Home Cart Sign in  
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 499770-76-2 Chemical Structure| 499770-76-2
Chemical Structure| 499770-76-2

5-(Bromomethyl)-1-methyl-1H-benzo[d][1,2,3]triazole

CAS No.: 499770-76-2

4.5 *For Research Use Only !

Cat. No.: A304390 Purity: 98%

Change View

Size Price

USA Stock *0-1 Day

Global Stock *5-7 Days

In Stock
250mg łÇÍď¶ÊÊ Inquiry 1-2 weeks
1g łÍÍǶÊÊ Inquiry 1-2 weeks

  • 250mg

    łÇÍď¶ÊÊ

  • 1g

    łÍÍǶÊÊ

In Stock

- +

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of [ 499770-76-2 ]

CAS No. :499770-76-2
Formula : C8H8BrN3
M.W : 226.07
SMILES Code : BrCC2=CC1=C([N](N=N1)C)C=C2
MDL No. :MFCD03407338
InChI Key :OSUZHHPMRAIJDY-UHFFFAOYSA-N
Pubchem ID :2795418

Safety of [ 499770-76-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:8
UN#:3261
Packing Group:

Calculated chemistry of [ 499770-76-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 9
Fraction Csp3 0.25
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 51.63
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

30.71 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.69
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.71
Log Po/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.

2.13
Log Po/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

1.9
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.89

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.8
Solubility 0.362 mg/ml ; 0.0016 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.95
Solubility 2.54 mg/ml ; 0.0112 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

-3.37
Solubility 0.0976 mg/ml ; 0.000432 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

Yes
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

Yes
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.

-6.48 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

0.0
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

1.0 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)

2.04

Application In Synthesis [ 499770-76-2 ]

* 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 [ 499770-76-2 ]

[ 499770-76-2 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 120321-72-4 ]
  • [ 499770-76-2 ]
YieldReaction ConditionsOperation in experiment
With phosphorus tribromide; In diethyl ether; at 20℃; Phosphorus tribromide (0.230 ml, 2.45 mmol) is added to a stirred solution of (1-methyl-1 H- 1 ,2,3-benzotriazole-5-yl)methano. (0.4 g, 2.45 mmol) in diethyl ether (25 mi) under an inert atmosphere of Argon. After stirring overnight at room temperature, the reaction mixture is diluted with water (5 ml) and stirred vigorously for 10 minutes. The organic portion is <n="64"/>separated, washed with water (2 x 5 ml), brine (2 x 5 ml) and concentrated in vacuo to yield the titled product which is used crude in the next step. (MH+ 226).
With phosphorus tribromide; In diethyl ether; at 20℃; 5-Bromomethyl-1-methyl-1 H-benzotriazole: Phosphorus tribromide (0.230 ml, 2.45 mmol) is added to a stirred solution of (I -methyl-I H- 1,2,3-benzotriazole-5-yl) methanol (0.4 g, 2.45 mmol) in diethyl ether (25 ml) under an inert atmosphere of Argon. After stirring overnight at room temperature, the reaction mixture is diluted with water (5 ml) and stirred vigorously for 10 minutes. The organic portion is separated, washed with water (2 x 5 ml), brine (2 x 5 ml) and concentrated in vacuo to yield the titled product which is used crude in the next step. (MH+ 226).
  • 2
  • [ 499770-76-2 ]
  • [2-methyl-1-(3-methyl-3H-benzotriazol-5-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of (2-methyl-1 H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester ( (0.025 g, 0.122 mmol) in dry DMF (1 ml) under an inert atmosphere of Argon is added dropwise, BEMP (56.6 //I, 0.196 mmol). The mixture is agitated at room temperature for 1 hour before cooling to 0 0C with an ice-bath. A solution of 5-bromomethyl-1-methyl-1H- benzotriazole (0.044 g, 0.196 mmol) in DMF (1 ml) is added to the cooled solution and the resulting mixture is agitated at room temperature for 2 days. The solvent is removed in vacuo and purification of the crude by chromatography on silica eluting with iso- hexane/ethyl acetate (0 %- 20 % ethyl acetate) yields the titled product. (MH+ 350).
  • 3
  • [ 499770-76-2 ]
  • [ 875318-60-8 ]
  • [ 944556-01-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 140℃; for 6h; A mixture of intermediate 18 (0.01 mol) and 5 -(bromo methyl)- 1 -methyl- IH- benzotriazole (0.0035 mol) in DMF (30ml) was stirred at 1400C for 6 hours. The solvent was evaporated. The residue was taken up in EtOAc. The organic layer was washed with water, then with saturated sodium chloride, dried (MgSO4), filtered and the solvent was evaporated. The residue was combined with another fraction made in a <n="41"/>similar way, yielding 4g, and then purified by column chromatography over silica gel (15-40mum) (eluent: DCM/MeOH 99/1). The pure fractions were collected and the solvent was evaporated. The residue (0.9g) was purified by column chromatography over silica gel (15-40mum) (eluent: DCM/MeOH 99/1). The pure fractions were collected and the solvent was evaporated, yielding 0.22g of intermediate 19.
  • 4
  • [ 499770-76-2 ]
  • [ 153172-31-7 ]
  • C22H36N4O3Si [ No CAS ]
  • 5
  • [ 7546-52-3 ]
  • [ 499770-76-2 ]
  • [2-methyl-1-(3-methyl-3H-benzotriazol-5-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
[2-Methyl-1-(3-methyl-3H-benzotriazol-5-ylmethyl)-1 H-pyrrolo[2,3-b]pyridin-3-yl]- acetic acid methyl ester: To a solution of (2-methyl-1 H-pyrrolo [2,3-b]pyridin-3-yl)-acetic methyl ester ( (0.025 g, 0.122 mmol) in dry DMF (1 ml) under an inert atmosphere of Argon is added dropwise, BEMP (56.6 pl, 0.196 mmol). The mixture is agitated at room temperature for 1 hour before cooling to 0 C with an ice-bath. A solution of 5-bromomethyl-1-methyl-1 H- benzotriazole (0.044 g, 0.196 mmol) in DMF (1 ml) is added to the cooled solution and the resulting mixture is agitated at room temperature for 2 days. The solvent is removed in vacuo and purification of the crude by chromatography on silica eluting with iso- hexane/ethyl acetate (0 %- 20 % ethyl acetate) yields the titled product. (MH+ 350).
  • 6
  • [ 499770-76-2 ]
  • [ 1395042-65-5 ]
  • [ 1395042-82-6 ]
  • 7
  • [ 499770-76-2 ]
  • (R)-tert-butyl 3-(5-chloro-4-(1H-pyrrolo[3,2-b]pyridin-6-yl)pyridin-2-ylcarbamoyl)piperidine-1-carboxylate [ No CAS ]
  • (3R)-N-(5-chloro-4-{1-[(1-methyl-1H-benzotriazol-6-yl)methyl]-1H-pyrrolo[3,2-b]pyridin-6-yl}pyridin-2-yl)piperidine-3-carboxamide bis trifluoroacetate salt [ No CAS ]
  • 8
  • [ 499770-76-2 ]
  • (R)-tert-butyl 3-(5-chloro-4-(1H-pyrrolo[3,2-b]pyridin-6-yl)pyridin-2-ylcarbamoyl)piperidine-1-carboxylate [ No CAS ]
  • (R)-tert-butyl 3-(5-chloro-4-(1-((1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)methyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)pyridin-2-ylcarbamoyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; at 75℃; for 16h; Example 305B (R)-tert-butyl 3-(5-chloro-4-(1-((1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)methyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)pyridin-2-ylcarbamoyl)piperidine-1-carboxylate To a two dram vial was added Example 305A (52 mg, 0.114 mmol), <strong>[499770-76-2]5-(bromomethyl)-1-methyl-1H-benzo[d][1,2,3]triazole</strong> (51.6 mg, 0.228 mmol), cesium carbonate (111 mg, 0.342 mmol) and tetrabutylammonium iodide (42.1 mg, 0.114 mmol) in N,N-dimethylformamide (570 mul). The vial was capped with a septa and the mixture was stirred at 75 C. for 16 hours. After cooling to ambient temperature, the mixture was partitioned between water and ethyl acetate (10 mL each). The organic layer was removed and dried over anhydrous magnesium sulfate, filtered and concentrated, and purified by silica gel flash chromatography (Isco, Redi-Sep column) eluting with a gradient of 40-100% ethyl acetate/hexane to give the title compound.
 

Historical Records

Technical Information

Categories