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4076-36-2

Basic Information
CAS No.: 4076-36-2
Name: 5-Methyl-1H-Tetrazole
Molecular Structure:
Molecular Structure of 4076-36-2 (5-Methyl-1H-Tetrazole)
Formula: C2H4N4
Molecular Weight: 84.08 .
Synonyms: 1H-Tetrazole,5-methyl- (8CI,9CI);5-Methyl-1,2,3,4-tetrazole;5-Methyl-2H-tetrazole;5-Methyltetrazole;NSC 11136;T 2588F;
EINECS: 609-862-8
Density: 1.319 g/cm3
Melting Point: 142-146 °C(lit.)
Boiling Point: 233.3 °C at 760 mmHg
Flash Point: 116.7 °C
Solubility: Soluble in water.
Appearance: white to yellowish crystals
Hazard Symbols: IrritantXi, FlammableF
Risk Codes: 36/37/38
Safety: 26-36-24/25-22
Transport Information: UN 1325
PSA: 54.46000
LogP: -0.49190
Synthetic route
75-05-8

acetonitrile

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
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-trityl-1H-tetrazole

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at -78℃; for 2.5h; Inert atmosphere;93%

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

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;61%
100-47-0

benzonitrile

75-05-8

acetonitrile

A

4076-36-2

5-methyl-1,2,3,4-tetrazole

B

18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With trimethylsilylazide; dibutyltin diacetate at 30℃; for 24h;A 40%
B 40%
109-95-5

ethyl nitrite

64-17-5

ethanol

39254-63-2

acetamidrazone hydrochloride

4076-36-2

5-methyl-1,2,3,4-tetrazole

109-95-5

ethyl nitrite

39254-63-2

acetamidrazone hydrochloride

4076-36-2

5-methyl-1,2,3,4-tetrazole

98071-92-2

1-ethoxy-1,1-diazido-ethane

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
With toluene; ethanethiol
62-55-5

thioacetamide

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
With tetrahydrofuran; aluminium trichloride; sodium azide
90040-43-0

1-Methoxy-5-methyl-1H-tetrazole

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
With phosphorus; hydrogen iodide for 2.5h; Heating;0.22 g
75-05-8

acetonitrile

azido-tetraphenylporphinato-Co(III)complex

azido-tetraphenylporphinato-Co(III)complex

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
With hydrogenchloride 1.) CH2Cl2, R.T., 7 d, 2.) EtOH, R.T., 1 h; Multistep reaction;
75-05-8

acetonitrile

polymeric Schiff Base cobalt(III) complex azid

polymeric Schiff Base cobalt(III) complex azid

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
With hydrogenchloride 1.) MeCN, reflux, 60 d, 2.) MeOH, 30 min; Yield given. Multistep reaction;
98071-92-2

1-ethoxy-1,1-diazido-ethane

108-88-3

toluene

75-08-1

ethanethiol

A

4076-36-2

5-methyl-1,2,3,4-tetrazole

B

nitrogen

nitrogen

1000-84-6

O-ethyl acetimidate

4076-36-2

5-methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
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
4076-36-2

5-methyl-1,2,3,4-tetrazole

75-65-0

tert-butyl alcohol

133500-31-9

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

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

957-68-6

7-Aminocephalosporanic acid

7-amino-3-[2-(5-methyl-2H-tetrazolyl)methyl]cephalosporanic acid

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

171364-79-7

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(4-methoxyphenyl)-5-methyl-2H-tetrazole

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

195062-61-4

4-chlorophenylboronic acid pinacol ester

2-(4-chlorophenyl)-5-methyl-2H-tetrazole

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

silver nitrate

5-methyl tetrazole

Conditions
ConditionsYield
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;
4076-36-2

5-methyl-1,2,3,4-tetrazole

67605-92-9

dimethylbis(η5-pentamethylcyclopentadienyl)uranium

(C5Me5)2U[η2-(N,N′)-tetrazolate]2

Conditions
ConditionsYield
In toluene at 20℃; for 2h; Inert atmosphere;91%
4076-36-2

5-methyl-1,2,3,4-tetrazole

silver nitrate

Ag(1+)*(x)C2H3N4(1-)

Conditions
ConditionsYield
In water at 121℃; for 70.5h;91%
4076-36-2

5-methyl-1,2,3,4-tetrazole

4755-77-5

Ethyl oxalyl chloride

888504-28-7

5-methyl-1,3,4-oxadiazole-2-carboxylic acid potassium salt

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

619-73-8

4-nitrobenzyl chloride

5-methyl-2-(4-nitrobenzyl)-2H-tetrazole

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 60℃; for 5h;90%
4076-36-2

5-methyl-1,2,3,4-tetrazole

2765-59-5

2-chloro-10-(3-chloropropyl)-10H-phenothiazine

C17H16ClN5S

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone at 80℃; for 72h;88.67%
4076-36-2

5-methyl-1,2,3,4-tetrazole

1165952-91-9

cyclohexa-1,3-diene

2-(2-cyclohexenyl)-5-methyltetrazole

Conditions
ConditionsYield
With phosphoric acid; water at 20℃; for 0.666667h;88%
4076-36-2

5-methyl-1,2,3,4-tetrazole

342028-87-9, 430431-14-4, 92275-25-7

trans-[PtCl4(propiononitrile)2]

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

dimethyl [2-(diisopropylamino)ethynyl]phosphonate

A

dimethyl [(Z)-2-diisopropylamino-2-(5-methyl-1H-tetrazol-1-yl)vinyl]-phosphonate

B

dimethyl [(Z)-2-diisopropylamino-2-(5-methyl-1H-tetrazol-2-yl)vinyl]-phosphonate

Conditions
ConditionsYield
In tetrachloromethane at 80℃; for 2h; Inert atmosphere; diastereoselective reaction;A 87%
B 11%
4076-36-2

5-methyl-1,2,3,4-tetrazole

ammonium hexafluorophosphate

[(η5-C5Me5)RhCl(2,2'-bipyridine)]Cl

75-05-8

acetonitrile

[[(η5-C5Me5)Ir(2,2'-bipyridine)]2(μ-(5-methyltetrazolato))][PF6]3*CH3CN

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

3282-30-2

pivaloyl chloride

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

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

536-80-1

iodosylbenzene

bis(5-methyltetrazolyl)iodobenzene

Conditions
ConditionsYield
In dichloromethane at 25℃; for 0.5h; Solvent; Darkness;85%
4076-36-2

5-methyl-1,2,3,4-tetrazole

93-97-0

benzoic acid anhydride

4046-03-1

2-methyl-5-phenyl-[1,3,4]oxadiazole

Conditions
ConditionsYield
84%
4076-36-2

5-methyl-1,2,3,4-tetrazole

7226-23-5

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

zinc(II) nitrate hexahydrate

64-17-5

ethanol

Zn(5-methyltetrazole(-H))2·0.5(tetrahydro-1,3-dimethyl-2(1H) pyrimidine)·0.5(ethanol)

Conditions
ConditionsYield
at 120℃; for 72h; Sealed tube;84%
4076-36-2

5-methyl-1,2,3,4-tetrazole

1199-63-9

1-methyl-3,5-dinitro-1H-[1,2,4]triazole

A

74245-88-8

5-Methyl-1-(2-methyl-5-nitro-2H-[1,2,4]triazol-3-yl)-1H-tetrazole

B

22244-55-9

1-methyl-3-nitro-1,2,4-triazol-5(1H,4H)-one

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 60℃; for 10h;A 6.6%
B 83%
4076-36-2

5-methyl-1,2,3,4-tetrazole

85829-45-4

dimethyl <2-(tert-butylimino)vinyl>phosphonate

[2-tert-butylimino-2-(5-methyltetrazol-1-yl)ethyl]phosphonic acid dimethyl ester

Conditions
ConditionsYield
In tetrachloromethane for 15h; Reflux; regioselective reaction;83%
4076-36-2

5-methyl-1,2,3,4-tetrazole

zinc(II) nitrate hexahydrate

100-21-0

terephthalic acid

75-59-2

tetramethyl ammoniumhydroxide

68-12-2, 33513-42-7

N,N-dimethyl-formamide

C4H12N(1+)*2Zn(2+)*1.8C3H7NO*3C2H3N4(1-)*C8H4O4(2-)

Conditions
ConditionsYield
at 120℃; for 24h; Sealed tube;83%
4076-36-2

5-methyl-1,2,3,4-tetrazole

14947-26-3

C11H13BrN4O4

A

114065-08-6

N-[2,2-Dimethyl-1-(5-methyl-tetrazol-2-yl)-prop-(Z)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine

B

114064-55-0

N-[2,2-Dimethyl-1-(5-methyl-tetrazol-1-yl)-prop-(Z)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine

Conditions
ConditionsYield
With triethylamine In butanone for 1h; Ambient temperature;A 8%
B 82%
4076-36-2

5-methyl-1,2,3,4-tetrazole

26042-63-7

silver(I) hexafluorophosphate

68315-69-5

[(η5-pentamethylcyclopentadienyl)Ir(Me2dtc)Cl]

1003294-71-0

[((η5-pentamethylcyclopentadienyl)Ir(Me2dtc))2(μ-MeCN4-κN(1):κN(4))]PF6

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

N-adamant-1-yl(diethoxyphosphoryl)ketenimine

[2-(adamantan-1-ylimino)-2-(5-methyltetrazol-1-yl)ethyl]-phosphonic acid diethyl ester

Conditions
ConditionsYield
In tetrachloromethane for 15h; Reflux; regioselective reaction;82%
4076-36-2

5-methyl-1,2,3,4-tetrazole

lithium perchlorate trihydrate

366804-74-2

[(-CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)-)Ni2(μ-Cl)](perchlorate)

1156490-78-6

[Ni2(5-Me-1,2,3,4-tetrazole)(tBuC6H2CH2NMeC2H4NMeC2H4NMeCH2)2]ClO4

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

ammonium hexafluorophosphate

[(η5-C5Me5)RhCl(2-(2'-pyridyl)phenyl)]

[[(η5-C5Me5)Rh(2-(2'-pyridyl)phenyl)]2(μ-(5-methyltetrazolato))][PF6]

Conditions
ConditionsYield
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%
4076-36-2

5-methyl-1,2,3,4-tetrazole

zinc(II) nitrate hexahydrate

127-19-5

N,N-dimethyl acetamide

Zn(5-methyltetrazole(-H))2·N,N-dimethylacetamide

Conditions
ConditionsYield
In ethanol at 120℃; for 72h; Sealed tube;80%
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  • Casno:

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    BLOOM TECH Advanced API/Technology support 5-Methyl-1H-tertazole CAS 4076-36-2

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Chemistry

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

Uses

 5-Methyl-1H-Tetrazole (CAS NO.4076-36-2) is used as a cephalosporin side chain.

Safety Profile

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