Home Cart Sign in  
Chemical Structure| 22300-52-3 Chemical Structure| 22300-52-3
Chemical Structure| 22300-52-3

4,5-Dibromo-2H-1,2,3-triazole

CAS No.: 22300-52-3

4.5 *For Research Use Only !

Cat. No.: A190726 Purity: 98%

Change View

Size Price

US Stock

Global Stock

In Stock
250mg łÇʶÊÊ Inquiry Inquiry
1g łÇ˶ÊÊ Inquiry Inquiry
5g łËǶÊÊ Inquiry Inquiry
10g łËò¶ÊÊ Inquiry Inquiry
25g łÍǶÊÊ Inquiry Inquiry
100g łÇͧ¶ÊÊ Inquiry Inquiry
500g łďÇͶÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 250mg

    łÇʶÊÊ

  • 1g

    łÇ˶ÊÊ

  • 5g

    łËǶÊÊ

  • 10g

    łËò¶ÊÊ

  • 25g

    łÍǶÊÊ

  • 100g

    łÇͧ¶ÊÊ

  • 500g

    łďÇͶÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

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

Alternative Products

Product Details of [ 22300-52-3 ]

CAS No. :22300-52-3
Formula : C2HBr2N3
M.W : 226.86
SMILES Code : BrC1=NNN=C1Br
MDL No. :MFCD19440717
InChI Key :GUQUYKTWVBJKFL-UHFFFAOYSA-N
Pubchem ID :312397

Safety of [ 22300-52-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Calculated chemistry of [ 22300-52-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 31.78
TPSA ?

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

41.57 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.83
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

1.65
Log Po/w (WLOGP)?

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

1.33
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.

0.81
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

2.65
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.46

Water Solubility

Log S (ESOL):?

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

-2.81
Solubility 0.348 mg/ml ; 0.00153 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.

-2.14
Solubility 1.66 mg/ml ; 0.00731 mol/l
Class?

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

-2.58
Solubility 0.604 mg/ml ; 0.00266 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

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.

-6.51 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

1.0
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)

1.98

Application In Synthesis of [ 22300-52-3 ]

* 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 [ 22300-52-3 ]

[ 22300-52-3 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 176694-36-3 ]
  • [ 22300-52-3 ]
  • [ 1192847-36-1 ]
  • 2
  • [ 4548-45-2 ]
  • [ 22300-52-3 ]
  • [ 1192847-38-3 ]
  • 3
  • [ 5470-18-8 ]
  • [ 22300-52-3 ]
  • [ 1192847-41-8 ]
  • 4
  • [ 22300-52-3 ]
  • [ 369-34-6 ]
  • [ 1192847-34-9 ]
  • 5
  • [ 22300-52-3 ]
  • [ 27996-87-8 ]
  • [ 1192847-35-0 ]
  • 6
  • [ 22300-52-3 ]
  • [ 394-47-8 ]
  • [ 1192847-32-7 ]
  • 7
  • [ 22300-52-3 ]
  • [ 701-45-1 ]
  • [ 1192847-37-2 ]
  • 8
  • [ 22300-52-3 ]
  • [ 1427-06-1 ]
  • [ 1192847-39-4 ]
  • 10
  • [ 22300-52-3 ]
  • [ 72537-17-8 ]
  • [ 1192847-40-7 ]
  • 11
  • [ 69966-55-8 ]
  • [ 22300-52-3 ]
  • [ 1248676-31-4 ]
  • [ 1248676-67-6 ]
  • 12
  • [ 74-96-4 ]
  • [ 22300-52-3 ]
  • [ 1248676-21-2 ]
  • [ 1248676-59-6 ]
  • 13
  • [ 75-77-4 ]
  • [ 22300-52-3 ]
  • [ 1248676-08-5 ]
  • 14
  • [ 75-77-4 ]
  • [ 22300-52-3 ]
  • 4,5-bis(trimethylsilyl)-2H-1,2,3-triazole [ No CAS ]
  • 15
  • [ 22300-52-3 ]
  • [ 96-32-2 ]
  • [ 1248676-22-3 ]
  • [ 1248676-61-0 ]
  • 16
  • [ 22300-52-3 ]
  • [ 103-63-9 ]
  • [ 1248676-24-5 ]
  • [ 1248676-62-1 ]
  • 17
  • [ 22300-52-3 ]
  • [ 874-98-6 ]
  • [ 1248676-29-0 ]
  • [ 1248676-64-3 ]
  • 18
  • [ 22300-52-3 ]
  • [ 17201-43-3 ]
  • [ 1248676-26-7 ]
  • [ 1248676-63-2 ]
  • 19
  • [ 22300-52-3 ]
  • [ 402-49-3 ]
  • [ 1248676-30-3 ]
  • [ 1248676-65-4 ]
  • 20
  • [ 22300-52-3 ]
  • [ 74-88-4 ]
  • [ 28938-17-2 ]
  • [ 25537-64-8 ]
YieldReaction ConditionsOperation in experiment
57% With potassium carbonate; In tetrahydrofuran; at -10 - 40℃; The 10.0g (44.1mmol) 4,5- dibromo -2H-1,2,3- triazole (commercially available) was dissolved in 90ml of tetrahydrofuran was added 6.1g (44.2mmol) of potassium carbonate, cooled to -10 , was added 7.5g (53mmol) of methyl iodide.In the 35 ~ 40 to react until the reaction is complete.50ml of water was added, the tetrahydrofuran was distilled off, 90ml and extracted with methyl tert-butyl ether, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure, the residual solid was added methyl tert-butyl ether, 10ml, 70ml of n-hexane was added slowly, solid precipitation, the addition was completed, stirring at room temperature for 1 to 2 hours.Filtered to give pure 4,5-dibromo-1-methyl -1H-1,2,3- triazole 5.8g, 57percent yield.
  • 21
  • [ 288-36-8 ]
  • [ 22300-52-3 ]
YieldReaction ConditionsOperation in experiment
95% With bromine; In water; at 50℃; Into a 3000-mL 3-necked round-bottom flask, was placed 2H-1,2,3-triazole (100 g, 1.45 mol, 1.00 equiv), water (1000 mL), Br2 (522 g, 3.27 mol, 2.25 equiv). The resulting solution was stirred overnight at 50 C. in an oil bath. The reaction was then quenched by the addition of 1000 mL of Na2SO3 (aq). The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 313 g (95%) of 4,5-dibromo-2H-1,2,3-triazole as a white solid.
60.8% With bromine; In water; at 0 - 20℃; 4,5-dibromo-2H-l,2,3-triazole. Bromine (15 mL) was added dropwise to a stirred solution of 2H-l,2,3-triazole (15.0 g, 217 mmol) in water (200 mL) at 0C. Once addition was completed, the mixture was stirred for 12 hours at room temperature. The resultant mixture was filtered off and washed with water, dried over sodium sulfate and recrystallized from methanol to afford 4,5-dibromo-2H-l,2,3-triazole as a dark brown solid (29.8 g, 60.8%).
49% With bromine; In water; at 0 - 20℃; [0260] Bromine (11.59 g, 73.35 mmol) was added dropwise to a 0 C solution of 2H-l,2,3-triazole (5.00 g, 72.46 mmol) in water (50 mL), and the resulting solution was allowed to warm to room temperature and stir overnight. The precipitate was collected by filtration and dried to afford 4,5- dibromo-2H-l ,2,3-triazole (8.00 g, 49%) as a white solid. MS (ESI, pos. ion) m/z 228, 226, 230 [M+H]+.
With bromine; In water; at 0℃; for 7h; To a stirred solution of EE-1 (10 g, 144.79 mmol) in water (100 mL) is added EE-2 (13.73 g, 173.75 mmol) dropwise at 0 C and the reaction mixture is stirred at 0 C for 7 hours. The reaction mixture is filtered and extracted with diethyl ether. The combined organics are concentrated in vacuo to yield EE-3.

  • 22
  • [ 22300-52-3 ]
  • [ 74-88-4 ]
  • [ 28938-17-2 ]
YieldReaction ConditionsOperation in experiment
36.9% With potassium carbonate; In N,N-dimethyl-formamide; at -10 - 20℃; 4,5-dibromo-2-methyl-2H-l,2,3-triazole. Iodomethane (19.0 g, 133.8 mmol) was added to a solution of 4,5-dibromo-2H-l,2,3-triazole (15.0 g, 66.7 mmol) and potassium carbonate (18.1 g, 131.2 mmol) in N,N-dimethylformamide (100 mL) at -10°C. The mixture was warmed to room temperature and stirred for 12 hours. The reaction mixture was concentrated to give a residue. The residue was dissolved in ethyl acetate (200 mL), washed by brine (50 mL x 3), dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by column chramtography (silica gel, dichloromethane/methanol = 15 : 1) to afford 4,5-dibromo-2-methyl-2H-l,2,3-triazole as a white solid (5.9, 36.9 percent).
  • 23
  • [ 288-36-8 ]
  • [ 22300-52-3 ]
YieldReaction ConditionsOperation in experiment
70.8 g With N-Bromosuccinimide; potassium carbonate; In Isopropyl acetate; at 20℃; for 5h; Example 2 Preparation of 4,5-dibromo-2H-1,2,3-triazole NBS (123 g, 690 mmol), K2CO3 (0.8 g, 5.8 mmol) and IPAc (300 mL) are added into a round bottom flask with the internal temperature of the flask keep at 20 C. Then, 1H-1,2,3-triazole (19 mL, 330 mmol) is slowly added in the flask by keeping internal temperature of the reaction mixture below 40 C. The reaction mixture is stirred at 20 C. for 5 h, and then filtered. The filter cake is washed with IPAc (30 mL), and then the filter cake is discarded. The filtrate is washed with 2% NaS2O3 (100 mL). The solvent of the resulting organic layer is distilled under vacuum and the internal temperature of the solvent is kept below 45 C. After the distillation, the obtained product is recrystallized by hexanes (600 mL). The resulting solid is filtered, and the filter cake is washed with hexanes (60 mL). The resulting solid is dried under vacuum at a temperature of no more than 35 C. to afford 70.8 grams of the product. Other R1 heterocycles as contemplated in the present invention can be brominated via similar preparation procedures as outlined above.
  • 24
  • [ 22300-52-3 ]
  • [ 141699-59-4 ]
  • tert-butyl 4-(4-bromo-2H-1,2,3-triazol-2-yl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl 4-(4-bromo-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
33%; 20% Step 2. tert-butyl 4-(4,5-dibromo-2H-l,2,3-triazol-2-yl)piperidine-l-carboxylate and tert-butyl 4-(4,5-dibromo-lH-l,2,3-triazol-l-yl)piperidine-l-carboxylate [0261] A mixture of 4,5-dibromo-2H-l,2,3-triazole (2.27 g, 10.08 mmol), tert-butyl 4- (methylsulfonyloxy)piperidine-l -carboxylate (2.79 g, 10.00 mmol), and cesium carbonate (9.75 g, 29.91 mmol) in N,N-dimethylformamide (50 mL) stirred overnight at 100 °C. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford a mixture of tert-butyl 4-(4,5-dibromo-2H- 1 ,2,3- triazol-2-yl)piperidine- 1 -carboxylate and tert-butyl 4-(4,5-dibromo- 1 H- 1 ,2,3-triazol- 1 -yl)piperidine- 1-carboxylate (4.00 g, 97percent) as a yellow oil. MS (ESI, pos. ion) m/z 411 , 409, 413 [M+H]+. Step 3. tert-butyl 4-(4-bromo-2H-l,2,3-triazol-2-yl)piperidine-l-carboxylate (Intermediate 19) and tert-butyl 4-(4-bromo-lH-l,2,3-triazol-l-yl)piperidine-l-carboxylate (Intermediate 20) [0262] n-Butyllithium (2.5 M in hexanes, 2.92 mL, 7.30 mmol) was added dropwise to a -78 °C solution containing a mixture of tert-butyl 4-(4,5-dibromo-2H- 1,2, 3-triazol-2-yl)piperi dine- 1- carboxylate and tert-butyl 4-(4,5-dibromo-lH-l,2,3-triazol-l-yl)piperidine-l -carboxylate (3.00 g, 7.35 mmol) in tetrahydrofuran (20 mL). The resulting solution stirred for 1 hour at -78 °C, and then the reaction mixture was poured into saturated aqueous ammonium chloride solution (20 mL). The aqueous phase was separated and extracted with ethyl acetate (3 x 20 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 2: 1, ethyl acetate/petroleum ether) to afford tert-butyl 4-(4-bromo-2H-l,2,3-triazol-2-yl)piperidine-l- carboxylate (0. 800 g, 33percent) as a colorless oil. MS (ESI, pos. ion) m/z 331, 333[M+H]+. [0263] tert-Butyl 4-(4-bromo-lH-l ,2,3-triazol-l-yl)piperidine-l-carboxylate (0.500g, 20percent) was also obtained as a colorless oil. MS (ESI, pos. ion) m/z 331, 333 [M+H]+.
  • 25
  • [ 22300-52-3 ]
  • [ 141699-59-4 ]
  • tert-butyl 4-(4,5-dibromo-2H-1,2,3-triazol-2-yl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl 4-(4,5-dibromo-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; Step 2. tert-butyl 4-(4,5-dibromo-2H-l,2,3-triazol-2-yl)piperidine-l-carboxylate and tert-butyl 4-(4,5-dibromo-lH-l,2,3-triazol-l-yl)piperidine-l-carboxylate [0261] A mixture of 4,5-dibromo-2H-l,2,3-triazole (2.27 g, 10.08 mmol), tert-butyl 4- (methylsulfonyloxy)piperidine-l -carboxylate (2.79 g, 10.00 mmol), and cesium carbonate (9.75 g, 29.91 mmol) in N,N-dimethylformamide (50 mL) stirred overnight at 100 °C. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford a mixture of tert-butyl 4-(4,5-dibromo-2H- 1 ,2,3- triazol-2-yl)piperidine- 1 -carboxylate and tert-butyl 4-(4,5-dibromo- 1 H- 1 ,2,3-triazol- 1 -yl)piperidine- 1-carboxylate (4.00 g, 97percent) as a yellow oil. MS (ESI, pos. ion) m/z 411 , 409, 413 [M+H]+.
  • 26
  • [ 22300-52-3 ]
  • [ 4399-47-7 ]
  • C6H7Br2N3 [ No CAS ]
  • 27
  • [ 26272-85-5 ]
  • [ 22300-52-3 ]
  • C5H5Br2N3O [ No CAS ]
  • 28
  • [ 19752-84-2 ]
  • [ 22300-52-3 ]
  • C7H9Br2N3O [ No CAS ]
  • 29
  • [ 22300-52-3 ]
  • [ 23761-24-2 ]
  • 3-(4,5-dibromo-2H-1,2,3-triazol-2-yl)cyclobutanone [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 22300-52-3 ]

Bromides

Chemical Structure| 16681-67-7

A136090 [16681-67-7]

4-Bromo-2-methyl-2H-1,2,3-triazole

Similarity: 0.76

Chemical Structure| 942060-54-0

A157464 [942060-54-0]

4-Bromo-2,5-dimethyl-2H-1,2,3-triazole

Similarity: 0.62

Related Parent Nucleus of
[ 22300-52-3 ]

Triazoles

Chemical Structure| 16681-67-7

A136090 [16681-67-7]

4-Bromo-2-methyl-2H-1,2,3-triazole

Similarity: 0.76

Chemical Structure| 942060-54-0

A157464 [942060-54-0]

4-Bromo-2,5-dimethyl-2H-1,2,3-triazole

Similarity: 0.62