Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide at 120℃; for 3h; | 99% |
With sodium azide; nickel(II) ferrite; ammonium acetate In N,N-dimethyl-formamide at 100℃; for 1h; | 94% |
With sodium azide; zinc(II) sulfate In butan-1-ol at 110℃; for 16h; Reagent/catalyst; | 94% |
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
With naphthalene; lithium In tetrahydrofuran at -78℃; for 2.5h; Inert atmosphere; | 93% |
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
With naphthalene; lithium In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; | 61% |
benzonitrile
acetonitrile
A
5-methyl-1,2,3,4-tetrazole
B
5-Phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With trimethylsilylazide; dibutyltin diacetate at 30℃; for 24h; | A 40% B 40% |
ethyl nitrite
ethanol
acetamidrazone hydrochloride
5-methyl-1,2,3,4-tetrazole
1-ethoxy-1,1-diazido-ethane
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
With toluene; ethanethiol |
Conditions | Yield |
---|---|
With tetrahydrofuran; aluminium trichloride; sodium azide |
1-Methoxy-5-methyl-1H-tetrazole
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
With phosphorus; hydrogen iodide for 2.5h; Heating; | 0.22 g |
Conditions | Yield |
---|---|
With hydrogenchloride 1.) CH2Cl2, R.T., 7 d, 2.) EtOH, R.T., 1 h; Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride 1.) MeCN, reflux, 60 d, 2.) MeOH, 30 min; Yield given. Multistep reaction; |
1-ethoxy-1,1-diazido-ethane
toluene
ethanethiol
A
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
Stage #1: O-ethyl acetimidate With hydrazine hydrate at -15 - -10℃; Stage #2: With sodium nitrite In water at 5℃; for 0.5h; Reagent/catalyst; | 15.8 g |
5-methyl-1,2,3,4-tetrazole
tert-butyl alcohol
2-(tert-butyl)-5-methyl-2H-tetrazole
Conditions | Yield |
---|---|
With sulfuric acid for 0.5h; | 97% |
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20 - 25℃; for 48h; regioselective reaction; | 70% |
With trifluorormethanesulfonic acid at 20℃; for 2h; | 60% |
Conditions | Yield |
---|---|
Stage #1: 5-methyl-1,2,3,4-tetrazole With sulfuric acid at 20℃; for 0.333333h; Stage #2: 7-Aminocephalosporanic acid at 20℃; Reagent/catalyst; | 96.21% |
With borane-THF In tetrahydrofuran at 55℃; for 6h; Temperature; Concentration; | 95% |
5-methyl-1,2,3,4-tetrazole
2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With pyridine; 1,3-bis-(diphenylphosphino)propane; oxygen; silver trifluoroacetate; triphenylphosphine; copper(I) bromide In dichloromethane; acetonitrile at 0 - 20℃; for 10h; Reagent/catalyst; Solvent; | 93.7% |
5-methyl-1,2,3,4-tetrazole
4-chlorophenylboronic acid pinacol ester
Conditions | Yield |
---|---|
With pyridine; 1,3-bis-(diphenylphosphino)propane; oxygen; silver trifluoroacetate; triphenylphosphine; copper(I) bromide In dichloromethane; acetonitrile at 0 - 20℃; for 8h; Reagent/catalyst; Solvent; | 93.5% |
Conditions | Yield |
---|---|
In water at 120℃; for 72.5h; Temperature; Solvent; | 92% |
In water equiv. amounts of educts; filtered, washed with ethanol or aq. alcohol, dried at 70 - 90°C; | |
In water equiv. amounts of educts; filtered, washed with ethanol or aq. alcohol, dried at 70 - 90°C; |
5-methyl-1,2,3,4-tetrazole
dimethylbis(η5-pentamethylcyclopentadienyl)uranium
Conditions | Yield |
---|---|
In toluene at 20℃; for 2h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
In water at 121℃; for 70.5h; | 91% |
5-methyl-1,2,3,4-tetrazole
Ethyl oxalyl chloride
5-methyl-1,3,4-oxadiazole-2-carboxylic acid potassium salt
Conditions | Yield |
---|---|
Stage #1: 5-methyl-1,2,3,4-tetrazole; Ethyl oxalyl chloride With triethylamine In toluene at 0 - 65℃; for 3h; Stage #2: With potassium hydroxide; water In ethanol at 10 - 20℃; for 1.16667h; | 90.8% |
Stage #1: 5-methyl-1,2,3,4-tetrazole; Ethyl oxalyl chloride With triethylamine In toluene at 0 - 5℃; for 1h; Stage #2: In toluene at 50 - 65℃; for 1.66667 - 1.83333h; Stage #3: With potassium hydroxide In ethanol; water at 10 - 20℃; for 1.16667h; | 90.8% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 60℃; for 5h; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone at 80℃; for 72h; | 88.67% |
5-methyl-1,2,3,4-tetrazole
cyclohexa-1,3-diene
Conditions | Yield |
---|---|
With phosphoric acid; water at 20℃; for 0.666667h; | 88% |
5-methyl-1,2,3,4-tetrazole
trans-[PtCl4(propiononitrile)2]
Conditions | Yield |
---|---|
In dichloromethane byproducts: 2EtCN; other Radiation; microwave irradn. (40 °C), 4 h; ppt. was filtered off, washed with Et2O, dried in vac. at room temp., elem. anal.; | 87% |
In nitromethane byproducts: 2EtCN; reflux for 6 h; ppt. was filtered off, washed with Et2O, dried in vac. at room temp., elem. anal.; | 78% |
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
In tetrachloromethane at 80℃; for 2h; Inert atmosphere; diastereoselective reaction; | A 87% B 11% |
Conditions | Yield |
---|---|
Stage #1: [(η5-C5Me5)RhCl(2,2'-bipyridine)]Cl With silver trifluoromethanesulfonate In methanol at 20℃; for 24h; Darkness; Stage #2: 5-methyl-1,2,3,4-tetrazole In methanol for 1h; Stage #3: ammonium hexafluorophosphate; acetonitrile In methanol | 86% |
Conditions | Yield |
---|---|
Stage #1: 5-methyl-1,2,3,4-tetrazole With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: pivaloyl chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 0.5h; Solvent; Darkness; | 85% |
5-methyl-1,2,3,4-tetrazole
benzoic acid anhydride
2-methyl-5-phenyl-[1,3,4]oxadiazole
Conditions | Yield |
---|---|
84% |
5-methyl-1,2,3,4-tetrazole
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
ethanol
Conditions | Yield |
---|---|
at 120℃; for 72h; Sealed tube; | 84% |
5-methyl-1,2,3,4-tetrazole
1-methyl-3,5-dinitro-1H-[1,2,4]triazole
A
5-Methyl-1-(2-methyl-5-nitro-2H-[1,2,4]triazol-3-yl)-1H-tetrazole
B
1-methyl-3-nitro-1,2,4-triazol-5(1H,4H)-one
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 60℃; for 10h; | A 6.6% B 83% |
5-methyl-1,2,3,4-tetrazole
dimethyl <2-(tert-butylimino)vinyl>phosphonate
Conditions | Yield |
---|---|
In tetrachloromethane for 15h; Reflux; regioselective reaction; | 83% |
5-methyl-1,2,3,4-tetrazole
terephthalic acid
tetramethyl ammoniumhydroxide
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 120℃; for 24h; Sealed tube; | 83% |
5-methyl-1,2,3,4-tetrazole
C11H13BrN4O4
A
N-[2,2-Dimethyl-1-(5-methyl-tetrazol-2-yl)-prop-(Z)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine
B
N-[2,2-Dimethyl-1-(5-methyl-tetrazol-1-yl)-prop-(Z)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine
Conditions | Yield |
---|---|
With triethylamine In butanone for 1h; Ambient temperature; | A 8% B 82% |
5-methyl-1,2,3,4-tetrazole
silver(I) hexafluorophosphate
[(η5-pentamethylcyclopentadienyl)Ir(Me2dtc)Cl]
[((η5-pentamethylcyclopentadienyl)Ir(Me2dtc))2(μ-MeCN4-κN(1):κN(4))]PF6
Conditions | Yield |
---|---|
In methanol; acetonitrile to soln. Ir complex in MeOH-MeCN soln. AgPF6 in MeOH was added and stirred in the dark for 2 h, soln. was filtered and evapd., residue was extd.with MeCN, 5-methyltetrazole was added; Et2O vapor diffusion, ppt. was filtered and air-dried; elem. anal.; | 82% |
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
In tetrachloromethane for 15h; Reflux; regioselective reaction; | 82% |
5-methyl-1,2,3,4-tetrazole
[(-CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)-)Ni2(μ-Cl)](perchlorate)
[Ni2(5-Me-1,2,3,4-tetrazole)(tBuC6H2CH2NMeC2H4NMeC2H4NMeCH2)2]ClO4
Conditions | Yield |
---|---|
With Et3N In methanol 1.1 equiv. of Et3N was added to MeOH soln. of 1.1 equiv. of tetrazole-compd., 1 equiv. of Ni-compd. was added, stirring for 12 h, 1 equiv. of Li-compd. was added in MeOH, stirring for 2 h; ppt. was filtered off, washed with cold EtOH, dried in air; | 80% |
5-methyl-1,2,3,4-tetrazole
Conditions | Yield |
---|---|
Stage #1: [(η5-C5Me5)RhCl(2-(2'-pyridyl)phenyl)] With silver trifluoromethanesulfonate In methanol at 20℃; for 2h; Darkness; Stage #2: 5-methyl-1,2,3,4-tetrazole With triethylamine In methanol for 1h; Stage #3: ammonium hexafluorophosphate In methanol for 1h; | 80% |
Conditions | Yield |
---|---|
In ethanol at 120℃; for 72h; Sealed tube; | 80% |
Molecular Structure:
Molecular Formula: C2H4N4
Molecular Weight: 84.08
IUPAC Name: 5-Methyl-2H-tetrazole
Synonyms of 5-Methyl-1H-Tetrazole (CAS NO.4076-36-2): 1H-Tetrazole, 5-methyl-
CAS NO: 4076-36-2
Product Categories: Tetrazoles ; Building Blocks ; Heterocyclic Building Blocks
Melting point: 142-146 °C
Polar Surface Area: 43.6 Å2
Index of Refraction: 1.533
Molar Refractivity: 19.78 cm3
Molar Volume: 63.7 cm3
Surface Tension: 74.2 dyne/cm
Density: 1.319 g/cm3
Flash Point: 116.7 °C
Enthalpy of Vaporization: 47.01 kJ/mol
Boiling Point: 233.3 °C at 760 mmHg
Vapour Pressure: 0.0561 mmHg at 25°C
5-Methyl-1H-Tetrazole (CAS NO.4076-36-2) is used as a cephalosporin side chain.
Safety Information of 5-Methyl-1H-Tetrazole (CAS NO.4076-36-2):
Hazard Codes:Xi ,F
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-36-24/25-22
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
24/25:Avoid contact with skin and eyes
22:Do not breathe dust
RIDADR:1325
WGK Germany:3
Hazard Note:Flammable/Irritant/Keep Cold
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