benzonitrile
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide In dimethyl sulfoxide at 140℃; for 1h; Solvent; Time; Temperature; | 100% |
With sodium azide In dimethyl sulfoxide at 120℃; for 0.166667h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Green chemistry; | 100% |
With sodium azide In N,N-dimethyl-formamide at 120℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Green chemistry; | 100% |
2-(α,α-dimethylbenzyl)-5-phenyltetrazole
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With potassium formate; palladium on activated charcoal In ethanol for 4h; Hydrogenolysis; Heating; | 100% |
Benzaldoxime
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In 5,5-dimethyl-1,3-cyclohexadiene at 138 - 144℃; for 4h; Solvent; Reagent/catalyst; Temperature; Green chemistry; | 99% |
With sodium azide; hydroxylamine hydrochloride In water at 70℃; for 1.41667h; Green chemistry; | 98% |
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; | 93% |
Conditions | Yield |
---|---|
With sodium azide; sodium phosphate In N,N-dimethyl-formamide at 110℃; for 5.7h; | 99% |
benzaldehyde
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; hydroxylamine hydrochloride In water at 20℃; for 0.116667h; Solvent; Temperature; Reagent/catalyst; Green chemistry; | 98% |
With sodium azide; hydroxylamine hydrochloride In water at 70℃; for 1.41667h; Reagent/catalyst; | 98% |
With sodium azide; hydroxylamine hydrochloride In water at 60℃; for 0.25h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Green chemistry; | 97% |
(Z)-benzaldehyde oxime
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; copper diacetate In N,N-dimethyl-formamide at 120℃; for 12h; | 98% |
benzyl alcohol
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; hydroxylamine hydrochloride In water at 20℃; for 2h; Reagent/catalyst; | 98% |
Multi-step reaction with 2 steps 1: copper(II) nitrate trihydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; ammonia / dimethyl sulfoxide; water / 8 h / 80 °C / 760.05 Torr / Sealed tube 2: sodium azide; copper(II) nitrate trihydrate / N,N-dimethyl-formamide / 16 h / 120 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1 h / 20 °C / 760.05 Torr 2: sodium azide / 5 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 2.44 wtpercent Co(III) TEMPO-porphyrin copolymer complex immobilized on silica shell-functionalized magnetic nano-Fe3O4 nanocatalyst / water / 0.5 h / 20 °C 2: sodium azide; hydroxylamine hydrochloride / water / 1.42 h / 70 °C View Scheme |
N-(triphenylmethyl)phenyltetrazole
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With naphthalene; lithium In tetrahydrofuran at -78℃; for 3h; Inert atmosphere; | 97% |
Stage #1: N-(triphenylmethyl)phenyltetrazole With methanol; indium In tetrahydrofuran at 78℃; for 26h; Stage #2: With hydrogenchloride In water at 20℃; | 93% |
With methanol; zinc In tetrahydrofuran for 3h; Reflux; | 92% |
Conditions | Yield |
---|---|
With sodium azide; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6.4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; | 97% |
toluene
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; hydroxylamine hydrochloride In water at 20℃; for 3.33333h; Reagent/catalyst; | 97% |
Multi-step reaction with 2 steps 1: water / 3 h / 20 °C 2: sodium azide; hydroxylamine hydrochloride / water / 1.42 h / 70 °C View Scheme |
Conditions | Yield |
---|---|
With sodium azide; potassium carbonate In ethanol; water for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Reflux; Inert atmosphere; Green chemistry; | 97% |
2-acetylaminomethyl-5-phenyltetrazole
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With hydrogenchloride at 60 - 70℃; for 1h; Product distribution; Further Variations:; Reagents; | 95% |
2-allyl-5-phenyl-2H-tetrazole
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With t-ByMgCl; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; toluene at 20℃; for 0.0833333h; | 95% |
1-benzyl-5-phenyl-1H-tetrazole
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With indium In tetrahydrofuran; methanol for 20h; Reagent/catalyst; Time; Reflux; | 95% |
With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 50 - 65℃; for 22h; | 86% |
With Pd/C; hydrogen at 140℃; under 3000.3 Torr; for 6h; |
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With triazidochlorosilane In acetonitrile for 2h; Heating; | 92% |
With picoline; diphenyl phosphoryl azide for 16h; Reagent/catalyst; Reflux; Inert atmosphere; | 88% |
syn-benzaldehyde oxime
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; copper(II) ferrite In N,N-dimethyl-formamide at 120℃; for 12h; Sealed tube; | 92% |
Conditions | Yield |
---|---|
Stage #1: dimethyl sulfoxide; phenylboronic acid With C37H35N2O2PPd; ammonium bicarbonate; potassium hydroxide In water for 2h; Stage #2: With sodium azide In water at 90℃; Catalytic behavior; Reagent/catalyst; Solvent; | 92% |
benzenecarbothioamide
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; tetrachlorosilane In acetonitrile at 20 - 82℃; for 1.66667h; | 88% |
phenylacetylene
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; tetrabutylammomium bromide at 105℃; for 24h; Solvent; Temperature; Sealed tube; Green chemistry; | 87% |
Conditions | Yield |
---|---|
With sodium azide; sodium phosphate In N,N-dimethyl-formamide at 110℃; for 9h; | 86% |
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 65℃; for 3h; dealkylation; | 83% |
5-hydrazinyl-1H-tetrazole
triethoxyphenylsilane
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h; Hiyama Coupling; | 82% |
Conditions | Yield |
---|---|
With sodium azide; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 9.6h; | 79% |
With 1,4-diaza-bicyclo[2.2.2]octane; sodium azide; palladium diacetate; sodium carbonate; zinc dibromide In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere; | 69% |
1-benzyl-5-bromo-1H-tetrazole
phenylboronic acid
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
Stage #1: 1-benzyl-5-bromo-1H-tetrazole; phenylboronic acid With palladium on carbon; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1'-biphenyl)[2-(2-amino-1,1’-biphenyl)]palladium(II)methanesulfonate; caesium carbonate In water; toluene at 100℃; for 4h; Inert atmosphere; Stage #2: With hydrogen In ethanol; water; toluene at 40℃; under 1500.15 Torr; for 18h; Pressure; Solvent; Temperature; Reagent/catalyst; | 65% |
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With naphthalene; lithium In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
With copper diacetate; palladium dichloride In dimethyl sulfoxide; acetonitrile at 90℃; for 2h; | 62% |
5-(2-bromophenyl)-1H-tetrazole
3-Aminophenylboronic acid
B
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 115℃; for 0.5h; Suzuki-Miyaura reaction; microwave irradiation; | A 60% B n/a |
5-(2-bromophenyl)-1H-tetrazole
3-methoxyphenylboronic acid
B
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 115℃; under 6000.48 - 9000.72 Torr; for 0.5h; Suzuki-Miyaura reaction; microwave irradiation; | A 58% B n/a |
5-(2-bromophenyl)-1H-tetrazole
3-fluorophenylboronic acid
B
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 115℃; for 0.5h; Suzuki-Miyaura reaction; microwave irradiation; | A 58% B n/a |
5-Phenyl-1H-tetrazole
tert-butyl alcohol
2-(tert-butyl)-5-phenyl-2H-tetrazole
Conditions | Yield |
---|---|
With sulfuric acid for 0.5h; | 100% |
With sulfuric acid In chloroform Heating; | 98% |
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20 - 25℃; for 48h; regioselective reaction; | 74% |
5-Phenyl-1H-tetrazole
cyclohexene
2-cyclohexyl-5-phenyl-2H-tetrazole
Conditions | Yield |
---|---|
With sulfuric acid | 100% |
5-Phenyl-1H-tetrazole
p-methylbenzoic anhydride
2-(4-methylphenyl)-5-phenyl-1,3,4-oxadiazole
Conditions | Yield |
---|---|
99% |
5-Phenyl-1H-tetrazole
p-N,N-dimethylaminobenzoic anhydride
2-(N,N-dimethyl-4-aminophenyl)-5-phenyl-1,3,4-oxadiazole
Conditions | Yield |
---|---|
In xylene | 99% |
5-Phenyl-1H-tetrazole
2-methylbenzoic anhydride
2-(2-methylphenyl)-5-phenyl-1,3,4-oxadiazole
Conditions | Yield |
---|---|
99% |
Conditions | Yield |
---|---|
In methanol at 5 - 20℃; | 99% |
5-Phenyl-1H-tetrazole
N,N-dimethyl-formamide
2-(1H-tetrazol-5-yl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 5-Phenyl-1H-tetrazole With sec.-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; | 99% |
Conditions | Yield |
---|---|
With macrocyclic cyclooctene-supported AlCl-salen catalyst In toluene at 55℃; for 26h; | 98% |
Conditions | Yield |
---|---|
With {(2S)-2-{bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}-1-pyrrolidinyl}[4-(1-pyrrolidinyl)-3-pyridinyl]methanone; triethylamine In diethyl ether at 23℃; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 23℃; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 23℃; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
With C28H28N2O2; dibutylmagnesium In n-heptane; toluene at 20℃; for 2h; Inert atmosphere; Molecular sieve; | 98% |
5-Phenyl-1H-tetrazole
trityl chloride
N-(triphenylmethyl)phenyltetrazole
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium carbonate In chloroform; water at 0 - 5℃; for 3 - 4h; Product distribution / selectivity; | 97.66% |
With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate In dichloromethane; water at 0 - 5℃; for 3 - 4h; Product distribution / selectivity; | 97.5% |
With tetraheptylammonium bromide; sodium carbonate In dichloromethane; water at 0 - 5℃; for 3 - 4h; Product distribution / selectivity; | 95.9% |
5-Phenyl-1H-tetrazole
p-nitrobenzoic anhydride
2-(4-nitrophenyl)-5-phenyl-1,3,4-oxadiazole
Conditions | Yield |
---|---|
In xylene | 97% |
5-Phenyl-1H-tetrazole
2-fluorobenzoic anhydride
Conditions | Yield |
---|---|
97% |
5-Phenyl-1H-tetrazole
phenyl isocyanate
2-phenylamino-5-phenyl-1,3,4-oxadiazole
Conditions | Yield |
---|---|
In nitrobenzene at 150℃; for 2h; | 97% |
Conditions | Yield |
---|---|
With C28H28N2O2; dibutylmagnesium In n-heptane; toluene at 20℃; for 2h; Inert atmosphere; Molecular sieve; | 97% |
5-Phenyl-1H-tetrazole
tert-butyl alcohol
Conditions | Yield |
---|---|
With perchloric acid In acetic acid at 20℃; for 48h; Addition; | 96% |
The CAS registry number of 5-Phenyltetrazole is 18039-42-4. The IUPAC name is 5-phenyl-2H-tetrazole. Its EINECS registry number is 241-950-8. In addition, the molecular formula is C7H6N4 and the molecular weight is 146.15. It is a kind of white to almost white crystalline powder and belongs to the classes of Miscellaneous; Building Blocks; Heterocyclic Building Blocks; Tetrazoles. What's more, it should be stored in a airtight, cool and dry place.
Physical properties about this chemical are: (1)ACD/LogP: 1.65; (2)ACD/LogD (pH 5.5): 0.65; (3)ACD/LogD (pH 7.4): -0.3; (4)ACD/BCF (pH 5.5): 1.06; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 18.94; (7)ACD/KOC (pH 7.4): 2.12; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 43.6 Å2; (12)Index of Refraction: 1.619; (13)Molar Refractivity: 39.55 cm3; (14)Molar Volume: 112.7 cm3; (15)Polarizability: 15.67 ×10-24cm3; (16)Surface Tension: 67.1 dyne/cm; (17)Density: 1.296 g/cm3; (18)Flash Point: 161.3 °C; (19)Enthalpy of Vaporization: 57.31 kJ/mol; (20)Boiling Point: 330.5 °C at 760 mmHg; (21)Vapour Pressure: 0.000165 mmHg at 25°C.
Preparation of 5-Phenyltetrazole: firstly, let kenzonitrile reacting with the hydrazine or hydrazine salt, then react with nitrous acid to get the product. In addition, it also can be prepared by benzonitrile. This reaction will need reagents NaN3 and NH4Cl and solvent dimethylformamide. The reaction time is 17 hours by heating. The yield is about 89%.
Uses of 5-Phenyltetrazole: this chemical can be used as intermediates of ace transformation enzyme inhibitors. And it can react with chloroacetic acid to get 2-chloromethyl-5-phenyl-[1,3,4]oxadiazole. This reaction will need reagent dicyclohexylcarbodiimide and solvent toluene. The reaction time is 15 minutes at reaction temperature of 120 °C. The yield is about 81%.
When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, irritating to eyes, respiratory system and skin and harmful if swallowed. And it has risk of explosion if heated under confinement. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. You should keep away from sources of ignition. Although it is slightly harmful to the water, you can not let a large number of this products contact with the groundwater, the waterway or sewage system. If without government permission, do not put this material into surroundings.
You can still convert the following datas into molecular structure:
(1)SMILES: n1nnnc1c2ccccc2
(2)InChI: InChI=1/C7H6N4/c1-2-4-6(5-3-1)7-8-10-11-9-7/h1-5H,(H,8,9,10,11)
(3)InChIKey: MARUHZGHZWCEQU-UHFFFAOYAI
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 890mg/kg (890mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | National Technical Information Service. Vol. OTS0570992, |
rat | LD50 | oral | 1901mg/kg (1901mg/kg) | National Technical Information Service. Vol. OTS0570992, |
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