Home Cart Sign in  
Chemical Structure| 51686-78-3 Chemical Structure| 51686-78-3

Structure of 51686-78-3

Chemical Structure| 51686-78-3

*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 [ 51686-78-3 ]

CAS No. :51686-78-3
Formula : C6H3Br2NO2
M.W : 280.90
SMILES Code : O=[N+](C1=CC=C(Br)C=C1Br)[O-]
MDL No. :MFCD02660416
InChI Key :DXRVYZGVVFZCFP-UHFFFAOYSA-N
Pubchem ID :12315646

Safety of [ 51686-78-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 51686-78-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 50.66
TPSA ?

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

45.82 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.87
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

3.21
Log Po/w (WLOGP)?

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

3.12
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.

3.19
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

1.06
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.49

Water Solubility

Log S (ESOL):?

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

-3.94
Solubility 0.0321 mg/ml ; 0.000114 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.

-3.84
Solubility 0.0402 mg/ml ; 0.000143 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

-3.48
Solubility 0.0932 mg/ml ; 0.000332 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

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.

-5.73 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

2.0 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)

2.05

Application In Synthesis of [ 51686-78-3 ]

* 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 [ 51686-78-3 ]

[ 51686-78-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 51686-78-3 ]
  • [ 74-89-5 ]
  • [ 302800-13-1 ]
YieldReaction ConditionsOperation in experiment
76% In ethanol; water; for 2h;Heating / reflux; To a solution of intermediate 1 (8g, 28.5 mmol) in EtOH (200ml) was added a solution of methylamine 40% in water (200ml) and the mixture was heated under reflux for 2 hours and then cooled. The resulting precipitate was filtered and dried. The title compound was obtained as an orange solid (5g, 76%); m.p. 130-132C.
76% In ethanol; water; at 80℃; for 3h; Step 2: (5-Bromo-2-nitro-phenyl)-methyl-amine; [0310] To a solution of 2,4-dibromo-l-nitro-benzene (2.0 g, 7.14 mmol) in ethanol (50 mL) was added a 40% aqueous solution of methylamine (50 mL). The reaction mixture was stirred at 8O0C in a closed vessel for 3 h, then cooled to O0C. Water was added and the precipitate was filtered, washed with water, and dried in vacuo to give 1.26 g of (5-bromo- 2-nitro-phenyl)-methyl-amine as an orange solid (76% yield): 1H NMR (CDCl3) δ 3.04 (s, 3H), 6.79 (dd, IH), 7.03 (d, IH), 8.05 (d, IH), 8.0-8.1 (broad s, IH); MS (m/z) 231, 233 [M+H+]+.
76% In ethanol; water; for 2h;Heating / reflux; To a solution of intermediate 1 (8g, 28.5 mmol) in EtOH (200ml) was added asolution of methylamine 40% in water (200ml) and the mixture was heated under reflux for 2 hours and then cooled. The resulting precipitate was filtered and dried.The title compound was obtained as an orange solid (5g, 76%); m.p. 130-132C
68% In ethanol; water; for 2h;Heating / reflux; Example 14; 224 229 230 231232Part A:Compound 224 was prepared via the synthetic method described in Example 13 (Part A). A solution of compound 1 (10.0 g, 35.8 mmol) and 40% aqueous methylamine (270 ml_) in ethanol (270 ml_) was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature, resulting in the formation of a precipitate, which was filtered and dried to afford compound 229 as a yellow solid 5.6 g (68%). 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, 1 H), 7.14 (d, 1 H), 6.79 (dd, 1 H), 2.94 (d, 3H).

  • 2
  • [ 51686-78-3 ]
  • [ 593-51-1 ]
  • 4-bromo-<i>N</i>,<i>N</i>'-dimethyl-<i>o</i>-phenylenediamine [ No CAS ]
  • [ 302800-13-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 70℃; Step 2:; A mixture of compound 33-2 (6.3 g, 22.4 mmol) and methylamine hydrochloride (3.0 g, 44.8 mmol) in DMF (50 mL) and cooled to 0C. Triethylamine (9.4 mL, 67 mmol) was added and the mixture was allowed to stir at RT for 3.5 h, then heated at 70C overnight. The mixture was poured into water and the resulting precipitate was filtered. The filtrate was extracted with EtOAc (3X) and the extract was washed with water (3X) and saturated NaCI, dried (MgS04), filtered and concentrated to give a mixture of compounds 33-3 and 33-4 as an orange solid (4.8 g), which was used as is in the next step.
  • 3
  • [ 7311-95-7 ]
  • [ 51686-78-3 ]
  • ethyl 2-(5-bromo-2-nitroanilino)benzo[b]thiophene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
STARTING MATERIAL SYNTHESIS EXAMPLE 7 In the same manner as in Starting Material Synthesis Example 4 and using <strong>[7311-95-7]ethyl 2-aminobenzo[b]thiophene-3-carboxylate</strong>, 2,4-dibromonitrobenzene and dimethyl sulfoxide, ethyl 2-(5-bromo-2-nitroanilino)benzo[b]thiophene-3-carboxylate is obtained.
  • 4
  • [ 654664-63-8 ]
  • [ 51686-78-3 ]
  • 2-(5-bromo-2-nitrophenyl)triphenylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
93.5% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; for 2h;Reflux; 1000 ml of a bottle, with magnetic stirring, adding trimethylene benzene-2-boronic acid (molecular weight: 272, 0.02 mol) 2,48-dibromonitrobenzene (5.28 g (molecular weight: 278, 0.019 mol) Pd (PPh3) 4 used 1.3 g (molecular weight 1154, 0.001265 mol), Sodium carbonate 140 ml (2M), toluene 140 ml, ethanol 140 ml. After argon replacement, reflux, monitoring reaction with TLC, 2 hours after the reaction is complete, cooling, separated from the base layer, evaporated, with 1/10 ethyl acetate / petroleum ether column separation, To give 7.58 g of product having a molecular weight of 427 and a yield of 93.5%.
43% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃; for 12h; A 2 L reactor was charged with [Intermediate 1-a] (52 g, 177 mmol) 2-Biphenylboronic acid (42 g, 212 mmol),Tetrakis (triphenylphosphine) palladium (4.1 g, 3.5 mmol),Potassium carbonate (73.4 g, 531 mmol), toluene (600 mL) and distilled water (200 mL) were added, and the mixture was stirred at 100 C for 12 hours.After cooling to room temperature, the organic layer was extracted with ethyl acetate.The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain [intermediate 1-b]. (41 g, 72%). In Synthesis Example 1- (2) Using 2-triphenylboronic acid instead of [intermediate 1-a]Instead of 2-biphenylboronic acid 2,4-dibromonitrobenzeneSynthesis was carried out in the same way except for using[Intermediate 6-a] was obtained. (38 g, 43%).
  • 5
  • [ 51686-78-3 ]
  • [ 5470-65-5 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; cobalt(II) acetate; at 50℃; for 2h;Inert atmosphere; (1) After mixing 2,4-dibromonitrobenzene with water, heating to 50°C under inert gas protection,Cobalt acetate was added and stirred to mix well, then ammonia was added dropwise to carry out the reflux reaction. After the addition was complete, the reaction was continued for 2 hours while stirring.After completion of the reaction, centrifugation, liquid separation, collection of the organic phase, and distillation under reduced pressure yield a mixture of 3-bromo-4-nitrophenol and 5-bromo-2-nitrophenol.After steam distillation, ether extraction, recrystallization, separation of isomers to obtain 3-bromo-4-nitrophenol In step (1), the molar volume ratio of 2,4-dibromonitrobenzene to water is 0.4 mol/L;The inert gas is helium or argon; the molar ratio of 2,4-dibromonitrobenzene and cobalt acetate is 1.4:1;The molar volume ratio of 2,4-dibromonitrobenzene and ammonia was 0.6 mol/L, and the concentration of ammonia water was 1 mol/L.
  • 6
  • [ 51686-78-3 ]
  • [ 1698-16-4 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 51686-78-3 ]

Aryls

Chemical Structure| 13402-32-9

A158500 [13402-32-9]

1,3-Dibromo-2-nitrobenzene

Similarity: 0.92

Chemical Structure| 35757-20-1

A169418 [35757-20-1]

2-Bromo-3-nitroaniline

Similarity: 0.92

Chemical Structure| 10403-47-1

A130232 [10403-47-1]

2-Bromo-5-nitroaniline

Similarity: 0.92

Chemical Structure| 6311-60-0

A111519 [6311-60-0]

1,3-Dibromo-5-nitrobenzene

Similarity: 0.90

Chemical Structure| 59255-95-7

A203705 [59255-95-7]

2-Bromo-6-nitroaniline

Similarity: 0.88

Bromides

Chemical Structure| 13402-32-9

A158500 [13402-32-9]

1,3-Dibromo-2-nitrobenzene

Similarity: 0.92

Chemical Structure| 35757-20-1

A169418 [35757-20-1]

2-Bromo-3-nitroaniline

Similarity: 0.92

Chemical Structure| 10403-47-1

A130232 [10403-47-1]

2-Bromo-5-nitroaniline

Similarity: 0.92

Chemical Structure| 6311-60-0

A111519 [6311-60-0]

1,3-Dibromo-5-nitrobenzene

Similarity: 0.90

Chemical Structure| 59255-95-7

A203705 [59255-95-7]

2-Bromo-6-nitroaniline

Similarity: 0.88

Nitroes

Chemical Structure| 13402-32-9

A158500 [13402-32-9]

1,3-Dibromo-2-nitrobenzene

Similarity: 0.92

Chemical Structure| 35757-20-1

A169418 [35757-20-1]

2-Bromo-3-nitroaniline

Similarity: 0.92

Chemical Structure| 10403-47-1

A130232 [10403-47-1]

2-Bromo-5-nitroaniline

Similarity: 0.92

Chemical Structure| 6311-60-0

A111519 [6311-60-0]

1,3-Dibromo-5-nitrobenzene

Similarity: 0.90

Chemical Structure| 59255-95-7

A203705 [59255-95-7]

2-Bromo-6-nitroaniline

Similarity: 0.88