6154-04-7|5-Amino-2-methyl-2H-tetrazole| Ambeed

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Quality Control of [ 6154-04-7 ] Purity: 97% SDS Specification

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Product Details of [ 6154-04-7 ]

CAS No. :	6154-04-7
Formula :	C₂H₅N₅
M.W :	99.09
SMILES Code :	NC1=NN(C)N=N1
MDL No. :	MFCD01819831
InChI Key :	AZUKLCJYWVMPML-UHFFFAOYSA-N
Pubchem ID :	138677

Safety of [ 6154-04-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H228-H302-H315-H319-H335
Precautionary Statements:	P210-P233-P240-P241-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P370+P378-P403-P403+P233-P405-P501
Class:	4.1
UN#:	1325
Packing Group:	Ⅱ

Computational Chemistry of [ 6154-04-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	7
Num. arom. heavy atoms	5
Fraction Csp3	0.5
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	23.48
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	69.62 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.83
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.23
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-1.2
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.89
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.51
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.4

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.84
Solubility	14.4 mg/ml ; 0.145 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.77
Solubility	16.7 mg/ml ; 0.168 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.39
Solubility	242.0 mg/ml ; 2.44 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.07 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.33

Application In Synthesis of [ 6154-04-7 ]

* 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.

Downstream synthetic route of [ 6154-04-7 ]

[ 6154-04-7 ] Synthesis Path-Downstream 1~54

1
[ 186581-53-3 ]
[ 4418-61-5 ]
[ 6154-04-7 ]
[ 5422-44-6 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 411,414.

2
[ 4418-61-5 ]
[ 77-78-1 ]
[ 6154-04-7 ]
[ 5422-44-6 ]

Yield	Reaction Conditions	Operation in experiment
25%; 51%		A solution of sodium hydroxide (20%) was added dropwise to a suspension of 5-aminotetrazole monohydrate (10.3 g; 0.1 mol) in water (30 mL), with a drop of phenolphthalein. The mixture was stirred until complete dissolution of the suspended material. Dimethyl sulfate (20 mL; 0.11 mol) was then added in small portions, keeping an alkaline medium through addition of aqueous sodium hydroxide. The final mixture was refluxed for 1 h, then cooled, and finally left in an ice bath, in the fridge, for 2 days. Colorless needles of the desired compound were filtered (6.1 g; 51% yield), m.p. 220-221 C, 1H NMR (CDCl3): delta 4.15 (3H, s), MS (EI): m/z 99 [M+].
25%; 51%	With phenolphthalein; sodium hydroxide; In water; for 1h;Reflux;	General procedure: A solution of sodium hydroxide (20%) was added dropwise to a suspension of 5aminotetrazole monohydrate (120 mmol) in water (30 mL), with a drop of phenolphthalein. The mixture was stirred until complete dissolution of the suspended material. Dimethyl sulphate (110 mmol) was then added in small portions, keeping an alkaline medium through addition of aqueous sodium hydroxide. The final mixture was refluxed for 1 h, then cooled, and finally left in ice bath for 48h. Colourless needles of the desired compound were filteredand dried (51% yield).

References: [1]Journal of Molecular Structure,2012,vol. 1023,p. 128 - 142.
[2]Molecules,2020,vol. 25.
[3]Pharmaceuticals,2019,vol. 12.
[4]New Journal of Chemistry,2019,vol. 43,p. 609 - 616.
[5]Journal of the American Chemical Society,1954,vol. 76,p. 923,924.
[6]New Journal of Chemistry,2009,vol. 33,p. 136 - 147.
[7]Chemistry - A European Journal,2009,vol. 15,p. 1164 - 1176.
[8]Polyhedron,2019,vol. 162,p. 100 - 110.

3
[ 6154-04-7 ]
[ 100-39-0 ]
1-benzyl-3-methyl-5-(N'-phenyl-thioureido)-tetrazolium betaine [ No CAS ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 2894,2896.

4
[ 6154-04-7 ]
[ 100-39-0 ]
5-amino-1-benzyl-3-methyl-tetrazolium; chloride [ No CAS ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 2894,2896.

5
[ 6154-04-7 ]
[ 100-52-7 ]
benzylidene-(2-methyl-2H-tetrazol-5-yl)-amine [ No CAS ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 923,924.

6
[ 6154-04-7 ]
[ 103-72-0 ]
N-(2-methyl-2H-tetrazol-5-yl)-N'-phenyl-thiourea [ No CAS ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 923,924.

7
[ 6154-04-7 ]
[ 75-36-5 ]
[ 6154-06-9 ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 923,924.

8
[ 6154-04-7 ]
[ 80-18-2 ]
5-amino-1,3-dimethyl-tetrazolium betaine [ No CAS ]
[ 88511-19-7 ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 2894,2896.

9
[ 6154-04-7 ]
[ 80-18-2 ]
phenyl-(1,2,3-trimethyl-2,3-dihydro-1H-tetrazol-5-yl)-carbodiimide [ No CAS ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 2894,2896.

10
[ 6154-04-7 ]
[ 80-18-2 ]
5-amino-1,3-dimethyl-tetrazolium betaine [ No CAS ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 2894,2896.

11
[ 6154-04-7 ]
bis(2-methyltetrazol-5-yl)amine [ No CAS ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 411,414.

12
[ 6154-04-7 ]
[ 41463-69-8 ]

References: [1]Journal of Physical Chemistry,1957,vol. 61,p. 261,264.

13
[ 6154-04-7 ]
[ 26621-43-2 ]
[ 7593-32-0 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 411,414.

14
[ 26621-43-2 ]
[ 6154-04-7 ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 923,924.

15
[ 4418-61-5 ]
[ 74-88-4 ]
[ 6154-04-7 ]
[ 5422-44-6 ]

Yield	Reaction Conditions	Operation in experiment
18%; 50%		A 500 mL R.B. flask was fitted with a magnetic stirrer andcharged with 30 mL of distilled water and 5-aminotetrazole monohydrate(17, 10.3 g, 0.1 mol), which formed a suspension. The flaskwas fitted with a pressure equalizing addition funnel containing25 mL of 20% NaOH solution (5 g, 0.125 mol). The solution wasadded dropwise to the flask over 0.5 h. A clear solution wasobtained in the flask. Then the pressure equalizing addition funnelwas replaced by another pressure equalizing addition funnel containinga solution of methyl iodide (14.2 g, 6.22 mL, 0.1 mol) in160 mL of acetone. The methyl iodide solution was added dropwiseto the flask over an hour. Afterwords, the reaction solution wasstirred at room temperature for three days and monitored by tlcas it proceeded to completion. During this 72 h period most ofthe acetone evaporated. The reaction solution was transferred to500 mL beaker and left in the hood overnight. A white solidprecipitated (6.6 g), which was spectroscopically identified as95:5 mixture of 1methyl5aminotetrazole ( 18) and 2methyl5aminotetrazole (19). This mixture was recrystallized from an acetone-water mixture yielding pure product 18 (5 g, 0.05 mol,50% yield); m.p. 220 C. TLC (acetonitrile) Rf = 0.65. The originalmother liquor (from which the 6.6 g precipitated) was evaporated,and 150 mL chloroform was added to the remaining white solid(which contained the minor product 19 and the inorganic saltNaI). The slurry was magnetically stirred overnight in order toextract the organic material, and the solid sodium iodide was filtered off. The yellow chloroform was evaporated yielding thedesired product 19. The latter was obtained pure via recrystallizationfrom water (1.8 g, 0.018 mol, 18% yield); M.p. 105 C. TLC (acetonitrile):Rf = 0.55.18: 1H NMR (DMSO-d6): delta 6.66 (s, 2H), 3.70 (s, 3H) ppm. 13CNMR (DMSO-d6): delta 155.71, 32.03 ppm. HRMS (m/z): calcd for[C2H6N5]+ 100.06185, obsd 100.06177.19: 1H NMR (DMSO-d6): delta 5.96 (s, 2H), 4.07(s, 3H) ppm. 13CNMR (DMSO-d6): delta 167.05, 38.68 ppm. HRMS (m/z): calcd for[C2H6N5]+ 100.06181, obsd 100.06177.
	With caesium carbonate; In acetonitrile; for 7h;Heating / reflux;	A mixture of 5-aminotetrazole (24.4 g, 0.29 mol), methyliodide (48.8 g, 0.34 mol), and Cs2CO3 (112.0 g, 0.34 mol) in acetonitrile (700 mL) is stirred and refluxed for 7 hours. The mixture is cooled to 50 0C and filtrated. The resulting filtrate is concentrated to give a mixture of 5-amino-2-methyltetrazole and 5-amino-1-methyltetrazole.
	With caesium carbonate; In acetonitrile; for 7h;Heating / reflux;	A mixture of 5-aminotetrazole (24.4 g, 0.29 mol), methyliodide (48.8 g, 0.34 mol), and Cs2CO3 (112.0 g, 0.34 mol) in acetonitrile (700 mL) is stirred and refluxed for 7 hours. The mixture is cooled to 50 0C and filtrated. The resulting filtrate is concentrated to give the mixture of 5-amino-2-methyltetrazole and 5-amino-1-methyltetrazole.

With caesium carbonate; In acetonitrile; for 7h;Heating / reflux;

A mixture of 5-aminotetrazole (24.4 g, 0.29 mol), methyliodide (48.8 g, 0.34 mol), and Cs2CO3 (112.0 g, 0.34 mol) in acetonitrile (700 mL) is stirred and refluxed for 7 hours. The mixture is cooled to 50 0C and filtrated. The resulting filtrate is concentrated to give the mixture of 5-amino-2-methyltetrazole and 5-amino-1-methyltetrazole.

References: [1]Polyhedron,2019,vol. 157,p. 71 - 89.
[2]Australian Journal of Chemistry,1984,vol. 37,p. 2453 - 2468.
[3]Patent: WO2007/73934,2007,A1 .Location in patent: Page/Page column 100-101.
[4]Patent: WO2008/58961,2008,A1 .Location in patent: Page/Page column 45.
[5]Patent: WO2008/58967,2008,A1 .Location in patent: Page/Page column 44.

16
[ 6154-04-7 ]
[ 13987-61-6 ]
[ 136670-17-2 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1991,vol. 27,p. 358 - 359.
Zhurnal Organicheskoi Khimii,1991,vol. 27,p. 419 - 420.

17
[ 6154-04-7 ]
[ 459-57-4 ]
[ 868-85-9 ]
[ 145181-82-4 ]

References: [1]Journal of general chemistry of the USSR,1992,vol. 62,p. 456 - 460.
Zhurnal Obshchei Khimii,1992,vol. 62,p. 556 - 561.

18
[ 6154-04-7 ]
[ 106-40-1 ]
[ 93680-38-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1589 - 1592.

19
[ 6154-04-7 ]
[ 61734-80-3 ]

References: [1]Helvetica Chimica Acta,2007,vol. 90,p. 2132 - 2150.
[2]Chemistry of Heterocyclic Compounds,1984,vol. 20,p. 1298 - 1300.
Khimiya Geterotsiklicheskikh Soedinenii,1984,p. 1569 - 1571.

20
[ 6154-04-7 ]
[ 41463-69-8 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1991,vol. 40,p. 1727.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1991,p. 1940 - 1941.

21
[ 6154-04-7 ]
[ 140861-19-4 ]