Home Cart Sign in  
Chemical Structure| 23842-82-2 Chemical Structure| 23842-82-2

Structure of 2-Amino-5-methoxybenzonitrile
CAS No.: 23842-82-2

Chemical Structure| 23842-82-2

*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 [ 23842-82-2 ]

CAS No. :23842-82-2
Formula : C8H8N2O
M.W : 148.16
SMILES Code : N#CC1=CC(OC)=CC=C1N
MDL No. :MFCD05149280
InChI Key :SRWMPAZUWXLIPG-UHFFFAOYSA-N
Pubchem ID :3513002

Safety of [ 23842-82-2 ]

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

Computational Chemistry of [ 23842-82-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 42.05
TPSA ?

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

59.04 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.58
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

1.48
Log Po/w (WLOGP)?

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

1.16
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.

0.51
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

1.16

Water Solubility

Log S (ESOL):?

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

-2.03
Solubility 1.39 mg/ml ; 0.00936 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.

-2.33
Solubility 0.698 mg/ml ; 0.00471 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

-2.23
Solubility 0.868 mg/ml ; 0.00586 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.

-6.15 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)

1.28

Application In Synthesis of [ 23842-82-2 ]

* 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 [ 23842-82-2 ]

[ 23842-82-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 38469-84-0 ]
  • [ 23842-82-2 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; at 20℃; under 1292.9 Torr; for 0.333333h; Step 2: A solution of the nitro compound from Step 1 (6.5 g, 36 mmol) in 4:1 EtOAc: MeOH (150 ml_) in a pressure vessel was degassed with by bubbling N2 through the solution for 10 min. To this solution was added 10% Pd/C (300 mg). The vessel was sealed and pressurized with H2 to 25 psi. The vessel was then shaken at RT for 20 min. Once the reaction was complete, the vessel was purged with N2. The mixture was filtered through Celite and concentrated. The crude product was purified via flash chromatography (SiO2: gradient elution, 100:0 to 60:40 hexanes: EtOAc) to afford the aniline (6.4 g, 100%) as a light yellow solid.
84% With sodiumsulfide nonahydrate; acetic acid; In N,N-dimethyl-formamide; at 20℃; for 20h;Green chemistry; General procedure: Condition B: An oven-dried pressure tube (10 mL) was charged with sodium sulfide nonahydrate (144 mg, 0.6 mmol), acetic acid (36 mg, 0.6 mmol), nitrobenzene (24.6 mg, 0.2 mmol), DMF (0.8 mL). The reaction vessel was closed under air and the resulting solution was stirred at room temperature for 20 h. Then the reaction mixture was filtered through a pad of silica gel and washed with 5 mL ethyl acetate for three times. The filtrate was removed under vacuum and the residue was purified by flash column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the desired product.
With sodium dithionite; water; In ethanol; for 1h;Reflux; Step 3 2-Amino-5-methoxybenzonitrile A 100 mL round bottom flask was charged with <strong>[38469-84-0]5-methoxy-2-nitrobenzonitrile</strong> (1.7 g, 9.55 mmol), sodium dithionite (4.99 g, 29 mmol), water (15 mL) and EtOH (50 mL). The resulting mixture was heated at reflux for 1 h. Work-up: the reaction mixture was concentrated in vacuo to remove ethanol then extracted with EtOAc (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, to afford 1.4 g (quantitative) of the product as yellow oil. It was used in the next step without further purification.
With sodium dithionite; water; In ethanol; for 1h;Reflux; 2-Amino-5-methoxybenzonitrile: [0441] A 100 mL round bottom flask was charged with 5-methoxy-2- nitrobenzonitrile (1.7 g, 9.55 mmol), sodium dithionite (4.99 g, 29 mmol), water (15 mL) and EtOH (50 mL). The resulting mixture was heated at reflux for 1 h. Work-up: the reaction mixture was concentrated in vacuo to remove ethanol then extracted with EtOAc (50 mL). The organic layer was dried over anhydrous Na2S04 and concentrated in vacuo, to afford 1.4 g (quantitative) of the product as yellow oil. It was used in the next step without further purification.

  • 2
  • [ 32315-10-9 ]
  • [ 23842-82-2 ]
  • [ 105763-77-7 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 23842-82-2 ]

Aryls

Chemical Structure| 38487-85-3

A171574 [38487-85-3]

2-Amino-4-methoxybenzonitrile

Similarity: 1.00

Chemical Structure| 116423-58-6

A108487 [116423-58-6]

2-Amino-5-hydroxybenzonitrile

Similarity: 0.92

Chemical Structure| 148932-68-7

A115487 [148932-68-7]

2-Amino-3-methoxybenzonitrile

Similarity: 0.91

Chemical Structure| 269411-71-4

A110591 [269411-71-4]

3-Amino-5-methoxybenzonitrile

Similarity: 0.90

Chemical Structure| 214623-57-1

A113814 [214623-57-1]

5-Amino-2-methoxybenzonitrile

Similarity: 0.87

Ethers

Chemical Structure| 38487-85-3

A171574 [38487-85-3]

2-Amino-4-methoxybenzonitrile

Similarity: 1.00

Chemical Structure| 148932-68-7

A115487 [148932-68-7]

2-Amino-3-methoxybenzonitrile

Similarity: 0.91

Chemical Structure| 269411-71-4

A110591 [269411-71-4]

3-Amino-5-methoxybenzonitrile

Similarity: 0.90

Chemical Structure| 214623-57-1

A113814 [214623-57-1]

5-Amino-2-methoxybenzonitrile

Similarity: 0.87

Chemical Structure| 60979-25-1

A251846 [60979-25-1]

3-Amino-4-methoxybenzonitrile

Similarity: 0.84

Amines

Chemical Structure| 38487-85-3

A171574 [38487-85-3]

2-Amino-4-methoxybenzonitrile

Similarity: 1.00

Chemical Structure| 116423-58-6

A108487 [116423-58-6]

2-Amino-5-hydroxybenzonitrile

Similarity: 0.92

Chemical Structure| 148932-68-7

A115487 [148932-68-7]

2-Amino-3-methoxybenzonitrile

Similarity: 0.91

Chemical Structure| 269411-71-4

A110591 [269411-71-4]

3-Amino-5-methoxybenzonitrile

Similarity: 0.90

Chemical Structure| 214623-57-1

A113814 [214623-57-1]

5-Amino-2-methoxybenzonitrile

Similarity: 0.87

Nitriles

Chemical Structure| 38487-85-3

A171574 [38487-85-3]

2-Amino-4-methoxybenzonitrile

Similarity: 1.00

Chemical Structure| 116423-58-6

A108487 [116423-58-6]

2-Amino-5-hydroxybenzonitrile

Similarity: 0.92

Chemical Structure| 148932-68-7

A115487 [148932-68-7]

2-Amino-3-methoxybenzonitrile

Similarity: 0.91

Chemical Structure| 269411-71-4

A110591 [269411-71-4]

3-Amino-5-methoxybenzonitrile

Similarity: 0.90

Chemical Structure| 214623-57-1

A113814 [214623-57-1]

5-Amino-2-methoxybenzonitrile

Similarity: 0.87