Home Cart Sign in  
Chemical Structure| 98592-34-8 Chemical Structure| 98592-34-8

Structure of 98592-34-8

Chemical Structure| 98592-34-8

*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 [ 98592-34-8 ]

CAS No. :98592-34-8
Formula : C9H6ClNO2
M.W : 195.60
SMILES Code : O=C(OC)C1=CC=C(C#N)C=C1Cl
MDL No. :MFCD14635863
InChI Key :GLZBUNHGODEJPT-UHFFFAOYSA-N
Pubchem ID :53845357

Safety of [ 98592-34-8 ]

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

Computational Chemistry of [ 98592-34-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.11
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 47.45
TPSA ?

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

50.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.0
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

3.15
Log Po/w (WLOGP)?

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

2.0
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.

1.86
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

2.33
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.27

Water Solubility

Log S (ESOL):?

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

-3.25
Solubility 0.111 mg/ml ; 0.000567 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.

-3.87
Solubility 0.0263 mg/ml ; 0.000134 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

-3.18
Solubility 0.129 mg/ml ; 0.000661 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

No
Log Kp (skin permeation)?

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

-5.26 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

0.0 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)

1.77

Application In Synthesis of [ 98592-34-8 ]

* 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 [ 98592-34-8 ]

[ 98592-34-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 98592-34-8 ]
  • [ 117738-77-9 ]
YieldReaction ConditionsOperation in experiment
97% Lithium hydroxide (1.12 g, 26.69 mmol) was added to a solution of 2-chloro-4-cyano-benzoic acid methyl ester (2.60 g, 13.29 mmol) in dioxan/water (4:1, 100ml). The mixture was stirred at room temperature for 3h and concentrated in vacuo. The residue was partitioned between 1N hydrochloric acid and chloroform and the organic layer was washed with brine and concentratedin vacuo. The residue was recrystallised from a mixture of dioxan and pet. ether to give a pale orange solid identified as 2-chloro-4-cyanobenzoic acid (2.33 g, 97%).
63.3% Intermediate 125b was dissolved in a 0.5molar 1 : 1 mixture of MeOH / THF and LiOH.H20 (302 mg, 7.21 mmol. The reaction was stirred for 5hrs before the solvent was removes under vaccuum.The residue was suspended in water and acidified with aqueous HCI (2M). A pink precipitate was filtered off and dried under HV + cold trap to yield intermediate 125c (569.2 mg, 3.04 mmol, 63.3 % yield) as pinkish solid.1 H NMR (400 MHz, DMSO-c 6) delta ppm 13.95 (br. S., 1 H), 8.18 (s, 1 H), 7.85 - 7.96 (m, 2 H). RtMSi= 1.21 min., [M+H]+ = 182.1.
55% With lithium hydroxide; water; In tetrahydrofuran; for 18h; 2-Chloro-4-cyanobenzoic acid Lithium hydroxide monohydrate (1.18g, 28mmol) was added to a solution of 2-chloro-4-cyanobenzoic acid methyl ester (2.61g, 13mmol) in a mixture of THF and water (4:1, 100ml) and stirred for 18h. The mixture was reduced in vacuo, the residue was acidified with 1N hydrochloric acid and extracted with a mixture of methanol and chloroform (5:95). The organic extracts were washed with brine, dried and reduced. The residue was recrystallized from dioxan/pet. ether to give a pale orange solid identified as 2-chloro-4-cyanobenzoic acid, yield 1.34g, 55%.
With sodium hydroxide; In methanol; water; EXAMPLE 76 2-Chloro-4-cyanobenzoic Acid To a stirred solution of 2-chloro-4-cyanobenzoic acid, methyl ester (24.3 g) in methanol (150 ml) was added 2.5N sodium hydroxide (54.5 ml). After stirring at room temperature. for 45 minutes, the solvent was removed in vacuo. The residue was dissolved in water, cooled in an ice bath, and made acidic with 2N hydrochloric acid (14 ml). The resulting precipitate was filtered and dried in vacuo to yield the title compound as a solid (22.55 g) m.p. 154-158 C.
To a stirred solution of 2-chloro-4-cyanobenzoic acid, methyl ester (24.3 g) in methanol (150 ml) was added 2.5N sodium hydroxide (54.5 ml). After stirring at room temperature. for 45 minutes, the solvent was removed in vacuo. The residue was dissolved in water, cooled in an ice bath, and made acidic with 2N hydrochloric acid (14 ml). The resulting precipitate was filtered and dried in vacuo to yield the title compound as a solid (22.55 g) m.p. 154-158 C.

 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 98592-34-8 ]

Aryls

Chemical Structure| 409127-32-8

A487149 [409127-32-8]

Methyl 2,6-dichloro-4-cyanobenzoate

Similarity: 0.94

Chemical Structure| 117738-77-9

A153399 [117738-77-9]

2-Chloro-4-cyanobenzoic acid

Similarity: 0.92

Chemical Structure| 58331-97-8

A179890 [58331-97-8]

Methyl 4-chloro-2-cyanobenzoate

Similarity: 0.92

Chemical Structure| 89891-83-8

A156198 [89891-83-8]

2-Chloro-5-cyanobenzoic acid

Similarity: 0.90

Chemical Structure| 214759-66-7

A394089 [214759-66-7]

Methyl 3-chloro-4-cyanobenzoate

Similarity: 0.88

Chlorides

Chemical Structure| 409127-32-8

A487149 [409127-32-8]

Methyl 2,6-dichloro-4-cyanobenzoate

Similarity: 0.94

Chemical Structure| 117738-77-9

A153399 [117738-77-9]

2-Chloro-4-cyanobenzoic acid

Similarity: 0.92

Chemical Structure| 58331-97-8

A179890 [58331-97-8]

Methyl 4-chloro-2-cyanobenzoate

Similarity: 0.92

Chemical Structure| 89891-83-8

A156198 [89891-83-8]

2-Chloro-5-cyanobenzoic acid

Similarity: 0.90

Chemical Structure| 214759-66-7

A394089 [214759-66-7]

Methyl 3-chloro-4-cyanobenzoate

Similarity: 0.88

Esters

Chemical Structure| 409127-32-8

A487149 [409127-32-8]

Methyl 2,6-dichloro-4-cyanobenzoate

Similarity: 0.94

Chemical Structure| 58331-97-8

A179890 [58331-97-8]

Methyl 4-chloro-2-cyanobenzoate

Similarity: 0.92

Chemical Structure| 214759-66-7

A394089 [214759-66-7]

Methyl 3-chloro-4-cyanobenzoate

Similarity: 0.88

Chemical Structure| 2905-69-3

A122739 [2905-69-3]

Methyl 2,5-dichlorobenzoate

Similarity: 0.85

Chemical Structure| 651058-97-8

A141026 [651058-97-8]

2-Chloro-5-(methoxycarbonyl)benzoic acid

Similarity: 0.85

Nitriles

Chemical Structure| 409127-32-8

A487149 [409127-32-8]

Methyl 2,6-dichloro-4-cyanobenzoate

Similarity: 0.94

Chemical Structure| 117738-77-9

A153399 [117738-77-9]

2-Chloro-4-cyanobenzoic acid

Similarity: 0.92

Chemical Structure| 58331-97-8

A179890 [58331-97-8]

Methyl 4-chloro-2-cyanobenzoate

Similarity: 0.92

Chemical Structure| 89891-83-8

A156198 [89891-83-8]

2-Chloro-5-cyanobenzoic acid

Similarity: 0.90

Chemical Structure| 214759-66-7

A394089 [214759-66-7]

Methyl 3-chloro-4-cyanobenzoate

Similarity: 0.88