13726-16-4|4-Chloro-3-methoxybenzaldehyde| Ambeed

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

Quality Control of [ 13726-16-4 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 13726-16-4 ]

CAS No. :	13726-16-4
Formula :	C₈H₇ClO₂
M.W :	170.59
SMILES Code :	O=CC1=CC=C(Cl)C(OC)=C1
MDL No. :	MFCD07787490
Boiling Point :	No data available
InChI Key :	BZCOHGUBYSDFET-UHFFFAOYSA-N
Pubchem ID :	12909725

Safety of [ 13726-16-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 13726-16-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	43.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.83
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	2.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.16
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.	1.71
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	2.61
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.1

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.55
Solubility	0.482 mg/ml ; 0.00282 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.	-2.38
Solubility	0.718 mg/ml ; 0.00421 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	-3.08
Solubility	0.141 mg/ml ; 0.000824 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.	-5.79 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	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)	1.25

Application In Synthesis of [ 13726-16-4 ]

* 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 [ 13726-16-4 ]

[ 13726-16-4 ] Synthesis Path-Downstream 1~36

1
[ 13726-16-4 ]
4,4'-dichloro-3,3'-dimethoxy-benzil [ No CAS ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546.

2
[ 56962-12-0 ]
[ 77-78-1 ]
[ 13726-16-4 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1757 - 1763.
[2]Journal of the American Chemical Society,1955,vol. 77,p. 543,546.

3
[ 79-24-3 ]
[ 13726-16-4 ]
[ 27572-01-6 ]

Yield	Reaction Conditions	Operation in experiment
20 g	With potassium fluoride; N,N-dimethylammonium chloride; In toluene; for 20h;Reflux; Dean-Stark;	To a solution of <strong>[13726-16-4]4-chloro-3-methoxy-benzaldehyde</strong> (25 g, 150 mmol) in toluene (300 mL) was added nitroethane (27 g, 300 mol), dimethyamine hydrochloride (36.5 g, 450 mmol) and potassium fluoride (8.7 g, 150 mmol). The mixture was refluxed for 20 hours with a Dean-Stark trap. The reaction mixture was diluted with ethyl acetate (500 mL) and then quenched with 10percent HCl (150 mL). The organic layer was separated, washed with water (150 mL) and brine (150 mL), and then dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The residue was purified by column chromatography to give 1-chloro-2-methoxy-4-[2-nitroprop-1-enyl]benzene (20 g) as a yellow solid.
20 g	With potassium fluoride; N,N-dimethylammonium chloride; In toluene; for 20h;Dean-Stark; Reflux;	Step 1: Preparation of l-ehloro-2-methox -4-\|2-nitroprop-l-enyl\| benzene To a solution of <strong>[13726-16-4]4-chloro-3-methoxy-benzaldehyde</strong> (25 g, 150 mmol) in toluene (300 ml.) was added nitroethane (27 g, 300 mol), dimethyamine hydrochloride (36.5 g, 450 mmol) and potassium fluoride (8.7 g, 1 50 mmol ). The mixture was refluxed for 20 hours with a Dean-Stark trap. The reaction mixture was diluted with ethyl acetate (500 ml . ) and then quenched with 10percent HC1 ( 1 50 ml. ). The organic layer was separated, washed w ith water ( 1 50 mL) and brine ( 1 50 ml. ), and then dried over anhydrous Na2S04 and then concentrated under reduced pressure. The residue was purified by column chromatography to give 1 -chloro-2-metho.xy-4-[ 2-nitroprop- 1 - enyl jbenzene (20 g) as a yellow solid.

References: [1]Journal of Medicinal Chemistry,1974,vol. 17,p. 1100 - 1111.
[2]Patent: US2015/210682,2015,A1 .Location in patent: Paragraph 0989; 0990.
[3]Patent: WO2015/113990,2015,A1 .Location in patent: Page/Page column 113; 114.

4
[ 13726-16-4 ]
[ 768-94-5 ]
Adamantan-1-yl-(4-chloro-3-methoxy-benzyl)-amine [ No CAS ]

References: [1]Patent: AT335420,1976, .
Patent: DE2403138,1975, .
Chem.Abstr.,1975,vol. 83.

5
[ 13726-16-4 ]
[ 5452-37-9 ]
[ 769062-56-8 ]

References: [1]Patent: AT335420,1976, .
Patent: DE2403138,1975, .
Chem.Abstr.,1975,vol. 83.

6
[ 75-52-5 ]
[ 13726-16-4 ]
[ 144181-28-2 ]

Yield	Reaction Conditions	Operation in experiment
66.6%	With sodium hydroxide; In ethanol; at 0℃; for 3h;	4-Chloro-3-methoxybenzaldehyde (lg, 5.88mmol) in ethanol (lOmL) was reacted with nitro methane (358mg,5.88mmol) and ION NaOH (0.6mL, 28.1 lmmol). The resulting mixture was stirred at 0°C for 3 hours to afford 800 mg of the product (66.6percent yield).1H NM (CDC13, 300 MHz): delta 7.97-7.93 (m, 1H), 7.59-7.55 (m, 1H), 7.45- 7.426 (m, 1 H), 7.1-7.09 (dd, 1H), 7.03-7.0 (d, 1H), 3.95 (s, 3H).
66.6%	With sodium hydroxide; In ethanol; at 0℃; for 3h;	Preparation of Intermediate 1-chloro-2-methoxy-4-(2-nitrovinyl)benzene (I-86a) 4-Chloro-3-methoxybenzaldehyde (1 g, 5.88 mmol) in ethanol (10 mL) was reacted with nitro methane (358 mg, 5.88 mmol) and 10N NaOH (0.6 mL, 28.11 mmol). The resulting mixture was stirred at 0° C. for 3 hours to afford 800 mg of the product (66.6percent yield). 1H NMR (CDCl3, 300 MHz): delta 7.97-7.93 (m, 1H), 7.59-7.55 (m, 1H), 7.45-7.426 (m, 1H), 7.1-7.09 (dd, 1H), 7.03-7.0 (d, 1H), 3.95 (s, 3H).

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4408 - 4414.
[2]Patent: WO2012/35078,2012,A1 .Location in patent: Page/Page column 192.
[3]Patent: US2014/45872,2014,A1 .Location in patent: Paragraph 1175.

7
[ 7677-24-9 ]
[ 13726-16-4 ]
(4-Chloro-3-methoxy-phenyl)-trimethylsilanyloxy-acetonitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1887 - 1891.

8
[ 13726-16-4 ]
[ 2181-42-2 ]
2-(4-Chloro-3-methoxy-phenyl)-oxirane [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 352 - 358.

9
[ 13726-16-4 ]
[ 13726-17-5 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1757 - 1763.
[2]Bulletin de la Societe Chimique de France,1966,p. 3311 - 3318.

10
[ 13726-17-5 ]
[ 13726-16-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With manganese dioxide; In dichloromethane; benzene;	D. Synthesis of 4-chloro-3-methoxybenzaldehyde To a solution of (4-chloro-3-methoxyphenyl)methan-1-ol (5.08 g, 29.4 mmol) in benzene (120 mL) was added MnO2 (5.65 g, 65 mmol). The reaction mixture was refluxed for 17 hr, chilled, and filtered through Celite, washing the cake with CH2Cl2 (300 mL). The filtrate was concentrated in vacuo to give 4-chloro-3-methoxybenzaldehyde (4.5 g, 89percent).
89%	With manganese dioxide; In dichloromethane; benzene;	D. Synthesis of 4-chloro-3-methoxybenzaldehyde To a solution of (4-chloro-3-methoxyphenyl)methan-1-ol (5.08 g, 29.4 mmol) in benzene (120 mL) was added MnO2 (5.65 g, 65 mmol). The reaction mixture was refluxed for 17 hr, chilled, and filtered through Celite, washing the cake with CH2Cl2 (300 mL). The filtrate was concentrated in vacuo to give 4-chloro-3-methoxybenzaldehyde (4.5 g, 89percent).
89%	With manganese(IV) oxide; In benzine; for 17h;Reflux;	D. Synthesis of 4-chloro-3-methoxybenzaldehyde (0202) To a solution of (4-chloro-3-methoxyphenyl)methan-1-ol (5.08 g, 29.4 mmol) in benzene (120 mL) was added MnO2 (5.65 g, 65 mmol). The reaction mixture was refluxed for 17 hr, chilled, and filtered through Celite, washing the cake with CH2Cl2 (300mL). The filtrate was concentrated in vacuo to give 4-chloro-3-methoxybenzaldehyde (4.5 g, 89percent).

87%

With pyridinium chlorochromate; In dichloromethane; at 20℃; for 3h;Molecular sieve;

[00154] Step 2. A suspension of pyridinium chlorochromate (1.37 g, 6.34 mmol) in dichloromethane (35 mL) was treated with Celite (2.0 g) and stirred at rt. A solution of (4-chloro-3-methoxyphenyl)methanol (730 mg, 4.23 mmol) in dichloromethane (5 mL) was added in one portion, and the resulting mixture was stirred at rt for 3 h. After this time, the mixture was diluted with diethyl ether, and stirred vigorously. The mixture was then filtered through a pad of silica gel and the collected solids were rinsed with additional diethyl ether. The combined filtrates were concentrated under vacuum to provide 4-chloro-3-methoxybenzaldehyde as a pale tan-yellow solid (630 mg, 87percent). 1H NMR (400 MHz, CDCl3) delta ppm 3.98 (s, 3 H) 7.41 (dd, J=I.9, 1.8 Hz, 1 H) 7.45 (d, J=2.0 Hz, 1 H) 7.55 (d, J=7.6 Hz, 1 H) 9.95 (s, I H).

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4408 - 4414.
[2]Patent: US2002/77486,2002,A1 .
[3]Patent: US6906063,2005,B2 .
[4]Patent: EP2314593,2016,B1 .Location in patent: Paragraph 0202.
[5]Tetrahedron Letters,2005,vol. 46,p. 5417 - 5419.
[6]Patent: WO2010/9069,2010,A1 .Location in patent: Page/Page column 47.
[7]Journal of Medicinal Chemistry,1987,vol. 30,p. 1887 - 1891.
[8]Journal of Medicinal Chemistry,1982,vol. 25,p. 352 - 358.
[9]Russian Chemical Bulletin,2012,vol. 61,p. 1616 - 1621.
Izv. Akad. Nauk, Ser. Khim.,2012,p. 1599 - 1604.

11
[ 75-17-2 ]
[ 13726-14-2 ]
[ 13726-16-4 ]

References: [1]Bulletin de la Societe Chimique de France,1966,p. 3311 - 3318.

14
[ 13726-16-4 ]
2-chloro-5-methoxy-phenyl magnesium bromide [ No CAS ]
2,4'-dichloro-5,3'-dimethoxy-benzophenone [ No CAS ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546.

15
[ 13726-16-4 ]
2-chloro-3-methoxy-phenyl magnesium bromide [ No CAS ]
[ 875844-45-4 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546.

16
[ 141-82-2 ]
[ 13726-16-4 ]
[ 475654-41-2 ]