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Chemical Structure| 81998-05-2 Chemical Structure| 81998-05-2

Structure of 81998-05-2

Chemical Structure| 81998-05-2

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Product Details of [ 81998-05-2 ]

CAS No. :81998-05-2
Formula : C12H11BrN2
M.W : 263.13
SMILES Code : CC1=CC(=NC=C1)C1=NC=CC(CBr)=C1
MDL No. :MFCD08275265
InChI Key :HUJZHWSADZZJAB-UHFFFAOYSA-N
Pubchem ID :10956379

Safety of [ 81998-05-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H290-H314
Precautionary Statements:P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 81998-05-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 12
Fraction Csp3 0.17
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 65.27
TPSA ?

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

25.78 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.69
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

2.4
Log Po/w (WLOGP)?

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

3.2
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.

1.89
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

3.94
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.82

Water Solubility

Log S (ESOL):?

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

-3.44
Solubility 0.0948 mg/ml ; 0.00036 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.

-2.58
Solubility 0.687 mg/ml ; 0.00261 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

-5.82
Solubility 0.000402 mg/ml ; 0.00000153 mol/l
Class?

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

Moderately 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

Yes
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.

-6.2 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<0.0
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)

2.44

Application In Synthesis of [ 81998-05-2 ]

* 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 [ 81998-05-2 ]

[ 81998-05-2 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 1134-35-6 ]
  • [ 81998-05-2 ]
  • [ 96897-04-0 ]
  • 4
  • [ 1468-95-7 ]
  • [ 81998-05-2 ]
  • [ 122020-07-9 ]
  • 5
  • [ 88351-40-0 ]
  • [ 81998-05-2 ]
  • [ 96897-04-0 ]
  • 6
  • [ 81998-04-1 ]
  • [ 81998-05-2 ]
YieldReaction ConditionsOperation in experiment
91.3% With sulfuric acid; hydrogen bromide; In water; for 40h;Reflux; A solution of 15(301 mg, 1.50 mmol) in 48% aqueous HBr solution (15 mL) andconcentrated H2SO4 (0.6 mL) was refluxed for 40 h. Aftercooling to room temperature, water (4 mL) was added to thereaction mixture and basified with sat. aqueous Na2CO3 solutionto pH 8. The aqueous solution was extracted with CH2Cl2 until the organic layer wascolorless. The combined organic layer was dried over anhydrous Na2SO4 andconcentrated. The residue was purified by silica gel column chromatography withchloroform / triethylamine (v/v, 40/1) to give 16 (361 mg, 1.37 mmol, 91.3%) as lightbrown . 1H NMR (CDCl3): = 8.66 (d, J = 5.1 Hz, 1H), 8.55 (d, J = 4.8 Hz, 1H), 8.41 (s, 1H),8.24 (s, 1H), 7.34 (dd, J1 = 5.1 Hz, J2 = 1.8 Hz, 1H), 7.16 (d, J = 4.8 Hz, 1H), 4.48 (s,2H), 2.45 (s, 3H). IR (NaCl): = 2918, 1632, 1597, 1567, 1517, 1444, 1379, 1038, 994,827, 749 cm-1
In dichloromethane; (c) 4-bromomethyl-4'-methyl-2,2'-bipyridine To a solution of crude 4-hydroxymethyl-4'-methyl-2,2'-bipyridine in methylene chloride at 0 C. were added a slight excess of both PPh3 and N-bromosuccinimide to immediately give a brown-orange solution. The mixture was stirred for 1 h, warmed to room temperature, and concentrated to a thick brown oil. Chromatography on silica with 1:1 hexanes:diethyl ether as eluent gave the product as a white powder. Yields 50%. 1H NMR spectra are consistent with structure.
(d) Preparation of 4-methyl-4'-bromomethyl-2,2'-bipyridine 1.5 g of 4-methyl-4'-hydroxymethyl-2,2'-bipyridine are reacted analogously to Example 2(e). This gives 1.74 g (88% of theory) of 4-methyl-4'-bromomethyl-2,2'-bipyridine as an unstable oil which is used immediately for the further reaction.
In dichloromethane; (c) 4-bromomethyl-4'-methyl-2,2'-bipyridine To a solution of crude 4-hydroxymethyl-4'-methyl-2,2'-bipyridine in methylene chloride at 0 C. were added a slight excess of both PPh3 and N-bromosuccinimide to immediately give a brown-orange solution. The mixture was stirred for 1 h, warmed to room temperature, and concentrated to a thick brown oil. Chromatography on silica with 1:1 hexanes:diethyl ether as eluent gave the product as a white powder. Yields 50%. 1H NMR spectra are consistent with structure.

  • 7
  • [ 2810-74-4 ]
  • [ 81998-05-2 ]
  • [ 191601-42-0 ]
  • 8
  • <i>N</i>,<i>N</i>'-dimethyl-benzidine; dihydrochloride [ No CAS ]
  • [ 81998-05-2 ]
  • N4,N4'-Dimethyl-N4,N4'-bis-(4'-methyl-[2,2']bipyridinyl-4-ylmethyl)-biphenyl-4,4'-diamine [ No CAS ]
  • 9
  • [ 81477-94-3 ]
  • [ 81998-05-2 ]
  • (R)-2-(Benzhydrylidene-amino)-3-(4'-methyl-[2,2']bipyridinyl-4-yl)-propionic acid tert-butyl ester [ No CAS ]
  • [ 402563-43-3 ]
  • 10
  • [ 39987-25-2 ]
  • [ 81998-05-2 ]
  • [ 344367-58-4 ]
  • 11
  • [ 81998-05-2 ]
  • [ 94789-61-4 ]
  • 6-mono[4-methyl-(4'-methyl-2,2'-bipyridyl)]-permethylated β-cyclodextrin [ No CAS ]
  • 12
  • [ 81998-05-2 ]
  • [ 603-35-0 ]
  • (4'-methyl-[2,2']bipyridinyl-4-ylmethyl)triphenylphosphonium bromide [ No CAS ]
  • 13
  • [ 295-37-4 ]
  • [ 81998-05-2 ]
  • [ 154324-58-0 ]
  • 14
  • [ 15435-71-9 ]
  • [ 81998-05-2 ]
  • [ 473546-17-7 ]
  • 15
  • [ 548-26-5 ]
  • [ 81998-05-2 ]
  • eosin (4'-methyl-2,2'-bipyridin-4-yl)methyl ester sodium salt [ No CAS ]
  • 16
  • [ 81998-05-2 ]
  • [ 104989-11-9 ]
  • [ 680571-09-9 ]
  • 17
  • [ 81998-05-2 ]
  • [ 221171-37-5 ]
  • 4-[4-(N,N-di-p-anisylamino)phenoxymethyl]-4'-methyl-2,2'-bipyridine [ No CAS ]
  • 18
  • [ 81998-05-2 ]
  • [ 153707-56-3 ]
  • [ 852567-35-2 ]
  • 19
  • [ 81998-05-2 ]
  • [ 121174-68-3 ]
  • 4'-methyl-[2,2']bipyridinyl-4-(2-anthracen-9-ylmethyl-1-methyl ether) [ No CAS ]
  • 20
  • [ 18928-34-2 ]
  • [ 81998-05-2 ]
  • 2-bromomethyl-11-methyl-6,7-dihydrodipyrido[1,2-a:2',1'-c]pyrazinediium ditriflate [ No CAS ]
  • 21
  • [ 81998-05-2 ]
  • [ 55804-65-4 ]
  • 10-oxo-2,3,5,6-tetrahydro-1<i>H</i>,4<i>H</i>,10<i>H</i>-11-oxa-3a-aza-benzo[<i>de</i>]anthracene-9-carboxylic acid 4'-methyl-[2,2']bipyridinyl-4-ylmethyl ester [ No CAS ]
  • 22
  • [ 81998-05-2 ]
  • [ 123-08-0 ]
  • [ 444201-13-2 ]
  • 24
  • [ 81998-05-2 ]
  • [ 444201-14-3 ]
  • 25
  • [ 81998-05-2 ]
  • 17-(4'-Methyl-2,2'-bipyridyl-4-yl)-2,6,11,15-tetramethylheptadeca-2,4,6,8,10,12,14,16-octaenal [ No CAS ]
  • 27
  • [ 81998-05-2 ]
  • (S)-2-Amino-3-(4'-methyl-[2,2']bipyridinyl-4-yl)-propionic acid methyl ester [ No CAS ]
  • 28
  • [ 81998-05-2 ]
  • [ 218910-10-2 ]
  • 29
  • [ 81998-05-2 ]
  • [ 218910-08-8 ]
  • 30
  • [ 81998-05-2 ]
  • 4'-Methyl-[2,2']bipyridinyl-4-carboxylic acid methyl-{4'-[methyl-(4'-methyl-[2,2']bipyridinyl-4-ylmethyl)-amino]-biphenyl-4-yl}-amide [ No CAS ]
  • 31
  • [ 81998-05-2 ]
  • [ 330649-41-7 ]
YieldReaction ConditionsOperation in experiment
With methylamine; In tetrahydrofuran; (d) 4-methylaminomethyl-4'-methyl-2,2'-bipyridine Methylamine was bubbled slowly through a solution of <strong>[81998-05-2]4-bromomethyl-4'-methyl-2,2'-bipyridine</strong> in THF for 10 min at 0 C. to give a white precipitate and a colorless solution. After bubbling, the solution was stirred for another hour at room temperature. The reaction was pumped dry to a pale off-white wax. The wax was extracted with diethyl ether and pumped dry to a pale yellow oil. Yields 80%. 1H NMR spectra are consistent with structure.
With methylamine; In tetrahydrofuran; (d) 4-methylaminomethyl-4'-methyl-2,2'-bipyridine Methylamine was bubbled slowly through a solution of <strong>[81998-05-2]4-bromomethyl-4'-methyl-2,2'-bipyridine</strong> in THF for 10 min at 0 C. to give a white precipitate and a colorless solution. After bubbling, the solution was stirred for another hour at room temperature. The reaction was pumped dry to a pale off-white wax. The wax was extracted with diethyl ether and pumped dry to a pale yellow oil. Yields 80%. 1H NMR spectra are consistent with structure.
  • 32
  • [ 81998-05-2 ]
  • [ 81370-49-2 ]
  • [ 1013915-36-0 ]
  • 33
  • ammonium hexafluorophosphate [ No CAS ]
  • Ammonium iron sulfate [ No CAS ]
  • [ 81998-05-2 ]
  • {Fe(4-bromomethyl-4`-methyl-2,2`-bipyridine)3}(PF6)2 [ No CAS ]
  • 34
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 81998-05-2 ]
  • [ 7646-85-7 ]
  • {Zn(II)(4-bromomethyl-4`-methyl-2,2`-bipyridine)3}(PF6)2 [ No CAS ]
  • 35
  • ammonium hexafluorophosphate [ No CAS ]
  • cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate [ No CAS ]
  • [ 2923-28-6 ]
  • [ 81998-05-2 ]
  • {ruthenium(2,2'-bipyridine)2(4-(bromomethyl)-4'-bipyridine)}(hexafluorophosphate)2 [ No CAS ]
 

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