74205-82-6|(1H-1,2,4-Triazol-1-yl)methanol| Ambeed

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Quality Control of [ 74205-82-6 ] Purity: 95% SDS Specification

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Product Details of [ 74205-82-6 ]

CAS No. :	74205-82-6
Formula :	C₃H₅N₃O
M.W :	99.09
SMILES Code :	OCN1N=CN=C1
MDL No. :	MFCD00227137
InChI Key :	WCRAKJMHCWUABB-UHFFFAOYSA-N
Pubchem ID :	1547783

Safety of [ 74205-82-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 74205-82-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	7
Num. arom. heavy atoms	5
Fraction Csp3	0.33
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	22.45
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	50.94 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.37
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	-0.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.92
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.	-1.03
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	-0.43
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.53

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.51
Solubility	30.8 mg/ml ; 0.311 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.	0.05
Solubility	112.0 mg/ml ; 1.13 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly 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	0.21
Solubility	162.0 mg/ml ; 1.64 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.	-7.37 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)	1.65

Application In Synthesis of [ 74205-82-6 ]

* 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 [ 74205-82-6 ]

[ 74205-82-6 ] Synthesis Path-Downstream 1~36

1
[ 288-88-0 ]
[ 50-00-0 ]
[ 74205-82-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran; water; at 20℃;	No.88 Triazole (1.00 g, 14.4 mmol) was placed in 100 mL flask. No.42 THF (40 mL) was added at 20C. to give a clear solution. To this, No.89 formaldehyde (1.31 g, 37% aqueous solution) was added and stirred for 4 h to give a homogeneous solution. The solvent was removed under reduced pressure with a rotary evaporator, and the residue was dried in vacuo to afford No.90 (1H-1,2,4-triazol-1-yl)methanol in 96% yield (1.38 g, 13.9 mmol) as a white solid.
89%	With triethylamine; at 140℃; for 0.5h;	Step 1. Preparation of (1H-1,2,4-triazol-1-yl)methanol A mixture of 1H-1,2,4-triazole (7.04 g, 102 mmol), paraformaldehyde (3.06 g, 102 mmol) and catalytic amount of triethylamine was heated to molten condition and stirred at the same temperature (140 C.) for 0.5 hour. Reaction mixture was then cooled to 30 C. to obtain the product (9.0 g, 89%) as white solid.
79%	In ethanol; water; at 20℃; for 13h;Reflux;	The compound was synthesized with some modifications compared to Ref. [14]: (1,2,4)-triazole [98 %(Aldrich), 1,73 g, 25 mmol] in 20 ml of ethanol (absolute ethanol, ≥99.8 %, Sigma-Aldrich) and 3.5 ml of formaldehyde solution (≥36,5 %, Sigma-Aldrich) were stirred, refluxed for 1 h, and mixing was continued at room temperature for 12 h. After the elimination of the solvent under reduced pressure, the obtained residue was treated with cold water. A white solid appeared, which was collected by filtration, washed with diethyl ether (99 %, Sigma-Aldrich) and dried under vacuum to yield the pure product (79 %).

References: [1]Heterocyclic Communications,2001,vol. 7,p. 577 - 582.
[2]Phosphorus and Sulfur and the Related Elements,1987,vol. 33,p. 41 - 52.
[3]Patent: US2020/399196,2020,A1 .Location in patent: Paragraph 0152.
[4]Tetrahedron,2010,vol. 66,p. 9145 - 9150.
[5]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 189 - 194.
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 251 - 256.
[6]Patent: US2016/83380,2016,A1 .Location in patent: Paragraph 0240; 0241.
[7]Structural Chemistry,2016,vol. 27,p. 697 - 704.
[8]Research on Chemical Intermediates,2020,vol. 46,p. 1453 - 1467.

2
[ 116-17-6 ]
[ 74205-82-6 ]
[ 84595-23-3 ]

References: [1]Phosphorus and Sulfur and the Related Elements,1987,vol. 30,p. 201 - 204.

3
[ 74205-82-6 ]
[ 288-88-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 189 - 194.
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 251 - 256.

4
[ 74205-82-6 ]
[ 84387-62-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With thionyl chloride; In dichloromethane; at 70℃; for 4h;	In a 50 mL round-bottomed flask was charged No.90 <strong>[74205-82-6](1H-1,2,4-triazol-1-yl)methanol</strong> (1.00 g, 10.1 mmol) in No.92 DCM (50 mL). No.30 SOCl2 (2.93 mL, 40.4 mmol) was added dropwise with stirring. The mixture was heated gently for 4 h at 70C., and then cooled. A vacuum was applied, and the bath temperature was slowly increased to 45C. to afford No.93 1-(chloromethyl)-1H-1,2,4-triazole in 81% yield (0.960 g, 8.21 mmol) as a white solid.
48%	With thionyl chloride; In 1,2-dichloro-ethane; at 100℃; for 4h;	Step 2. Preparation of 1-(chloromethyl)-1H-1,2,4-triazole To a solution of <strong>[74205-82-6](1H-1,2,4-triazol-1-yl)methanol</strong> (1.0 g, 10.09 mmol) in dichloroethane (20 ml) thionyl chloride (1.105 ml, 15.14 mmol) was added and the reaction mixture was stirred at 100 C. for 4 hours. The reaction mixture was cooled to 30 C., poured into H2O (25 mL) and extracted with dichloromethane (3*20 mL). The combined organic layers was washed with H2O (50 mL) & brine solution (50 mL), dried over Na2SO4 and evaporated in rotavapor under vacuum to yield 1-(chloromethyl)-1H-1,2,4-triazole (0.570 g, 48%) as brown liquid.

References: [1]Patent: US2020/399196,2020,A1 .Location in patent: Paragraph 0153.
[2]Patent: US2016/83380,2016,A1 .Location in patent: Paragraph 0242.
[3]Phosphorus and Sulfur and the Related Elements,1987,vol. 30,p. 201 - 204.

5
[ 74205-82-6 ]
C₅H₆N₆ [ No CAS ]

References: [1]Phosphorus and Sulfur and the Related Elements,1987,vol. 30,p. 201 - 204.

6
[ 74205-82-6 ]
(1H-1,2,4-triazol-1-yl)methyl chloride hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.2%	With thionyl chloride; In tetrahydrofuran;	Step 2--Preparation of 1-(chloromethyl)-1,2,4-triazole hydrochloride A 4 neck 1 liter flask equipped with condenser, addition funnel and mechanical stirrer was charged 45 gms of <strong>[74205-82-6]1-(hydroxymethyl)-1,2,4-triazole</strong> (0.464 mole) in 500 ml of THF was heating to 40 C. with vigorous stirring. Then SOCl2 (61 ml, 0.84 mole) was added dropwise maintaining the temperature at 45 C. During the addition, a precipitate formed and the mixture was stirred for an additional 2 hours. The product was filtered, washed three times with ethyl acetate and vacuum dried at room temperature. 67.3 gms of product having a melting point of 118-130 C. resulted (94.2% yield).

References: [1]Patent: US5087635,1992,A .
[2]Phosphorus and Sulfur and the Related Elements,1987,vol. 33,p. 41 - 52.

7
[ 74205-82-6 ]
[ 122-52-1 ]
[ 84595-22-2 ]

References: [1]Phosphorus and Sulfur and the Related Elements,1987,vol. 30,p. 201 - 204.

8
[ 89-72-5 ]
[ 74205-82-6 ]
2-sec-Butyl-6-[1,2,4]triazol-1-ylmethyl-phenol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

9
[ 106-44-5 ]
[ 74205-82-6 ]
4-Methyl-2-[1,2,4]triazol-1-ylmethyl-phenol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.
[2]Pest Management Science,2001,vol. 57,p. 707 - 712.

10
[ 121-72-2 ]
[ 74205-82-6 ]
Dimethyl-(3-methyl-4-[1,2,4]triazol-1-ylmethyl-phenyl)-amine [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

11
[ 90-15-3 ]
[ 74205-82-6 ]
2-(1H-1,2,4-triazol-1-ylmethyl)-1-naphthol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.
[2]Pest Management Science,2001,vol. 57,p. 707 - 712.

12
[ 2409-55-4 ]
[ 74205-82-6 ]
2-tert-Butyl-4-methyl-6-[1,2,4]triazol-1-ylmethyl-phenol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

13
[ 88-18-6 ]
[ 74205-82-6 ]
2-tert-Butyl-6-[1,2,4]triazol-1-ylmethyl-phenol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

14
[ 142-04-1 ]
[ 74205-82-6 ]
[ 101-77-9 ]
[ 119192-10-8 ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

15
[ 74205-82-6 ]
[ 95-48-7 ]
2-Methyl-6-[1,2,4]triazol-1-ylmethyl-phenol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.
[2]Pest Management Science,2001,vol. 57,p. 707 - 712.

16
[ 74205-82-6 ]
[ 121-69-7 ]
4-((1H-1,2,4-triazol-1-yl)methyl)-N,N-dimethylaniline [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

17
[ 74205-82-6 ]
[ 103-69-5 ]
[ 843-29-8 ]
Ethyl-(4-[1,2,4]triazol-1-ylmethyl-phenyl)-amine [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

18
[ 74205-82-6 ]
[ 62-53-3 ]
N-(1H-1,2,4-triazol-1-ylmethyl)aniline [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

19
[ 74205-82-6 ]
[ 100-61-8 ]
[ 1807-55-2 ]
Methyl-(4-[1,2,4]triazol-1-ylmethyl-phenyl)-amine [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

20
[ 74205-82-6 ]
[ 135-19-3 ]
1-(1H-1,2,4-triazol-1-ylmethyl)-2-naphthol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.
[2]Pest Management Science,2001,vol. 57,p. 707 - 712.

21
[ 74205-82-6 ]
[ 102-27-2 ]
Ethyl-(3-methyl-4-[1,2,4]triazol-1-ylmethyl-phenyl)-amine [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.

22
[ 74205-82-6 ]
[ 108-95-2 ]
o-(1H-1,2,4-triazol-1-ylmethyl)phenol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.
[2]Pest Management Science,2001,vol. 57,p. 707 - 712.

23
[ 1603-40-3 ]
[ 74205-82-6 ]
2-[(1,2,4-triazole-1-ylmethyl)amino]-3-methylpyridine [ No CAS ]