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Chemical Structure| 5131-60-2 Chemical Structure| 5131-60-2

Structure of 5131-60-2

Chemical Structure| 5131-60-2

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Product Citations

Product Citations

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski ; Michael Zimmermann ;

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

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Product Details of [ 5131-60-2 ]

CAS No. :5131-60-2
Formula : C6H7ClN2
M.W : 142.59
SMILES Code : NC1=CC=C(Cl)C(N)=C1
MDL No. :MFCD00025284
Boiling Point : No data available
InChI Key :ZWUBBMDHSZDNTA-UHFFFAOYSA-N
Pubchem ID :21209

Safety of [ 5131-60-2 ]

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

Computational Chemistry of [ 5131-60-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 2.0
Molar Refractivity 40.26
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.

1.17
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

0.85
Log Po/w (WLOGP)?

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

1.52
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.

1.41
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

1.07
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.2

Water Solubility

Log S (ESOL):?

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

-1.75
Solubility 2.52 mg/ml ; 0.0177 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.

-1.53
Solubility 4.25 mg/ml ; 0.0298 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

-2.27
Solubility 0.766 mg/ml ; 0.00537 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.

-6.57 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)

1.37

Application In Synthesis of [ 5131-60-2 ]

* 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 [ 5131-60-2 ]

[ 5131-60-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 674-82-8 ]
  • [ 5131-60-2 ]
  • [ 25781-49-1 ]
  • 2
  • [ 75-44-5 ]
  • [ 5131-60-2 ]
  • [ 4998-28-1 ]
  • 4
  • [ 302-17-0 ]
  • [ 5131-60-2 ]
  • 4-chloro-1,3-bis-(2-hydroxyimino-acetylamino)-benzene [ No CAS ]
  • 5
  • [ 5131-60-2 ]
  • [ 3964-52-1 ]
  • chloro-[1,4]benzoquinone-4-(2,4-diamino-5-chloro-phenylimine) [ No CAS ]
  • 6
  • [ 5131-60-2 ]
  • 6-chloro-[1,7]phenanthroline [ No CAS ]
  • 7
  • [ 5131-60-2 ]
  • [ 95-88-5 ]
  • 8
  • [ 5131-60-2 ]
  • [ 40505-09-7 ]
  • 10
  • [ 5131-60-2 ]
  • 4-acetylamino-2-amino-5-chloro-benzenesulfonic acid [ No CAS ]
  • 12
  • [ 136833-36-8 ]
  • [ 5131-60-2 ]
  • 13
  • [ 5131-60-2 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 62595-00-0 ]
  • 14
  • [ 5131-60-2 ]
  • [ 123-30-8 ]
  • [1,4]benzoquinone-mono-(2,4-diamino-5-chloro-phenylimine) [ No CAS ]
  • 15
  • [ 5131-60-2 ]
  • [ 98-88-4 ]
  • [ 30716-46-2 ]
  • 16
  • [ 5131-60-2 ]
  • [ 138-89-6 ]
  • 3-chloro-<i>N</i>8,<i>N</i>8-dimethyl-phenazine-2,8-diyldiamine [ No CAS ]
  • 17
  • [ 5131-60-2 ]
  • [ 98-59-9 ]
  • <i>N</i>,<i>N</i>'-(4-chloro-<i>m</i>-phenylene)-bis-toluene-4-sulfonamide [ No CAS ]
References: [1]Patent: DE166600, .
  • 18
  • [ 97-00-7 ]
  • [ 5131-60-2 ]
YieldReaction ConditionsOperation in experiment
100% With tin(II) chloride dihdyrate; In ethanol; at 20℃; A mixture of 1-chloro-2,4-dinitro-benzene (100 mg, 0.5 mmol) and SnCl2.2H2O (1.12 g, 5 mmol) in ethanol (2.5 mL) was stirred at room temperature overnight. Water was added and then the mixture was basified to pH 7-8 with saturated NaHCO3 solution. The solution was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to yield 4-chloro-benzene-1,3-diamine (D-1) (79 mg, quant.). HPLC ret. time 0.38 min, 10-99% CH3CN, 5 min run; ESI-MS 143.1 m/z (MH+).
With platinum on activated charcoal; In methanol; at 30℃; under 3750.38 Torr; for 1.5h;Autoclave;Catalytic behavior; General procedure: PtL1/L2/C (25.0 mg, 1.282 mol of Pt) and the desired amountof substrate were placed in a Teflon-coated stainless steel auto-clave (80.0 mL), equipped with magnetic stirrer, temperature andpressure controller. The autoclave was then sealed and evacu-ated, followed by charging it with deaerated MeOH (10.0 mL)by suction. Afterwards, the autoclave was placed in an oil pathwhich was heated to 30.0C. Once the latter temperature wasreached, the autoclave was pressurized with hydrogen (5.0 bar) and stirred at 800 rpm. After the desired reaction time, the auto-clave was removed from the oil bath and cooled to 20.0C, followedby venting the excess hydrogen. The suspension was centrifugedand the catalytic solution separated from catalyst by decantationin air atmosphere. To the latter solutions n-dodecane (100.0 L,0.44 mmol) was added as external standard and analyzed by GC.Recycling experiments were conducted by using recovered PtL1/2,applying the above descript protocol. The Ptsurface-atom related TOF(h-1) values were calculated according to the following equation:mmol(converted substrate) × [mmol(Ptsurface) × h]-1.The mmolof Ptsurface(i.e. amount of Pt atoms exposed to the substrate)using 25.0 mg of catalyst for the hydrogenation reactions were0.7179 mol for PtL1and 0.7948 mol for PtL2and PtC,according to the percentage of Pt-atoms localized on the NPs? sur-face (i.e. 56% (PtL1) and 62% for PtL2/C), using a HRTEM-basedcalculation [35].
  • 19
  • [ 5131-60-2 ]
  • [ 56-81-5 ]
  • [ 40505-09-7 ]
  • bis-(3,6-diamino-2,7-dichloro-9,10-dihydro-acridin-9-yl)-ether [ No CAS ]
  • 20
  • [ 6374-26-1 ]
  • [ 5131-60-2 ]
  • [ 66608-28-4 ]
  • 21
  • [ 5131-60-2 ]
  • [ 556-61-6 ]
  • [ 16349-68-1 ]
  • 22
  • [ 109-04-6 ]
  • [ 5131-60-2 ]
  • 4-chloro-N,N'-bis(2-pyridyl)-1,3-phenylenediamine [ No CAS ]
  • 23
  • [ 634-47-9 ]
  • [ 5131-60-2 ]
  • 4-chloro-N,N'-bis(4-methyl-2-quinolyl)-1,3-phenylenediamine [ No CAS ]
  • 24
  • [ 5131-60-2 ]
  • [ 58593-78-5 ]
  • 25
  • [ 4472-44-0 ]
  • [ 5131-60-2 ]
  • 1,3-bis(4,6-dimethyl-2-pyrimidyl)-4-chloro-1,3-phenylenediamine [ No CAS ]
  • 26
  • [ 97-00-7 ]
  • HCl-salt tin dichloride solution [ No CAS ]
  • [ 5131-60-2 ]
YieldReaction ConditionsOperation in experiment
(b) Amino compounds of the formula (XV) and (XV a)1,3-Diamino-benzene, 4-chloro-1,3-diamino-benzene, 2,4-diaminotoluene, 2,6-diamino-toluene, 1,4-diamino-naphthalene, 2,7-diamino-naphthalene, 1,5-diamino-naphthalene-3,7-disulphonic acid, 1,6-diamino-naphthalene-4,8-disulphonic acid, 1,4-diamino-naphthalene-6-sulphonic acid, ...
methylamine, ...2-ethyl-n-butylenediamine, 2-hydroxy-n-propylenediamine, 1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-diamino-4-chlorobenzene, 1,3-diamino-4-methylbenzene, 1,3-diamino-4-ethylbenzene, 1,3-diamino-4-methoxybenzene, ...
...he aromatic nucleus, for example alkyl groups and halogen atoms. ...1,4-phenylenediamine2,4-tolylenediamine2,4-diaminoanisole2,4-diaminochlorobenzene2,5-diaminoanisole1,2-phenylenediamine2,6-tolylenediamine1,4-diaminonaphthalene...
  • 29
  • [ 60-29-7 ]
  • [ 5131-60-2 ]
  • [ 7732-18-5 ]
  • [ 7553-56-2 ]
  • calcium carbonate [ No CAS ]
  • [ 858013-04-4 ]
  • 30
  • [ 67-56-1 ]
  • [ 5131-60-2 ]
  • [ 7553-56-2 ]
  • lead smoothness [ No CAS ]
  • [ 858013-04-4 ]
  • 31
  • [ 5131-60-2 ]
  • carbamoylguanidine-hydrogen sulfate [ No CAS ]
  • <i>N</i>,<i>N</i>'-bis-(3-amino-4-chloro-phenyl)-urea [ No CAS ]
  • 32
  • [ 13243-32-8 ]
  • [ 5131-60-2 ]
  • 33
  • [ 108-24-7 ]
  • [ 97-00-7 ]
  • [ 5131-60-2 ]
  • [ 51867-83-5 ]
  • [ 62595-00-0 ]
  • 34
  • [ 851875-39-3 ]
  • [ 5131-60-2 ]
  • [4-({5-[2-(4-<i>tert</i>-butoxyoxalyl-phenoxy)-acetylamino]-2-chloro-phenylcarbamoyl}-methoxy)-phenyl]-oxo-acetic acid <i>tert</i>-butyl ester [ No CAS ]
  • 35
  • [ 5131-60-2 ]
  • [ 75561-94-3 ]
YieldReaction ConditionsOperation in experiment
With benzoyl chloride; triethylamine; In dichloromethane; at 0℃; for 16h; benzoyl chloride (5.2 ml) was added to a stirred mixture of 2,4-diaminochlorobenzene (6.42 g), triethylamine (12.5 ml) and methylene chloride (100 ml) which had been cooled to 0°C. The mixture was allowed to warm to ambient temperature and was stirred for 16 hours.. The mixture was evaporated and the residue was triturated under a saturated aqueous sodium bicarbonate solution.. The resultant solid was isolated, washed in turn with water and isohexane and dried under vacuum at 55°C. There was thus obtained N-(3-amino-4-chlorophenyl)benzamide as a solid (10.38 g); NMR Spectrum: (DMSOd6) 5.32 (s, 2H), 6.9 (m, 1H), 7.1 (d, 1H), 7.37 (d, 1H), 7.52 (m, 3H), 7.9 (d, 2H), 10.05 (s, 1H).
 

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