Home Cart 0 Sign in  

[ CAS No. 16687-61-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 16687-61-9
Chemical Structure| 16687-61-9
Structure of 16687-61-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 16687-61-9 ]

Related Doc. of [ 16687-61-9 ]

Alternatived Products of [ 16687-61-9 ]

Product Details of [ 16687-61-9 ]

CAS No. :16687-61-9 MDL No. :MFCD00040952
Formula : C7H5ClN4 Boiling Point : -
Linear Structure Formula :- InChI Key :BGKOVWIBDZMJPN-UHFFFAOYSA-N
M.W : 180.59 Pubchem ID :257758
Synonyms :

Calculated chemistry of [ 16687-61-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.62
TPSA : 54.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 1.98
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 1.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.335 mg/ml ; 0.00186 mol/l
Class : Soluble
Log S (Ali) : -2.6
Solubility : 0.449 mg/ml ; 0.00249 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0431 mg/ml ; 0.000239 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 16687-61-9 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:1325
Hazard Statements:H315-H319-H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16687-61-9 ]

* 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.

  • Upstream synthesis route of [ 16687-61-9 ]
  • Downstream synthetic route of [ 16687-61-9 ]

[ 16687-61-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 3848-36-0 ]
  • [ 16687-61-9 ]
YieldReaction ConditionsOperation in experiment
99% With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In 5,5-dimethyl-1,3-cyclohexadiene for 4 h; Reflux; Green chemistry General procedure: DPPA (0.15 mmol) and DBU (0.30 mmol) were added to a solution of the appropriate aldoxime (0.10 mmol) in xylenes (0.5 mL). After stirring for 2–16 h at reflux, the mixture was cooled to r.t. and sat. aq NaHCO3 (2.0 mL) was added. After stirring for 5 min, the mixture was diluted with water (20 mL). The aqueous layer was then washed with EtOAc (25 mL) and acidified with 1 N aq HCl to pH 2. The aqueous layer was extracted with EtOAc (2 x 30 mL) and the combined organic extracts were washed with brine (30 mL) and dried over Na2SO4. Concentration of the solvent in vacuo followed by purification of the residue on a short column (silica gel, EtOAc–n-hexane, 1:1 to 3:1) gave the desired tetrazole.
90% With sodium azide; copper diacetate In N,N-dimethyl-formamide at 120℃; for 12 h; General procedure: A mixture of oxime (1 mmol), sodium azide (1.5 mmol), catalyst (25 mol percent), and DMF (3 mL) was taken in a 25 ml round bottomed flask and heated at 120 °C temperature for 12 h. under vigorous stirring. After completion of the reaction (observed on TLC) the reaction mass was cooled to rt. 5 ml of water was added followed by 5 mL of 2 N HCl. The mixture was stirred for 10 min. and the product was extracted with dichloromethane (3 .x. 10 mL). The organic layer was washed with water and dried over anhydrous sodium sulphate. Solvent was evaporated under reduced pressure to obtain the product. The crude product was purified on silica gel column by using pet ether and ethyl acetate as solvent to obtain the pure product. (98percent). The obtained product was analyzed by FTIR, 1H NMR and mass spectra.
89% With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene for 16 h; Reflux General procedure: DPPA (0.30 mmol) and DBU (0.60 mmol) were added to a solution of aldoxime (0.20 mmol) intoluene (1.0 mL). After stirring for 16 h at reflux, the mixture was cooled to room temperature andsaturated NaHCO3 aq. (2.0 mL) was added. After stirring for 5 min, the mixture was diluted withwater (20 mL). The aqueous layer was then washed with AcOEt (25 mL) and acidified with 1.0 NHCl aq. to pH 2. The aqueous layer was extracted with AcOEt (30 mL × 2), and the combinedorganic extracts were washed with brine (30 mL) and dried over Na2SO4. The concentration of thesolvent in vacuo followed by the purification of the residue through a short silica gel column(AcOEt:n-hexane 1:1-3:1) gave desired tetrazole
379.2 mg With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; Inert atmosphere General procedure: n-BuLi (1.55 M solution in hexane, 2.32 mL, 3.6 mmol) was added dropwise to a solution of 4-methylphenyl bromide (513 mg, 3.0 mmol) in THF (6.0 mL) at −50 °C under Ar atmosphere. After 30 min, DMF (278 μL, 3.6 mmol) was added and the obtained mixture was gradually warmed to r.t. After 1 h at the same temperature, NH2OHxHCl (313 mg, 4.5 mmol) and K2CO3 (622 mg, 4.5 mmol) were added and the obtained mixture was stirred for 2 h at r.t. Then, after removal of the solvent under reduced pressure, toluene (3.0 mL), DPPA (1.61 mL, 7.5 mmol), and DBU (1.57 mL, 10.5 mmol) were added to the obtained residue under Ar atmosphere. After being stirred for 16 h under refluxing conditions, the mixture was cooled to r.t. and then, saturated NaHCO3 aq. (15.0 mL) was added. After being stirred for 5 min, the mixture was diluted with water (5.0 mL). The aqueous layer was then washed with AcOEt (25.0 mL) and acidified with 1.0 M HCl aq. to pH 2. The aqueous layer was extracted with AcOEt (2 x 25.0 mL). Removal of the solvent, followed by purification of the residue by short column chromatography on neutral silica gel (AcOEt: hexane = 1:3–1:1) gave 5-(4′-methylphenyl)tetrazole 3A (336.1 mg, 70percent).

Reference: [1] Synthesis (Germany), 2018, vol. 50, # 6, p. 1293 - 1300
[2] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3706 - 3709
[3] Synlett, 2016, vol. 27, # 15, p. 2225 - 2228
[4] Tetrahedron Letters, 2016, vol. 57, # 5, p. 523 - 524
[5] Tetrahedron, 2018, vol. 74, # 31, p. 4226 - 4235
  • 2
  • [ 623-03-0 ]
  • [ 16687-61-9 ]
YieldReaction ConditionsOperation in experiment
99% With sodium azide; ammonium cerium (IV) nitrate In N,N-dimethyl-formamide at 110℃; for 6 h; Inert atmosphere; Green chemistry General procedure: sodiumazide (1.5 mmol) was added to a magnetically stirred solution of nitrile 1a(1 mmol) in anhydrous DMF and the CAN (10 mmol percent) was added. The reactionmixture was constantly stirred for another 6 h at 110 C under nitrogenatmosphere. After the completion of reaction as seen by TLC, the reactionmixture was brought to room temperature and the solvent was evaporatedunder vacuum. The crude thus obtained, was dissolved in ethyl acetate (20 mL)and solution was washed with acidified water (4 M HCl, 15 mL) twice.Separated organic layer was washed with brine solution dried overanhydrous Na2SO4, and solvent was removed under high vacuum to obtaintetrazole 1b as a white crystalline solid in 97percent yield.
99% With sodium azide In N,N-dimethyl-formamide at 120℃; for 4 h; General procedure: Cu(II)-NaY (0.1 g) was added to a mixture of benzonitrile (0.206 g, 2.0 mmol) and sodium azide (0.169 g, 2.6 mmol) in DMF (5 mL) and mixture was stirred at 120 °C for 3 h. After completion of reaction (as monitored by TLC), the catalyst was centrifuged, washed with ethyl acetate and the centrifugate was treated with ethyl acetate (30 mL) and 5 N HCl (20 mL) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined organic layers were washed with water and concentrated to give the crude solid crystalline 5-phenyltetrazole. The product was characterizedby 1H NMR , 13C NMR and mass spectroscopic analysis.
97% With sodium azide In N,N-dimethyl-formamide at 90℃; for 3 h; General procedure: In a double-necked round bottom flask (100 mL) equippedwith a condenser was added a mixture consisting ofnitrile (0.005 mol), NaN3 (0.006 mol), and monodisperse Pt NPsVC in DMF (1.5 mL). The mixture washeated at reflux until TLC monitoring indicated no furtherimprovement in the conversion. The reaction mixture wasthen cooled to room temperature, vacuum-filtered usinga sintered-glass funnel and the residue was washed withethyl acetate (3×10 mL). The filtrate was treated with5 mL HCl (4 mol L−1 to reach pH= 3 and it was allowedto stir for 30 minutes. Subsequently, the organic layer wasseparated, dried over anhydrous Na2SO4 and evaporated.The crude product was purified by recrystallization and/orcolumn chromatography on silica gel eluted with propersolvents to get pure 5-Phenyl 1H-tetrazole.
96% With sodium azide In water at 100℃; for 2 h; Green chemistry General procedure: Benzonitrile (1 mmol, 0.103 g), sodium azide (1.1 mmol, 0.0759 g), and 2 mL water were taken in a reaction tube and stirred at room temperature to make homogeneous suspension, and then 20 wtpercent catalyst (ZnO–RGO) was added to the reaction mixture. The reaction mixture was heated to 100 °C for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and centrifuged. The filtrate was treated with 5N HCl (10 mL) and then with ethyl acetate. The organic layer was separated, washed with deionized water, and then dried over anhydrous sodium sulfate and concentrated to give the crude solid crystalline 5-phenyl-1H-tetrazole. It was recrystallized from n-hexane, ethyl acetate, and the yield was about 0.143 g.
95% at 120℃; for 4 h; General procedure: A mixture of the required nitrile (1 mmol), sodium azide(1 mmol) and the catalyst MNP (0.05 g) was stirred at 120° C in PEG (1 mL) as solvent. After completion of the reaction, as indicated by TLC, the mixture was cooled to room temperature and diluted with 1:1 H2O:Ethyl acetate(10 mL) and then stirred at ambient temperature (10 min). The catalyst was removed by applying a magnetic field, and the decantate was treated with HCl (4 N, 10 mL). The organic layer was separated, washed with water, dried over sodium sulfate and concentrated to precipitate the crude crystalline solid. The pure tetrazoles were characterized bytheir spectroscopic data and melting points.
95% With sodium azide; aminosulfonic acid In N,N-dimethyl-formamide at 120℃; for 5 h; General procedure: A mixture of 4-nitrobenzonitrile (0.296 g, 2 mmol), sodium azide (0.195 g, 3 mmol), and sulfamic acid (0.0097 g, 0.1 mmol) was stirred at 120°C in DMF (5 mL) for the appropriate time (Table 2) until TLC (4:1 n-hexane:ethyl acetate) indicated no further progress in the conversion. After completion of the reaction (as monitored by TLC), the reaction mixture was cooled to room temperature, then 20 mL diethyl ether was added to the mixture and stirred for 10 minutes. The catalyst was separated by simple gravity filtration, washed with diethyl ether (2 £ 10 mL) and dried at 40°C for 30 min. The recovered catalyst wasused for three additional cycles and gave the tetrazole in 95, 85 and 75percent (with 4-nitrobenzonitrile). The filtrate was treated with ethyl acetate (30 mL) and 6 N HCl(20 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 5-(4-nitrophenyl) tetrazole (0.363 g), 95percent yield.
95% at 120℃; for 2 h; General procedure: To a stirred mixture of sodium azide (1.2 mmol) in PEG-400(2 mL), a nitrile compound (1 mmol) and NiNP-PNF (200 mL) were added and heated at 120°C under atmospheric conditions.The reaction progress was monitored by TLC. Upon reaction completion, the mixture was allowed to cool to ambient temperature and then filtered and extracted with ethyl acetate. The organic layer was washed with 1N HCl, dried with anhydrous Na2SO4, and filtered to afford pure 5-substituted tetrazoles.
95% at 120℃; for 0.333333 h; Green chemistry General procedure: To a suspension of the catalyst (0.004 g) in PEG (2 mL), nitrile (1 mmol) and sodium azide (1.2 mmol) were added and the mixture was stirred vigorously at 120 °C for the required time (Table 6). After the reaction was completed (as monitored by TLC), the catalyst was separated with a magnet. HCl (4 N, 10 mL) was then added to the residue, and the tetrazole was extracted with ethyl acetate. The organic extract was washed with distilled water, dried over anhydrous Na2SO4 and then evaporated to give the desired tetrazole.
95% With sodium azide; C19H17N3O4(2-)*Cu(2+) In ethylene glycol at 120℃; for 3 h; General procedure: In 25mL round-bottomed flask, sodium azide (0.076g, 1.2mmol) and polymeric copper (II) complex (0.005g) were added to a solution of benzonitrile (0.103g, 1mmol) in ethylene glycol (3mL) with stirring at room temperature. The reaction temperature was raised up to 120°C for 3h. The reaction was monitored by TLC at regular intervals. After completion of the reaction, the reaction mixture was cooled to room temperature and treated with 10mL HCl (2N) and extracted with 10mL ethyl acetate. The resulted organic layers were separated and washed with 2×10mL distilled water, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel (100–200 mesh) to afford the corresponding products.
94% With sodium azide In N,N-dimethyl-formamide at 110℃; for 2.5 h; Green chemistry General procedure: A mixtureof benzonitrile and sodium azide was added to 0.5g of 30molpercent CAN supportedHY-zeolite in DMF. Then the reaction mixture was stirred at 110 °C forspecified time. The progress of the reaction was monitored by TLC. Aftercompletion of the reaction the catalyst was removed by simple filtration andthe filtrate was treated with 1N HCl solution followed by extraction with ethylacetate twice. The combined organic layer was finally washed with water anddried over anhydrous sodium sulfate and was evaporated under reduced pressure.The crude product was recrystallized from hot ethanol to obtain pure 5-phenyl-1H-tetrazole. The same procedure has beenfollowed for other tetrazole derivatives. All the synthesized compounds except 10& 11 (Table 4) are known compounds and their spectral dataand physical properties are identical with those reported in literature.
94% at 140℃; for 0.833333 h; Green chemistry General procedure: NaN3 (0.975 g, 15 mmol) was dissolved in DES (10 mL) at room temperature by stirring until a clear solution was formed. Then benzonitrile (10 mmol) was added. The reaction mixture was constantly stirred at 140 °C and monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and poured into the cold water (10 mL). The solid was obtained and filtered. The obtained solid is taken into cold water (10 mL). Then it was acidified carefully to pH 5 with 5 M HCl. The organic material was extracted thrice with ethyl acetate; the resultant organic layer was washed with distilled water, dried over anhydrous sodium sulfate, and concentrated to give the crude solid crystalline 5-substituted 1H-tetrazole. The resulting product, although evident as a single compound by TLC, was purified by simple recrystallization from aqueous ethanol giving pure 5-substituted 1H-tetrazoles.
94% With sodium azide; <i>L</i>-proline In N,N-dimethyl-formamide at 110℃; Green chemistry General procedure: The mixture of organic nitrile (1 mmol), NaN3 (1.25 mmol) and L-proline (30 molpercent) in DMF (5mL) was stirred at 110 °C for 1-2 h. The progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the reaction mixture was allowed to cool to room temperature. Thecooled reaction mixture was poured in ice water (15 mL) with stirring. The resulting mixture wasacidified with dilute HCl under vigorous stirring. The solid product* was filtered under suction,washed with sufficient cold water till free of acid. The product was air dried to obtain the pureproduct.*In cases where solid product was not obtained after acidification, like benzyl cyanide andaliphatic nitriles, the acidified aqueous phase was extracted with ethyl acetate (2 X 20 mL), thecombined organic phase was washed with brine, dried over anhydrous sodium sulfate andconcentrated in vacuo to get the corresponding pure product.
93% With sodium azide In dimethyl sulfoxide at 85℃; for 12 h; General procedure: General procedure for the synthesis of Tetrazole. A mixture of benzonitrile (103 mg, 1 mmol), sodium azide (97.5 mg, 1.5 mmol), and 3 mL DMSO solvent was added in a 25 mL round bottomed flask. Further (50 mg, 23 mol percent, w/w) catalyst was added to the reaction mixture. The reaction mixture was heated to 85 °C for 12 h. After completion of the reaction (as monitored by TLC), the catalyst was separated by simple filtration, washed with diethyl ether and the filtrate was treated with ethyl acetate (30 mL) and 5 N HCl (20 mL) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined organic layers were washed with water and dried over anhydrous sodium sulfate and were evaporated under reduced pressure to give the product. The product was purified by the column chromatography. The structure was confirmed by spectral analysis (1H NMR, mass and elemental analysis).
93% With sodium azide In N,N-dimethyl-formamide at 110℃; for 4 h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), Cu complex catalyst (0.4 molpercent) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 110 °C temperature. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (2 × 20 mL) and 1 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2 × 15 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product.
93% With sodium azide; Acetate de N,N-dimethylamino-4 pyridinium In neat (no solvent) at 100℃; for 2 h; General procedure: To a round-bottomed flask containing 4-(N,N-dimethylamino)pyridiniumacetate (0.15 mmol, 0.02 g) at 100 C, 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.06 g) were added and the mixture was stirred. After1 h, the reaction was complete. The mixture was cooled and washed with coldEtOH (2 5 mL), each time it was permitted to stir for 1 h. Filtration followed bydrying of the precipitate gave the corresponding pure tetrazole
93% With sodium azide; silver(I) triflimide In toluene at 85℃; for 3 h; General procedure: A mixture of the appropriate nitrile (1 mmol), NaN3 (1.5 mmol),toluene (2 mL) and AgNTf2 (5 molpercent) was placed in a round bottomed flask and heated at 85 oC. The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was cooled and treated with ethyl acetate (15 mL) and 1M HCl (15 mL)and stirred vigorously. The resultant organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with water and concentrated to give the pure tetrazole. All the products are known compounds and the spectral data and melting points were identical to those reported in the literature. The disappearance of one strong and sharp absorption band (CN stretching band), and the appearance of an NH stretching band in the IR spectra, were characteristic of the formation of 5-substituted 1H-tetrazoles.
93% at 100℃; for 2 h; General procedure: In a roundbottom flask in 100°C, consecutively, the catalyst (0.015mmol, 0.004 g), 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.065 g) were added and the mixturewas stirred for 90 min until it was completed. Then, thereaction mixture was cooled to room temperature andwashed with ethanol (25 mL). After filtration, the white In a roundbottom flask in 100°C, consecutively, the catalyst (0.015mmol, 0.004 g), 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.065 g) were added and the mixturewas stirred for 90 min until it was completed. Then, thereaction mixture was cooled to room temperature andwashed with ethanol (25 mL). After filtration, the white
93% With sodium azide; copper(II) nitrate trihydrate In N,N-dimethyl-formamide at 120℃; for 16 h; General procedure: Cu(NO3)2·3H2O (0.10 mmol), the appropriate nitrile 1 (1.0 mmol), NaN3(2.0 mmol) and DMF (1 mL) were added to a 50 mL round-bottomed flask equipped with a magnetic stirrer. The reaction mixture was stirred in an oil bath at 120 °C for 16 h. After cooling to room temperature, the reaction was acidified HCl (3 M, pH 1.0). Ethyl acetate (~30 mL) wasadded, and stirring was continued until no solid was present. The organic layer was separated, and the aqueous layer was extracted with ethylacetate twice. The combined organic layers were washed with saturatedbrine, and concentrated in vacuo. The residue was purified by columnchromatography (silica gel, EtOAc-PE) to afford the product 2.
92% With Nano TiO2/SO42- In N,N-dimethyl-formamide for 2 h; Green chemistry General procedure: In a round-bottom flask, benzonitrile (1 mmol), sodiumazide (1 mmol), and nano TiO2/SO42 (0.2 g) were charged.Then the reaction mixture was stirred in distilleddimethylformamide (1 mL) at 120 8C. The progress ofthe reaction was followed by TLC (75:25 ethyl acetate:n-hexane). After completion of the reaction, the catalystwas separated by centrifugation, washed with doublydistilled water and acetone, and the centrifugate wastreated with 5 N HCl (20 mL) under vigorous stirring. Theaqueous solution finally obtained was extracted twice with ethyl acetate. The combined organic phase was washedwith water and concentrated to precipitate the crudecrystalline solid. All products were characterized by NMR,IR, mass spectra, and CHN analysis and the data for theknown compounds were found to be identical with theliterature. The complete spectroscopic data are describedin the supporting information. Yield: 92percent. White solid. M.p. 262–263 8C (lit. [11] 261–263 8C) 1H-NMR (250 MHz; DMSO-d6): d 8.04 (d, 2H,J = 8.52 Hz, Ar–H), 7.62 (d, 2H, J = 8.52 Hz, Ar–H), 4.15 (brs,1H,–NH); 13C-NMR (62.9 MHz, DMSO-d6): d 154.8, 135.8,129.4, 128.6, 123.1; IR (KBr): n = 3419, 2927, 2816, 2723,1602, 1457, 1437, 1383, 1350, 1161, 1095, 1055, 875,765 cm1.
91% With sodium azide In N,N-dimethyl-formamide at 90℃; for 8 h; Inert atmosphere General procedure: 5-Benzyl-1H-tetrazole (2a). To a DMF solution of benzyl cyanide (1a, 100 mg, 0.85 mmol) and NaN3(67 mg, 1.02 mmol, 1.2 eq) was added OSU-6 (15 mg, 15 wtpercent relative to 1a). The reaction mixturewas heated at 90 °C (oil bath temperature 95–100 °C) for 4 h at which time TLC indicated the reactionwas complete. The crude reaction mixture was filtered to remove the catalyst, and the filtrate was added to water and extracted with EtOAc (3 x 15 mL). The combined extracts were washed with H2O (3 x 15 mL) and saturated aq. NaCl (1 x 15 mL), dried (MgSO4), filtered, and concentrated under vacuum to give 2a (129 mg, 94percent).
91% at 120℃; for 10 h; Green chemistry General procedure: In a round-bottomed flask, a mixture of nitrile (1 mmol) and sodium azide (1.2 mmol) in the presence of 40 mg of Fe3O4*SBTU*Ni(II) was stirred at 120 °C in PEG for an appropriate time (monitored by TLC). Then, the reaction mixture was cooled down to room temperature. After magnetic separation of catalyst, HCl (4 N, 10 mL) was added to the filtrate and the product extracted with ethyl acetate (2 × 10 mL). The organic layer was washed with water several times, dried with anhydrous Na2SO4 and concentrated to give the crude solid crystalline product.
90% With sodium azide; ammonium acetate In N,N-dimethyl-formamide at 70℃; for 2.5 h; General procedure: The [AMWCNTs-O–Cu(II)–PhTPY] heterogeneous catalyst was subjected to 5 successive reuses under the reaction conditions: For each reaction, nitrile (1.0mmol), NaN3 (1.3mmol) and NH4OAc (1.0mmol) were mixed and stirred in DMF (1mL) in the presence of 4mol-percent of [AMWCNTs-O–Cu(II)–PhTPY] at 70°C in an uncapped vial. After the completion of the reaction, as monitored by TLC using n-hexane/ethyl acetate, the mixture was diluted by H2O (5mL), then the mixture was vacuum-filtered onto a sintered-glass funnel, and the residue was consecutively washed with ethyl acetate (30mL), water (5mL). The heterogeneous catalyst was recharged for another reaction run. The combined supernatant and organic washings were extracted with ethyl acetate (3×10mL), the combined organic layer was dried over anhydrous Na2SO4. Removal of the solvent under vacuum, followed by purification on silica gel using hexane/ethyl acetate as the eluent afforded the pure products.
90% With lithium tetraazidoborate; ammonium acetate In methanol; N,N-dimethyl-formamide at 100℃; for 8 h; General procedure: NH4OAc (15 mg) was added to a mixture of benzonitrile(103 mg, 1 mmol) and LiB(N3)4(93 mg, 0.5 mmol) in DMF/MeOH (9/1) solution (5 mL) and stirred the mixture was at 100 oC for 8 h. After completion of reaction (monitored by TLC),the mixture was cooled to room temperature and diluted with ethyl acetate. The resulting solution was washed with 1 M HCl, dried over anhydrous Na2SO4, and concentrated. An aqueous solution of NaOH (1 M) was added to the residue, and the mixture was stirred for 30 min at room temperature. The resulting solution was washed with ethyl acetate, and then 2 M HCl was added until the pH value of the water layer became 1~2. The aqueous layer was extracted with ethyl acetate three times, and the combined organic layers were washed with 1M HCl.The organic layer was dried over anhydrous Na2SO4 and concentrated to furnish pure 5-phenyl-1-H-tetrazole 1b as a white solid (125 mg) in 86percent yield.
90% With sodium azide; copper(l) chloride In N,N-dimethyl-formamide at 120℃; for 12 h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol) and copper(I) chloride (4 mole percent) in DMF (2 mL) was stirred at 120 °C for the appropriate time period. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled and treated with 5 mL of HCl (4 mol L−1) and 10 mL of ethyl acetate, successively. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The product thus obtained was recrystallised from acetic acid to afford pure 5-substituted 1H-tetrazoles.
90% With sodium azide; activated Fuller’s earth In dimethyl sulfoxide at 120℃; for 1.5 h; Green chemistry General procedure: To a DMSO (3 ml) solution of nitrile (1 mmol), and sodium azide (1.5 mmol), was added catalyst (10 wt percent). The reaction mixture was stirred to 120 0C in an oil bath. The reaction was monitored by TLC. After completion of the reaction, the mixture was filtered to separate the catalyst. The filtrate was quenched with water (30 ml), acidified with 5N HCl (20 ml) to precipitate the product, extracted with ethyl acetate (2 X 20 ml). The combined organic layers were washed with water, dried over sodium sulphate and evaporated under reduced pressure to give the product.
90% at 90℃; for 0.5 h; Green chemistry General procedure: A mixture of benzonitriles (2a-p) (0.009 mol), sodium azide (0.009 mol) was dissolved in DIPEAc (5 ml) and allowed to stirr for 30 min at 80° FontWeight="Bold" FontSize="10" C. After completion of the reaction (monitored by thin-layer chromatography, TLC), the reaction mixture was cooled to room temperature and poured on crushed ice. To it 5N HCl (10 mL) was added and stirred vigorously. Otained solid products was filtered and crystallized from ethanol. The synthesized compounds were confirmed by Melting points, IR, 1H and 13C NMR which were in good agreement with those reported in the literature.
90% With sodium azide; (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate In water; isopropyl alcohol at 65℃; for 0.25 h; Inert atmosphere; Microwave irradiation; Green chemistry General procedure: In a round-bottomed flask, a mixture of organic nitrile 1 (1.0 equiv) and NaN3 (1.5 equiv) was added to 5 ml solution of H2O-IPA (1:1) containing 10 molpercent [Cu(phen)(PPh3)2]NO3 as catalyst under N2 atmosphere. The reaction mixture was irradiated under microwave heating at 245 W for 15–25 min at 65°C. Reaction progress was monitored by thin-layer chromatography (TLC). After reaction completion, the mixture was filtered to remove the catalyst. The filtrate was acidified with 5 N HCl (20 ml) to neutralize the product, extracted with ethyl acetate (2 9 10 ml). The combined organic layer was dried over anhydrous MgSO4. The combined filtrate was subjected to evaporation to obtain the crude compound, which was purified over silica gel column (60–120 mesh) using 50 percent ethyl acetate in hexane as eluent to obtain corresponding 5-substituted 1H-tetrazoles 2 as product.
89% With sodium azide; copper(II) ferrite In N,N-dimethyl-formamide at 120℃; for 12 h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), catalyst (40 molpercent) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 120 °C temperature for 12 h. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (30 mL) and 5 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product. refText
89% With sodium azide; scandium tris(trifluoromethanesulfonate) In water; isopropyl alcohol at 160℃; for 1 h; Microwave irradiation; Sealed tube General procedure: Synthesis of 5-(4-chlorophenyl)-1H-tetrazole (2c) was achieved as follows: 4-chlorobenzonitrile 1c (274 mg, 2 mmol), NaN3 (260 mg, 4 mmol), Sc(OTf)3(197 mg, 0.4 mmol), and 8mL of a 3:1 isopropanol=water mixture were added to a30-mL Pyrex microwave vessel and capped. The microwave vessel was then placedin a Milestone Start Synth microwave reactor. The reaction was magnetically stirredand heated for 1 h at 160 C. The reaction was monitored by thin-layer chromatography(TLC) using an ether=hexane mixture (typically 50=50) for development.The reaction mixture was then diluted with saturated aqueous sodium bicarbonate(20 mL) and washed with ethyl acetate (215mL). The aqueous sodium bicarbonatelayer was cooled with ice and acidified to a pH of 2 or less with concentratedhydrochloric acid, which was added dropwise. The precipitate formed was extractedwith ethyl acetate (315 mL). The combined organic layers were dried with anhydroussodium sulfate and decanted into a tared round-bottom flask. The organiclayer was concentrated under reduced pressure by rotary evaporation at 40 C andthen under high vacuum. The tetrazole product was recrystallized from ethyl acetateand hexane. All reagents mentioned were not unpurified.NMR spectra were acquired on a spectrometer at 300MHz for 1H and 75MHzfor 13C acquisitions. All 1H NMR spectra were taken in dimethylsulfoxide (DMSOd6)using DMSO as a standard at 2.52 ppm. All 13C NMR spectra were taken inDMSO-d6 using DMSO as a standard at 40.5 ppm. An IR spectrum was obtainedusing a Fourier transform infrared (FTIR) spectrophotometer. A melting point wasalso obtained for the solid products. 5-(4-Chlorophenyl)-1H-tetrazole (2c) is a whitesolid. IR (KBr, thin film) vmax (cm1): 3385 (br), 1645 (m), 1634 (m); 1H NMR(DMSO-d6, d): 11.60 (s, br, 1H), 8.07 (d, J8.28 Hz, 2H), 7.70 (d, J8.25 Hz,2H); 13C NMR (DMSO-d6, d): 155.8 (br), 136.9, 130.6, 129.7, 124.1; mp 250251 C.
89% With sodium azide In N,N-dimethyl-formamide at 120℃; for 1.5 h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol),catalyst (25 mg), and DMF (3 mL) was taken in a 5 mLround bottomed flask and heated at 120C. After completionof the reaction (observed on TLC) the reactionmixture was cooled to r.t. and separated from catalyst bycentrifugation. The solvent was removed under reducedpressure. The residue was dissolved in water (5 mL) andacidified with HCl (37percent). The precipitation was filteredand crystallized in a mixture of water and ethanol. Furtherpurification with column chromatography was notnecessary.
88% at 120℃; for 1.83333 h; General procedure: In order to the synthesis of 5-substituted tetrazoles, 0.005g of SBA-15(at)serine(at)Pd was added to a mixture of nitrile (1mmol) and sodium azide (1.2mmol) under stirring conditions at 120°C in PEG, and the completion of the reaction progress was monitored by TLC with n-hexane-ethylacetate (4:1). Then, the catalyst was separated by simple filtration after completion of reaction. Finally, HCl (4N, 10mL) added to the filtrate and then the resultant organic layers were extract with ethyl acetate and washed with distilled water in order to give corresponding tetrazole.
84% With sodium azide In N,N-dimethyl-formamide at 120℃; for 6 h; General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol) and catalyst (0.02 g, contains 0.4 molpercent of Cu(II)) in DMF (3 mL) was taken in a round-bottomed flask and stirred at 120 °C. The progress of the reaction was followed by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (3×20 mL). The catalyst was removed by using magnetic field or filtration and then the resulting solution was washed with 1N HCl, dried over anhydrous Na2SO4 and then was evaporated. The crude products were obtained in excellent yields. All products were characterized by 1H, 13C NMR, FT-IR, and melting point which were in agreement with literature. We have reported the spectral data of some aromatic and heteroaromatic synthesized compounds
84% With sodium azide In methanol; N,N-dimethyl-formamide at 20 - 100℃; for 8 h; General procedure: A mixture of benzonitrile (1 mmol), sodium azide (2 mmol), Ln(OTf)3-SiO2 (2008 mg) and DMF/MeOH (4:1, 5 mL) in a pressure vial was initially stirred at room temperature. After 30 min, the temperature of the reaction mixture was raised to 100 °C and stirred for another 7 h. After consumption of 1a (as indicated by TLC), the catalyst was separated by filtration and the filtrate was treated with ethyl acetate (15 mL). The organic layer was washed with 4 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was extracted with ethyl acetate (15 mL). The combined organic layer was washed with water (2 × 10 mL), dried over anhydrous sodium sulfate and concentrated to afford white crystalline solid.5-Phenyl-1H-tetrazole(3a)IR (KBr, cm−1): 3331, 2907, 2850, 2611, 1607, 1485, 1433, 1050, 828, 742. 1H NMR (300 MHz, CDCl3): 8.04–8.007 (m, 1H), 7.611–7.574 (m, 2H). 13C NMR (75 MHz, CDCl3): 156.03, 131.19, 129.08, 126.805, 123.924. MS: m/z = 146 [M]+.
82% With indium(III) chloride; sodium azide In water; isopropyl alcohol at 160℃; Microwave irradiation General procedure: Synthesis of 4-acetylbenzotetrazole (2c). 4-Acetylbenzonitrile 3c (290 mg, 2 mmol), NaN3 (260 mg, 4 mmol), InCl3(89 mg, 0.4 mmol), and 8 mL of a 3:1 isopropanol/water mixture were added to a 30-mL Pyrex microwave vessel and capped. The microwave vessel was then placed in a Milestone Start Synth microwave reactor. The reaction was magnetically stirred and heated for 1 hour at 160 oC. The pressure in the vessels was not determined. The reaction was monitored by TLC using an ether/hexane mixture (typically50/50) for development. After cooling, the reaction mixture was diluted with saturated aqueous sodium bicarbonate (20mL) and washed with ethyl acetate (2 x 15 mL). The aqueous sodium bicarbonate layer was cooled to 0 oC and acidified to a pH of 2 or less with concentrated hydrochloric acid,which was added drop-wise. The precipitate formed was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were dried over anhydrous sodium sulfate and decanted into a tared round bottom flask. The organic layer was concentrated under reduced pressure. The tetrazole product was recrystallized from ethyl acetate and hexane. All reagents mentioned above were used unpurified
80% With sodium azide; silver nitrate In N,N-dimethyl-formamide at 20 - 120℃; for 5 h; General procedure: Sodiumazide (0.378 g, 0.046 mmol) was added to a solution of AgNO3 (5 mg, 10 mmol)in DMF (5 ml) and reaction mixture was stirred for 5 min, to this stirredsolution benzonitrile 1a (0.4 ml, 0.033 mmol) was added dropwise over theperiod of 1 min at room temperature and stirring continued for 10 min at thesame temperature and then heated at 120 C for 5 h. After consumption of 1a,the reaction mixture was cooled to room temperature and chilled by addingcrushed ice into the reaction mixture followed by addition of 2 N HCl tillreaction mixture reached the pH 2. The reaction mixture was then extractedwith ethyl acetate. The organic layer was dried with anhydrous Na2SO4, andconcentrated to obtain tetrazole 2a in 83percent yield as an off white solid (268 mg).
80% With sodium azide In N,N-dimethyl-formamide at 120℃; for 16 h; General procedure: In a round-bottom flask, 0.2 g benzonitrile (2 mmol) and0.4 g sodium azide (6 mmol), were added to 10 mL DMF.To this mixture, 20 mg of functionalized KIT-6 was addedand the reaction mixture was refluxed. The progress ofreaction was monitored by TLC (75:25 ethyl acetate/nhexane).After completion of the reaction, the reactionmixture was cooled and filtered. The solid materials werewashed three times with acetone and then with the water.The catalyst was collected and dried to activation for nextrun. The product was obtained by acidification of solutionwith hydrochloric acid (5 mL, 6 M). The precipitate wasfiltered and recrystallized from a water/ethanol mixture toget pure product as a white powder, yield: 88percent.
77% With sodium azide; lead(II) chloride In N,N-dimethyl-formamide at 120℃; for 8 h; Inert atmosphere General procedure: Benzonitrile (103 mg, 1 mmol) and sodium azide (97.5 mg, 1.5 mmol) were dissolved in 2 ml of dry DMF in a 25 ml round bottom flask. PbCl2 (27.8 mg, 0.1 mmol, 10 mol percent) was added to the reaction mixture and stirred at 120 °C for 8 h under nitrogen. After completion of the reaction (as monitored by TLC), the reaction mixture was cooled to room temperature and 10 ml of ice water was added followed by addition of 3 N HCl until the reaction mixture became strongly acidic (pH 2-3). The reaction mixture was extracted three times with 20 ml ethyl acetate. The organic layer was washed with brine solution and dried over anhydrous sodium sulfate, and was evaporated under reduced pressure to give a white solid product of 5-phenyl 1H-tetrazole with 81percent yield.
75% With sodium azide; ammonium chloride In N,N-dimethyl-formamide for 24 h; Reflux General procedure: In a typical procedure, 5-aryl-1H-tetrazoles (1–24) were synthesized by adding aryl nitriles (1 eq.), sodium azide (1.2 eq.), and ammonium chloride (1 eq.) in solvent, the mixture was refluxed for 24 h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 2.5 mL of 2M NaOH was added and the solution was stirred for half an hour. The reaction mixture was concentrated on reduced pressure, and dissolved in water. 3M HCl was added to the reaction mixture until precipitates formed. The precipitates were filtered and washed with distilled water. The yields of title compounds were found to be moderate to high.
74% With sodium azide In N,N-dimethyl-formamide for 24 h; Sealed tube; Green chemistry General procedure: The benzonitrile derivatives (2 mmol), sodium azide (3.2 mmol), and DMF (2 mL) were mixed in a sealed tube, then 30 mg of catalyst MSS-SO3H (or catalyst MSS-SO3Zn) was added into the tube, which was heated for 24 h under 140 C. After 24 hours’ reaction,the catalyst was separated by magnetic force, and the solution was poured into water.The liquid was acidified to pH 1, then ethyl acetate was added to extract the tetrazoles. Carefully evaporating the solvent under reduced pressure, we got the isolated tetrazoles. A sample for characterization was purified on a flash silica column.

Reference: [1] Journal of the Brazilian Chemical Society, 2012, vol. 23, # 12, p. 2197 - 2203
[2] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10882 - 10890
[3] Tetrahedron Letters, 2014, vol. 55, # 44, p. 6034 - 6038
[4] Asian Journal of Chemistry, 2017, vol. 29, # 4, p. 864 - 866
[5] Chemical Communications, 2010, vol. 46, # 3, p. 448 - 450
[6] Angewandte Chemie - International Edition, 2010, vol. 49, # 39, p. 7101 - 7105
[7] RSC Advances, 2015, vol. 5, # 84, p. 68558 - 68564
[8] Applied Organometallic Chemistry, 2015, vol. 29, # 11, p. 730 - 735
[9] Catalysis Science and Technology, 2015, vol. 5, # 9, p. 4452 - 4457
[10] RSC Advances, 2015, vol. 5, # 62, p. 49849 - 49860
[11] Journal of Nanoscience and Nanotechnology, 2017, vol. 17, # 3, p. 1992 - 1999
[12] Heterocycles, 2014, vol. 89, # 9, p. 2137 - 2150
[13] Synthetic Communications, 2018, vol. 48, # 2, p. 175 - 187
[14] Research on Chemical Intermediates, 2018, vol. 44, # 2, p. 1363 - 1380
[15] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 390 - 393
[16] Synthetic Communications, 2009, vol. 39, # 24, p. 4479 - 4485
[17] RSC Advances, 2016, vol. 6, # 38, p. 31850 - 31860
[18] RSC Advances, 2016, vol. 6, # 39, p. 32653 - 32660
[19] RSC Advances, 2016, vol. 6, # 79, p. 75227 - 75233
[20] Transition Metal Chemistry, 2017, vol. 42, # 2, p. 131 - 136
[21] Organic Preparations and Procedures International, 2017, vol. 49, # 4, p. 346 - 354
[22] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5278 - 5289
[23] Australian Journal of Chemistry, 2017, vol. 70, # 10, p. 1127 - 1137
[24] Transition Metal Chemistry, 2017, vol. 42, # 8, p. 703 - 710
[25] MedChemComm, 2017, vol. 8, # 10, p. 1953 - 1964
[26] Journal of Organometallic Chemistry, 2018, vol. 870, p. 16 - 22
[27] E-Journal of Chemistry, 2012, vol. 9, # 3, p. 1145 - 1152
[28] New Journal of Chemistry, 2014, vol. 38, # 7, p. 3078 - 3083
[29] Tetrahedron Letters, 2014, vol. 55, # 41, p. 5683 - 5686
[30] RSC Advances, 2015, vol. 5, # 126, p. 104087 - 104094
[31] Synthetic Communications, 2017, vol. 47, # 8, p. 779 - 787
[32] Synlett, 2018, vol. 29, # 7, p. 874 - 879
[33] Chemical Biology and Drug Design, 2018, vol. 91, # 6, p. 1101 - 1112
[34] Tetrahedron Letters, 2013, vol. 54, # 1, p. 106 - 109
[35] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 18 - 29
[36] Tetrahedron Letters, 2015, vol. 56, # 5, p. 739 - 742
[37] Journal of Chemical Research, 2015, vol. 39, # 6, p. 321 - 323
[38] Letters in Organic Chemistry, 2016, vol. 13, # 2, p. 113 - 119
[39] Applied Organometallic Chemistry, 2016, vol. 30, # 8, p. 705 - 712
[40] Journal of Chemical Research, 2017, vol. 41, # 1, p. 25 - 29
[41] New Journal of Chemistry, 2017, vol. 41, # 16, p. 8084 - 8091
[42] Applied Organometallic Chemistry, 2018, vol. 32, # 8,
[43] New Journal of Chemistry, 2018, vol. 42, # 16, p. 13754 - 13762
[44] New Journal of Chemistry, 2013, vol. 37, # 10, p. 3261 - 3266
[45] Monatshefte fur Chemie, 2013, vol. 144, # 9, p. 1407 - 1410
[46] Comptes Rendus Chimie, 2014, vol. 17, # 10, p. 1007 - 1012
[47] RSC Advances, 2015, vol. 5, # 16, p. 12372 - 12381
[48] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9090 - 9095
[49] RSC Advances, 2015, vol. 5, # 28, p. 21651 - 21658
[50] Molecules, 2015, vol. 20, # 12, p. 22757 - 22766
[51] Applied Organometallic Chemistry, 2017, vol. 31, # 9,
[52] Applied Organometallic Chemistry, 2017, vol. 31, # 12,
[53] Journal of Sulfur Chemistry, 2018, vol. 39, # 3, p. 237 - 251
[54] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 75 - 79
[55] Chemistry Letters, 2012, vol. 41, # 8, p. 814 - 816
[56] Journal of the Iranian Chemical Society, 2012, vol. 9, # 5, p. 799 - 803
[57] Journal of Organometallic Chemistry, 2013, vol. 738, p. 41 - 48
[58] Tetrahedron Letters, 2013, vol. 54, # 49, p. 6779 - 6781
[59] Chemical Papers, 2015, vol. 69, # 9, p. 1231 - 1236
[60] Tetrahedron Letters, 2016, vol. 57, # 51, p. 5815 - 5819
[61] Synthetic Communications, 2017, vol. 47, # 7, p. 695 - 703
[62] Research on Chemical Intermediates, 2017, vol. 43, # 12, p. 7365 - 7374
[63] Applied Organometallic Chemistry, 2017, vol. 31, # 7,
[64] Synthetic Communications, 2010, vol. 40, # 17, p. 2624 - 2632
[65] Tetrahedron Letters, 2011, vol. 52, # 28, p. 3565 - 3569
[66] Synthetic Communications, 2011, vol. 41, # 20, p. 3053 - 3059
[67] Chinese Chemical Letters, 2010, vol. 21, # 9, p. 1029 - 1032
[68] Chinese Journal of Chemistry, 2011, vol. 29, # 1, p. 131 - 134
[69] Synthetic Communications, 2015, vol. 45, # 2, p. 218 - 225
[70] Journal of Chemical Sciences, 2016, vol. 128, # 1, p. 93 - 99
[71] Applied Organometallic Chemistry, 2016, vol. 30, # 11, p. 897 - 904
[72] Applied Organometallic Chemistry, 2018, vol. 32, # 6,
[73] Polyhedron, 2019, vol. 157, p. 374 - 380
[74] Synthetic Communications, 2009, vol. 39, # 3, p. 426 - 432
[75] RSC Advances, 2016, vol. 6, # 61, p. 56638 - 56646
[76] RSC Advances, 2016, vol. 6, # 99, p. 96623 - 96634
[77] Applied Organometallic Chemistry, 2018, vol. 32, # 8,
[78] Chinese Chemical Letters, 2012, vol. 23, # 2, p. 161 - 164
[79] RSC Advances, 2013, vol. 3, # 13, p. 4362 - 4371
[80] Journal of Organometallic Chemistry, 2013, vol. 743, p. 87 - 96
[81] Tetrahedron Letters, 2014, vol. 55, # 25, p. 3557 - 3560
[82] Synthetic Communications, 2006, vol. 36, # 12, p. 1809 - 1814
[83] Synlett, 2010, # 3, p. 391 - 394
[84] Journal of the American Chemical Society, 2011, vol. 133, # 12, p. 4465 - 4475
[85] Medicinal Chemistry, 2017, vol. 13, # 4, p. 359 - 364
[86] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 11, p. 4001 - 4004
[87] Tetrahedron Letters, 2014, vol. 55, # 11, p. 1879 - 1882
[88] RSC Advances, 2014, vol. 4, # 69, p. 36713 - 36720
[89] Journal of the Iranian Chemical Society, 2018, vol. 15, # 4, p. 831 - 838
[90] New Journal of Chemistry, 2015, vol. 39, # 6, p. 4814 - 4820
[91] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4435 - 4438
[92] Comptes Rendus Chimie, 2016, vol. 19, # 3, p. 305 - 312
[93] Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6468 - 6476
[94] Bioorganic Chemistry, 2018, vol. 79, p. 201 - 211
[95] Advanced Synthesis and Catalysis, 2005, vol. 347, # 9, p. 1212 - 1214
[96] Synthetic Communications, 2018, vol. 48, # 20, p. 2652 - 2662
[97] Heteroatom Chemistry, 2011, vol. 22, # 2, p. 168 - 173
[98] RSC Advances, 2014, vol. 4, # 12, p. 6116 - 6119
[99] European Journal of Organic Chemistry, 2005, # 2, p. 326 - 333
[100] RSC Advances, 2015, vol. 5, # 115, p. 95061 - 95072
  • 3
  • [ 104-88-1 ]
  • [ 16687-61-9 ]
YieldReaction ConditionsOperation in experiment
66% With sodium azide; cerium(IV) tetraammonium sulfate dihydrate; hydroxylamine hydrochloride In N,N-dimethyl-formamide for 6 h; Reflux; Green chemistry General procedure: Aldehyde (1 mmol), hydroxylamine hydrochloride (2 mmol) and sodium azide (2 mmol) were added successively to a solution of (NH4)4Ce(SO4)4·2H2O (20 molpercent) in 5 mL DMF. The mixture was reflux for appropriate time (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, the solution was treated with HCl (4N, 10  mL) and then the solution was poured into 100 mL water and extract with ethyl acetate, washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ethyl acetate (75:25) as eluent to afford the pure solid tetrazole. All the products were characterized by 1H NMR, 13C NMR and HRMS.
Reference: [1] RSC Advances, 2016, vol. 6, # 94, p. 91999 - 92006
[2] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2116 - 2122
[3] Applied Organometallic Chemistry, 2018, vol. 32, # 4,
[4] Synlett, 2012, vol. 23, # 20, p. 2927 - 2930
[5] Synthesis (Germany), 2013, vol. 45, # 4, p. 507 - 510
[6] Tetrahedron Letters, 2018, vol. 59, # 14, p. 1385 - 1389
[7] Synthetic Communications, 2011, vol. 41, # 14, p. 2081 - 2085
[8] Tetrahedron Letters, 2016, vol. 57, # 5, p. 523 - 524
[9] Journal of Chemical Research, 2017, vol. 41, # 1, p. 25 - 29
[10] Synthetic Communications, 2017, vol. 47, # 7, p. 695 - 703
  • 4
  • [ 3717-24-6 ]
  • [ 16687-61-9 ]
YieldReaction ConditionsOperation in experiment
89% With sodium azide; copper(II) ferrite In N,N-dimethyl-formamide at 120℃; for 12 h; Sealed tube General procedure: A mixture of oxime (1 mmol), NaN3 (1.5 mmol), catalyst(30 mol percent) and DMF (3 mL) was taken in a sealed tube and stirred at 120 °C for 12 h. After completion of the reaction,the catalyst was separated from the reaction mixture with an external magnet kept at RT for 5 min. Then H2O (5 mL) and3N HCl (5 mL) were added, and an extraction with ethylacetate was performed. Resultant organic layer was washedwith water, dried over sodium sulfate, and the solvent was removed by distillation. The crude material was purified by column chromatography on silica gel (hexane/AcOEt 1:1)and afforded the pure tetrazole derivatives.
Reference: [1] Letters in Organic Chemistry, 2014, vol. 11, # 6, p. 440 - 445
  • 5
  • [ 2521-24-6 ]
  • [ 16687-61-9 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 11, p. 2226 - 2235
  • 6
  • [ 619-56-7 ]
  • [ 16687-61-9 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1257 - 1260
  • 7
  • [ 623-03-0 ]
  • [ 4648-54-8 ]
  • [ 16687-61-9 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 54, p. 34197 - 34207
  • 8
  • [ 637-87-6 ]
  • [ 16687-61-9 ]
Reference: [1] Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2135 - 2142
[2] Tetrahedron, 2018, vol. 74, # 31, p. 4226 - 4235
  • 9
  • [ 1679-18-1 ]
  • [ 67-68-5 ]
  • [ 16687-61-9 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 887 - 892
  • 10
  • [ 873-76-7 ]
  • [ 16687-61-9 ]
Reference: [1] Journal of Chemical Research, 2017, vol. 41, # 1, p. 25 - 29
  • 11
  • [ 106-39-8 ]
  • [ 16687-61-9 ]
Reference: [1] Tetrahedron, 2018, vol. 74, # 31, p. 4226 - 4235
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 16687-61-9 ]

Aryls

Chemical Structure| 18039-42-4

[ 18039-42-4 ]

5-Phenyl-1H-tetrazole

Similarity: 0.86

Chemical Structure| 51449-86-6

[ 51449-86-6 ]

5-(o-Tolyl)tetrazole

Similarity: 0.83

Chemical Structure| 50907-23-8

[ 50907-23-8 ]

5-(4-Bromophenyl)-1H-tetrazole

Similarity: 0.75

Chemical Structure| 73096-42-1

[ 73096-42-1 ]

5-(2-Bromophenyl)tetrazole

Similarity: 0.71

Chemical Structure| 34114-12-0

[ 34114-12-0 ]

4-(1H-Tetrazol-5-yl)benzoic acid

Similarity: 0.67

Chlorides

Chemical Structure| 5685-72-3

[ 5685-72-3 ]

3-Amino-5-chloro-1H-indazole

Similarity: 0.65

Chemical Structure| 20925-60-4

[ 20925-60-4 ]

4-Chloro-1H-indazol-3-amine

Similarity: 0.63

Chemical Structure| 1185303-65-4

[ 1185303-65-4 ]

(4-Chlorobenzyl)hydrazine dihydrochloride

Similarity: 0.58

Chemical Structure| 1427430-82-7

[ 1427430-82-7 ]

4-Chloro-7-methyl-1H-indazole

Similarity: 0.57

Chemical Structure| 885519-32-4

[ 885519-32-4 ]

6-Chloro-1H-indazol-4-amine

Similarity: 0.57

Related Parent Nucleus of
[ 16687-61-9 ]

Tetrazoles

Chemical Structure| 18039-42-4

[ 18039-42-4 ]

5-Phenyl-1H-tetrazole

Similarity: 0.86

Chemical Structure| 242815-91-4

[ 242815-91-4 ]

6-Chlorotetrazolo[1,5-a]pyridine

Similarity: 0.57

Chemical Structure| 274-87-3

[ 274-87-3 ]

Tetrazolo[1,5-a]pyridine

Similarity: 0.51