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Chemical Structure| 3001-15-8 Chemical Structure| 3001-15-8

Structure of 3001-15-8

Chemical Structure| 3001-15-8

4,4'-Diiodo-1,1'-biphenyl

CAS No.: 3001-15-8

4.5 *For Research Use Only !

Cat. No.: A629328 Purity: 98%

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Product Details of [ 3001-15-8 ]

CAS No. :3001-15-8
Formula : C12H8I2
M.W : 406.00
SMILES Code : IC1=CC=C(C2=CC=C(I)C=C2)C=C1
MDL No. :MFCD00001057
InChI Key :GPYDMVZCPRONLW-UHFFFAOYSA-N
Pubchem ID :76348

Safety of [ 3001-15-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 3001-15-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 77.31
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.98
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

5.66
Log Po/w (WLOGP)?

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

4.56
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.

5.45
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

5.45
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.82

Water Solubility

Log S (ESOL):?

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

-6.49
Solubility 0.000131 mg/ml ; 0.000000323 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-5.42
Solubility 0.00153 mg/ml ; 0.00000376 mol/l
Class?

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

Moderately 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

-6.73
Solubility 0.0000756 mg/ml ; 0.000000186 mol/l
Class?

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

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
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

Yes
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.

-4.76 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

1.0
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

2.0
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<2.0
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 of [ 3001-15-8 ]

* 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.

  • Downstream synthetic route of [ 3001-15-8 ]

[ 3001-15-8 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 3001-15-8 ]
  • [ 626-13-1 ]
  • [ 184104-80-1 ]
  • 2
  • [ 3001-15-8 ]
  • [ 1205-64-7 ]
  • [ 65181-78-4 ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate;PEG-6000; In 1,2-dichloro-benzene; for 22h;Heating / reflux; (Synthetic Example 1) N,N'-diphenyl-N,N'-bis(3-tolyl)-4,4'-diaminobiphenyl (3,3-TPD) was synthesized as follows. 1.0g (2.46mmol) of 4,4'-diiodobiphenyl and 20 ml of o-dichlorobenzene were added to a 100 ml four-necked flask made of glass. Furthermore 1.08g (5.90mmol) of m-methyldiphenylamine, 0.104g of poly(ethylene glycol) PEG-6000 as a reaction accelerator that was available from Wako Pure Chemical Industries, Ltd., 2.73g (0.0198mol) of potassium carbonate and 0.635g (9.87mmol) of powdered copper were added thereto. It was determined for tracing by the high-speed liquid chromatography. And it was stirred and refluxed for 22 hours until no peaks of starting materials and intermediates were determined. It was filtrated at the hot temperature. The product was washed with dichloromethane until color of the filtrate was to be light. The solvent was distilled under reduced pressure. Residual product was purified by silica gel column chromatography to obtain 3,3-TPD that is represented by Compound Example 1.
  • 3
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 3001-15-8 ]
  • [ 792-74-5 ]
  • 4
  • [ 56525-79-2 ]
  • [ 3001-15-8 ]
  • [ 524067-29-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; copper(II) sulfate; In tridecane; at 230℃; for 24h; (Compound 1): In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane.. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours.. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water.. The solid resulting was then dissolved in hot toluene.. The insoluble residue was filtered hot.. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder.. This compound had a melting point of 294° C.
  • 5
  • [ 3001-15-8 ]
  • [ 1205-64-7 ]
  • [ 620-84-8 ]
  • [ 20441-06-9 ]
  • [ 65181-78-4 ]
  • N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
(Synthetic Example 3) The mixture of 3,3-TPD, 4,4-TPD and N,N'-diphenyl-N-(3-tolyl)-N'-(4-tolyl)-4,4'-diaminobiphenyl (3,4-TPD) that is represented by Compound Example 3 was synthesized as follows. Mixture of 438g (2.43mol) of 3-methyldiphenylamine and 49g (0.27mol) of 4-methyldiphenylamine whose mol ratio is 90: 10 were added to a 5000 ml four-necked flask made of glass. Further 28g (4.4mol) of powdered copper was added thereto. It was heated at 30 degrees Centigrade. 450g (1.1mol) of 4,4'-diiodobiphenyl and 47g of poly(ethylene glycol) PEG-6000 that was available from Wako Pure Chemical Industries, Ltd. were added thereto. It was heated at 100 degrees Centigrade, and then 307g (2.2mol) of powdered potassium carbonate was added thereto. It was heated at 205 degrees Centigrade, and stirred for 14 hours. After cooling, DMF was added thereto, and stirred at 130 degrees Centigrade for 1 hour. After cooling till 90 degrees Centigrade, hot water was added thereto. It was stirred for 2 hours. After filtration, filtrated cake was washed with hot water to obtain brown solid. The obtained brown solid was dispersed and stirred into DMF for 1 hour, filtrated and washed with DMF and methanol. The obtained solid was refluxed with activated carbon in xylene for 1 hour. After cooling till 70 degrees Centigrade, it was filtrated. The filtrate was passed through a column packing adsorbent to obtain colorless solution. The solvent was distilled under reduced pressure. Precipitated crystals were filtrated out and dried to obtain 455g of mixture of TPD.
  • 6
  • [ 3001-15-8 ]
  • [ 92115-21-4 ]
  • [ 65181-78-4 ]
  • 7
  • copper(ll) sulfate pentahydrate [ No CAS ]
  • [ 56525-79-2 ]
  • [ 629-50-5 ]
  • [ 3001-15-8 ]
  • [ 584-08-7 ]
  • [ 524067-29-6 ]
  • 4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE II Synthesis of 4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water. The solid resulting was then dissolved in hot toluene. The insoluble residue was filtered hot. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder. This compound had a melting point of 294° C. Its chemical structure was confirmed by proton analysis.
  • 8
  • [ 3001-15-8 ]
  • [ 1205-64-7 ]
  • [ 12775-96-1 ]
  • [ 65181-78-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; EXAMPLE V Preparation of N,N'-diphenyl-N,N'-bis-(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine in the absence of the aliphatic hydrocarbon solvent. A 500 milliliter 3 necked round bottom flask equipped with an argon purge, a condenser and an overhead mechanical stirrer was charged with 81.2 grams (0.2 mole) of 4,4'-diiodobiphenyl, 146.4 grams (0.8 mole) of 3-methyl-diphenylamine, 89.6 grams (1.6 moles) of KOH flake and 80 grams (1.0 mole) of copper powder. The flask was immersed in a 165° C. oil bath and the two-phase melt was stirred for 3 hours. Hot (140° C.) Soltrol.(R). 170 was added and the inorganic solid separated by vacuum filtration. On cooling, the product crystallized from the filtrate and was isolated in 89percent yield by filtration. Purification was accomplished by slurrying the product with neutral alumina (10 grams) in 1 liter of Soltrol.(R). 170 at 150° C. for six hours, the alumina was removed by filtration and the purified product crystallized from the filtration on cooling. Isolation by filtration was accomplished with a 95percent recovery of the product.
  • 9
  • [ 3001-15-8 ]
  • [ 97963-62-7 ]
  • [ 1312711-67-3 ]
YieldReaction ConditionsOperation in experiment
81% With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h; General procedure: CuI (0.05 equiv), 1,10-phenanthroline (0.1 equiv) and K2CO3 (2 equiv) were placed in an oven-dried screw-capped test tube with Teflon-lined septum that was filled with nitrogen. About 2.5 mL of dry DMF was then added at room temperature. Now the corresponding aryl iodide (1.0 mmol) was added followed by MBI or FMBI (1.0 equiv) and the tube was placed in the preheated oil bath at 140 C and the reaction mixture was magnetically stirred for 22 h. After complete disappearance of iodobenzene (the progress of the reaction was followed by TLC), the reaction mixture was allowed to cool to room temperature. Then water was added and the reaction mixture was extracted with ethyl acetate. After removal of the solvent in vacuum, the crude residue was purified by column chromatography.5- (or 6-) (Difluoromethoxy)-2-(phenylsulfanyl)-1H-benzimidazole (1).
  • 11
  • [ 366-18-7 ]
  • [ 52522-40-4 ]
  • [ 3001-15-8 ]
  • PdI(C<SUB>6</SUB>H<SUB>4</SUB>-4-C<SUB>6</SUB>H<SUB>4</SUB>-4-I)(2,2'-bipyridine) [ No CAS ]
  • 12
  • [ 3001-15-8 ]
  • [ 630127-51-4 ]
  • 4,4'''-bis(trimethylsilylethynyl)-1,1':4',1'':4'',1'''-quaterphenyl [ No CAS ]
 

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