[ CAS No. 28539-02-8 ] {[proInfo.proName]}

Name: 28539-02-8|1-(Hydroxymethyl)benzotriazole|95%
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Quality Control of [ 28539-02-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 28539-02-8 ]

CAS No. :	28539-02-8	MDL No. :	MFCD00179118
Formula :	C₇H₇N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MXJIHEXYGRXHGP-UHFFFAOYSA-N
M.W :	149.15	Pubchem ID :	224169
Synonyms :

Calculated chemistry of [ 28539-02-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.95
TPSA :	50.94 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.4
Log Po/w (XLOGP3) :	0.63
Log Po/w (WLOGP) :	0.23
Log Po/w (MLOGP) :	0.88
Log Po/w (SILICOS-IT) :	0.33
Consensus Log Po/w :	0.69

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.7
Solubility :	2.97 mg/ml ; 0.0199 mol/l
Class :	Very soluble
Log S (Ali) :	-1.27
Solubility :	7.92 mg/ml ; 0.0531 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.52
Solubility :	4.47 mg/ml ; 0.03 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 28539-02-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 28539-02-8 ]

* 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 [ 28539-02-8 ]
Downstream synthetic route of [ 28539-02-8 ]

[ 28539-02-8 ] Synthesis Path-Upstream 1~9

1
[ 109-06-8 ]
[ 28539-02-8 ]
[ 103-74-2 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 6, p. 1165 - 1167

2
[ 1072-97-5 ]
[ 28539-02-8 ]
[ 84539-30-0 ]

Reference： [1] Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 805 - 812

3
[ 95-14-7 ]
[ 50-00-0 ]
[ 28539-02-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	at 25℃; for 0.0833333 h;	Example 30 1-Hydroxymethyl-1H-benzotriazole [0464] Dissolve 10 g (83.94 mmol) of 1H-benzotriazole in 6.81 mL (83.94 mmol) of a 37percent aqueous solution of formaldehyde. Stir and bring the mixture to a temperature of 25° C. After 5 minutes, the reaction mixture solidifies. Cool the solution to ambient temperature. Filter and wash with diethyl ether. Triturate the residue in the cold in tetrahydrofuran and filter (Int. 94). [0465] Yield: 94percent [0466] Melting point: 148-150° C. (tetrahydrofuran and diethyl ether)
90%	at 20℃; for 2 h;	Weigh benzotriazole (5mmol, 596mg), 40percent formic acid (5mmol, 375mg) placed in 100mL round bottomBottles , 60mL of methanol was added , stirred for 2 hours at room temperature , there are a lot of white solid precipitated , suction filtered , the filter cake washed with cold methanol , and dried ,To give 1-hydroxymethyl benzene and triazole , quality 671mg ( 90percent yield ) . Weigh 1-hydroxymethyl benzo triazole (lmmol,149mg), 4_ (4_ morpholinyl ) aniline (lmmol, 178mg) a 50mL round bottom flask was added 20mL of methanol , stirred at room temperatureMixed 3h, has a large amount of solid precipitated , suction filtered , the filter cake washed with cold methanol , and dried to give the title compound . An off-white solid , mass :278mg ( 90percent yield ) .
35%	at 80℃; for 1 h;	(1) 11.9 g of benzotriazole,30ml water and30ml formaldehyde mixture,Heating to dissolve the solid,At 80 water bath heating 1h,Cool and filter to give white needles,Recrystallization from ethyl acetate gave white crystals,Namely hydroxymethyl benzotriazole;

Reference： [1] Patent: US2004/67998, 2004, A1, . Location in patent: Page/Page column 24
[2] Journal of the American Chemical Society, 2017, vol. 139, # 27, p. 9281 - 9290
[3] Patent: CN102688233, 2016, B, . Location in patent: Paragraph 0095; 0098
[4] Patent: CN106188103, 2016, A, . Location in patent: Paragraph 0035; 0037
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 3868
[6] Justus Liebigs Annalen der Chemie, 1934, vol. 511, p. 213,240
[7] Recueil des Travaux Chimiques des Pays-Bas, 1988, vol. 107, # 11, p. 641 - 646
[8] Journal of Organic Chemistry, 1989, vol. 54, # 26, p. 6022 - 6029
[9] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 15, p. 2009 - 2014
[10] Organic Preparations and Procedures International, 1992, vol. 24, # 4, p. 475 - 478
[11] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8981 - 8982
[12] Organic Letters, 2012, vol. 14, # 8, p. 2138 - 2141
[13] Patent: , 2016, , . Location in patent: Paragraph 0037
[14] Patent: CN108774252, 2018, A, . Location in patent: Paragraph 0032; 0034

4
[ 1073609-15-0 ]
[ 62-53-3 ]
[ 28539-02-8 ]
[ 5335-37-5 ]

Reference： [1] Heterocycles, 2008, vol. 75, # 9, p. 2201 - 2211

5
[ 100726-41-8 ]
[ 28539-02-8 ]

Reference： [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1574

6
[ 50-00-0 ]
[ 1352930-09-6 ]
[ 28539-02-8 ]

Reference： [1] Chemical Communications, 2012, vol. 48, # 4, p. 552 - 554

7
[ 95-14-7 ]
[ 50-00-0 ]
[ 28539-02-8 ]
[ 136969-48-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2, 1990, # 6, p. 921 - 924
[2] Journal of the Chemical Society, Perkin Transactions 2, 1990, # 6, p. 921 - 924
[3] Journal of the Chemical Society, Perkin Transactions 2, 1990, # 6, p. 921 - 924

8
[ 28539-02-8 ]
[ 91-66-7 ]
[ 135-91-1 ]

Reference： [1] Synthesis, 1990, p. 341 - 346

9
[ 28539-02-8 ]
[ 91-66-7 ]
[ 135-91-1 ]
[ 129075-92-9 ]

Reference： [1] Synthesis, 1990, p. 341 - 346

[ 28539-02-8 ] Synthesis Path-Downstream 1~88

1
[ 95-14-7 ]
[ 50-00-0 ]
[ 28539-02-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	In water; at 25℃; for 0.0833333h;	Example 30 1-Hydroxymethyl-1H-benzotriazole [0464] Dissolve 10 g (83.94 mmol) of 1H-benzotriazole in 6.81 mL (83.94 mmol) of a 37% aqueous solution of formaldehyde. Stir and bring the mixture to a temperature of 25 C. After 5 minutes, the reaction mixture solidifies. Cool the solution to ambient temperature. Filter and wash with diethyl ether. Triturate the residue in the cold in tetrahydrofuran and filter (Int. 94). [0465] Yield: 94% [0466] Melting point: 148-150 C. (tetrahydrofuran and diethyl ether)
90%	In methanol; at 20℃; for 2h;	Weigh benzotriazole (5mmol, 596mg), 40% formic acid (5mmol, 375mg) placed in 100mL round bottomBottles , 60mL of methanol was added , stirred for 2 hours at room temperature , there are a lot of white solid precipitated , suction filtered , the filter cake washed with cold methanol , and dried ,To give 1-hydroxymethyl benzene and triazole , quality 671mg ( 90% yield ) . Weigh 1-hydroxymethyl benzo triazole (lmmol,149mg), 4_ (4_ morpholinyl ) aniline (lmmol, 178mg) a 50mL round bottom flask was added 20mL of methanol , stirred at room temperatureMixed 3h, has a large amount of solid precipitated , suction filtered , the filter cake washed with cold methanol , and dried to give the title compound . An off-white solid , mass :278mg ( 90% yield ) .
35%	In water; at 80℃; for 1h;	(1) 11.9 g of benzotriazole,30ml water and30ml formaldehyde mixture,Heating to dissolve the solid,At 80 water bath heating 1h,Cool and filter to give white needles,Recrystallization from ethyl acetate gave white crystals,Namely hydroxymethyl benzotriazole;

	In water; at 80℃; for 1h;	11.9 g of benzotriazole, 30 ml of water and 30 ml of formaldehyde were mixed, and the mixture was heated with stirring to dissolve the solid.Heating to lh, cooling, filtering to obtain white needle-like product, recrystallization from ethyl acetate to obtain white crystals, namely hydroxylMethylbenzotriazole; (2) 7.4 g of hydroxymethylbenzotriazole was added to a single-necked flask, 25 ml of S0C12 was added dropwise, and the mixture was stirredMixed 30min, 80 C reflux 3h; with rotary evaporator to excess S0C12, obtained white crystals, namely chloromethyl benzotriazoleOxazole;(3) 40 mmol of 2-ethylimidazole was dissolved in 20 ml of dimethylsulfoxide (DMS0), and the mixture was milledNa0H80mmol, heated to 60 C, then add 40mmol chloromethyl benzotriazole, 60 C water bath heating lh, cooling to room temperature,Poured into 100g of ice water, stirring, precipitation, filtration, precipitation washed with water 3 times to get crude;(4) The crude product was recrystallized from ethyl acetate to give the colored crystals as the ligand 1- (benzotriazole-1-methyl) -1- (2-ethylimidazole).
	In water; at 80℃; for 1h;	(1) Mix 50 mmol of benzotriazole with 15 mL of water and 15 mL of formaldehyde, and heat to 80 C for 60 min in a water bath.Cooling and filtering to obtain a white needle-like product.Recrystallization from ethyl acetate gave white crystals.It is hydroxymethylbenzotriazole;
	In water; at 80℃; for 1h;	The preparation method of the ligand 1-(benzotriazol-1-methyl)-1-(2-ethyl-4-methylimidazole) of the invention comprises the following steps:(1) Mix 50 mmol of benzotriazole with 15 mL of water and 15 mL of formaldehyde. The water bath was heated to 80 C and refluxed for 60 min. Cooling and filtering to obtain a white needle-like product. Recrystallization from ethyl acetate gave white crystals. It is hydroxymethylbenzotriazole;

Reference： [1]Patent: US2004/67998,2004,A1 .Location in patent: Page/Page column 24
[2]Journal of the American Chemical Society,2017,vol. 139,p. 9281 - 9290
[3]Journal of the American Chemical Society,2020
[4]Patent: CN102688233,2016,B .Location in patent: Paragraph 0095; 0098
[5]Patent: CN106188103,2016,A .Location in patent: Paragraph 0035; 0037
[6]Journal of the American Chemical Society,1952,vol. 74,p. 3868
[7]Recueil des Travaux Chimiques des Pays-Bas,1988,vol. 107,p. 641 - 646
[8]Journal of Organic Chemistry,1989,vol. 54,p. 6022 - 6029
[9]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2009 - 2014
[10]Organic Preparations and Procedures International,1992,vol. 24,p. 475 - 478
[11]Tetrahedron Letters,2006,vol. 47,p. 8981 - 8982
[12]Organic Letters,2012,vol. 14,p. 2138 - 2141
[13]Patent: ,2016, .Location in patent: Paragraph 0037
[14]Patent: CN108774252,2018,A .Location in patent: Paragraph 0032; 0034
[15]Patent: CN108659022,2018,A .Location in patent: Paragraph 0031-0033

2
[ 28539-02-8 ]
[ 75-36-5 ]
[ 99358-56-2 ]
[ 18773-93-8 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 1022,1023

3
[ 28539-02-8 ]
[ 54187-96-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With thionyl chloride; at 0℃; for 1h;Heating / reflux;	Example 31 1-Chloromethyl-1H-benzotriazole [0467] To 8.91 g (59.7 mmol) of 1-hydroxymethyl-1H-benzotriazole cooled to 0 C. in an ice bath, add, progressively, using a dropping funnel, 26 mL (360 mmol) of thionyl chloride. Stir and bring to reflux for 1 hour. Evaporate to dryness. Take up the residue in methanol. Cool the solution, filter and dry (Int. 95). [0468] Yield: 93% [0469] Melting point: 136-138 C. (methanol)
	With thionyl chloride; at 80℃; for 3.5h;	7.4 g of hydroxymethylbenzotriazole was added to a single-necked flask, 25 ml of S0C12 was added dropwise,After the end of the mixing, the mixture was stirred for 30 min and refluxed at 80 C for 3 h. The excess S0C12 was distilled off with a rotary evaporator, To give a white crystal, i. EforChloromethyl benzotriazole
	With thionyl chloride; at 80℃; for 3.5h;	(2) The hydroxymethyl benzotriazole 7.4g added to a single-necked flask,Dropping 25ml SOCl2,After the dropwise addition and stirring 30min,80 reflux 3h;Excess amount of SOCl2 was distilled off by a rotary evaporator,Get white crystals,Namely chloromethyl benzotriazole;

	With thionyl chloride; at 80℃; for 3h;	(2) Weigh 25mmol of hydroxymethylbenzotriazole into a single-mouth bottle,Then add 12.5mL of thionyl chloride,After the completion of the dropwise addition, the mixture was stirred for 20 min, and refluxed at 80 C for 180 min;The remaining thionyl chloride is distilled off using a rotary evaporator.Get yellow-white crystals, That is chloromethylbenzotriazole;
	With thionyl chloride; at 80℃; for 3.33333h;	Weigh 25mmol of hydroxymethylbenzotriazole into a single-mouth bottle, Then add 12.5mL of thionyl chloride, Mix and stir for 20 min after the end of the addition. Reflow at 80 C for 180 min; The remaining thionyl chloride is distilled off using a rotary evaporator. Get yellow-white crystals, That is chloromethylbenzotriazole;

Reference： [1]Patent: US2004/67998,2004,A1 .Location in patent: Page/Page column 23
[2]Journal of the American Chemical Society,2017,vol. 139,p. 9281 - 9290
[3]Journal of the American Chemical Society,2020
[4]Journal of the American Chemical Society,1952,vol. 74,p. 3868
[5]Recueil des Travaux Chimiques des Pays-Bas,1988,vol. 107,p. 641 - 646
[6]Journal of Organic Chemistry,1989,vol. 54,p. 6022 - 6029
[7]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2009 - 2014
[8]Organic Letters,2012,vol. 14,p. 2138 - 2141
[9]Patent: ,2016, .Location in patent: Paragraph 0038
[10]Patent: CN106188103,2016,A .Location in patent: Paragraph 0035; 0038
[11]Patent: CN108774252,2018,A .Location in patent: Paragraph 0032-0035
[12]Patent: CN108659022,2018,A .Location in patent: Paragraph 0031; 0034

4
[ 1072-97-5 ]
[ 28539-02-8 ]
[ 84539-30-0 ]

Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 805 - 812

5
[ 50-00-0 ]
[ 28539-02-8 ]
[ 111184-76-0 ]
[ 121238-82-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	In benzene for 5h; Heating; Dean-Stark adapter;

Reference： [1]Katritzky, Alan R.; Yannakopoulou, Konstantina; Lue, Ping; Rasala, Danuta; Urogdi, Laszlo [Journal of the Chemical Society. Perkin transactions I, 1989, p. 225 - 233]

6
[ 28539-02-8 ]
[ 627-45-2 ]
N-Benzotriazol-1-ylmethyl-N-ethyl-formamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With toluene-4-sulfonic acid In toluene for 8h; Heating;

Reference： [1]Katritzky, Alan R.; Yao, Guowei; Lan, Xiangfu; Zhao, Xiaohong [Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2086 - 2093]

7
[ 28539-02-8 ]
[ 637-53-6 ]
N-Benzotriazol-1-ylmethyl-N-phenyl-thioacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With toluene-4-sulfonic acid In toluene for 72h; Heating;

Reference： [1]Katritzky, Alan R.; Yao, Guowei; Lan, Xiangfu; Zhao, Xiaohong [Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2086 - 2093]

8
[ 28539-02-8 ]
[ 142-04-1 ]
[ 129075-89-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	In acetic acid for 0.25h; Heating;

Reference： [1]Katritzky, Alan R.; Lan, Xiangfu; Lam, Jamshed N. [Synthesis, 1990, p. 341 - 346]

9
[ 28539-02-8 ]
[ 91-66-7 ]
[ 135-91-1 ]

Reference： [1]Synthesis,1990,p. 341 - 346

10
[ 28539-02-8 ]
[ 91-66-7 ]
[ 135-91-1 ]
[ 129075-92-9 ]

Reference： [1]Synthesis,1990,p. 341 - 346

11
[ 28539-02-8 ]
[ 111184-76-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With ammonium hydroxide; acetic acid In methanol at 25℃; for 5h;

Reference： [1]Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila [Journal of the Chemical Society. Perkin transactions I, 1987, p. 799 - 804]

12
[ 28539-02-8 ]
[ 86-86-2 ]
N-Benzotriazol-1-ylmethyl-2-naphthalen-1-yl-acetamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 4002 - 4005

13
[ 28539-02-8 ]
[ 15862-72-3 ]
[ 170164-57-5 ]

Reference： [1]Synthetic Communications,1995,vol. 25,p. 2751 - 2762

14
[ 28539-02-8 ]
[ 163808-09-1 ]
[ 163808-10-4 ]

Reference： [1]Heterocycles,1995,vol. 41,p. 345 - 352

15
[ 28539-02-8 ]
[ 3195-78-6 ]
[ 146041-90-9 ]
N-Methyl-N-[(1S,7S)-7-(2-oxo-pyrrolidin-1-yl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-1-yl]-acetamide [ No CAS ]
1-((1S,7S)-7-Benzotriazol-1-yl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-1-yl)-pyrrolidin-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 3117 - 3126
[2]Journal of Organic Chemistry,1996,vol. 61,p. 3117 - 3126

16
[ 88-12-0 ]
[ 28539-02-8 ]
[ 66943-05-3 ]
13-[3-(pyrrolidin-1-yl)propyl]-1,4,7,10-tetraoxa-13-azacyclopentadecane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7578 - 7584

17
[ 28539-02-8 ]
[ 3195-78-6 ]
[ 66943-05-3 ]
13-(4-methyl-4-azahexyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7578 - 7584

18
[ 28539-02-8 ]
[ 1975-78-6 ]
N-(Benzotriazol-1-ylmethyl)decanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With boron trifluoride diethyl etherate at 120℃; for 8h;

Reference： [1]Katritzky, Alan R.; Galuszka, Barbara; Zhang, Yongmin; Rachwal, Stanislaw [Organic Preparations and Procedures International, 1992, vol. 24, # 4, p. 475 - 478]

19
[ 2362-64-3 ]
[ 28539-02-8 ]
[ 301344-07-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With toluene-4-sulfonic acid In toluene for 24h; Heating;

Reference： [1]Katritzky; Huang; Voronkov; Wang; Kolb [Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8819 - 8821]

20
[ 28539-02-8 ]
[ 312327-16-5 ]
[ 312327-19-8 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 8001 - 8010

21
[ 28539-02-8 ]
[ 527-20-8 ]
benzotriazol-1-ylmethyl-pentachlorophenyl-amine [ No CAS ]

Reference： [1]Bollettino Chimico Farmaceutico,2001,vol. 140,p. 215 - 220

22
[ 28539-02-8 ]
[ 126208-61-5 ]
[ 402519-07-7 ]