96516-29-9|2-Fluoro-3-nitrobenzaldehyde| 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 [ 96516-29-9 ] Purity: 95% 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 [ 96516-29-9 ]

CAS No. :	96516-29-9
Formula :	C₇H₄FNO₃
M.W :	169.11
SMILES Code :	FC1=C(C=O)C=CC=C1[N+](=O)[O-]
MDL No. :	MFCD08669885
InChI Key :	WLDHPJSICUOHTH-UHFFFAOYSA-N
Pubchem ID :	10487325

Safety of [ 96516-29-9 ]

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

Computational Chemistry of [ 96516-29-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	40.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.94
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	1.31
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.97
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.	0.69
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	0.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.95
Solubility	1.89 mg/ml ; 0.0112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.23
Solubility	0.993 mg/ml ; 0.00587 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	-2.0
Solubility	1.69 mg/ml ; 0.01 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	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.	-6.4 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	3.0 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)	1.65

Application In Synthesis of [ 96516-29-9 ]

* 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 [ 96516-29-9 ]

[ 96516-29-9 ] Synthesis Path-Downstream 1~35

1
[ 58755-57-0 ]
[ 96516-29-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium fluoride; In N,N-dimethyl-formamide; at 150℃; for 5.0h;	To a solution of 2-chloro-3-nitrobenzaldehyde (9.5 g, 51.2 mmol) in DMF (100 mL) was added KF (8.9 g, 154 mmol). The reaction mixture was heated to 150 C and stirred at that temperature for 5 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude material was poured into H20 (400 mL) and extracted with DCM (100 mL x 4). The combined organic extracts were concentrated in vacuo and the crude material was purified by silica-gel column chromatography (petroleum ether/EtOAc, 20: 1) to give 2-fluoro-3- nitrobenzaldehyde as a yellow oil (6.7 g, yield: 77%). 1H NMR (400 MHz, CDCI3) d: 10.44 (s, 1H), 8.36-8.30 (m, 1H), 8.22-8.16 (m, 1H), 7.47 (t, J = 8.0 Hz, 1H).

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2049 - 2054.
[2]Patent: WO2019/222101,2019,A1 .Location in patent: Page/Page column 154.

2
[ 105-45-3 ]
[ 96516-33-5 ]
[ 96516-29-9 ]
4-(2-Fluoro-3-nitro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-[3-(benzyl-methyl-amino)-2,2-dimethyl-propyl] ester 5-methyl ester; hydrochloride [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2049 - 2054.

3
[ 54527-65-0 ]
[ 96516-29-9 ]
[ 14205-39-1 ]
2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2049 - 2054.

4
[ 96516-25-5 ]
[ 96516-29-9 ]
[ 14205-39-1 ]
3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2049 - 2054.

5
[ 446-52-6 ]
[ 96516-29-9 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 7348 - 7350.

6
[ 3970-40-9 ]
[ 96516-29-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2049 - 2054.

7
[ 626-34-6 ]
[ 96516-25-5 ]
[ 96516-29-9 ]
3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl ethyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol;	EXAMPLE 19 Synthesis of 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl ethyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (162) A mixture of 184 mg of <strong>[96516-29-9]2-fluoro-3-nitrobenzaldehyde</strong>, 324 mg of 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl acetoacetate and 138 mg of ethyl 3-aminocrotonate in 1 ml of 2-propanol was reacted and then purified in the same way as in Example 8 to yield 120 mg of the desired compound (162). IR (CHCl3) numaxcm-1: 1680, 1348, 1096 NMR (CDCl3) deltappm: 7.8-6.8 (m, 8H), 6.35 (brs, 1H), 5.27 (s, 1H), 4.00 (q, 2H, J=7 Hz), 3.84 (s, sH), 3.39 (s, 2H), 2.25 (s, 8H), 2.03 (s, 3H), 1.18 (t, 3H, J=7 Hz), 0.85 (s, 6H),

References: [1]Patent: US4578395,1986,A .

8
[ 54527-65-0 ]
[ 21731-17-9 ]
[ 96516-29-9 ]
2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol;	EXAMPLE 3 Synthesis of 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (104) A mixture of 330 mg of <strong>[96516-29-9]2-fluoro-3-nitrobenzaldehyde</strong>, 252 mg of methyl 3-aminocrotonate and 506 mg of 2-(N-benzyl-N-methylamino)ethyl acetoacetate in 2 ml of 2-propanol was refluxed for 12 hours, and then the solvent was distilled off in vacuo. The residue was purified by the method of a column chromatography on silica gel to provide 492 mg of the desired compound (104). IR (CHCl3) numaxcm-1: 1692, 1614, 1462 NMR (CDCl3) deltappm: 7.94-7.55 (m, 2H), 7.27 (s, 5H), 7.06 (m, 1H), 5.83 (brs, 1H), 5.31 (s, 1H), 4.13 (t, 2H, J=6 Hz), 3.59 (s, 3H), 3.48 (s, 2H), 2.60 (t, 2H, J=6 Hz), 2.30 (s, 6H), 2.15 (s, 3H)

References: [1]Patent: US4578395,1986,A .

9
3-chloro-2,2-dimethylpropyl acetoacetate [ No CAS ]
[ 21731-17-9 ]
[ 96516-29-9 ]
3-chloro-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol;	(v) To a solution of 1.70 g of <strong>[96516-29-9]2-fluoro-3-nitrobenzaldehyde</strong> in 10 ml of isopropanol were added 1.15 g of methyl 3-aminocrotonate and 2.10 g of 3-chloro-2,2-dimethylpropyl acetoacetate. The mixture was refluxed for 5 hours. Solvent was distilled off under reduced presoure to leave a residue. The residue was chromatographed on silica gel to give 2.09 g of 3-chloro-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

References: [1]Patent: US4578395,1986,A .

10
[ 96516-29-9 ]
5-Iodopyrrolo<2,3-d>pyrimidine [ No CAS ]
[ 1318945-46-8 ]

Yield	Reaction Conditions	Operation in experiment
		To 5-iodo-7H-pyrrolo[2,3-d]pyrimidine (35, 1.911 g, 7.799 mmol) 9.75 mL of tetrahydrofuran was added, the suspension was cooled to -5 C., and o-tolylmagnesium chloride (8.19 mL, 1.00 M in tetrahydrofuran, 8.19 mmol) was added. The reaction solution was stirred and kept between -5 C. and 0 C. for 30 minutes, then isopropylmagnesium chloride (4.29 mL, 2.0 M in tetrahydrofuran, 8.58 mmol) was slowly added dropwise. The reaction mixture was stirred and kept at 0 C. for 30 minutes, then <strong>[96516-29-9]2-fluoro-3-nitro-benzaldehyde</strong> (36, 1.58 g, 9.36 mmol) in 4 mL of tetrahydrofuran was added dropwise using a syringe. The reaction mixture was stirred at -5 C. for 30 minutes and quenched with 1 N hydrochloric acid (1 equivalent) and extracted with ethyl acetate and saturated sodium bicarbonate in water. The organic layer was dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluding with a gradient of 60-80% ethyl acetate in hexanes (with 4% acetic acid). Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (37, 699 mg). MS(ESI) [M+H+]+=289.4.

References: [1]Patent: US2009/286783,2009,A1 .Location in patent: Page/Page column 59-60.

11
[ 96516-29-9 ]
[ 873697-69-9 ]

References: [1]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 472 - 477.

12
[ 96516-29-9 ]
[ 873697-70-2 ]

References: [1]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 472 - 477.

13
[ 96516-29-9 ]
[ 317-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chlorite; aminosulfonic acid; water; In 1,4-dioxane; at 20℃; for 0.5h;	In a round bottom flask, <strong>[96516-29-9]2-fluoro-3-nitro-benzaldehyde</strong> (15, 1 .02 g, 6.03 mmol) is combined with sodium chlorite ( 1.26 g, 1 1.15 mmol), 60 mL of 1 ,4-dioxane, 20 mL of water, and sulfamic acid (4.47 g, 46.0 mmol) and the reaction is stirred at room temperature for 30 minutes. The mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with water, then brine, dried over magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified on column chromatography, eluting with methanol and dichloromethane. Appropriate fractions are combined and concentrated under vacuum, then suspended in dichloromethane. The resulting solid is collected by filtration to provide the desired compound (16, 151 mg). MS (ESI) [M-H+]' = 184.4.

References: [1]Patent: WO2011/79133,2011,A2 .Location in patent: Page/Page column 152.

14
[ 96516-29-9 ]
[ 1214341-16-8 ]

References: [1]Patent: WO2011/79133,2011,A2 .

15
[ 96516-29-9 ]
[ 1254567-33-3 ]

References: [1]Patent: WO2011/79133,2011,A2 .

16
[ 96516-29-9 ]
[ 1312942-00-9 ]

References: [1]Patent: WO2011/79133,2011,A2 .

17
[ 96516-29-9 ]
[ 1312942-01-0 ]

References: [1]Patent: WO2011/79133,2011,A2 .

18
[ 96516-29-9 ]
[ 1312940-70-7 ]

References: [1]Patent: WO2011/79133,2011,A2 .

19
[ 612-96-4 ]
[ 96516-29-9 ]
[ 1354658-52-8 ]