Home Cart Sign in  
Chemical Structure| 66490-33-3 Chemical Structure| 66490-33-3

Structure of 66490-33-3

Chemical Structure| 66490-33-3

*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 [ 66490-33-3 ]

CAS No. :66490-33-3
Formula : C8H5ClS
M.W : 168.64
SMILES Code : ClC1=C(C=CS2)C2=CC=C1
MDL No. :MFCD18451627
InChI Key :YGYUMNQONHLLNC-UHFFFAOYSA-N
Pubchem ID :12398605

Safety of [ 66490-33-3 ]

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

Computational Chemistry of [ 66490-33-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 46.84
TPSA ?

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

28.24 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.28
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

3.57
Log Po/w (WLOGP)?

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

3.55
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.

3.23
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

4.33
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.39

Water Solubility

Log S (ESOL):?

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

-3.8
Solubility 0.0267 mg/ml ; 0.000158 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.

-3.85
Solubility 0.0239 mg/ml ; 0.000142 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

-3.95
Solubility 0.0189 mg/ml ; 0.000112 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

Yes
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.

-4.79 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

2.0
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<2.0
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)

2.19

Application In Synthesis of [ 66490-33-3 ]

* 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 [ 66490-33-3 ]

[ 66490-33-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 17402-83-4 ]
  • [ 66490-33-3 ]
  • 2
  • [ 205054-85-9 ]
  • [ 66490-20-8 ]
  • [ 66490-33-3 ]
YieldReaction ConditionsOperation in experiment
With phosphoric acid; In chlorobenzene; for 6h;Heating / reflux; A solution containing polyphosphoric acid (8 g) and chlorobenzene (50 mL) is heated at reflux. A solution containing 1-chloro-3-(2,2-dimethoxyethylsulfanyl)benzene (2.7 g, 11.6 mmol) in chlorobenzene (5 mL) is added dropwise to the refluxing polyphosphoric acid solution. After 6 hours, the solution is cooled to ambient temperature. The solution is diluted with CH2Cl2 and washed with water and saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with hexanes to yield the title compounds (2.4 g, 9.0 mmol) as a 1:1 isomeric mixture. 1H NMR (CDCl3, 300 MHz) δ7.88 (m, 1H), 7.75 (m, 2H), 7.42 (m, 2H). MS (EI): m/z 168, 170 (M+), Cl pattern
  • 3
  • [ 66490-20-8 ]
  • [ 66490-33-3 ]
  • [ 128852-00-6 ]
  • [ 128852-07-3 ]
YieldReaction ConditionsOperation in experiment
To a solution of 4-chloro-benzo[b]thiophene and <strong>[66490-20-8]6-chlorobenzo[b]thiophene</strong> (11.8 g, 88.1 mmol), in 400 mL of THF at -78 C. is added n-BuLi (55 mL of a 1.6M solution in hexanes, 88.1 mmol). After 15 minutes, the solution is added by cannula to a precooled (-78 C.) solution of SO2 (200 g) in 100 mL of THF. After addition, the solution is allowed to warm to ambient temperature. After 0.5 hour, the solution is concentrated. The residue is suspended in hexanes (400 mL) and is cooled to 0 C. To the solution is added SO2Cl2 (12.5 g, 92.5 mmol). After stirring for 15 minutes, the solution is concentrated. The residue is dissolved in EtOAc. The organic solution is washed with saturated NH4Cl (aq.), H2O and saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is dissolved in CH2Cl2 and filtered through a plug of silica gel. The crude product is purified by column chromatography eluting with hexanes to yield the title compound as well as 4-chlorobenzo[b]thiophene-2-sulfonyl chloride as white solids. [1511] 4-Chlorobenzo[b]thiophene-2-sulfonyl chloride: 1H NMR (CDCl3, 300 MHz) δ8.32 (m, 1H), 7.81 (m, 1H), 7.53 (m, 2H). [1512] 6-Chlorobenzo[b]thiophene-2-sulfonyl chloride: 1H NMR (CDCl3, 300 MHz) δ8.11 (s, 1H), 7.88 (m, 2H), 7.50 (m, 1H)
  • 4
  • [ 180160-64-9 ]
  • [ 66490-20-8 ]
  • [ 66490-33-3 ]
  • [ 19742-92-8 ]
YieldReaction ConditionsOperation in experiment
51%; 40% With PPA; Polyphosphoric acid (PPA); In chlorobenzene; for 3.75h;Heating / reflux; Preparation of 4-Chlorobenzo[b]thiophene and 6-Chlorobenzo[b]thiophene. [CHEMMOL-00085] [0265] A mixture of 3-chlorobenzenethiol (9.9 g, 68.5 mmol), K2CO3 (11.35 g, 82.1 mmol), and bromoacetaldehyde diethyl acetal (8.1 mL, 68.5 mmol) in acetone (250 mL) was stirred at room temperature for 24 h. The base and the salt formed were removed by filtration with ethereal rinse. The filtrate and washings were combined, concentrated, taken up in 250 mL of Et2O, and washed with 200 mL each of 0.5 N KOH and brine. The aqueous layers were back-extracted with 2×250 mL of Et2O. Combined organic layers were dried over MgSO4, concentrated, and dried under vacuum. [0266] To a heated and vigorously stirred biphasic solution of polyphosphoric acid (PPA) (ca. 35 g) and chlorobenzene (350 mL) was added dropwise the crude acetal in 100 mL of chlorobenzene over 2.5 h period. After heating at reflux for 1.25 h, the mixture was stirred overnight while allowed to cool to room temperature. The organic layer was separated by decantation, concentrated, taken up in EtOAc (300 mL), and washed with 200 mL each of saturated aqueous NaHCO3 and brine. The PPA layer was dissolved in H2O (ca. 500 mL) and extracted with 3×300 mL of EtOAc which was washed with the saturated aqueous NaHCO3 and brine used above. Combined organic layers were dried over MgSO4, concentrated, and purified by PrepLC 500A with hexanes as eluent to yield 4-chlorobenzo[b]thiophene (4.269 g, 40%) and 6-chlorobenzo[b]thiophene (5.896 g, 51%) which was contaminated with 3-chlorobenzenedisulfide. FDMS 168(M)+
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 66490-33-3 ]

Chlorides

Chemical Structure| 20532-33-6

A155777 [20532-33-6]

5-Chlorobenzothiophene

Similarity: 0.80

Chemical Structure| 26018-73-5

A433573 [26018-73-5]

6-Chlorobenzo[b]thiophene-2-carboxylic acid

Similarity: 0.72

Chemical Structure| 132740-14-8

A195755 [132740-14-8]

1-(3-Chlorobenzo[b]thiophen-2-yl)-N-methylmethanamine hydrochloride

Similarity: 0.69

Chemical Structure| 1198-51-2

A124149 [1198-51-2]

3-(Bromomethyl)-5-chlorobenzo[b]thiophene

Similarity: 0.67

Chemical Structure| 90407-16-2

A195796 [90407-16-2]

7-Chloro-1-benzothiophene-2-carboxylic acid

Similarity: 0.67

Related Parent Nucleus of
[ 66490-33-3 ]

Benzothiophenes

Chemical Structure| 20532-33-6

A155777 [20532-33-6]

5-Chlorobenzothiophene

Similarity: 0.80

Chemical Structure| 16587-47-6

A298899 [16587-47-6]

6-Methylbenzo[b]thiophene

Similarity: 0.77

Chemical Structure| 26018-73-5

A433573 [26018-73-5]

6-Chlorobenzo[b]thiophene-2-carboxylic acid

Similarity: 0.72

Chemical Structure| 6179-28-8

A160405 [6179-28-8]

Benzo[b]thiophen-6-ylmethanol

Similarity: 0.69

Chemical Structure| 132740-14-8

A195755 [132740-14-8]

1-(3-Chlorobenzo[b]thiophen-2-yl)-N-methylmethanamine hydrochloride

Similarity: 0.69