Home Cart Sign in  
Chemical Structure| 175883-60-0 Chemical Structure| 175883-60-0

Structure of 175883-60-0

Chemical Structure| 175883-60-0

*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 [ 175883-60-0 ]

CAS No. :175883-60-0
Formula : C7H8BClO3
M.W : 186.40
SMILES Code : COC1=C(Cl)C=C(C=C1)B(O)O
MDL No. :MFCD04039888
InChI Key :VUTJHOWRPUPHIG-UHFFFAOYSA-N
Pubchem ID :3247522

Safety of [ 175883-60-0 ]

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

Computational Chemistry of [ 175883-60-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 47.77
TPSA ?

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

49.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

1.43
Log Po/w (WLOGP)?

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

0.03
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.

0.6
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

-0.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.39

Water Solubility

Log S (ESOL):?

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

-2.13
Solubility 1.37 mg/ml ; 0.00734 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.

-2.08
Solubility 1.56 mg/ml ; 0.00834 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

-2.03
Solubility 1.73 mg/ml ; 0.00927 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

No
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.

-6.42 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)

1.9

Application In Synthesis of [ 175883-60-0 ]

* 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 [ 175883-60-0 ]

[ 175883-60-0 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 29022-11-5 ]
  • [ 175883-60-0 ]
  • [ 210282-31-8 ]
  • 2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • [(5S,10bR)-8-(3-Chloro-4-methoxy-phenyl)-3-oxo-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline-5-carbonyl]-amino}-acetic acid [ No CAS ]
  • 2
  • [ 29022-11-5 ]
  • [ 175883-60-0 ]
  • [ 210282-31-8 ]
  • 2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 2-{2-[1-(carboxymethyl-carbamoyl)-2-(3'-chloro-4'-methoxy-biphenyl-3-yl)-ethylcarbamoyl]-ethyl}-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 3
  • [ 50638-47-6 ]
  • [ 175883-60-0 ]
YieldReaction ConditionsOperation in experiment
Step 2 Preparation of 3-chloro-4-methoxyphenylboronic acid Following the general procedure outlined in Synthetic Scheme I, 10.2 g (46.2 mmol) of <strong>[50638-47-6]4-bromo-2-chloroanisole</strong> (Step 1) was converted to 3-chloro-4-methoxyphenylboronic acid: NMR (CDCl3) delta 3.83 (s, 3H), 6.57 (s, 2H), 6.83 (d, J=8 Hz, 1H), 7.64 (dd, J=1.5, 8 Hz, 1H), 7.77 (d, J=1.5 Hz, 1H).
To a THF solution of <strong>[50638-47-6]4-bromo-2-chloroanisole</strong> was added an n-butyllithium/n-hexane solution at -78C, followed by 30 minutes of stirring. Then, trimethyl borate was added and the whole was warmed to room temperature, followed by 30 minutes of stirring. Using the residue obtained by evaporation of the solvent instead of 3,4-dimethoxyphenylboric acid, an objective compound was obtained in a similar manner to Reference Example 1.
  • 4
  • [ 175883-60-0 ]
  • [ 75676-72-1 ]
  • 5
  • [ 5419-55-6 ]
  • [ 50638-47-6 ]
  • [ 175883-60-0 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of compound 1a-e (10.0 mmol,1.0 eq) in anhydrousTHF (20 mL) was slowly added n-BuLi (6 mL of 2.5 M solution inhexane, 15.0 mmol, 1.5 eq) at 78 C. The mixture was stirred for1 h and triisopropyl borate (50.0 mmol, 5.0 eq) was added by syringe.The solutionwas stirred for another 1 h and allowed towarmto 25 C overnight. The reactionwas cooled to 0 C, followed by thesequential addition ofwater (5 mL) and 2N HCl (5 mL). After 10 min,an additional 35 mL of 2N HCl was added and the mixture wasfurther stirred for 30 min. The mixture was extracted with ethylacetate (20 mL * 3) and the combined organic layers wereconcentrated to a thick oil under reduced pressure. Crystallizationwith cold hexane yielded a white solid.
  • 6
  • [ 6627-22-1 ]
  • [ 175883-60-0 ]
  • [ 1207724-96-6 ]
YieldReaction ConditionsOperation in experiment
With tripotassium phosphate tribasic; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; In N,N-dimethyl-formamide; at 60℃; for 3h;Inert atmosphere; A mixture of <strong>[6627-22-1]methyl 6-chloropyrimidine-4-carboxylate</strong> (200 mg, 1.16 mmol), (3-chloro-4-10 methoxy-phenyl)boronic acid (432 mg, 2.32 mmol), dichloro[1,1'- bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (85 mg, 0.12 mmol) and potassium phosphate (738 mg, 3.48 mmol) in DMF (10 mL) was purged with argon and heated in a sealed tube at 60 C for 3 h. After this time, the reaction mixture was concentrated under reduced pressure, and the residue obtained was purified by FCC (Silica, 0-5% MeOH in DCM) to give the title compound. m/z (ES+) (M+H)+ 279.0.1H NMR (300 MHz, DMSO-d6) δ 9.35 (d, J = 1.2 Hz, 1H), 8.53 5 (d, J = 1.2 Hz, 1H), 8.39 (d, J = 2.1 Hz, 1H), 8.31 (dd, J = 8.7, 2.4 Hz, 1H), 7.34 (d, J = 9.0 Hz, 1H), 3.97 (s, 3H), 3.95 (s, 3H).
With tripotassium phosphate tribasic; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; In N,N-dimethyl-formamide; at 60℃; for 3h;Inert atmosphere; A mixture of <strong>[6627-22-1]methyl 6-chloropyrimidine-4-carboxylate</strong> (200 mg, 1.16 mmol), (3-chloro-4-10 methoxy-phenyl)boronic acid (432 mg, 2.32 mmol), dichloro[1,1'- bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (85 mg, 0.12 mmol) and potassium phosphate (738 mg, 3.48 mmol) in DMF (10 mL) was purged with argon and heated in a sealed tube at 60 C for 3 h. After this time, the reaction mixture was concentrated under reduced pressure, and the residue obtained was purified by FCC (Silica, 0-5% MeOH in DCM) to give the title compound. m/z (ES+) (M+H)+ 279.0.1H NMR (300 MHz, DMSO-d6) δ 9.35 (d, J = 1.2 Hz, 1H), 8.53 5 (d, J = 1.2 Hz, 1H), 8.39 (d, J = 2.1 Hz, 1H), 8.31 (dd, J = 8.7, 2.4 Hz, 1H), 7.34 (d, J = 9.0 Hz, 1H), 3.97 (s, 3H), 3.95 (s, 3H).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 175883-60-0 ]

Organoborons

Chemical Structure| 480438-55-9

A158221 [480438-55-9]

(4-Butoxy-3-chlorophenyl)boronic acid

Similarity: 0.92

Chemical Structure| 854778-30-6

A121579 [854778-30-6]

(2-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.91

Chemical Structure| 1256346-35-6

A139606 [1256346-35-6]

(4-Chloro-3-isopropoxyphenyl)boronic acid

Similarity: 0.89

Chemical Structure| 89694-48-4

A175212 [89694-48-4]

(5-Chloro-2-methoxyphenyl)boronic acid

Similarity: 0.86

Chemical Structure| 89694-47-3

A219688 [89694-47-3]

(4-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.86

Aryls

Chemical Structure| 480438-55-9

A158221 [480438-55-9]

(4-Butoxy-3-chlorophenyl)boronic acid

Similarity: 0.92

Chemical Structure| 854778-30-6

A121579 [854778-30-6]

(2-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.91

Chemical Structure| 1256346-35-6

A139606 [1256346-35-6]

(4-Chloro-3-isopropoxyphenyl)boronic acid

Similarity: 0.89

Chemical Structure| 89694-48-4

A175212 [89694-48-4]

(5-Chloro-2-methoxyphenyl)boronic acid

Similarity: 0.86

Chemical Structure| 89694-47-3

A219688 [89694-47-3]

(4-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.86

Chlorides

Chemical Structure| 480438-55-9

A158221 [480438-55-9]

(4-Butoxy-3-chlorophenyl)boronic acid

Similarity: 0.92

Chemical Structure| 854778-30-6

A121579 [854778-30-6]

(2-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.91

Chemical Structure| 1256346-35-6

A139606 [1256346-35-6]

(4-Chloro-3-isopropoxyphenyl)boronic acid

Similarity: 0.89

Chemical Structure| 89694-48-4

A175212 [89694-48-4]

(5-Chloro-2-methoxyphenyl)boronic acid

Similarity: 0.86

Chemical Structure| 89694-47-3

A219688 [89694-47-3]

(4-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.86

Ethers

Chemical Structure| 480438-55-9

A158221 [480438-55-9]

(4-Butoxy-3-chlorophenyl)boronic acid

Similarity: 0.92

Chemical Structure| 854778-30-6

A121579 [854778-30-6]

(2-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.91

Chemical Structure| 1256346-35-6

A139606 [1256346-35-6]

(4-Chloro-3-isopropoxyphenyl)boronic acid

Similarity: 0.89

Chemical Structure| 89694-48-4

A175212 [89694-48-4]

(5-Chloro-2-methoxyphenyl)boronic acid

Similarity: 0.86

Chemical Structure| 89694-47-3

A219688 [89694-47-3]

(4-Chloro-3-methoxyphenyl)boronic acid

Similarity: 0.86