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18039-42-4

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18039-42-4 Usage

Synthesis

5-Phenyltetrazole can be prepared by reacting benzonitrile with hydrazine or hydrazine salt, and then reacting with nitrous acid.

Chemical Properties

white to almost white crystalline powder

Uses

Different sources of media describe the Uses of 18039-42-4 differently. You can refer to the following data:
1. 5-Phenyl-1H-tetrazole can be used as an etching solution composing metal wire layer to improve the production efficiency of panel manufacturing and cost reduction.
2. 5-Phenyl-1H-tetrazole may be used as ligand in the solvothermal synthesis of 3D polyoxometalate-based silver coordination polymers. It was used in the synthesis of 5-phenyltetrazolate organolanthanide complexes. It was used to investigate the corrosion inhibition of copper in salt water.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 3908, 1958 DOI: 10.1021/ja01548a028Tetrahedron Letters, 38, p. 1257, 1997 DOI: 10.1016/S0040-4039(97)00052-XTetrahedron, 51, p. 11737, 1995 DOI: 10.1016/0040-4020(95)00725-N

General Description

Nucleophilic substitution reactions on 1,4-dimethoxybenzene and 1,3,5-trimethoxybenzene by the anions of 5-phenyl-1H-tetrazole has been investigated by paired electrosynthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 18039-42-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,0,3 and 9 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 18039-42:
(7*1)+(6*8)+(5*0)+(4*3)+(3*9)+(2*4)+(1*2)=104
104 % 10 = 4
So 18039-42-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H5N4/c1-2-4-6(5-3-1)7-8-10-11-9-7/h1-5H/q-1

18039-42-4 Well-known Company Product Price

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  • Alfa Aesar

  • (B25664)  5-Phenyl-1H-tetrazole, 99%   

  • 18039-42-4

  • 25g

  • 354.0CNY

  • Detail
  • Alfa Aesar

  • (B25664)  5-Phenyl-1H-tetrazole, 99%   

  • 18039-42-4

  • 100g

  • 667.0CNY

  • Detail
  • Aldrich

  • (347744)  5-Phenyl-1H-tetrazole  99%

  • 18039-42-4

  • 347744-25G

  • 567.45CNY

  • Detail
  • Aldrich

  • (347744)  5-Phenyl-1H-tetrazole  99%

  • 18039-42-4

  • 347744-100G

  • 1,223.82CNY

  • Detail

18039-42-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Phenyltetrazole

1.2 Other means of identification

Product number -
Other names 5-phenyl-1,2,3,4-tetrazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:18039-42-4 SDS

18039-42-4Synthetic route

benzonitrile
100-47-0

benzonitrile

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
165670-57-5

2-(α,α-dimethylbenzyl)-5-phenyltetrazole

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With potassium formate; palladium on activated charcoal In ethanol for 4h; Hydrogenolysis; Heating;100%
Benzaldoxime
932-90-1

Benzaldoxime

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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%
iodobenzene
591-50-4

iodobenzene

potassium tetracyanonickelate(II)

potassium tetracyanonickelate(II)

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; sodium phosphate In N,N-dimethyl-formamide at 110℃; for 5.7h;99%
benzaldehyde
100-52-7

benzaldehyde

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
622-32-2

(Z)-benzaldehyde oxime

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; copper diacetate In N,N-dimethyl-formamide at 120℃; for 12h;98%
benzyl alcohol
100-51-6

benzyl alcohol

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
154750-11-5

N-(triphenylmethyl)phenyltetrazole

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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%
iodobenzene
591-50-4

iodobenzene

potassium ferrocyanide

potassium ferrocyanide

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6.4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;97%
toluene
108-88-3

toluene

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
potassium cyanide

potassium cyanide

phenylboronic acid
98-80-6

phenylboronic acid

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
659741-18-1

2-acetylaminomethyl-5-phenyltetrazole

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With hydrogenchloride at 60 - 70℃; for 1h; Product distribution; Further Variations:; Reagents;95%
2-allyl-5-phenyl-2H-tetrazole
65103-37-9

2-allyl-5-phenyl-2H-tetrazole

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
28386-90-5

1-benzyl-5-phenyl-1H-tetrazole

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With triazidochlorosilane In acetonitrile for 2h; Heating;92%
With picoline; diphenyl phosphoryl azide for 16h; Reagent/catalyst; Reflux; Inert atmosphere;88%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; copper(II) ferrite In N,N-dimethyl-formamide at 120℃; for 12h; Sealed tube;92%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

phenylboronic acid
98-80-6

phenylboronic acid

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
2227-79-4

benzenecarbothioamide

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; tetrachlorosilane In acetonitrile at 20 - 82℃; for 1.66667h;88%
phenylacetylene
536-74-3

phenylacetylene

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; tetrabutylammomium bromide at 105℃; for 24h; Solvent; Temperature; Sealed tube; Green chemistry;87%
bromobenzene
108-86-1

bromobenzene

potassium tetracyanonickelate(II)

potassium tetracyanonickelate(II)

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; sodium phosphate In N,N-dimethyl-formamide at 110℃; for 9h;86%
2-benzyloxymethyl-5-phenyl-2H-tetrazole

2-benzyloxymethyl-5-phenyl-2H-tetrazole

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With hydrogenchloride In methanol at 65℃; for 3h; dealkylation;83%
5-hydrazinyl-1H-tetrazole
40925-73-3

5-hydrazinyl-1H-tetrazole

triethoxyphenylsilane
780-69-8

triethoxyphenylsilane

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h; Hiyama Coupling;82%
bromobenzene
108-86-1

bromobenzene

potassium ferrocyanide

potassium ferrocyanide

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
79344-08-4

1-benzyl-5-bromo-1H-tetrazole

phenylboronic acid
98-80-6

phenylboronic acid

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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%
2,2-dimethyl-1-(5-phenyl-1H-tetrazol-1-yl)propan-1-one

2,2-dimethyl-1-(5-phenyl-1H-tetrazol-1-yl)propan-1-one

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;63%
CHN4O2S(1-)*Na(1+)

CHN4O2S(1-)*Na(1+)

phenylboronic acid
98-80-6

phenylboronic acid

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With copper diacetate; palladium dichloride In dimethyl sulfoxide; acetonitrile at 90℃; for 2h;62%
5-(2-bromophenyl)-1H-tetrazole
73096-42-1

5-(2-bromophenyl)-1H-tetrazole

3-Aminophenylboronic acid
30418-59-8

3-Aminophenylboronic acid

A

2'-(1H-tetrazol-5-yl)biphenyl-3-ylamine

2'-(1H-tetrazol-5-yl)biphenyl-3-ylamine

B

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
73096-42-1

5-(2-bromophenyl)-1H-tetrazole

3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

A

5-(3'-methoxy-biphenyl-2-yl)-1H-tetrazole

5-(3'-methoxy-biphenyl-2-yl)-1H-tetrazole

B

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
73096-42-1

5-(2-bromophenyl)-1H-tetrazole

3-fluorophenylboronic acid
768-35-4

3-fluorophenylboronic acid

A

5-(3'-fluoro-biphenyl-2-yl)-1H-tetrazole

5-(3'-fluoro-biphenyl-2-yl)-1H-tetrazole

B

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
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
18039-42-4

5-Phenyl-1H-tetrazole

tert-butyl alcohol
75-65-0

tert-butyl alcohol

2-(tert-butyl)-5-phenyl-2H-tetrazole
59772-96-2

2-(tert-butyl)-5-phenyl-2H-tetrazole

Conditions
ConditionsYield
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
18039-42-4

5-Phenyl-1H-tetrazole

cyclohexene
110-83-8

cyclohexene

2-cyclohexyl-5-phenyl-2H-tetrazole
140406-56-0

2-cyclohexyl-5-phenyl-2H-tetrazole

Conditions
ConditionsYield
With sulfuric acid100%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

p-methylbenzoic anhydride
13222-85-0

p-methylbenzoic anhydride

2-(4-methylphenyl)-5-phenyl-1,3,4-oxadiazole
1874-47-1

2-(4-methylphenyl)-5-phenyl-1,3,4-oxadiazole

Conditions
ConditionsYield
99%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

p-N,N-dimethylaminobenzoic anhydride
7474-31-9

p-N,N-dimethylaminobenzoic anhydride

2-(N,N-dimethyl-4-aminophenyl)-5-phenyl-1,3,4-oxadiazole
1874-35-7

2-(N,N-dimethyl-4-aminophenyl)-5-phenyl-1,3,4-oxadiazole

Conditions
ConditionsYield
In xylene99%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

2-methylbenzoic anhydride
607-86-3

2-methylbenzoic anhydride

2-(2-methylphenyl)-5-phenyl-1,3,4-oxadiazole
59663-63-7

2-(2-methylphenyl)-5-phenyl-1,3,4-oxadiazole

Conditions
ConditionsYield
99%
morpholine
110-91-8

morpholine

formaldehyd
50-00-0

formaldehyd

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

4-(5-phenyltetrazol-1-ylmethyl)-morpholine

4-(5-phenyltetrazol-1-ylmethyl)-morpholine

Conditions
ConditionsYield
In methanol at 5 - 20℃;99%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-(1H-tetrazol-5-yl)benzaldehyde
205452-86-4

2-(1H-tetrazol-5-yl)benzaldehyde

Conditions
ConditionsYield
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%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

C11H11NO2
247043-59-0

C11H11NO2

C18H17N5O2
1136090-60-2

C18H17N5O2

Conditions
ConditionsYield
With macrocyclic cyclooctene-supported AlCl-salen catalyst In toluene at 55℃; for 26h;98%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

isobutyraldehyde
78-84-2

isobutyraldehyde

(S)-2-methyl-1-(5-phenyl-2H-tetrazol-2-yl)propyl isobutyrate

(S)-2-methyl-1-(5-phenyl-2H-tetrazol-2-yl)propyl isobutyrate

Conditions
ConditionsYield
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%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

acetaldehyde
75-07-0

acetaldehyde

diethyl dicarbonate
1609-47-8

diethyl dicarbonate

ethyl (1-(5-phenyl-2H-tetrazol-2-yl)ethyl) carbonate

ethyl (1-(5-phenyl-2H-tetrazol-2-yl)ethyl) carbonate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 23℃; regioselective reaction;98%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

acetaldehyde
75-07-0

acetaldehyde

ethyl (1-(5-phenyl-2H-tetrazol-2-yl)ethyl) carbonate

ethyl (1-(5-phenyl-2H-tetrazol-2-yl)ethyl) carbonate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 23℃; regioselective reaction;98%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

C10H12N2O

C10H12N2O

C17H18N6O

C17H18N6O

Conditions
ConditionsYield
With C28H28N2O2; dibutylmagnesium In n-heptane; toluene at 20℃; for 2h; Inert atmosphere; Molecular sieve;98%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

trityl chloride
76-83-5

trityl chloride

N-(triphenylmethyl)phenyltetrazole
154750-11-5

N-(triphenylmethyl)phenyltetrazole

Conditions
ConditionsYield
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
18039-42-4

5-Phenyl-1H-tetrazole

p-nitrobenzoic anhydride
902-47-6

p-nitrobenzoic anhydride

2-(4-nitrophenyl)-5-phenyl-1,3,4-oxadiazole
1090-82-0

2-(4-nitrophenyl)-5-phenyl-1,3,4-oxadiazole

Conditions
ConditionsYield
In xylene97%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

2-fluorobenzoic anhydride
64508-63-0

2-fluorobenzoic anhydride

2-(2-fluorophenyl)-5-phenyl-1,3,4-oxadiazole

2-(2-fluorophenyl)-5-phenyl-1,3,4-oxadiazole

Conditions
ConditionsYield
97%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

phenyl isocyanate
103-71-9

phenyl isocyanate

2-phenylamino-5-phenyl-1,3,4-oxadiazole
1148-89-6

2-phenylamino-5-phenyl-1,3,4-oxadiazole

Conditions
ConditionsYield
In nitrobenzene at 150℃; for 2h;97%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

C12H16N2O

C12H16N2O

C19H22N6O

C19H22N6O

Conditions
ConditionsYield
With C28H28N2O2; dibutylmagnesium In n-heptane; toluene at 20℃; for 2h; Inert atmosphere; Molecular sieve;97%
5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

tert-butyl alcohol
75-65-0

tert-butyl alcohol

1-H-3-tret-butyl-5-phenyltetrazolium perchlorate

1-H-3-tret-butyl-5-phenyltetrazolium perchlorate

Conditions
ConditionsYield
With perchloric acid In acetic acid at 20℃; for 48h; Addition;96%

18039-42-4Relevant articles and documents

Tetrazoles: XLV. Amidoalkylation of 5-Substituted Tetrazoles

Myznikov,Esikov,Artamonova,Koldobskii

, p. 731 - 734 (2003)

Amidoalkylation of 5-aryl(hetaryl)tetrazoles with N-hydroxymethylamides of aliphatic and aromatic carboxylic acids occurs regioselectively and yields mainly 5-aryl(hetaryl)-2-acylaminomethyltetrazoles. These compounds are fairly stable in neutral media bu

Tetrazoles: Calcium oxalate crystal growth modifiers

McMulkin, Calum J.,Massi, Massimiliano,Jones, Franca

, p. 2675 - 2681 (2015)

Molecules containing tetrazole substituents have become of interest due to their being bioisosteres of carboxylic acids and like their carboxylate counterparts, tetrazolate anions have been able to affect the crystal growth of barium sulphate and calcium carbonate. In this proof of principle study, we show that this behaviour also extends to calcium oxalate and therefore opens the possibility of using tetrazole-based additives for investigating mineralization processes of human pathological relevance. This journal is

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Washburne,Peterson

, p. 427 (1970)

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Non-catalyzed addition of heterocyclic thiols and 5-substituted-1H-tetrazoles to vinyl ethers

Melnikova, Iuliia,Roh, Jaroslav,Kune?, Ji?í,Artamonova, Tatiana,Zevatskii, Yuri,Myznikov, Leonid

, p. 3842 - 3845 (2017)

The alkylation of 1-substituted 1H-tetrazole-5-thiols and 4-substituted 4 H-1,2,4-triazole-3-thiols with alkyl halides or sulfonates lead to the formation of S-alkylated products regardless of the substituent on the heterocycle. In this work, we found that substituted 1H-tetrazole-5-thiols and 4 H-1,2,4-triazole-3-thiols readily reacted with vinyl ethers in the absence of a catalyst to exclusively form N-substituted 1H-tetrazole-5(4H)-thiones and 1H-1,2,4-triazole-5(4H)-thiones, respectively. Furthermore, the reactions of 5-substituted-1H-tetrazoles with vinyl ethers under the same conditions selectively yielded 2,5-disubstitued tetrazoles.

A novel route for the synthesis of 5-substituted 1-: H tetrazoles in the presence of polymer-supported palladium nanoparticles

Darbandizadeh Mohammad Abadi, Seyed Shahab Addin,Karimi Zarchi, Mohammad Ali

, p. 10397 - 10406 (2017)

A novel method for the synthesis of 5-substituted 1-H tetrazoles has been developed using one-pot tandem reactions of aryl halides with K4[Fe(CN)6] and sodium azide in the presence of cross-linked poly(4-vinylpyridine)-stabilized Pd(0) nanoparticles, [P4-VP]-PdNPs. The catalyst was characterized using various techniques such as FT-IR and UV-vis spectroscopy, AAS, TEM, FESEM, EDX analysis, XRD and XPS. The results confirm a good dispersion of palladium nanoparticles on the polymer support. The catalyst is reusable many times without a significant loss in its activity.

Dendron-functionalized Fe3O4 magnetic nanoparticles with palladium catalyzed CN insertion of arylhalide for the synthesis of tetrazoles and benzamide

Karimi Zarchi, Mohammad Ali,Darbandizadeh Mohammad Abadi, Seyed Shahab Addin

, p. 196 - 212 (2019)

A novel method for the one-pot synthesis of 5-substituted 1H-tetrazoles and Benzamide from arylhalide containing in situ CN insertion from inorganic salt source was accomplished in presence of a new magnetically catalyst, palladium on surface-modified Schiff-Base complex. K2[Ni(CN)4] plays a role of nontoxic inorganic cyanide source in arylhalide Nucleophilic substitution. The synthesized Pd-Schiff-Base@Fe3O4MNPs was characterized by various techniques such as FT-IR, TGA, SEM, VSM, XRD, TEM, ICP-AES, EDX, BET and XPS. The nano structure catalyst was easily recovered by external magnetic field and reused several times without noticeable loss of its catalytic activity. Leaching study of Pd-Schiff-Base@Fe3O4 MNPs shows palladium strong bonded to different active parts of catalyst surface. Heterogeneity of this catalyst has been examined using hot filtration and ICP-AES techniques.

1-Disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1H-tetrazoles

Aali, Elaheh,Gholizadeh, Mostafa,Noroozi-Shad, Nazanin

, (2021/08/30)

A simple, green and efficient method has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction in good to excellent yields between various benzonitriles and sodium azide. For this purpose, 1-disulfo-[2,2-bipyridine]-1,1-diium chloride ([BiPy](HSO3)2Cl2) system as an ionic liquid catalyst have been extended for the construction of these valuable products. This procedure has significant advantages, including using ethylene glycol as a green solvent. The other advantages of this method are inexpensive and ease the preparation of the catalyst, mild reaction conditions, green reaction medium, easy workup, short reaction time, and simple experimental process.

Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) Nanostructures

Baghershiroudi, Mahrokh,Bafandeh, Fereshteh Taghipour,Safa, Kazem D.,Panahi, Parvane Nakhostin

, p. 230 - 236 (2021/04/09)

Abstract: The synthesis of 5-substituted 1H-tetrazoles by use of a series of M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) nanocatalysts are presented. Following the optimized conditions, Co-SAPO-34 nanocatalyst has been found to effectively catalyze the 5-substi

Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex

Mahmoudi, Boshra,Rostami, Amin,Kazemnejadi, Milad,Hamah-Ameen, Baram Ahmed

, (2020/12/21)

A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.

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