Home Cart Sign in  
Chemical Structure| 666727-31-7 Chemical Structure| 666727-31-7

Structure of 666727-31-7

Chemical Structure| 666727-31-7

*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 [ 666727-31-7 ]

CAS No. :666727-31-7
Formula : C6H4ClIO
M.W : 254.45
SMILES Code : OC1=CC=CC(I)=C1Cl
MDL No. :MFCD08166415
Boiling Point : No data available
InChI Key :OXCDLZCOMWIYQR-UHFFFAOYSA-N
Pubchem ID :11379814

Safety of [ 666727-31-7 ]

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

Computational Chemistry of [ 666727-31-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 46.19
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.99
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

2.84
Log Po/w (WLOGP)?

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

2.65
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.

2.99
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

2.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.69

Water Solubility

Log S (ESOL):?

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

-3.7
Solubility 0.0508 mg/ml ; 0.000199 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.

-2.92
Solubility 0.304 mg/ml ; 0.00119 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

-3.39
Solubility 0.103 mg/ml ; 0.000405 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

Yes
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.

-5.84 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<0.0
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)

1.93

Application In Synthesis of [ 666727-31-7 ]

* 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.

  • Upstream synthesis route of [ 666727-31-7 ]

[ 666727-31-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 56962-01-7 ]
  • [ 666727-31-7 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h;
Stage #2: With sulfuric acid; potassium iodide In water at 20℃; for 2 h;
Example 10 [:] Synthesis of [2-CHLORO-3- (2, 2-DIMETHYL-4-PHENETHYLSULFANYLMETHYL-1,] 2- dihydroquinoline-6-yl) phenol OH z O < \\ CI 8r OrB/ H H Suzuki OH OH ci ci \\I \\I I/ \\ \\ I \\ N N H H 10 To a suspension of 2-amino-3-nitrophenol (10 g, 65 mmol) in concentrated [HC1] (10 mL) at [0°C,] sodium nitrite (5.1 g, 73.3 mmol) in water (60 [ML)] was added dropwise. After stirring for 30 minutes at [0°C,] CuCl (12.8 g, [130] mmol) in 10percent [H2SO4] (3 mL) was added and the reaction was stirred for 18 hours. The heterogeneous mixture was filtered and washed with water. The filtrate was extracted three times with 70 mL portions of EtOAc. Evaporation of EtOAc extractions afforded 7 grams (62percent yield) of pure [2-CHLORO-3-NITROPHENOL,] 2-Chloro-3- nitrophenol (6 g, 35 mmol) was dissolved in methanol (100 [ML)] and treated with ammonium chloride (9.4 g, 175.7 mmol) and zinc dust (46 g, 702.8 mmol). The resulting mixture was refluxed for one hour. After filtration and evaporation, 2-chloro-3-aminophenol was collected (4.5 g, 90percent yield) as a purple solid. To a suspension of 2-chloro-3-aminophenol (4.5 g, 31 mmol) in concentrated [HCI] (10 mL) at [0°C] was added dropwise sodium nitrite (2.5 g, 35 mmol) in water (50 mL). After stirring for 30 minutes at [0°C,] [I (I] (10.4 g, 63 mmol) in 10percent [H2SO4] (3 mL) was added dropwise. The reaction was stirred at room temperature for 2 hours, then filtered, extracted with EtOAc, and concentrated in vacuo to afford 2-chloro-3-iodophenol as a dark purple solid (6 g, 75percent yield). 6-Bromo-2,2, [4-TRIMETHYL-1,] 2-dihydroquinoline (2.3 g, 9.2 mmol) (Example 8) and bis (pinacol) diborane (4.2 g, 16.5 mmol) were combined in DMSO (2 mL). [KOAC] (2.7 g, 27.4 mmol) was added, followed by [PDCL2] (dppf) (100 mg). The contents were placed into a microwave reaction vessel assembly and irradiated at [120°C] for 15 minutes. After cooling to room temperature, purification by chromatography afforded 2,2, [4-TRIMETHYL-6- (4,] 4,5, 5- tetramethyl- [1, 3,2] [DIOXABOROLAN-2-YL)-1,] 2-dihydroquinoline (2.3 g, [84percent] yield) as a white crystalline solid. 2,2, [4-TRIMETHYL-6- (4,] 4,5, [5-TETRAMETHYL- [1,] 3,2] [DIOXABOROLAN-2-YL)-1,] 2-dihydroquinoline [(308] mg) and 393 mg of 2-chloro-3-iodophenol were coupled using of 100 mg [OF PDCL2 (DPPF)] and [300 MG OF KOAC TO GIVE 250 MG OF 2-CHLORO-3- (2, 2, 4-TRIMETHYL-1, 2-DIHYDROQUINOLIN-6-YL) -] phenol. Using the procedures described in Example 7, this (85 mg) was reacted with NBS to give 56 mg [OF 3- (4-BROMOMETHYL-2, 2-DIMETHYL-1, 2-DIHYDROQUINOLIN-6-YL)-2-CHLOROPHENOL.] The product (50 mg) was coupled with 0.04 mL of 2-phenylethanethiol to give 40 mg of the title compound as an oil.
References: [1] Patent: WO2004/18429, 2004, A2, . Location in patent: Page 87.
  • 2
  • [ 626-02-8 ]
  • [ 666727-31-7 ]
  • [ 289039-26-5 ]
  • [ 202982-72-7 ]
References: [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479.
[2] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479.
  • 3
  • [ 863870-84-2 ]
  • [ 666727-31-7 ]
References: [1] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6548 - 6551.
[2] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5113 - 5118.
[3] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437.
  • 4
  • [ 626-02-8 ]
  • [ 666727-31-7 ]
References: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 4, p. 485 - 493.
[2] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6548 - 6551.
  • 5
  • [ 863870-73-9 ]
  • [ 666727-31-7 ]
References: [1] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5113 - 5118.
[2] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6548 - 6551.
[3] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 666727-31-7 ]

Aryls

Chemical Structure| 116130-33-7

A103766 [116130-33-7]

2-Chloro-4-iodophenol

Similarity: 0.90

Chemical Structure| 289039-26-5

A304497 [289039-26-5]

2-Chloro-5-iodophenol

Similarity: 0.90

Chemical Structure| 858854-82-7

A379289 [858854-82-7]

3-Chloro-2-iodophenol

Similarity: 0.84

Chemical Structure| 161949-50-4

A103230 [161949-50-4]

2-Chloro-5-iodoanisole

Similarity: 0.81

Chemical Structure| 34074-22-1

A275136 [34074-22-1]

2,6-Dichloro-4-iodophenol

Similarity: 0.81

Chlorides

Chemical Structure| 116130-33-7

A103766 [116130-33-7]

2-Chloro-4-iodophenol

Similarity: 0.90

Chemical Structure| 289039-26-5

A304497 [289039-26-5]

2-Chloro-5-iodophenol

Similarity: 0.90

Chemical Structure| 858854-82-7

A379289 [858854-82-7]

3-Chloro-2-iodophenol

Similarity: 0.84

Chemical Structure| 161949-50-4

A103230 [161949-50-4]

2-Chloro-5-iodoanisole

Similarity: 0.81

Chemical Structure| 34074-22-1

A275136 [34074-22-1]

2,6-Dichloro-4-iodophenol

Similarity: 0.81