90-15-3|1-Naphthol| Ambeed

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Product Citations

Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto ; Prathamesh M. Datar ; Daniel J. DiRocco ; Katherine Huntera and E. Neil G. Marsh

DOI: 10.1039/D4FD00006D PubMed ID: 38837123 Faraday Discuss.,2024,252,208-222.

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Purchased from AmBeed: 27916-43-4 ; 2438-05-3 ; 501-89-3 ; 42287-94-5 ; 776-79-4 ; 53473-36-2 ; 7251-61-8 ; 42287-97-8 ; 1621-91-6 ; 37718-11-9 ; 288-13-1 ; 86-73-7 ; 104-53-0 ; 2018-90-8 ; 87-66-1 ; 135-19-3 ; 1664-57-9 ; 289-80-5 ; 693-95-8 ; 55-22-1 ; 102-93-2 ; 1477-50-5 ; 1632-76-4 ; 4780-79-4 ; 16642-79-8 ; 3581-89-3 ; 501-97-3 ; 771-50-6 ; 98-98-6 ; 619-64-7 ; 100-51-6 ; 402-45-9 ; 59-67-6 ; 93-60-7 ; 273-53-0 ; 2084-13-1 ; 51-17-2 ; 2459-09-8 ; 2459-07-6 ; 95-16-9 ; 459-31-4 ; 90-05-1 ; 150-76-5 ; 103-25-3 ; 271-44-3 ; 6293-56-7 ; 2550-26-7 ; 288-32-4 ; 501-52-0 ; 2001-32-3 ; 1592-38-7 ; 95-15-8 ; 91-19-0 ; 1122-61-8 ; 3724-19-4 ; 20173-24-4 ; 118-31-0 ; 6125-24-2 ; 60-12-8 ; 90-15-3 ; 120-72-9 ; 822-36-6 ; 288-47-1 ; 288-42-6 ; 2038-57-5 ; 38628-51-2 ; 1929-29-9 ; 15009-91-3 ; 1505-50-6 ; 581-40-8 ; 616-47-7 ; 1571-33-1

Product Details of 1-Naphthol

CAS No. :	90-15-3
Formula :	C₁₀H₈O
M.W :	144.17
SMILES Code :	OC1=C2C=CC=CC2=CC=C1
Synonyms :	Furro ER; NSC 9586; Nako TRB
MDL No. :	MFCD00003930
InChI Key :	KJCVRFUGPWSIIH-UHFFFAOYSA-N
Pubchem ID :	7005

Safety of 1-Naphthol

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H311-H302-H315-H318-H371-H335-H410
Precautionary Statements:	P501-P273-P260-P270-P271-P264-P280-P391-P308+P311-P361+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338+P310-P403+P233-P405
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of 1-Naphthol

* 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 [ 90-15-3 ]
Downstream synthetic route of [ 90-15-3 ]

[ 90-15-3 ] Synthesis Path-Upstream 1~4

1
[ 107-94-8 ]
[ 90-15-3 ]
[ 16563-41-0 ]

References: [1] Journal of the Indian Chemical Society, 1939, vol. 16, p. 639,644.
[2] Bioorganic Chemistry, 2015, vol. 59, p. 151 - 167.

2
[ 90-15-3 ]
[ 16563-41-0 ]

References: [1] Synthesis, 1984, # 12, p. 1063 - 1065.

3
[ 90-15-3 ]
[ 110387-88-7 ]
[ 98-22-6 ]
[ 115-11-7 ]

References: [1] Tetrahedron, 1987, vol. 43, # 5, p. 835 - 844.

4
[ 90-15-3 ]
[ 3562-99-0 ]

References: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 4970.

[ 90-15-3 ] Synthesis Path-Downstream 1~34

1
[ 507-19-7 ]
[ 90-15-3 ]
[ 571-57-3 ]
[ 771-15-3 ]

References: [1]Chemistry and industry,1957,p. 660.

2
[ 507-19-7 ]
[ 90-15-3 ]
[ 771-15-3 ]

References: [1]Chemistry and industry,1957,p. 660.

3
[ 90-15-3 ]
[ 771-15-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,2-ethanediylbis(triphenylphosphonium) ditribromide; In methanol; dichloromethane; at 20℃; for 0.0833333h;	General procedure: To a mixture of anilines or phenols (0.7 mmol) the brominatingagent (1) (0.72 g, 0.7 mmol) in dichloromethane(30 ml)-methanol (15 ml) was added. The reactionmixture was stirred at room temperature until decolorizationof the orange solution took place. The progress of thereaction was monitored by TLC (eluent: n-hexane/ethylacetate, 7:3). After completion of the reaction, the solventwas evaporated and diethyl ether (10 ml) was added to theresidue. The supernatant was decanted and the insolubleresidue was washed by ether (3 × 10 ml). The combinedether extracts were dried on magnesium sulfate and also evaporated under vacuum to afford monobromo anilines ormonobromo phenols which was purified by flash columnchromatography over silica gel (n-hexane/ethyl acetate,7:3).
84%	With polyethylene glycol entrapped potassium tribromide; In neat (no solvent); for 0.2h;Green chemistry;	The bromination reactions were carried out in solvent free manner. In a typical reaction, PEG·KBr3 (1mmol, 4.3g) was added to the aromatic substrate (1mmol) in a mortar and was ground for the desired reaction time. The progress of the reaction was monitored by TLC (10% ethyl acetate/hexane). After completion of the reaction, the product was extracted with ethyl acetate and evaporated under vacuum to obtain the pure brominated product. The products were characterized by IR and NMR spectra (see Supporting information).
72.4%	With N-Bromosuccinimide; In dichloromethane; at 40℃;Alkaline conditions;	1-Naphthol (10 g, 69.36 mmol)and diisopropylamine (0.972 mL, 6.94 mmol) was dissolved indichloromethane (100 mL). N-Bromosuccinimide (13.58 g, 76.3 mmol)was carefully added and the reaction mixture was stirred at 40 Covernight. The resulting mixture was allowed to cool to roomtemperature, quenched with 2M H2SO4, and extracted withdichloromethane. The combined organic layer was dried overanhydrous sodium sulfate and concentrated in vacuo. The crudeproduct was purified by silica gel column eluting with petroleumether: ethyl acetate (20/1) to give the desired product (11.2 g, yield72.4%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.23 - 8.21 (m,1H), 7.76 - 7.73 (m, 1H), 7.50 - 7.48 (m, 2H), 7.44 (d, J=8.8 Hz, 1H),7.28 (d, J=8.8 Hz, 1H), 5.97 (s, 1H). ESI-MS: [M-H]- m/z :221.0.

70%	With tetrabutylammomium bromide; isoquinolinium chlorochromate; In water; at 25 - 30℃; for 5h;	General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.
69%	With potassium hydrogensulfate; potassium bromide; isoquinolinium chlorochromate; In water; at 20℃;	General procedure: A centimolar (0.01mol) organic substrate (phenols, anilines,or acetanilides), about 0.01 mol of potassium halide (KBr orKI), 0.001 mol hypervalent Cr (VI) reagent (IQCC orIQDC), and solvent (DCE or ACN) were taken in a previouslycleaned round-bottom flask. About 50 mg of KHSO4 isalso added to the reaction flask. The reaction mixture isrefluxed for about 4-5 h at 50-60C. Progress of the reactionwas monitored by TLC technique. After completion, thereaction mixture is treated with 5% sodium thiosulfate solutionfollowed by the addition of ether. The aqueous layer wasseparated, dried, and evaporated under vacuum, and purifiedwith column chromatography using chloroform:n-hexane(9:1) as eluent to get pure product.General.

References: [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1309 - 1315.
[2]Journal of Organic Chemistry,2005,vol. 70,p. 4267 - 4271.
[3]Chinese Journal of Chemistry,2010,vol. 28,p. 2221 - 2225.
[4]RSC Advances,2014,vol. 4,p. 25898 - 25903.
[5]Journal of the Iranian Chemical Society,2016,vol. 13,p. 2019 - 2028.
[6]Tetrahedron Letters,2006,vol. 47,p. 8693 - 8697.
[7]Tetrahedron Letters,2015,vol. 56,p. 5646 - 5650.
[8]Journal of the American Chemical Society,2013,vol. 135,p. 18052 - 18055.
[9]Journal of Organic Chemistry,2014,vol. 79,p. 3725 - 3730.
[10]Chinese Chemical Letters,2013,vol. 24,p. 866 - 868.
[11]Tetrahedron,2005,vol. 61,p. 1863 - 1870.
[12]International Journal of Chemical Kinetics,2018,vol. 50,p. 804 - 812.
[13]Bioorganic and Medicinal Chemistry,2019,vol. 27.
[14]Tetrahedron Letters,2009,vol. 50,p. 4781 - 4784.
[15]Asian Journal of Chemistry,2018,vol. 30,p. 1892 - 1896.
[16]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2016,vol. 46,p. 832 - 837.
[17]Organic Letters,2015,vol. 17,p. 1126 - 1129.
[18]Chemische Berichte,1957,vol. 90,p. 1537,1541.
[19]Journal of Organic Chemistry,1967,vol. 32,p. 2358 - 2360.
[20]Journal fur praktische Chemie (Leipzig 1954),1985,vol. 327,p. 998 - 1006.
[21]Organometallics,2010,vol. 29,p. 478 - 483.
[22]European Journal of Medicinal Chemistry,2013,vol. 68,p. 58 - 71.
[23]European Journal of Organic Chemistry,2014,vol. 2014,p. 4315 - 4326.

4
[ 462-06-6 ]
[ 90-15-3 ]
[ 79836-47-8 ]
[ 82101-34-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 754 - 760.
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 870 - 878.

5
[ 462-06-6 ]
[ 90-15-3 ]
[ 79836-47-8 ]
[ 82101-34-6 ]
[ 82101-35-7 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 754 - 760.
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 870 - 878.

6
[ 5394-23-0 ]
[ 90-15-3 ]
[ 156492-34-1 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1994,vol. 49,p. 675 - 682.

7
[ 6642-30-4 ]
[ 90-15-3 ]
[ 63-25-2 ]

References: [1]Tetrahedron,1991,vol. 47,p. 1249 - 1256.
[2]Tetrahedron,1991,vol. 47,p. 1249 - 1256.

8
[ 90-15-3 ]
[ 571-57-3 ]
[ 2050-49-9 ]
[ 771-15-3 ]

References: [1]Gazzetta Chimica Italiana,1987,vol. 117,p. 83 - 86.

9
[ 90-15-3 ]
[ 571-57-3 ]
[ 771-15-3 ]

References: [1]Synlett,1997,vol. 1997,p. 1241 - 1242.
[2]Synlett,1997,vol. 1997,p. 1241 - 1242.
[3]Chemistry - An Asian Journal,2011,vol. 6,p. 2130 - 2146.
[4]Canadian Journal of Chemistry,1988,vol. 66,p. 2556 - 2564.
[5]Synthesis,1980,p. 487 - 489.
[6]Catalysis Letters,2010,vol. 137,p. 190 - 201.

10
[ 51114-70-6 ]
[ 90-15-3 ]
[ 771-15-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 1745 - 1752.

11
[ 90-15-3 ]
[ 632-80-4 ]
[ 76622-68-9 ]

References: [1]Journal of general chemistry of the USSR,1980,vol. 50,p. 2055 - 2062.
Zhurnal Obshchei Khimii,1980,vol. 50,p. 2539 - 2547.

12
[ 90-15-3 ]
[ 625-51-4 ]
[ 81471-59-2 ]
[ 81471-61-6 ]
[ 81471-60-5 ]

References: [1]Archiv der Pharmazie,1982,vol. 315,p. 222 - 227.

13
[ 90-15-3 ]
[ 74205-82-6 ]
2-(1H-1,2,4-triazol-1-ylmethyl)-1-naphthol [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1813 - 1822.
[2]Pest Management Science,2001,vol. 57,p. 707 - 712.

14
[ 90-15-3 ]
[ 1119-34-2 ]
2-Brom-naphthochinon-(1,4)-4-<(4-γ-cyanpropyl)-semicarbazon> [ No CAS ]

References: [1]Chemische Berichte,1963,vol. 96,p. 2170 - 2172.

15
[ 90-15-3 ]
[ 1119-34-2 ]
2-Brom-naphthochinon-(1,4)-4-<(4-δ-carboxy-δ-amino-butyl)-semicarbazon> [ No CAS ]

References: [1]Chemische Berichte,1963,vol. 96,p. 2170 - 2172.

16
[ 13195-50-1 ]
[ 90-15-3 ]
[ 190966-77-9 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 779 - 786.

17
[ 90-15-3 ]
[ 2050-49-9 ]
[ 771-15-3 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4865 - 4868.

18
[ 90-15-3 ]
[ 63558-65-6 ]
5-iodo-4-(naphthalen-1-yloxy)-pyrimidine [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 8235 - 8239.

19
[ 90-15-3 ]
[ 2033-42-3 ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 77 - 82.

20
[ 90-15-3 ]
[ 32024-15-0 ]
[ 109-77-3 ]
C₂₂H₁₇IN₂O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2858 - 2864.

21
[ 90-15-3 ]
3.4.5-trimethoxy-benzenediazonium-⁽¹⁾-salt [ No CAS ]
[ 771-15-3 ]

References: [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 1371 - 1385.

22
[ 90-15-3 ]
[ 1200828-74-5 ]
[ 1185387-69-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	To a solution of 1-naphthol (170 mg, 1.18 mmol) in anhydrous DMF (10 mL) was added K2CO3 (510 mg, 3.53 mmol) and ethyl alpha-bromocyclopropaneacetate (295 mg, 1.41 mmol). The mixture was stirred at room temperature for 2 h and then diluted with water (50 mL) and then extracted with ethyl acetate (3*50 mL). The organic extracts were combined, washed with brine, dried over anhydrous MgSO4, filtered, concentrated in vacuo and purified by flash column chromatography using a mixture of ethyl acetate and n-hexane (1:9) to furnish ethyl 2-cyclopropyl-2-(1-naphthalenyloxy)acetate (8, R=c-Pr, 296 mg, 93%) as a white solid. The ester (250 mg, 0.92 mmol) was dissolved in 20 mL THF: H2O (2:1) and then 3M NaOH (111 mg, 2.77 mmol) was added. The reaction was heated at 80 C. for 6 h. After cooling, the reaction mixture was quenched with 1N HCL to a pH ?7 and then extracted with chloroform. The organic extract was dried over anhydrous MgSO4, filtered, concentrated in vacuo and purified by flash column chromatography eluting with a mixture of ethyl acetate/n-hexane (a gradient of 2:1) to furnish 2-cyclopropyl-2-(1-naphthalenyloxy)acetic acid (41, R=c-Pr) (136 mg, 61%) as a white solid.

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4623 - 4630.
[2]Patent: US10125116,2018,B2 .Location in patent: Page/Page column 5; 132.

23
[ 90-15-3 ]
[ 13920-91-7 ]
[ 1374558-43-6 ]

References: [1]Polyhedron,2012,vol. 38,p. 50 - 57.

24
[ 90-15-3 ]
[ 81-16-3 ]
[ 1383124-83-1 ]

References: [1]Dyes and Pigments,2012,vol. 95,p. 304 - 312.

25
[ 90-15-3 ]
[ 19047-31-5 ]
[ 931081-80-0 ]

References: [1]Synthesis,2013,vol. 45,p. 1039 - 1044.

26
[ 90-15-3 ]
[ 60827-45-4 ]
[ 56715-19-6 ]

References: [1]Journal of Molecular Structure,2013,vol. 1045,p. 104 - 111.

27
[ 90-15-3 ]
[ 79-07-2 ]
[ 86-86-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7851 - 7861.

28
[ 90-15-3 ]
[ 1835-65-0 ]
[ 25579-66-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium fluoride; In acetonitrile; at 20 - 25℃; for 2h;	Thetetrafluoro Phthalo nitrile 6.0 g (30mmol), and the potassium fluoride 15 g(1.2eq.) and acetonitrile 20ml were put in the reactor in which the entrance of100ml placing the thermometer was 4 and it was stirred and it cooled to 0. Here, alpha - naphthol 4.3 g(1.0eq.) waslittle by little injected. In 5 orless the mixture after the input end, after it reacted at 1 hour thetemperature was increased to 20 and itreacted 2 hours at 20 through 25. Thereaction mixture was emitted to water after the completion of reaction and the segregatedsolid was filtered and it took out. The obtained crude product was well wipedoff with the methanol and the compound (4-3) 7.2g of the white solid wasobtained (the yield 74percent).

References: [1]Patent: KR2015/107729,2015,A .Location in patent: Paragraph 0289-0292.

29
[ 90-15-3 ]
[ 108149-63-9 ]
1,1-dimethylethyl (S)-2,2-dimethyl-4-[[(1-naphthyl)oxy]methyl]-3-oxazolidinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 80℃; for 3h;	General procedure: To a stirred solution of 39 (0.100g, 0.433mmol), appropriate substituted phenol (0.649mmol) and PPh3 (0.182g, 0.693mmol) in anhydrous toluene (5mL) was added DIAD (0.14mL, 0.693mmol) at 80C. After 3h, EtOAc (40mL) was added to the resulting solution. The organic layer was washed with 0.5M aqueous NaOH (40mL) and water (2×40mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash silica gel column chromatography eluting with Hexanes/EtOAc (9:1) or (95:5).

References: [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 13 - 25.

30
[ 3325-11-9 ]
[ 90-15-3 ]
C₁₆H₁₁N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: To a mixture of compound 3(1.5 mmol) and 3M HCl (1.53 mL) at 0 °C, a solution of sodium nitrite (NaNO2, 1.58mmol) in water (3 mL) was added dropwise while maintaining the temperaturebelow 5 °C. After stirring for 30 min, asolution of diazonium chloride was prepared. Subsequently, a solution ofdiazonium chloride was added gradually to a mixture of phenols/anilines (4a,b; 6a?f;8a?k or 9a?e, 1.5 mmol), and ethanol (3 mL) at 0-5 °C. The reaction mixture was adjusted to pH 8-9 with 1 Maq. NaOH. After addition, the mixture was continued to stir for 3-6 h. Thesolid was collected, washed with water (3×15 mL), dried and purified by PTLC orsilica gel column chromatography to give the target products IIa?x.

References: [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 181 - 187.

31
[ 90-15-3 ]
[ 118591-58-5 ]
[ 95510-00-2 ]

Yield	Reaction Conditions	Operation in experiment
94.8%	With potassium carbonate; In acetonitrile; at 80℃; for 12h;Inert atmosphere;	In a 250 mL three-necked flask, 1-naphthol 6.00 g, F 9.75 g, and potassium carbonate 20.70 g were added.The nitrogen gas is circulated for 3 to 5 times by continuous vacuuming, and oxygen and water in the system are discharged to reach a nitrogen atmosphere.Then, 70 mL of anhydrous CH3CN was added as a solvent, and the mixture was stirred at 80 ° C for 12 hours.After the reaction is completed, the reaction is stopped.The temperature of the reaction system was cooled to room temperature.250 mL of water was added to the reaction solution, and the solid was dissolved. Extract with ethyl acetate, with water,Washed with saturated NaHCO3 solution, saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and evaporated.A pale red wine viscous liquid of 8.25 g was obtained with a yield of 94.8percent.

References: [1]Patent: CN109369542,2019,A .Location in patent: Paragraph 0026; 0028.

32
[ 41042-12-0 ]
[ 90-15-3 ]
[ 105-56-6 ]
ethyl 2-amino-2′-oxo-1′-propyl-1′,2′-dihydrospiro[benzo[h]chromene-4,3′-indole]-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With trimethylamine; In ethanol; water; for 2h;Reflux;	General procedure: A mixture of 20 mmol of naphthol 9 or 10, 10 mL of aqueous trimethylamine, 20 mmol of ethyl cyanoacetate (7) or malononitrile (8), and 20 mmol of substituted isatin 1-6 in 80 mL of ethanol was refluxed for 2 h with stirring. A part of the solvent (40 mL) was distilled off, the residue was cooled, and the crystalline solid was filtered off and recrystallized from ethanol.

References: [1]Russian Journal of Organic Chemistry,2019,vol. 55,p. 1821 - 1825.
Zh. Org. Khim.,2019,vol. 55,p. 1822 - 1826,5.

33
[ 41042-12-0 ]
[ 90-15-3 ]
[ 109-77-3 ]
2-amino-2′-oxo-1′-propyl-1′,2′-dihydrospiro[benzo[h]chromene-4,3′-indole]-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With trimethylamine; In ethanol; water; for 2h;Reflux;	General procedure: A mixture of 20 mmol of naphthol 9 or 10, 10 mL of aqueous trimethylamine, 20 mmol of ethyl cyanoacetate (7) or malononitrile (8), and 20 mmol of substituted isatin 1-6 in 80 mL of ethanol was refluxed for 2 h with stirring. A part of the solvent (40 mL) was distilled off, the residue was cooled, and the crystalline solid was filtered off and recrystallized from ethanol.

References: [1]Russian Journal of Organic Chemistry,2019,vol. 55,p. 1821 - 1825.
Zh. Org. Khim.,2019,vol. 55,p. 1822 - 1826,5.

34
[ 90-15-3 ]
[ 143982-40-5 ]
[ 109-77-3 ]
2‑amino‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑4H‑benzo[h]-chromene‑3‑carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium carbonate; In ethanol; water; at 25.0℃; for 7.0h;	General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.

References: [1]Monatshefte fur Chemie,2020,vol. 151,p. 781 - 789.

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• Reactions of Benzene and Substituted Benzenes

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
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

Product Citations

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Product Details of 1-Naphthol

Safety of 1-Naphthol

Application In Synthesis of 1-Naphthol

[ 90-15-3 ] Synthesis Path-Upstream 1~4

[ 90-15-3 ] Synthesis Path-Downstream 1~34

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