / Ambient temperature 3: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

12
[ 5565-72-0 ]
[ 92906-13-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: benzene / Ambient temperature

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

13
[ 5565-72-0 ]
[ 92906-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: benzene / Ambient temperature

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

14
[ 5565-72-0 ]
[ 1071691-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

15
[ 5565-72-0 ]
4-acetylamino-<i>N</i>-(3-[1,3,4]oxadiazol-2-yl-phenyl)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C

Reference： [1]Vincent,M. [Bulletin de la Societe Chimique de France, 1962, p. 1587 - 1591]

16
[ 5565-72-0 ]
[ 1448308-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C
	Multi-step reaction with 2 steps 1: methanol

Reference： [1]Current Patent Assignee: SERVIER MONDE - WO2013/107405, 2013, A1
[2]Current Patent Assignee: SERVIER MONDE - US2015/87600, 2015, A1

17
[ 5565-72-0 ]
[ 5378-35-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 16h;	4.B Step B: 3-(1,3,4-oxadiazol-2-yl)aniline. A mixture of 2-(3-nitrophenyl)-l ,3,4-oxadiazole (1 g, 5.2 mmol) and 10% palladium on carbon (0.1 g) in methanol (20 mL) was stirred at r.t. for 16 h under the atmosphere of hydrogen. The mixture was filtered through Celite and the filtrate was concentrated to give the desired compound (840 mg, quant.). MS: 162.2 (M+l)+.
	In methanol	4.B Step B: Step B: 3-(1,3,4-oxadiazol-2-yl)aniline A mixture of 2-(3-nitrophenyl)-1,3,4-oxadiazole (1 g, 5.2 mmol) and 10% palladium on carbon (0.1 g) in methanol (20 mL) was stirred at r.t. for 16 h under the atmosphere of hydrogen. The mixture was filtered through Celite and the filtrate was concentrated to give the desired compound (840 mg, quant.). MS: 162.2 (M+1)+.

Reference： [1]Current Patent Assignee: SERVIER MONDE - WO2013/107405, 2013, A1 Location in patent: Paragraph 65
[2]Current Patent Assignee: SERVIER MONDE - US2015/87600, 2015, A1 Location in patent: Page/Page column

18
[ 591-50-4 ]
[ 5565-72-0 ]
2-(3-nitrophenyl)-5-(phenylseleno)-1,3,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With selenium; copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere;	18 Synthesis of 2- (3-nitrobenzene) -5-phenylseleno-1,3,4-oxadiazole in room temperature,Iodobenzene (1.2 mmol, 3 equiv),Elemental selenium (1.2 mmol, 3 equiv),2- (3-nitrobenzene) -1,3,4-oxadiazole (0.4 mmol, 1 equiv)Cu (OAc) 2 (0.04 mmol),Potassium carbonate (1.2 mmol, 3 equiv) was added to the reaction tube,Then filled with nitrogen, and replaced three times, in the nitrogen reaction environment,Then, 2 mL of DMF was added to the reaction solvent and stirred at 140 ° C for 24 h.After the reaction was monitored by thin layer chromatography, the reaction mixture was cooled,Then diluted with ethyl acetate, and the diluted solution was transferred to a separatory funnel,Extracted with saturated brine, separated from the aqueous phase and organic phase, and then extracted with ethyl acetate 3 times,The organic phases were combined, 5 g of anhydrous sodium sulfate was added,Wash the filter cake with 5 mL of ethyl acetate each time 3 times, then spin off the solvent,The product was isolated by column chromatography (eluent: petroleum ether: ether = 98: 2)The product was a yellow solid in 95% yield and 131 mg of product.

Reference： [1]Current Patent Assignee: WENZHOU MEDICAL UNIVERSITY - CN107056727, 2017, A Location in patent: Paragraph 0269-0272

19
benzene-1,3,5-triyl triformate [ No CAS ]
[ 618-94-0 ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With trifluoroacetic acid In toluene at 130℃; for 12h;	1,3,4-Oxadiazoles 2; General Procedure General procedure: A 25 mL pressure tube was charged with arylhydrazide 1 (0.5 mmol), TFBen (53 mg, 0.25 mmol, white solid, mp 57.2-58.5 °C), TFA (38 μL, 1.0 equiv), and toluene (4 mL). The tube was then heated by stirring the contents at 130 °C for 12 h. Afterwards, the mixture was cooled to r.t., quenched with sat. aq NaHCO3 (3 mL), and extracted with EtOAc (3 4 mL). The combined organic layers were dried (anhyd Na2SO4), filtered, and concentrated under reduced pressure. The pure product 2 was obtained after purification by column chromatography (EtOAc/ pentane 1:3).

Reference： [1]Yin, Zhiping; Power, Dennis J.; Wang, Zechao; Stewart, Scott G.; Wu, Xiao-Feng [Synthesis, 2018, vol. 50, # 16, p. 3238 - 3242]

20
[ 758-96-3 ]
[ 618-94-0 ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With titanium tetrachloride; at 110℃; for 1.5h;	General procedure: To a 10mL three-necked round bottle was charged with benzoylhydrazine (0.30 g,2.2 mmol), TiCl4 (0.83 g, 4.4 mmol) and DMA (3 mL, 32.1 mmol). The resulting solutionwas warmed to 110 C and stirred at this temperature for 1.5 h. When the reaction wascompleted, 50mL water was added and the resulting mixture was extracted with 50mLethyl acetate three times. The combined organic layer was successively washed withH2O (50 mL) and then brine (50 mL), then dried over anhydrous Na2SO4, filtered andconcentrated under reduced pressure. The residue was purified by column chromatographyon silica gel with petroleum ether and ethyl acetate to give the title products.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 423 - 431

21
[ 645-00-1 ]
C₄H₂N₄O₂Zn*Cl₂Li₂ [ No CAS ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
37 mg	With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In tetrahydrofuran at 25℃; for 2h; Inert atmosphere;

Reference： [1]Schwärzer, Kuno; Tüllmann, Carl Phillip; Graßl, Simon; Górski, Bartosz; Brocklehurst, Cara E.; Knochel, Paul [Organic Letters, 2020, vol. 22, # 5, p. 1899 - 1902]

22
[ 1895-39-2 ]
[ 618-94-0 ]
[ 5565-72-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium phosphate In acetonitrile at 100℃; for 1h; Sealed tube; Inert atmosphere;	2. General procedure for the synthesis of 3 General procedure: CH3CN (2 mL) was added to a mixture of ClCF2COONa 2a (0.3 mmol, 1.5 equiv) and hydrazides 1 (0.2 mmol, 1 equiv) in the presence of K3PO4 (0.3 mmol, 1.5 equiv). Then the sealed tube was stirred at 100 °C under N2 for 1 h. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatograph (silica gel, petroleum ether:EtOAc = 2:1, v/v) to give the desired product 3.

Reference： [1]Wang, Ya; Mu, Shiqiang; Li, Xin; Song, Qiuling [Chinese Chemical Letters, 2022, vol. 33, # 3, p. 1511 - 1514]

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 5565-72-0 ]

Quality Control of [ 5565-72-0 ]

Related Doc. of [ 5565-72-0 ]

Product Details of [ 5565-72-0 ]

Safety of [ 5565-72-0 ]

Application In Synthesis of [ 5565-72-0 ]

[ 5565-72-0 ] Synthesis Path-Downstream 1~22

Related Functional Groups of [ 5565-72-0 ]

Aryls

Nitroes

Related Parent Nucleus of [ 5565-72-0 ]

Oxadiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5565-72-0 ]

Related Parent Nucleus of
[ 5565-72-0 ]