Home Cart Sign in  
Chemical Structure| 70977-72-9 Chemical Structure| 70977-72-9

Structure of 70977-72-9

Chemical Structure| 70977-72-9

*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 [ 70977-72-9 ]

CAS No. :70977-72-9
Formula : C8H9NO2
M.W : 151.16
SMILES Code : CC(C1=CC=CC(N)=C1O)=O
MDL No. :MFCD03428566
Boiling Point : No data available
InChI Key :NLLYXOVHEQVWJF-UHFFFAOYSA-N
Pubchem ID :459294

Safety of [ 70977-72-9 ]

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

Computational Chemistry of [ 70977-72-9 ] 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 2.0
Molar Refractivity 43.06
TPSA ?

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

63.32 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.4
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

1.12
Log Po/w (WLOGP)?

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

1.18
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

0.95
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.03

Water Solubility

Log S (ESOL):?

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

-1.82
Solubility 2.29 mg/ml ; 0.0151 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.

-2.04
Solubility 1.37 mg/ml ; 0.00905 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

-1.78
Solubility 2.5 mg/ml ; 0.0166 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

Yes
Log Kp (skin permeation)?

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

-6.43 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

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<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 [ 70977-72-9 ]

* 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 [ 70977-72-9 ]

[ 70977-72-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 70977-72-9 ]
  • [ 1836-05-1 ]
YieldReaction ConditionsOperation in experiment
25% Lastly, the Sandemeyer reaction was carried out to obtain the desired bromo derivative Va in 25percent yield.
25% With cis-nitrous acid; copper(I) bromide; 1. Para-anisidine was acylated at the amino center with acetic anhydride in dichloromethane and the product was obtained in 91 percent yield. Then, Friedel Craft's acyla- tion was carried out to get the hydroxyl acetophenone with acetyl chloride in the presence of anhydrous aluminium chloride in dichloromethane to give the product in 70percent yield. Nitration of acetanilide derivative was carried out with nitric acid in aqueous acetic acid to get the product in 45percent yield. Acetyl group of acetamido functionality was removed by refluxing in dilute hydrochloric acid for 2.5 h to get the aniline derivative in quantitative yield. Deamination was done by diazotization and treating the diazonium salt with ethanol to get the 3-nitro-2-hydroxyacetophenone. The nitro group was reduced by heating the reaction mixture in ethyl acetate with tin in hydrochloric acid resulting in the formation of corresponding amino compound. Lastly, Sandemeyer reaction was carried out to get the desired bromo derivative Va in 25percent yield.
  • 2
  • [ 30131-16-9 ]
  • [ 70977-72-9 ]
  • [ 136450-06-1 ]
YieldReaction ConditionsOperation in experiment
84% 270 g of 4- (phenylbutoxy) benzoic acid was added, 270 g of thionyl chloride was added and incubated at 50 C for 3 hours. After completion of the reaction, the unreacted thionyl chloride was recovered under reduced pressure. Nitrogen blowing into the thiophene chloride. Cooled to room temperature by adding 270 g of dichloromethane. Weigh 151 g of 3-amino-2-hydroxyacetophenone in 200 g of methylene chloride, 160 g of pyridine was added, and a solution of 4- (phenylbutoxy) benzoyl chloride in methylene chloride was added dropwise to the ice bath. The temperature is not more than 10 , dripping finished, 10 incubation reaction 2h, after the end of the reaction, adding to the reaction system dilute hydrochloric acid, adjust the pH to 2-3, liquid, methyl chloride layer washed to neutral, anhydrous Dried over sodium sulfate, filtered and concentrated to give a reddish brown solid, petroleum ether: ethyl acetate = 1: 1 recrystallization to give 334 g, yield 84%.
 

Historical Records

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Grignard Reaction • Halogenation of Phenols • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Reimer-Tiemann Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 70977-72-9 ]

Aryls

Chemical Structure| 50-80-6

A151117 [50-80-6]

1-(5-Amino-2-hydroxyphenyl)ethanone

Similarity: 0.93

Chemical Structure| 376592-93-7

A259179 [376592-93-7]

3'-Amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid

Similarity: 0.84

Chemical Structure| 871101-87-0

A161747 [871101-87-0]

1-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

Similarity: 0.82

Chemical Structure| 28177-69-7

A112781 [28177-69-7]

1-(2-Hydroxy-3-nitrophenyl)ethanone

Similarity: 0.80

Chemical Structure| 2476-29-1

A193469 [2476-29-1]

1-(4-Amino-2-hydroxyphenyl)ethanone

Similarity: 0.80

Ketones

Chemical Structure| 50-80-6

A151117 [50-80-6]

1-(5-Amino-2-hydroxyphenyl)ethanone

Similarity: 0.93

Chemical Structure| 871101-87-0

A161747 [871101-87-0]

1-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

Similarity: 0.82

Chemical Structure| 28177-69-7

A112781 [28177-69-7]

1-(2-Hydroxy-3-nitrophenyl)ethanone

Similarity: 0.80

Chemical Structure| 2476-29-1

A193469 [2476-29-1]

1-(4-Amino-2-hydroxyphenyl)ethanone

Similarity: 0.80

Chemical Structure| 40547-58-8

A161672 [40547-58-8]

N-(4-Acetyl-3-hydroxyphenyl)acetamide

Similarity: 0.77

Amines

Chemical Structure| 50-80-6

A151117 [50-80-6]

1-(5-Amino-2-hydroxyphenyl)ethanone

Similarity: 0.93

Chemical Structure| 376592-93-7

A259179 [376592-93-7]

3'-Amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid

Similarity: 0.84

Chemical Structure| 871101-87-0

A161747 [871101-87-0]

1-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

Similarity: 0.82

Chemical Structure| 2476-29-1

A193469 [2476-29-1]

1-(4-Amino-2-hydroxyphenyl)ethanone

Similarity: 0.80

Chemical Structure| 112725-89-0

A218666 [112725-89-0]

3,5-Diamino-2-hydroxybenzoic acid

Similarity: 0.79