[ CAS No. 97-51-8 ] {[proInfo.proName]}

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2D 3D

Structure of 97-51-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 97-51-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 97-51-8 ]

SDS Specification

Alternatived Products of [ 97-51-8 ]

Product Details of [ 97-51-8 ]

CAS No. :	97-51-8	MDL No. :	MFCD00007337
Formula :	C₇H₅NO₄	Boiling Point :	-
Linear Structure Formula :	NO₂C₆H₃OHCHO	InChI Key :	IHFRMUGEILMHNU-UHFFFAOYSA-N
M.W :	167.12	Pubchem ID :	66808
Synonyms :

Calculated chemistry of [ 97-51-8 ] Expand+

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 :	1.0
Molar Refractivity :	42.67
TPSA :	83.12 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.55
Log Po/w (XLOGP3) :	0.72
Log Po/w (WLOGP) :	1.11
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	-0.64
Consensus Log Po/w :	0.29

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.57
Solubility :	4.52 mg/ml ; 0.0271 mol/l
Class :	Very soluble
Log S (Ali) :	-2.04
Solubility :	1.51 mg/ml ; 0.00904 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.15
Solubility :	12.0 mg/ml ; 0.0716 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 97-51-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 97-51-8 ]

* 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.

Upstream synthesis route of [ 97-51-8 ]
Downstream synthetic route of [ 97-51-8 ]

[ 97-51-8 ] Synthesis Path-Upstream 1~2

1
[ 97-51-8 ]
[ 39835-28-4 ]
[ 39835-09-1 ]

Reference： [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8657 - 8667

2
[ 97-51-8 ]
[ 39835-28-4 ]
[ 64037-16-7 ]

Reference： [1] Gazzetta Chimica Italiana, 1959, vol. 89, p. 1009,1013

[ 97-51-8 ] Synthesis Path-Downstream 1~10

1
[ 97-51-8 ]
[ 1569-16-0 ]
[ 123302-66-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 362 - 364

2
[ 526-08-9 ]
[ 97-51-8 ]
Sulphaphenazole 5-nitrosalicylaldimine [ No CAS ]

Reference： [1]Revue Roumaine de Chimie,1992,vol. 37,p. 433 - 438

3
aqueous sodium chloride [ No CAS ]
[ 5394-18-3 ]
[ 4591-55-3 ]
[ 97-51-8 ]
5-nitro-2-(4-phthalimidobutoxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; potassium carbonate; In N-methyl-acetamide; ethyl acetate;	The <strong>[4591-55-3]dimethyl pyridine-3,5-dicarboxylate</strong> used as starting material was obtained as follows: A stirred mixture of 5-nitrosalicylaldehyde (8.36 g.), potassium carbonate (11.04 g.), potassium iodide (0.2 g.), N-(4-bromobutyl)phthalimide (15.6 g.) and dimethylformamide (120 ml.) was heated at 100 C. for 48 hours and then cooled to laboratory temperature. Saturated aqueous sodium chloride solution (1200 ml.) and ethyl acetate (300 ml.) were added and the mixture was shaken and filtered, the solid residue being retained. The layers of the filtrate were separated, the aqueous layer was extracted with ethyl acetate (200 ml.) and the combined ethyl acetate solutions were washed three times with saturated aqueous sodium chloride solution (100 ml. each time), dried over magnesium sulphate and evaporated to dryness. The combined residue and retained solid were crystallized from methanol and there was thus obtained 5-nitro-2-(4-phthalimidobutoxy)benzaldehyde, m.p. 145-148 C.

Reference： [1]Patent: US4873254,1989,A

4
[ 52851-41-9 ]
[ 52147-97-4 ]
[ 97-51-8 ]
rac-(6bR,14S,14aR)-5-nitro-14-phenyl-14,14a-dihydro-6bH-benzo[5',6'][1,2]oxathiino [4',3':4,5]pyrano[3,2-c]quinolin-7(8H)-one 1,1-dioxide [ No CAS ]
rac-(6aR,7S,14bR)-2-nitro-7-phenyl-9,14b-dihydro-6aH-benzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[2,3-b]quinolin-14(7H)-one 6,6-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%; 23%		General procedure: To a stirring solution of 2-hydroxybenzaldehyde derivative 1 (1.0 mmol), styrenesulfonyl chloride (0.20 g, 1.0 mmol), and K2CO3 (0.14 g, 1.0 mmol) in H2O (15 mL) for 2 h was added 4-hydroxycoumarin derivative 2 (1.2 mmol) or 4-hydroxyquinolinone (0.19 g, 1.2 mmol) and EDDA (20 mmol%) and the mixture was heated at reflux for 12 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature and the organics were extracted using CH2Cl2 (30 mL). Evaporation of the solvent under reduced pressure followed by column chromatography on silica gel using hexane-ethyl acetate (3:1), afforded products 3 and 4.

Reference： [1]Tetrahedron,2013,vol. 69,p. 4979 - 4989

5
[ 57497-39-9 ]
[ 97-51-8 ]
[ 255052-03-0 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 84 - 91

6
[ 78364-55-3 ]
[ 97-51-8 ]
6-fluoro-2-(2-(2-hydroxy-5-nitrobenzylidene)hydrazino)benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With acetic acid; In ethanol; at 80℃; for 0.166667h;Microwave irradiation;	General procedure: A mixture of compound 2 (0.0549 g, 0.0003 mol), the appropriate aromatic aldehyde (0.00033 mol) and glacial acetic acid (0.1 mL) in ethanol (5 mL) was heated under microwave (20 W) at 80 °C for 10 min. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized to give compounds 3-29.

Reference： [1]Chinese Chemical Letters,2016,vol. 27,p. 380 - 386

7
[ 10167-97-2 ]
[ 97-51-8 ]
(E)-2-(((5-methoxypyridin-2-yl)imino)methyl)-4-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol; for 6h;Reflux;	2-hydroxy-5-nitrobenzaldehyde (0.84g 5 mmol) and 5-methoxypyridin-2-amine(0.62g 5 mmol) were added to the roundbottom flask with 20 ml absolute methanol. After refluxing 2h, alarge amount of yellow is precipitated. Then the mixture was cooledto room temperature and filtered the solid. The crude product waswashed three times with methanol. Bright yellow solid: 83percent.m.p.169.6?176.2 °C. 1H NMR (400 MHz, CDCl3) delta ppm=14.69 (s,1H, OH), 9.50 (s, 1H, CH), 8.51 (s,1H, ArH), 8.51 (d, 2H, ArH), 7.39 (s,2H, ArH), 7.12 (d, 1H, ArH), 3.97 (s, 3H, CH3). 13C NMR (126 MHz,CDCl3) delta 165.36 (s), 159.89 (s), 154.05 (s), 152.22 (s), 151.53 (s),135.60 (s), 134.74 (s), 122.98 (s), 119.41 (s), 109.13 (s), 97.67 (s),55.92 (s), 44.62 (s), 12.76 (s). MS (ESI) (CH2Cl2) m/z: 272.05 (M?1).Calcd. For C13H11N3O4: C, 57.14; H, 4.06; N, 15.38; O,23.42. Found:C,57.62; H, 4.27; N, 15.69; O,23.51;

Reference： [1]Dyes and Pigments,

8
[ 5369-19-7 ]
[ 97-51-8 ]
2-(((3-(tert-butyl)phenyl)amino)methyl)-4-nitrophenol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 214 - 231

9
[ 5369-19-7 ]
[ 97-51-8 ]
(E)-2-(((3-(tert-butyl)phenyl)imino)methyl)-4-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In ethanol; at 20℃;	General procedure: To a solution of benzaldehydes (1 equiv) in ethanol (10 mL) wasadded anilines (1 equiv), and the reaction mixture was stirred at roomtemperature overnight. The solid was collected by filtration and washedwith cold ethanol and hexane.
68%	In ethanol; at 20℃;	General procedure: To a solution of benzaldehydes (1 equiv) in ethanol (10 mL) was added anilines (1 equiv), and the reaction mixture was stirred atroom temperature overnight. The solid was collected by filtration,and washed with cold ethanol and hexane. 5.4.1 (E)-2-(((3-ethynylphenyl)imino)methyl)-4-nitrophenol (1) The title compound was prepared according to general procedure (A) using 5-nitrosalicylaldehyde (200mg, 1.20mmol) and 3-aminophenylacetylene 1a (135muL, 1.20mmol, 1 equiv), yielding the pure product as a yellow solid (242mg, 76%),

Reference： [1]Bioorganic Chemistry,2019,vol. 92
[2]European Journal of Medicinal Chemistry,2019,vol. 178,p. 214 - 231

10
[ 7504-94-1 ]
[ 97-51-8 ]
(E)-5-nitro-2-((2-(pyrimidin-2-yl)hydrazono)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol; at 20℃;	General procedure: Compounds 2 were prepared by the reaction between <strong>[7504-94-1]2-hydrazinylpyrimidine</strong> 1 (0.04 g, 0.36 mmol) and the appropriate aromatic or heteroaromatic aldehyde (1.0 eq., 0.36 mmol) in ethanol (3.0 mL) [27]. The reaction mixture was stirred for between 20 min and 5 h at room temperature. After rotary evaporation, the product was purified by washing with cold ethanol (2.0 mL) and cold diethyl ether (2.0 mL), leading to the pure derivatives 2a-f as solid in 27-75% yields.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 184

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Isomers

Technical Information

? Acidity of Phenols ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Pharmaceutical Intermediates of
[ 97-51-8 ]

Vilazodone Intermediates

[ 183288-46-2 ]

5-(Piperazin-1-yl)benzofuran-2-carboxamide

[ 183288-43-9 ]

tert-Butyl 4-(2-(ethoxycarbonyl)benzofuran-5-yl)piperazine-1-carboxylate

[ 174775-48-5 ]

Ethyl 5-aminobenzofuran-2-carboxylate

[ 56-12-2 ]

4-Aminobutyric acid

[ 15861-24-2 ]

Indole-5-carbonitrile

Telcagepant Related Intermediates

[ 127474-54-8 ]

(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

[ 1068-90-2 ]

Diethyl 2-acetamidomalonate

[ 6298-19-7 ]

2-Chloropyridin-3-amine

[ 452-58-4 ]

2,3-Diaminopyridine

[ 29976-53-2 ]

N-Carbethoxy-4-piperidone

Related Functional Groups of
[ 97-51-8 ]

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2-Hydroxy-5-nitrobenzoic acid

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H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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. 97-51-8 ] {[proInfo.proName]}

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[ 97-51-8 ] Synthesis Path-Upstream 1~2

[ 97-51-8 ] Synthesis Path-Downstream 1~10

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Aryls

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