89942-77-8|Methyl 3-hydroxy-2-nitrobenzoate| 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 [ 89942-77-8 ] 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 [ 89942-77-8 ]

CAS No. :	89942-77-8
Formula :	C₈H₇NO₅
M.W :	197.14
SMILES Code :	COC(=O)C1=C(C(O)=CC=C1)[N+]([O-])=O
MDL No. :	MFCD09951956
Boiling Point :	No data available
InChI Key :	FHCNMPYMCKHBTK-UHFFFAOYSA-N
Pubchem ID :	13659833

Safety of [ 89942-77-8 ]

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

Computational Chemistry of [ 89942-77-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	3
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	48.57
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	92.35 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.44
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	1.86
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.09
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.	0.3
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	-0.9
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.76

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.35
Solubility	0.874 mg/ml ; 0.00443 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.	-3.42
Solubility	0.0748 mg/ml ; 0.00038 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	-1.28
Solubility	10.3 mg/ml ; 0.052 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	No
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.	-6.18 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	2.0 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)	2.06

Application In Synthesis of [ 89942-77-8 ]

* 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 [ 89942-77-8 ]

[ 89942-77-8 ] Synthesis Path-Downstream 1~35

1
[ 602-00-6 ]
[ 89942-77-8 ]

Yield	Reaction Conditions	Operation in experiment
100%		SOCI2 (0.6 mL) was added dropwise to anhydrous MeOH (10 mL) at O0C. The mixture was stirred at this temperature for 0.5 h, then 3-hydroxy-2-nitrobenzoic acid (0.6 g, 3.2 mmol) was added to the mixture. The resulting mixture was heated at reflux for 4 h. TLC (petroleum ether: ethyl acetate = 1 :1) showed the <n="74"/>reaction was complete. The resulting mixture was concentrated in vacuo to give the title compound (0.63 g 100%) as a brown solid.
	With thionyl chloride; In methanol;	Step 1 To a methanol solution (15 mL) at 0 C. was dropwise added thionyl chloride (6.4 mL, 0.088 mol). After 15 minutes, 3-hydroxy-2-nitrobenzoic acid (4 g, 0.022 mol) was added and the resulting mixture was stirred at room temperature for 72 hours. Volatile was removed under vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and saturated sodium chloride, and was dried over sodium sulfate. After concentration, the crude product was recrystallized from dichloromethane and hexane to gave 4.5 g of methyl 3-hydroxy-2-nitrobenzoate.
	With hydrogenchloride; sodium chloride; sodium hydrogencarbonate; In methanol; dichloromethane; water;	1st Stage Preparing Methyl (3-Hydroxy-2-nitro)benzoate 3-hydroxy-2-nitrobenzoic acid (5 g; 27.32 mM) was dissolved in anhydrous methanol (200 ml). Anhydrous hydrogen chloride gas was bubbled through the solution until saturated. The mixture was then refluxed for 20 hours (reaction followed by T.L.C.: 10% methanol/90% dichloromethane). Next, the solvent was removed under vacuum to yield a brown solid. The solid was dissolved in water (100 ml) and sodium bicarbonate was added until effervescence stopped. Sodium chloride (15 g) was added to the aqueous solution, and the product was extracted into ethyl acetate (3*50 ml). The pooled aliquots were dried over magnesium sulphate and the solvent removed under vacuum to yield a malty brown solid.

References: [1]Patent: WO2007/125405,2007,A2 .Location in patent: Page/Page column 24; 72-73.
[2]Nippon Kagaku Zasshi,1953,vol. 74,p. 251.
Chem.Abstr.,1954,p. 3959.
[3]Patent: US2002/52397,2002,A1 .
[4]Patent: US5756510,1998,A .

2
[ 89942-77-8 ]
[ 17672-21-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With palladium on activated charcoal; hydrogen;	Our next target was the synthesis of 2-aminophenol derivative 8, which was desirable for the construction of 4 (Scheme 5). Selective reduction of the carboxyl ester 11 by LiAlH4 in dry THF or NaBH4 in THF/MeOH gave 13 in up to 92-98% yield (Scheme 6). The deprotection of methoxyl group of 13 by AlCl3, however, gave 14 in only 61% yield, along with some unreacted 13. Although the deprotection of 13 by BBr3 also gave 14, the reaction mixture contained several unidentified by-products. Selective reduction of ester 12 by NaBH4 in THF/MeOH even did not proceed. We finally found 12 could be reduced by LiAlH4 in anhydrous THF to afford 14 in about 82% yield. Then the desirable 8 was prepared by hydrogenation catalyzed by Pd/C.
95%	With iron; acetic acid; In ethanol; for 2h;Heating;	At room temperature, 8 g (40.58 mmol) of <strong>[89942-77-8]methyl <strong>[89942-77-8]3-hydroxy-2-nitrobenzoate</strong></strong> were dissolved in 160 ml of a mixture (1:1) of acetic acid and ethanol. 9.971 g (178.55 mmol) of iron powder were added to the solution, and the mixture was heated at the boil for 2 h. The mixture was cooled to room temperature, 50 ml of water were added and the mixture was extracted twice with 100 ml of ethyl acetate. The organic phase was washed with dilute sodium bicarbonate solution until neutral and dried over sodium sulfate. The solvent was removed under reduced pressure, giving 6.50 g (95% of theory) of the desired methyl 2-amino-3-hydroxybenzoate. 1H-NMR (400 MHz, DMSO-d6 delta in ppm) 9.66 (s, 1H), 7.20 (d, 1H), 6.81 (d, 1H), 6.39 (t, 1H), 6.09 (br. s, 2H), 3.78 (s, 3H). 700 mg (4.19 mmol) of methyl 2-amino-3-hydroxybenzoate, 877 mg (4.19 mmol) of 2,4-dichlorobenzoyl chloride and 210 mg (0.838 mmol) of 4-methylbenzenesulfonic acid monohydrate were suspended 10 ml of xylene in a microwave vial. The vial was sealed with a septum cap and the mixture was heated in a Biotage Initiator Sixty microwave at 160 C. for 25 min. After cooling to room temperature, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (n-heptane:ethyl acetate 4:1?ethyl acetate), giving 500 mg (35% of theory) of methyl 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylate. 1H-NMR (CDCl3 delta in ppm): 8.21 (d, 1H), 8.08 (d, 1H), 7.81 (dd, 1H), 7.59 (d, 1H), 7.48 (t, 1H), 7.42 (dd, 1H), 4.05 (s, 3H). 450 mg (1.40 mmol) of methyl 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylate and 0.838 ml of 2 N aqueous sodium hydroxide solution were dissolved in 10 ml of THF and 2 ml of water. The solution was stirred at room temperature overnight, resulting in the precipitation of a solid. The suspension was acidified with 2 N hydrochloric acid and the resulting solid was filtered off with suction. The solid was air-dried, giving 300 mg (66% of theory) of the desired 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylic acid. 1H-NMR (CDCl3 delta in ppm): 11.62 (br. s, 1H), 8.23-8.18 (m, 2H), 7.88 (d, 1H), 7.67 (d, 1H), 7.60 (t, 1H), 7.49 (dd, 1H). 250 mg (0.81 mmol) of 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylic acid, 132 mg (0.97 mmol) of 1-hydroxy-1H-benzotriazole, 171 mg (0.89 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 10 mg of DMAP were dissolved in 5 ml of dichloromethane. The mixture was stirred at room temperature for 15 min, and 1.78 ml of a 0.5 M solution of ammonia in 1,4-dioxane were then added dropwise. The mixture was stirred at room temperature for 2 h and the organic phase was washed twice with 0.5 N hydrochloric acid and once with dilute sodium bicarbonate solution. The solvent was removed under reduced pressure and the residue was suspended in acetonitrile and then heated in an ultrasonic bath. The solid was filtered off with suction and air-dried. This gives 120 mg (45% of theory) of 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxamide. 1H-NMR (DMSO-d6 delta in ppm): 8.42 (br. s, 1H), 8.33 (d, 1H), 8.07-8.01 (m, 3H), 7.98 (d, 1H), 7.71 (d, 1H), 7.62 (dd, 1H).
	palladium/carbon catalyst; In methanol;	2nd Stage Preparation of Methyl (2-Amino-3-hydroxy)benzoate Under a nitrogen atmosphere a palladium/carbon catalyst was suspended in anhydrous methanol (150 ml). To this suspension was added methyl (3-hydroxy-2-nitro) benzoate from Stage 1 (4 g; 20.3 mM). The mixture was left under a hydrogen atmosphere for 41/2 hours. The catalyst was removed by filtration through a "celite" pad, and the solvent removed from the filtrate to yield an orange/brown product.

With hydrogen;palladium on activated charcoal; In ethyl acetate; at 25℃; under 760.051 Torr; for 4h;

Example 113 Cmethyl 2-amino-3-hydroxybenzoate; A suspension of [89942-77-8]methyl [89942-77-8]3-hydroxy-2-nitrobenzoate (14 g, 71 mmol) and 10% Pd/C (1.4 g) in ethyl acetate (300 mL) was purged in 1 atm hydrogen and stirred at 25 C. for 4 hr. The mixture was filtered, and the filtrate was concentrated to give methyl 2-amino-3-hydroxybenzoate (11.5 g, yield 97%) as a light yellow solid. 1H-NMR (400 MHz, CDCl3-d) delta 3.88 (s, 1H), 5.84 (s, br 3H), 6.50-6.54 (t, J=8.0 Hz, 1H), 6.84-6.86 (d, J=7.2 Hz, 1H), 7.47-7.49 (d, J=7.6 Hz, 1H); LC-MS (ESI) m/z 168 [M+1]+.

References: [1]RSC Advances,2013,vol. 3,p. 10208 - 10212.
[2]Patent: US2014/303376,2014,A1 .Location in patent: Paragraph 0098.
[3]Journal of Medicinal Chemistry,2013,vol. 56,p. 3310 - 3317.
[4]Patent: US2015/216168,2015,A1 .Location in patent: Paragraph 0154.
[5]Tetrahedron Letters,2001,vol. 42,p. 6969 - 6971.
[6]Acta Chemica Scandinavica (1947),1959,vol. 13,p. 1305,1307.
[7]Journal of the Chemical Society,1957,p. 1592,1599.
[8]Patent: US5756510,1998,A .
[9]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 55-56.

3
[ 89942-77-8 ]
[ 108-24-7 ]
[ 90945-76-9 ]

References: [1]Acta Chemica Scandinavica (1947),1959,vol. 13,p. 1305,1307.

4
[ 89942-77-8 ]
[ 100-44-7 ]
[ 533897-93-7 ]

References: [1]Nippon Kagaku Zasshi,1953,vol. 74,p. 251.
Chem.Abstr.,1954,p. 3959.

5
[ 4437-18-7 ]
[ 89942-77-8 ]
[ 105918-52-3 ]

References: [1]Australian Journal of Chemistry,1986,vol. 39,p. 635 - 645.

6
[ 89942-77-8 ]
[ 92252-50-1 ]
[ 105918-47-6 ]

References: [1]Australian Journal of Chemistry,1986,vol. 39,p. 635 - 645.

8
[ 89942-77-8 ]
[ 100-52-7 ]
[ 128156-57-0 ]
3-Hydroxy-2-[1-phenyl-meth-(E)-ylidene]-amino}-benzoic acid methyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 991 - 996.

9
[ 89942-77-8 ]
[ 2577-48-2 ]
9-hydroxy-1,2,3,11a-tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione [ No CAS ]