93490-31-4|4-Chloro-6-methoxy-1H-indole| Ambeed

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Quality Control of [ 93490-31-4 ] Purity: 95% SDS Specification

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Product Details of [ 93490-31-4 ]

CAS No. :	93490-31-4
Formula :	C₉H₈ClNO
M.W :	181.62
SMILES Code :	COC1=CC2=C(C=CN2)C(Cl)=C1
MDL No. :	MFCD00238559
InChI Key :	ROZQWTXWGPFHST-UHFFFAOYSA-N
Pubchem ID :	124511

Safety of [ 93490-31-4 ]

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

Computational Chemistry of [ 93490-31-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.11
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	49.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	25.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.02
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.83
Log P_o/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.	1.8
Log P_o/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	3.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.49

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.12
Solubility	0.136 mg/ml ; 0.000751 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.	-2.83
Solubility	0.271 mg/ml ; 0.00149 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	-4.03
Solubility	0.0171 mg/ml ; 0.0000942 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.53 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)	1.53

Application In Synthesis of [ 93490-31-4 ]

* 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 [ 93490-31-4 ]

[ 93490-31-4 ] Synthesis Path-Downstream 1~16

1
[ 108-05-4 ]
[ 117970-20-4 ]
[ 93490-31-4 ]
6-chlor-4-methoxyindol [ No CAS ]

References: [1]Helvetica Chimica Acta,1988,vol. 71,p. 344 - 347.
[2]Helvetica Chimica Acta,1988,vol. 71,p. 344 - 347.

2
[ 4637-24-5 ]
[ 102735-89-7 ]
[ 93490-31-4 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 4115 - 4119.

3
[ 93490-31-4 ]
[ 99684-91-0 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 4115 - 4119.

4
[ 618-86-0 ]
[ 93490-31-4 ]

References: [1]Helvetica Chimica Acta,1988,vol. 71,p. 344 - 347.

5
[ 55910-07-1 ]
[ 93490-31-4 ]

References: [1]Helvetica Chimica Acta,1988,vol. 71,p. 344 - 347.

6
[ 446-10-6 ]
[ 93490-31-4 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 4115 - 4119.

7
[ 16024-30-9 ]
[ 93490-31-4 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 4115 - 4119.

8
[ 16024-29-6 ]
[ 93490-31-4 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 4115 - 4119.

9
[ 102735-88-6 ]
[ 93490-31-4 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 4115 - 4119.

10
[ 3332-29-4 ]
[ 93490-31-4 ]
[ 530-62-1 ]
4-chloro-2-N-ethoxy-6-methoxy-1H-indole-1-carboxamide [ No CAS ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 7320 - 7330.

11
[ 93490-31-4 ]
C₁₄H₁₃ClF₂N₂O₃ [ No CAS ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 7320 - 7330.

12
[ 93490-31-4 ]
[ 76-02-8 ]
2,2,2-trichloro-1-(4-chloro-6-methoxy-1H-indol-3-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
320 mg	With pyridine; In dichloromethane; at 0 - 20℃;	4-Chloro-6-methoxy-1H-indole (250 mg, 1.38 mmol) was dissolved in DCM (5 mL) and pyridine (0.334 mL, 4.13 mmol) was added. The solution was cooled to ~ 0 ^C, and a solution of trichloroacetyl chloride (0.231 mL, 2.07 mmol) in DCM (1 mL) was added over the course of about 30 min. The cooling bath was removed and the reaction mixture was stirred at rt overnight. All the volatiles are removed under reduced pressure. The mixture was then stirred with ethanol-water (1:1, 15 mL) for 10 min, and the product was filtered off and dried. Further purification by silica gel flash chromatography eluting with 0-100% ethyl acetate gradient in hexanes to give 2,2,2-trichloro-1-(4-chloro-6-methoxy-1H-indol-3- yl)ethanone (320 mg).

References: [1]Patent: WO2018/9539,2018,A1 .Location in patent: Page/Page column 120; 121.

13
[ 93490-31-4 ]
2,2,2-trichloro-1-[4-chloro-6-methoxy-1-(2-naphthylmethyl)indol-3-yl]ethanone [ No CAS ]

References: [1]Patent: WO2018/9539,2018,A1 .

14
[ 93490-31-4 ]
4-chloro-6-methoxy-1-(2-naphthylmethyl)indole-3-carboxylic acid [ No CAS ]

References: [1]Patent: WO2018/9539,2018,A1 .

15
[ 93490-31-4 ]
4-chloro-6-methoxy-1-(2-naphthylmethyl)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-3,6-bis(hydroxymethyl)tetrahydropyran-3-yl]indole-3-carboxamide [ No CAS ]

References: [1]Patent: WO2018/9539,2018,A1 .

16
[ 93490-31-4 ]
4-chloro-6-methoxy-1-(2-naphthylmethyl)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)-3-methyltetrahydropyran-3-yl]indole-3-carboxamide [ No CAS ]

References: [1]Patent: WO2018/9539,2018,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Ethers • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 93490-31-4 ]

Chlorides

A221172 [117970-23-7]

6-Chloro-4-methoxy-1H-indole

Similarity: 0.82

A258254 [25235-85-2]

4-Chloroindole

Similarity: 0.74

A139898 [162100-43-8]

4-Chloro-5-methyl-1H-indole

Similarity: 0.73

A233973 [885521-78-8]

4-Chloro-6-methyl-1H-indole

Similarity: 0.73

A157075 [101495-18-5]

4,6-Dichloro-1H-indole

Similarity: 0.72

Ethers

A221172 [117970-23-7]

6-Chloro-4-methoxy-1H-indole

Similarity: 0.82

A179099 [1076-74-0]

5-Methoxy-2-methyl-1H-indole

Similarity: 0.73

A105085 [1006-94-6]

5-Methoxyindole

Similarity: 0.72

A111612 [14430-23-0]

5,6-Dimethoxyindole

Similarity: 0.71

A171054 [1071973-95-9]

6-Methoxy-5-methyl-1H-indole

Similarity: 0.71

Related Parent Nucleus of
[ 93490-31-4 ]

Indoles

A221172 [117970-23-7]

6-Chloro-4-methoxy-1H-indole

Similarity: 0.82

A258254 [25235-85-2]

4-Chloroindole

Similarity: 0.74

A139898 [162100-43-8]

4-Chloro-5-methyl-1H-indole

Similarity: 0.73

A179099 [1076-74-0]

5-Methoxy-2-methyl-1H-indole

Similarity: 0.73

A233973 [885521-78-8]

4-Chloro-6-methyl-1H-indole

Similarity: 0.73

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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 93490-31-4

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