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Chemical Structure| 3171-45-7 Chemical Structure| 3171-45-7

Structure of 3171-45-7

Chemical Structure| 3171-45-7

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Product Citations

Product Citations

Andressa V. Müller ; Shahbaz Ahmad ; Jake T. Sirlin ; Mehmed Z. Ertem ; Dmitry E. Polyansky ; David C. Grills , et al.

Abstract: The reaction steps for the selective conversion of a carbonyl complex to a hydroxymethyl complex that releases methanol upon irradiation with visible light have been successfully quantified in solution with dihydrobenzimidazole organic hydride reductants. Dihydrobenzimidazole reductants have been shown to be inactive toward H2 generation in the presence of a wide range of proton sources and have been regenerated electrochemically or photochemically. Specifically, the reaction of cis-[Ru(bpy)2(CO)2]2+ (bpy = 2,2′-bipyridine) with one equivalent of a dihydrobenzimidazole quantitatively yields a formyl complex, cis-[Ru(bpy)2(CO)(CHO)]+, and the corresponding benzimidazolium on a seconds time scale. Kinetic experiments revealed a first-order dependence on the hydride concentration and an unusually large kinetic isotope effect, inconsistent with direct hydride transfer and more likely to occur by an electron transfer-proton-coupled electron transfer (EΤ−PCET) or related mechanism. Further reduction/protonation of cis-[Ru(bpy)2(CO)(CHO)]+ with two equivalents of the organic hydride yields the hydroxymethyl complex cis-[Ru(bpy)2(CO)(CH2OH)]+. Visible light excitation of cis-[Ru(bpy)2(CO)(CH2OH)]+ in the presence of excess organic hydride was shown to yield free methanol. Identification and quantification of methanol as the sole CO product was confirmed by 1H NMR spectroscopy and gas chromatography. The high selectivity and mild reaction conditions suggest a viable approach for methanol production from CO, and from CO2 through cascade catalysis, with renewable organic hydrides that bear similarities to Nature’s NADPH/NADP+.

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Alternative Products

Product Details of [ 3171-45-7 ]

CAS No. :3171-45-7
Formula : C8H12N2
M.W : 136.19
SMILES Code : CC1=CC(N)=C(N)C=C1C
MDL No. :MFCD00007729
InChI Key :XSZYBMMYQCYIPC-UHFFFAOYSA-N
Pubchem ID :76635

Safety of [ 3171-45-7 ]

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

Computational Chemistry of [ 3171-45-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 2.0
Molar Refractivity 45.18
TPSA ?

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

52.04 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.21
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

1.29
Log Po/w (WLOGP)?

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

1.48
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.

1.48
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

1.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.35

Water Solubility

Log S (ESOL):?

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

-1.94
Solubility 1.56 mg/ml ; 0.0115 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.98
Solubility 1.42 mg/ml ; 0.0104 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

-2.42
Solubility 0.514 mg/ml ; 0.00378 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

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.21 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

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)

1.0

Application In Synthesis of [ 3171-45-7 ]

* 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 [ 3171-45-7 ]

[ 3171-45-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 98541-64-1 ]
  • [ 3171-45-7 ]
  • [ 183953-82-4 ]
  • 2
  • [ 422-64-0 ]
  • [ 3171-45-7 ]
  • 5,6-dimethyl-2-pentafluoroethyl-1<i>H</i>-benzoimidazole [ No CAS ]
  • 3
  • [ 3973-08-8 ]
  • [ 3171-45-7 ]
  • 4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)thiazole [ No CAS ]
  • 4
  • [ 3171-45-7 ]
  • [ 162709-84-4 ]
  • [ 916815-63-9 ]
  • 5
  • [ 1635-84-3 ]
  • [ 3171-45-7 ]
  • [ 3171-46-8 ]
YieldReaction ConditionsOperation in experiment
1.300 g (96%) palladium-carbon; In ethanol; 1,2-Diamino-4,6-dimethylbenzene. A mixture of 4,6-dimethyl-2-nitroaniline (1.66 g, 10.0 mmole) and 10% Pd/C (200 mg) in ethanol (35 mL) was hydrogenated for 2 h at room temperature under 25 psi H2. The catalyst was removed by filtration with celite and the solvent was removed by rota-evaporation to give 1.300 g (96%) of 1,2-diamino-4,5-dimethylbenzene as a brown solid. 1 H NMR (CDCl3): 6.449 (s, 1H), 6.469 (s, 1H), 3.327 (br, 2H), 3.259 (br, 2H), 2.190 (s, 3H), 2.159 (s, 3H).
  • 6
  • [ 3171-45-7 ]
  • [ 4494-26-2 ]
  • [ 1425795-63-6 ]
  • 7
  • [ 5424-47-5 ]
  • [ 3171-45-7 ]
  • 7,8-dimethyl-4-(thiophen-2-yl)-2,3-dihydro-1H-1,5-benzodiazepine [ No CAS ]
  • 8
  • [ 1072960-66-7 ]
  • [ 3171-45-7 ]
  • (4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]
  • 9
  • [ 4079-54-3 ]
  • [ 3171-45-7 ]
  • 6,7-dimethyl-2-(p-tolyl)quinoxaline [ No CAS ]
  • 10
  • [ 3171-45-7 ]
  • [ 90176-80-0 ]
  • 2-(4-fluoro-2-(trifluoromethyl)phenyl)-5,6-dimethyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In ethanol; at 80℃; for 1h; General procedure: ZrO2-Al2O3 solid acid catalytic material was added to the stirred solution of O-phenylenediamines and different substituted aromatic aldehydes in a suitable solvent, and the resulting mixture was heated at a particular temperature and monitored by TLC. After the completion of the reaction, the reaction mixture was cooled and filtered and the residue was washed with ethanol to recover the solid acid catalyst. Filtrate was evaporated in vacuum to get the crude reaction product, which was then purified by silica-gel column chromatography using a suitable mobile phase to separate the desired product. The reaction products were characterized by melting point, 1H NMR and 13C NMR spectroscopy (Bruker, 400 MHz), LC-MS (Varian), and HPLC (Waters) techniques
  • 11
  • [ 59046-72-9 ]
  • [ 3171-45-7 ]
  • C23H18N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With ammonium bromide; In dimethyl sulfoxide; at 20℃; for 24h; General procedure: A solution of o-diaminobenzene 2 (1 mmol) in anhydrousDMSO (2 ml) was slowly added to a solution of the correspondingaldehyde 1 (1 mmol) in DMSO (2 ml). Then, NH4Br (39 mg, 0.4 mmol)was added and the resulting mixture was stirred in the contact with dryair at room temperature for 24 h
  • 12
  • [ 41042-12-0 ]
  • [ 504-02-9 ]
  • [ 3171-45-7 ]
  • 7,8-dimethyl-1’-propyl-3,4,5,10-tetrahydrospiro(dibenzo[b,e][1,4]diazepine-11,3’-indoline)-1,2’(2H)-dione [ No CAS ]
  • 13
  • [ 667463-64-1 ]
  • [ 3171-45-7 ]
  • 3-bromo-5,9,10-trimethylbenzo[4,5]imidazo[1,2-c]quinazolin-6(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tert.-butylhydroperoxide; In dimethyl sulfoxide; at 90℃; for 0.5h; N-methyl indole (0.5 mmol), DMSO (5 ml) were added into reaction tube and stirred at 90 C. Then the I2 (0.6 mmol) and TBHP (2.5 mmol) were added into the reaction tube. After 24 h the o-benzenediamine (0.34 mmol) was added into the mixture. The reaction was stopped until the o-benzenediamine was completely consumed as monitored by TLC analysis. After the completion of reaction, 5% Na2S2O3 solution (30 mL) was added to the mixture. The mixture was extracted with EtOAc (3 * 20 ml) and the organic layer was dried by Na2SO4. Then the crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate/dichloromethane 3/1/1).
  • 14
  • [ 26767-16-8 ]
  • [ 3171-45-7 ]
  • 3-(2-bromophenyl)-6,7-dimethylquinoxalin-2(1H)-one [ No CAS ]
 

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Technical Information

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