Home Cart Sign in  
Chemical Structure| 21190-87-4 Chemical Structure| 21190-87-4

Structure of 21190-87-4

Chemical Structure| 21190-87-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 21190-87-4 ]

CAS No. :21190-87-4
Formula : C6H4BrNO2
M.W : 202.01
SMILES Code : OC(=O)C1=NC(Br)=CC=C1
MDL No. :MFCD00093197
InChI Key :XURXQNUIGWHWHU-UHFFFAOYSA-N
Pubchem ID :593919

Safety of [ 21190-87-4 ]

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

Computational Chemistry of [ 21190-87-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 38.9
TPSA ?

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

50.19 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.05
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

1.56
Log Po/w (WLOGP)?

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

1.54
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.

-0.34
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

1.43
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.05

Water Solubility

Log S (ESOL):?

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

-2.45
Solubility 0.711 mg/ml ; 0.00352 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.

-2.22
Solubility 1.21 mg/ml ; 0.00597 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

-2.26
Solubility 1.12 mg/ml ; 0.00555 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.

-6.42 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.

0.56

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)

1.66

Application In Synthesis of [ 21190-87-4 ]

* 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 [ 21190-87-4 ]

[ 21190-87-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 21190-87-4 ]
  • [ 210366-15-7 ]
  • 2
  • [ 21190-87-4 ]
  • [ 62058-03-1 ]
  • 6-bromo-N-((1R,2s,3S,5s,7s)-5-hydroxyadamantan-2-yl)picolinamide [ No CAS ]
  • 3
  • [ 21190-87-4 ]
  • [ 637336-53-9 ]
  • 4-[(6-bromo-pyridine-2-carbonyl)-amino]-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; 4-[(6-Bromo-pyridine-2-carbonyl)-amino]-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester A mixture of 6-Bromo-pyridine-2-carboxylic acid (3000 mg; 14.85 mmol; 1.00 eq.), 4-Amino-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester (2765 mg; 17.82 mmol; 1.20 eq.), Ethyl-diisopropyl-amine (6.57 mL; 37.13 mmol; 2.50 eq.) and 3-[chloro-(2-oxooxazolidin-3-yl)phosphoryl]oxazolidin-2-one (4536 mg; 17.82 mmol; 1.20 eq.) in DCM (20 mL) were stirred at RT for overnight. The reaction was filtered, the solid was washed with water, and then acetonitile, the title compound was obtained as a white solid. The filtrate was washed with water, the organic layer was separated, concentrated, washed with methanol, and collected the title compound (combined portions: gave product 5000 mg, which was quantitative yield). LC-MS (M+1): 339/341.
  • 4
  • [ 21190-87-4 ]
  • [ 4506-66-5 ]
  • C18H10Br2N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With acetic acid; at 70℃; for 12h; 6-bromo-2-picolinic acid 2 (0.40 g, 2.00 mmol), tetraaminobenzene hydrochloride 3 (0.28 g, 1.00 mmol) in glacial acetic acid,The reaction was stirred at 70 ° C for 12 hours.After cooling to room temperature, filter the diatomaceous earth.Wash the dichloromethane several times until there is no product.Spin the solvent and separate it by column chromatography.Yellow solid 1 was obtained as the objective product (0.11 g, yield 23percent). The target product was confirmed by nuclear magnetic resonance spectroscopy.
  • 5
  • [ 21190-87-4 ]
  • [ 22259-53-6 ]
  • N-((1H-indol-3-yl)methyl)-6-bromopicolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.9% General procedure: The corresponding carboxylic acid (1 equiv), benzotriazol-1-yloxytripyrrolidinophosphoniumhexafluorophosphate (PyBOP) (1equiv), and triethylamine (TEA) (3 equiv) were dissolved in anhydrousDMF under argon and stirred for 15 min at RT. The appropriate primaryamine (2 equiv) was then added in one portion and the reaction wasallowed to stir for 18 h at RT and then poured into 75 mLs EtOAc and25 mLs deionized water. The aqueous layer was discarded and the organiclayer was washed twice with water (25 mLs) and once with brine(25 mLs). The organic layer was dried with magnesium sulfate andevaporated under reduced pressure. The crude solids were purified byflash chromatography (5-20% EtOAc/Hexanes) to afford pure products.
  • 6
  • [ 21190-87-4 ]
  • [ 140645-24-5 ]
  • tert-butyl (S)-3-((6-bromopicolinamido)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
900 mg To the suspension of 6-bromopicolinic acid (scheme 8-32 compound S1, 606 mg, 3.0mmol) in DCM (15.0mL), a catalytic amount of DMF was added, followed by dropwise addition of oxalyl chloride (495 mg, 3.9mmol, 0.34mL) at 0 C. The reaction mixture was warmed up to rt and kept stirring for additional 1 h. The volatiles were evaporated and the remaining material was dissolved in DCM (15.0 mL). The solution was cooled in an ice bath. To the solution, <strong>[140645-24-5]tert-butyl (S)-3-(aminomethyl)piperidine-1-carboxylate</strong> (535 mg, 2.5mmol) was added, followed by addition of TEA. The mixture was stirred overnight and quenched with saturated NaHCO3. The two layers are separated and the organic phase was dried over MgSO4, filtered and concentrated. The residue was purified to afford the title compound (900 mg). LC (method A): tR = 2.21min. LC/MS (EI) m/z: [M + H]+ 398.34, 400.37
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 21190-87-4 ]

Bromides

Chemical Structure| 1211516-25-4

A213235 [1211516-25-4]

6-Bromo-5-methylpicolinic acid

Similarity: 0.93

Chemical Structure| 1211516-18-5

A472589 [1211516-18-5]

6-Bromo-3-methylpicolinic acid

Similarity: 0.90

Chemical Structure| 21190-88-5

A151586 [21190-88-5]

Ethyl 6-bromopyridine-2-carboxylate

Similarity: 0.88

Chemical Structure| 321596-58-1

A803059 [321596-58-1]

6-Bromo-3-hydroxypicolinic acid

Similarity: 0.86

Chemical Structure| 1206679-66-4

A111089 [1206679-66-4]

5,6-Dibromopicolinic acid

Similarity: 0.86

Carboxylic Acids

Chemical Structure| 1211516-25-4

A213235 [1211516-25-4]

6-Bromo-5-methylpicolinic acid

Similarity: 0.93

Chemical Structure| 1211516-18-5

A472589 [1211516-18-5]

6-Bromo-3-methylpicolinic acid

Similarity: 0.90

Chemical Structure| 321596-58-1

A803059 [321596-58-1]

6-Bromo-3-hydroxypicolinic acid

Similarity: 0.86

Chemical Structure| 1206679-66-4

A111089 [1206679-66-4]

5,6-Dibromopicolinic acid

Similarity: 0.86

Chemical Structure| 1133116-49-0

A188957 [1133116-49-0]

3,6-Dibromopicolinic acid

Similarity: 0.85

Related Parent Nucleus of
[ 21190-87-4 ]

Pyridines

Chemical Structure| 1211516-25-4

A213235 [1211516-25-4]

6-Bromo-5-methylpicolinic acid

Similarity: 0.93

Chemical Structure| 1211516-18-5

A472589 [1211516-18-5]

6-Bromo-3-methylpicolinic acid

Similarity: 0.90

Chemical Structure| 21190-88-5

A151586 [21190-88-5]

Ethyl 6-bromopyridine-2-carboxylate

Similarity: 0.88

Chemical Structure| 321596-58-1

A803059 [321596-58-1]

6-Bromo-3-hydroxypicolinic acid

Similarity: 0.86

Chemical Structure| 1206679-66-4

A111089 [1206679-66-4]

5,6-Dibromopicolinic acid

Similarity: 0.86