Name: 132-75-2|2-(Naphthalen-1-yl)acetonitrile|97%
Brand: Ambeed
SKU: A104510
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1
[ 26421-44-3 ]
[ 132-75-2 ]
3c-(2,5-dimethyl-[3]thienyl)-2-[1]naphthyl-acrylonitrile [ No CAS ]

Reference： [1]Journal of the Chemical Society,1950,p. 2130,2134

2
[ 67-56-1 ]
[ 132-75-2 ]
[ 2876-78-0 ]

Reference： [1]Monatshefte fur Chemie,1950,vol. 81,p. 917,919
[2]Zeitschrift fur Chemie,1989,vol. 29,p. 283 - 284

3
[ 132-75-2 ]
[ 108-20-3 ]
[ 56477-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; sodium amide Behandeln des vom Ammoniak befreiten Reaktionsgemisches mit 1.2-Dichlor-aethan, anfangs bei -10grad, zuletzt bei Siedetemperatur;

Reference： [1]Cloke; Leary [Journal of the American Chemical Society, 1945, vol. 67, p. 1249]

4
[ 132-75-2 ]
[ 14034-59-4 ]
[ 835-31-4 ]

Reference： [1]Oxley; Short [Journal of the Chemical Society, 1947, p. 497,500]
[2]Current Patent Assignee: CIBA - US2505247, 1946, A [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.] Current Patent Assignee: CIBA - DE842063, 1948

5
[ 132-75-2 ]
[ 4735-50-6 ]

Yield	Reaction Conditions	Operation in experiment
40%	With lithium aluminium tetrahydride; In diethyl ether; at 20℃; for 12h;	2-(Naphthalen- 1 -yl)ethanamine (1616-63 a). 2-(Naphthalen- 1 -yl)acetonitrile (0.89 mL,6.0 mmol) in diethyl ether (5.0 mL, 1.2 M) was added dropwise to a solution of lithiumaluminum hydride (12 mL, 12 mmol, 2.0 equiv) in diethyl ether (20 mL, 0.30 M). Thesuspension was then allowed to stir at rt for 12 hrs. Water was added dropwise until nomore gas was given off, at which point 1.0 M NaOH was added to pH = 9. The mixturewas extracted with Et20 (2x) and washed with brine. The combined organic layers weredried over MgSO4, filtered and concentrated in vacuo. Purification was achieved via flashcolumn chromatography on Si02 (10% MeOH/DCM) to yield a yellow oil (0.41 g, 40 %).
32%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 25℃; for 24.1667h;	Step 5): 2-(Naphthalen- 1 -yl)ethanamine[00193] To 25 mL of tetrahydrofuran was added 2-(naphthalen-1-yl)acetonitrile (835 mg, 5.0 mmol) at 0 C, then LiA1H4 (950 mg, 25.0 mmol) was added slowly to the resulting solution. The mixture was reacted for 10 minutes, then warmed to 25 C and reacted for additional 24 hours. To the reaction solution were added water (1.24 g, 1.3 g/g LiA1H4), 15% NaOH solution (1.24 g, 1.3 g/g LiA1H4) and water (3.09 g, 3.25 g/g LiA1H4) in turn to quench the reaction. To the resulting mixture was added 30 mL of ethyl acetate and the mixture was filtered. The filtrate was washed with saturated aqueous sodium chloride (40 mL), then organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concerntrated in vacuo and the residue was purified by silica gel chromatography (DCMIMeOH (v/v) = 20/1) to give the title compound as yellow oil (274 mg, 32%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 172.2 [M+H] and ?H NMR (400 IVIFIz, CDC13) (ppm): 8.05 (d, J= 8.1 Hz, 1H), 7.88-7.83 (m, 1H), 7.73 (d, J= 8.1 Hz, 1H), 7.54-7.45 (m, 2H), 7.43 -7.37 (m, 1H), 7.34 (d, J = 6.2 Hz, 1H), 3.26 (t, J = 7.0 Hz, 2H), 3.12 (t, J = 7.0 Hz, 2H).
32%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 25℃; for 24h;	Add 2-(naphthalen-1-yl)acetonitrile (835 mg, 5.0 mmol) to tetrahydrofuran (25.0 mL). Then LiAlH4 (950 mg, 25.0 mmol) was slowly added. After reacting for ten minutes, the temperature was raised to 25 C, and the reaction was stirred for 24 hours. Then add H2O (1.23g, 1.3g/g LiAlH4), 15% NaOH solution (1.23g, 1.3g/g LiAlH4), H2O (3.08 g, 3.25 g/g LiAlH4) was quenched, then ethyl acetate (30 mL). After suction filtration, the filtrate was washed with a saturated sodium chloride solution (40 mL). After separation, the organic phase was dried over anhydrous sodium sulfate. Filtration, the filtrate was dried under reduced pressure and the crude material was applied to silica gel column (dichloromethane / methanol (v / v) = 20/1) The title compound was obtained as a yellow oil (yield: 274 mg, 32%).

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2868 - 2877
[2]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 3905 - 3909
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2068 - 2073
[4]Patent: WO2014/25942,2014,A1 .Location in patent: Page/Page column 63
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356
[6]Patent: WO2015/158313,2015,A1 .Location in patent: Paragraph 00193
[7]Patent: CN104725249,2019,B .Location in patent: Paragraph 0288; 0297-0300
[8]Archiv der Pharmazie,1939,vol. 277,p. 25,26 Anm.2
[9]Chemische Berichte,1923,vol. 56,p. 1413
[10]Journal of the American Chemical Society,1959,vol. 81,p. 3725,3726
[11]Journal of Medicinal Chemistry,1977,vol. 20,p. 771 - 776
[12]Journal of Heterocyclic Chemistry,1965,vol. 2,p. 379 - 384
[13]Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases,1982,vol. 78,p. 3467 - 3476
[14]Journal of medicinal chemistry,1988,vol. 31,p. 271 - 273
[15]Journal of Medicinal Chemistry,2007,vol. 50,p. 4898 - 4908

6
[ 132-75-2 ]
[ 86-87-3 ]

Yield	Reaction Conditions	Operation in experiment
74.8%		(3) The yellow oil obtained in step (2) was heated to reflux with sodium hydroxide solution with a solute mass fraction of 10% for 3 hours, cooled to room temperature, the aqueous solution was washed with recovered toluene solvent, the phases were separated, and the upper organic phase was solid hydrogen Sodium oxide is used as a reaction solvent after drying;(4) The aqueous phase is adjusted to pH = 2 by hydrochloric acid with a solute mass fraction of 30%, a white solid is precipitated, filtered, and the filtered solid is retained;(5) Dissolve the filter solid obtained in step (4) with hot water, slowly cool down to precipitate white crystals, and filter to obtain a wet product of naphthalene acetic acid;(6) The naphthaleneacetic acid wet product obtained in step (5) is blow-dried at 80 C to obtain a pure naphthaleneacetic acid product.As can be seen from Figure 2, the nuclear magnetic hydrogen spectrum data of naphthalene acetonitrile Through the above preparation steps, the pure naphthalene acetic acid product obtained was white needle-like crystals with a mass of 145.0 g. The content of naphthalene acetic acid was 96.0% and the yield was 74.8% after liquid phase detection.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1099 - 1104
[2]Patent: CN110818589,2020,A .Location in patent: Paragraph 0037; 0041-0046; 0047; 0051-0056; 0057; 0061-0067
[3]Canadian Journal of Research, Section B: Chemical Sciences,1939,vol. 17,p. 14,19
[4]Recueil des Travaux Chimiques des Pays-Bas,1937,vol. 56,p. 853,856
[5]Patent: US2166554,1938,
[6]Journal of the Chemical Society,1965,p. 2072 - 2078

7
[ 132-75-2 ]
[ 117070-77-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium azide; cerium(III) chloride heptahydrate; In water; isopropyl alcohol; at 160℃; for 4h;Microwave irradiation;	General procedure: Synthesis of 5-(thiophen-3-yl)-1H-tetrazole (2a). 3-Thiophenecarbonitrile 1a (218 mg, 2 mmol), NaN3 (260 mg,4 mmol), CeCl3·7H2O (75 mg, 0.2 mmol), and 8 mL of a 3:1isopropanol/water mixture were added to a 30-mL Pyrexmicrowave vessel and capped. The microwave vessel wasthen placed in a multi-mode microwave reactor. The reactionwas magnetically stirred and heated for 1 hour at 160 C.The pressure in the vessel was not determined. The reactionwas monitored by TLC using an ether/hexane mixture (typically50/50) for development. After cooling, the reactionmixture was diluted with saturated aqueous sodium bicarbonate(20 mL) and washed with ethyl acetate (2 x 15 mL).The aqueous sodium bicarbonate layer was cooled with iceand acidified to a pH of 2 or less with concentrated hydrochloricacid, which was added drop-wise. The precipitateformed was extracted with ethyl acetate (3 x 15 mL). Thecombined organic layers were dried over anhydrous sodiumsulfate and decanted into a tared round bottom flask. Theorganic layer was concentrated under reduced pressure. Thetetrazole product was recrystallized from ethyl acetate andhexane. All reagents mentioned above were used unpurified.

Reference： [1]Organic Letters,2019,vol. 21,p. 7069 - 7072
[2]Medicinal Chemistry,2018,vol. 14,p. 550 - 555
[3]Recueil des Travaux Chimiques des Pays-Bas,1958,vol. 77,p. 1107,1113

8
[ 132-75-2 ]
[ 86-86-2 ]

Reference： [1]Green Chemistry,2012,vol. 14,p. 921 - 924
[2]Journal of Organic Chemistry,1950,vol. 15,p. 548,549
Organic Syntheses,1963,vol. Coll. Vol. IV,p. 760,762
[3]Patent: US2331711,1942,

9
[ 132-75-2 ]
[ 5381-20-4 ]
3c(?)-benzo[b]thiophen-3-yl-2-[1]naphthyl-acrylonitrile [ No CAS ]

Reference： [1]Journal of the Chemical Society,1951,p. 255

10
[ 86-86-2 ]
[ 132-75-2 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 2203 - 2206
[2]Journal of the American Chemical Society,2018,vol. 140,p. 1627 - 1631
[3]Synthesis,1980,p. 657 - 658
[4]Synthesis,1980,p. 657 - 658
[5]Canadian Journal of Chemistry,1956,vol. 34,p. 1662,1666
[6]Organic Letters,2005,vol. 7,p. 5237 - 5239

11
[ 132-75-2 ]
[ CAS Unavailable ]
[ 835-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; zinc(II) chloride

Reference： [1]Kubiczek; Neugebauer [Monatshefte fur Chemie, 1949, vol. 80, p. 815,818]

12
[ 132-75-2 ]
[ 5326-50-1 ]
[ 20334-83-2 ]

Reference： [1]Monatshefte fur Chemie,1968,vol. 99,p. 1050 - 1055

13
[ 132-75-2 ]
[ 74-88-4 ]
[ 55615-31-1 ]

Yield	Reaction Conditions	Operation in experiment
77%		Step 1): 2-Methyl-2-(naphthalen- 1 -yl)propanenitrile[00224] To 10 mL of anhydrous DMF were added 2-(naphthalen-1-yl)acetonitrile (1.67 g, 10.0 mmol) and sodium hydride (60% dispersion in mineral oil, 2.0 g, 50.0 mmol) at -30 C. The mixture was stirred at -30 C for 1 hour, then iodomethane (5.0 mL, 80.0 mmol) was added. The mixture was heated slowly to 65 C and reacted overnight. After the reaction, the mixture was quenched with 30 mL of saturated brine, then extracted with ethyl acetate (30 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 50/1) to give the title compound as a light yellow solid (1.5 g, 77%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 196.1 [M+Hfb; ?H NMR (600 MHz, CDC13) (ppm): 8.57 (d, J = 8.7 Hz, 1H), 7.93 (d, J = 8.2 Hz, 1H), 7.86 (d, J = 8.1 Hz, 1H), 7.64-7.63 (m, 1H), 7.56 (d, J 7.5 Hz, 1H), 7.50 (d, J 7.0 Hz, 1H), 7.46 (t, J7.7 Hz, 1H), 1.99 (s, 6H); and ?3C NIVIR (150 IVIHz, CDC13) (ppm): 135.7, 134.7, 130.2, 129.6,129.5, 126.4, 125.8, 125.1, 125.0, 124.6, 122.8, 34.7, 28.8.
77%		At -30 C, 2-(Naphthalen-1-yl)acetonitrile (1.67 g, 10. Ommol) And sodium hydride (60% dispersion in mineral oil, 2.0 g, 50.0 mmol) Add to anhydrous DMF (10 mL), After stirring for 1 h, iodomethane (5.0 mL, 80.Ommol) was added. The temperature was slowly raised to 65 C and allowed to react overnight. The reaction was stopped and quenched by the addition of saturated brine (30 mL). It was extracted with ethyl acetate (30 mL EtOAc). Filtration, and the filtrate was evaporated to dryness. The title compound was obtained as a pale yellow solid (1.5 g, 77%).
	In N,N-dimethyl-formamide;	2-Methyl-2-(1-naphthyl)-propionitrile A solution of 16.7 g (100 mmol) of <strong>[132-75-2]1-naphthylacetonitrile</strong> in 200 m of DMF and 15 ml (240 mmol) of methyl iodide is mixed at 0 C. with 10.4 g (260 mmol) of sodium hydride (addition within 2.5 hours). The batch is stirred for 3 hours at 0 C. and for 18 hours at 25 C. It is mixed with ice and ethyl acetate. The organic phase is acidified with 10% H2SO41 washed three times with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. A large-scale purification is carried out by bulb tube distillation (boiling range 60-130 C.) in an oil pump vacuum; yield: 18.8 g. 1H-NMR (CDCl3), delta (ppm)=2.00 (s, 6H), 7.41-7.60 (m, 3H), (ddd, 1H), 7.87 (d br., 1H), 7.93 (dd, 1H), 8.55 (d, 1H).

Reference： [1]Synthesis,2010,p. 4242 - 4250
[2]Journal of the American Chemical Society,1989,vol. 111,p. 1804 - 1815
[3]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2945 - 2952
[4]Patent: WO2015/158313,2015,A1 .Location in patent: Paragraph 00224
[5]Patent: CN104725249,2019,B .Location in patent: Paragraph 0487; 0489-0493
[6]Tetrahedron,1975,vol. 31,p. 153 - 158
[7]Patent: US2002/77356,2002,A1

14
[ 186581-53-3 ]
[ 132-75-2 ]
[ 2876-78-0 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 1343 - 1346

15
[ 132-75-2 ]
[ 2082-66-8 ]
[ 5518-09-2 ]

Yield	Reaction Conditions	Operation in experiment
32%	With hydrogenchloride; lithium diisopropyl amide; In benzene;	EXAMPLE 5 1-Naphthylmalononitrile With stirring and cooling, 0.3 mol of 1-naphthylaceto-nitrile and then, dropwise, 0.6 mol of 2-chlorobenzyl thiocyanate are added to a solution of 0.65 mol of lithium diisopropylamide in benzene. After one hour, the reaction mixture is introduced into 1 l of 0.3 molar NaOH, and the mixture is allowed to stand for a while and then the two phases which are formed are separated. The aqueous solution is neutralized by adding hydrochloric acid and allowed to stand overnight. The precipitated product is filtered off with suction, dried and purified by recrystallization from ethanol. Yield: 32%, m.p.: 165 C.

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 2774 - 2775
[2]Patent: US6284889,2001,B1

16
[ 132-75-2 ]
[ 36321-73-0 ]
[ 144037-86-5 ]

Reference： [1]Synthesis,1992,p. 765 - 768

17
[ 90-14-2 ]
[ 105-56-6 ]
[ 132-75-2 ]
[ 13234-71-4 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7606 - 7607
[2]Journal of Organic Chemistry,1993,vol. 58,p. 7606 - 7607

18
[ 132-75-2 ]
[ 1732-26-9 ]
5-(1-naphthylmethyl)-4-pyrenecarbonitrile [ No CAS ]

Reference： [1]Synthesis,1995,p. 827 - 830

19
[ 132-75-2 ]
[ 533-68-6 ]
[ 194808-41-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2003,vol. 51,p. 779 - 789
[2]Acta Chemica Scandinavica,1997,vol. 51,p. 426 - 430
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3173 - 3176
[4]Monatshefte fur Chemie,2008,vol. 139,p. 967 - 974
[5]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1016 - 1023
[6]ChemMedChem,2011,vol. 6,p. 826 - 833
[7]Chemical Biology and Drug Design,2011,vol. 78,p. 596 - 602

20
[ 132-75-2 ]
[ 15328-32-2 ]
[ 5518-09-2 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 401 - 402

21
[ 132-75-2 ]
[ 99-58-1 ]
[ 100-09-4 ]
2-cyano-3-(1-naphthylmethyl)-4-methoxybenzoic acid [ No CAS ]
3-(Cyano-naphthalen-1-yl-methyl)-4-methoxy-benzoic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 2451 - 2455
[2]Journal of Organic Chemistry,1998,vol. 63,p. 2451 - 2455

22
[ 132-75-2 ]
[ 28733-43-9 ]
7-Naphthalen-1-ylmethyl-pyrrolo[3,4-c]pyridine-1,3-dione [ No CAS ]
4-Cyano-5-naphthalen-1-ylmethyl-nicotinamide [ No CAS ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 3391 - 3400

23
[ 132-75-2 ]
[ 835-31-4 ]

Reference： [1]Oxley; Short [Journal of the Chemical Society, 1947, p. 497,500]
[2]Current Patent Assignee: CIBA - US2505247, 1946, A [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.] Current Patent Assignee: CIBA - DE842063, 1948

24
[ 132-75-2 ]
[ 771-15-3 ]
1-Hydroxy-3-(1-naphythylmethyl)naphthalene-2-carbonitrile [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 3149 - 3153

25
[ 132-75-2 ]
[ 930-68-7 ]
[ 371917-37-2 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 6169 - 6173
[2]Journal of Organic Chemistry,2006,vol. 71,p. 5440 - 5447

26
[ 609-12-1 ]
[ 132-75-2 ]
[ 640724-25-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2003,vol. 51,p. 779 - 789
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3173 - 3176
[3]Monatshefte fur Chemie,2008,vol. 139,p. 967 - 974
[4]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1016 - 1023

27
[ 132-75-2 ]
[ 144223-33-6 ]
[ 63753-52-6 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 4932 - 4934

28
[ 132-75-2 ]
[ 64-17-5 ]
[ 56477-48-6 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 5662 - 5663
[2]Chemistry - A European Journal,2006,vol. 12,p. 8228 - 8239

29
[ 132-75-2 ]
[ 75-03-6 ]
[ 56477-48-6 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 949 - 952

30
[ 132-75-2 ]
[ 34800-90-3 ]

Reference： [1]Zeitschrift fur Chemie,1989,vol. 29,p. 283 - 284

31
[ 132-75-2 ]
[ 16275-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride;trimethylaluminum; In toluene;	EXAMPLE 7A 2-(1-Naphthyl)ethanamidine hydrochloride Analogously to Example 3A, starting from 32.9 g (614 mmol) of ammonium chloride, 307 ml of a 2M solution of trimethylaluminium in toluene and 51.4 g (307 mmol) of <strong>[132-75-2]1-naphthylacetonitrile</strong>, 56.3 g (83.1% of th.) of 2-(1-naphthyl)ethanamidine hydrochloride are obtained. 1H-NMR (DMSO-d6): delta/ppm 4.28 (s, 2 H), 7.48-8.06 (m, 7 H).
	With trimethylaluminum; ammonium chloride; In toluene; at 0 - 80℃; for 18h;	To a stirred suspension of NH4Cl (1.6 g, 30 mmol) in anhydrous toluene (50 mL) was added trimethyl aluminium (2M in toluene, 15 mL, 30 mmol) at 0 C. The mixture was then warmed to room temperature and stirred for 2 h. A solution of 2-(naphthalen-1-yl)acetonitrile (1.67 g, 10 mmol) in toluene (10 mL) was added to the above reaction mixture and the reaction mixture was stirred at 80 C. for 18 h. After completion of the reaction, the reaction mixture was quenched with a suspension of silica gel in chloroform. The mixture was stirred at room temperature for 0.5 h before being filtered through a sintered funnel. The silica gel was washed with methanol. The combined filtrate was concentrated under reduced pressure to give the crude product as an off-white solid (2 g, 91%), which was used directly without further purification. [0427] MS (M+H)=185.3.

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1085 - 1087
[2]Patent: US2002/198377,2002,A1
[3]Patent: US2014/194431,2014,A1 .Location in patent: Paragraph 0425-0427

32
[ 132-75-2 ]
[ 2876-78-0 ]

Reference： [1]Canadian Journal of Research, Section B: Chemical Sciences,1939,vol. 17,p. 14,19
[2]Journal of the Chemical Society,1965,p. 2072 - 2078

33
[ 132-75-2 ]
[ 97611-60-4 ]

Reference： [1]Journal of Organic Chemistry,1966,vol. 31,p. 3708 - 3711

34
[ 132-75-2 ]
[ 14660-52-7 ]
[ 183962-26-7 ]

Yield	Reaction Conditions	Operation in experiment
77.5%	In water; N,N-dimethyl-formamide;	Reference Example 17 Ethyl 6-cyano-6-(1-naphthyl)hexanoate In 125 ml of DMF was dissolved 12.54 g (75 mmol) of 1-naphthaleneacetonitrile. Then, 3.30 g (82.5 mmol) of 60% sodium hydride was added at room temperature and the mixture was heated to 60 C. and stirred for 30 minutes. After cooling to room temperature, 13.17 ml (82.5 mmol) of ethyl 5-bromovalerate was added. The reaction was further conducted at 60 C. for 30 minutes, after which the reaction mixture was cooled to <10 C. and diluted with 500 ml of pure water. The diluted mixture was extracted with 200 ml of ethyl acetate twice and the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was purified by silica gel column chromatography (hexane-CH2 Cl2 -ethyl acetate=4:2:1) to provide 17.16 g (yield 77.5%) of the title compound as light-yellow oil. 1 H-NMR (CDCl3) delta: 1.24 (3H, t, J=7.1 Hz), 1.59-1.78 (4H,m), 2.02-2.14 (2H, m), 2.30-2.37 (2H, m), 4.11 (2H, q, J=7.1 Hz), 4.55 (1H, t, J=7.1 Hz), 7.45-7.63 (3H, m), 7.68 (1H, dd, J=7.2 Hz, 1.2 Hz), 7.83-7.95 (3H, m).

Reference： [1]Patent: US5804601,1998,A

35
[ 132-75-2 ]
[ 75-36-5 ]
[ 39739-56-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	In methanol;	Step (1) Preparation of Methyl-2-(1-naphthalenyl)acetimidate Hydrochloride To a cooled (0 C.), stirred mixture of <strong>[132-75-2]1-naphthylacetonitrile</strong> (9.2 g, 0.055 mol), methanol (5.0 mL, 0.124 mol), and ether (5 mL) was added acetyl chloride (5.2 g, 0.066 mol) dropwise. Stirring was continued for 30 minutes and the mixture was allowed to stand at room temperature for 60 hours. The resulting precipitate was collected by filtration, washed with ether, crushed with a mortar and pestle, and again washed with ether. The product was dried in vacuo to give a white crystalline solid (11.7 g, 91%), which was used without further purification. NMR (CDCl3): delta4.22 (s, 3H), 4.58 (s, 2H), 7.53 (m, 4H), 7.88 (t, 2H, J=6.0 Hz), 8.12 (d, 1H, J=7.0 Hz), 11.95 (br s, 1H).

Reference： [1]Patent: US4786640,1988,A

36
[ 132-75-2 ]
[ 67843-74-7 ]
[ 923982-64-3 ]
(1R,2R)-2-hydroxymethyl-1-naphthalen-1-yl-cyclopropanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(3) (lRVZ-Hydroxytnethyl-l-d-naphthyD-cyclopropanecarbonitrile1-Naphthylacetonit?le (3Og, 180mmole) was dissolved in dry tetrahydrofuran(THF, 30OmL) under nitrogen atmosphere, cooled to -150C and sodium-bis EPO <DP n="95"/>(t?methylsilylamide) in IM tetrahydrofuran ( 180 mL) was added drop wise at -15C The resulting brown mixture was stirred for 45 min at -1O0C to O0C Then cooled the reaction mass to -150C A solution of S- (+) epichlorohyd?n (16 6g, 180mmol) in tetrahydrofuran (2OmL) was added drop wise at -150C and stirred for 30minutes Sodiumbis (t?methylsilylamide) in IM THF (18OmL) is added drop wise at -150C and the mixture was stirred for 45 mm The temperature of the reaction mass was then gradually raised to room temperature and maintained at room temperature for 30minutes The reaction is monitored by TLC (ethyl acetate/hexane (1 I )) The reaction was quenched with water (8OmL) The aqueous layer was extracted with ethyl acetate (2x75mL) The combined organic layer was washed with brine solution (20OmL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to yield 55g of crude oil, which was purified by column chromatography (silica gel, ethyl acetate/hexane (10 90) to yield 28g(69%) of product The 1H NMR shows mixture of diasteromers (2 1 cis /trans) 1H NMR delta(3OOMHz,CDC13, partial assignment) 1 57-1 62 (2H,m), 1 92-2 03 (l H,m), 3 10- 3 25 (l H,br, s), 3 91-3 97 (l H,m) 4 22-4 27 (l H,m), 7 37-7 69 (4H,m), 7 82-7 92 (2H,m), 8 36-8 49 ( lH,m)

Reference： [1]Patent: WO2008/57575,2008,A2 .Location in patent: Page/Page column 93-94

37
[ 132-75-2 ]
[ 51594-55-9 ]
[ 923982-65-4 ]
(1S,2S)-1-(1-naphthyl)-2-hydroxymethyl-cyclopropanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(4) (lSVl-Hydroxymethyl-l-d-napbthyD-cyclopropanecarbonitrile1-Naphthylacetonit?le (30g, 180mmole) was dissolved in dry tetrahydrofuran(THF, 30OmL) under nitrogen atmosphere, cooled to -150C and sodium -bis (t?methylsilylaniide) in I M tetrahydrofuran (180 mL) was added dropwise The resulting brown mixture was stirred for 45 min at -1O0C to O0C, cooled to -15C and added a solution of R- (+) epichlorohyd?n ( 16 6g, 180mmol) in tetrahydrofuran (2OmL) was added dropwise at -150C and stirred for 30min Sodiumbis(t?methylsilylamide) in IM tetrahydrofuran (18OmL) is added drop wise at -15C and the mixture was stirred for 45 min The temperature of the reaction mass was then gradually raised to room temperature and maintained at room temperature for 30min The reaction is monitored by TLC (ethyl acetate/hexane (1 I )) The reaction mass was EPO <DP n="96"/>quenched with water (8OmL) The aqueous layer was extracted with ethyl acetate (2x75mL) The combined organic layer was washed with b?ne solution (20OmL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to yield 55g of crude oil The oil was purified by column chromatography (silica gel, ethyl acetate /hexane ( 10 90) to yield 25g(62%) of product The ' H NMR shows mixture of diasteromers (2 1 cis /trans) 1H NMR delta(3OOMHz,CDC13, partial assignment) 1 55-1 59 (2H,m), 1 94-2 04 (l H,m), 2 42 (l H,m) 3 08 (l H,br,s), 3 32 (lH,m),7 42-7 68 (4H,m) ,7 72-7 93 (2H,m),8 37-8 40 (lH,d,J=8 4Hz)

Reference： [1]Patent: WO2008/57575,2008,A2 .Location in patent: Page/Page column 93-94

38
[ 132-75-2 ]
[ 13304-62-6 ]
[ 1201921-12-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 18252 - 18253

39
[ 132-75-2 ]
[ 383-63-1 ]
[ 1259537-04-6 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 4.1.2.1. 4-Phenyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (5a)2-Phenylacetonitrile (11.7 g, 100 mmol) was added to a fresh solution of Na (2.3 g, 100 mmol) in absolute alcohol (25 ml), then ethyl trifluoroacetate (17.0 g, 120 mmol) was added dropwise at about 50 C. The mixture of reaction was refluxed for 2 h. After this period, the solvent was removed under vacuum. The solid was dissolved in water (20 ml), washed by CH2Cl2 (4 × 15 ml) and the solution was concentrated to dryness under reduced pressure to obtain white solid (21 g, 90%), which was used in the next step without further purification. The white solid (11.8 g, 50 mmol), hydrazine sulfate (12.9 g, 100 mmol), and 3 A molecular sieve (10 g) in 120 ml DMC were stirred at 80 C for 4 h, and monitored by TLC (2:1 petroleum ether/EtOAc, Rf = 0.3). After this period, the solid was filtered off and washed with some DMC. The solution was reclaimed, and the residue was recrystallized from isopropyl ether to obtain the target compound as a white solid (7.5 g, 63%)

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 934 - 943

40
[ 90-11-9 ]
[ 1071-36-9 ]
[ 132-75-2 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4470 - 4474

41
[ 99747-74-7 ]
[ 1071-36-9 ]
[ 132-75-2 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4470 - 4474

42
[ 86-52-2 ]
potassium ferrocyanide [ No CAS ]
[ 132-75-2 ]

Yield	Reaction Conditions	Operation in experiment
5%Chromat.	With palladium diacetate; sodium carbonate; triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 10h;Inert atmosphere;	General procedure: 0.06 mmol PPh3, 0.02 mmol Pd(OAc)2, and 0.4 mL NMP were added into a dried 20 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 5 min to give a homogeneous solution, 0.3 mmol K4[Fe(CN)6], 1.5 mmol Na2CO3, 1 mmol benzyl chloride, and 0.4 mL NMP were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 140(+/-5) C to perform the reaction for 10 h. Once the reaction time was reached, the mixture was cooled to room temperature, then acetophenone was added as an internal standard. GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data.
	With copper(l) iodide; N-benzyl-N,N,N-triethylammonium chloride; In toluene; at 140℃; for 10h;Autoclave;	(1) Weigh 176.6g of 1-chloromethylnaphthalene, 110.5g of potassium ferrocyanide, and 1766.0g of toluene,19.0g of cuprous iodide and 22.8g of triethylbenzyl ammonium chloride were placed in a 5L autoclave to react, heated to 140 C, and reacted with stirring for 10 hours to obtain a mixed solution containing naphthalene acetonitrile;(2) The mixture containing naphthaleneacetonitrile obtained in step (1) is cooled to room temperature, filtered to remove insoluble matters, and the filtrate is retained. The filtrate is concentrated under negative pressure to obtain a yellow oil, and the distillate is toluene, which is recycled;

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5107 - 5109
[2]Patent: CN110818589,2020,A .Location in patent: Paragraph 0037; 0039; 0040; 0047; 0049; 0050; 0057; 0059

43
[ 132-75-2 ]
[ 1127-76-0 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 69 - 71

44
[ 132-75-2 ]
[ 1127-76-0 ]
[ 90-12-0 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 8362 - 8364

45
[ 110-52-1 ]
[ 132-75-2 ]
[ 56477-61-3 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium hydride; In diethyl ether; dimethyl sulfoxide; mineral oil; at 0 - 20℃; for 4.5h;	To a suspension of sodium hydride (60% in mineral oil, 5.24 g, 131.6 mmol) in dimethyl sulfoxide (50 mL) was added dropwise a mixture of naphthalen-1-yl-acetonitrile (337) (10.0 g, 59.8 mmol) and 1,4-dibromobutane (12.91 g, 59.8 mmol) dissolved in dimethyl sulfoxide-ether (1:1; 120 mL) at 0 C. and stirred for 30 min at the same temperature and then stirred at room temperature for 4 h (silica TLC, 10% ethyl acetate in hexane, Rf=0.65). The reaction mixture was quenched with HCl [1 N; 20 mL] at 0 C. Ethyl acetate (400 mL) was added and the mixture was washed with water (500 mL) and brine (2×200 ml) and dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using a gradient eluent; mixture of ethyl acetate and hexane to get pure 1-naphthalen-1-yl-cyclopentanecarbonitrile (338) (8.4 g, 63%) as a white solid.

Reference： [1]Patent: US2014/194431,2014,A1 .Location in patent: Paragraph 1227-1228

46
[ 132-75-2 ]
[ 3376-23-6 ]
[ 79271-56-0 ]
3-(methyl((triethylsilyl)oxy)amino)-2-(naphthalen-1-yl)-3-phenylpropanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In 1,2-dichloro-ethane; at -30℃; for 0.5h;Inert atmosphere;	General procedure: To a mixture of (Z)-N-benzylidenemethanamine oxide 10 (54.1 mg, 0.40 mmol),2-phenylpropanenitrile 13 (53 muL, 0.40 mmol) and Et3N (112 muL, 0.80 mmol) in DCE (2 mL) was added TESOTf (181 muL, 0.80 mmol) at -30 C, and the reaction mixture was stirred at this temperature for 30 min. Saturated aqueous sodium bicarbonate (1 mL) was added to the mixture,and the product was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography(SiO2, hexane-Et2O = 15:1) afforded O-TES beta-hydroxyamino nitrile 14c (143.5 mg, 0.377mmol, 94%) as an inseparable 55:45 mixture of diastereomers.

Reference： [1]Synlett,2014,vol. 25,p. 1863 - 1868

47
[ 132-75-2 ]
[ 123415-45-2 ]
NA-DBA [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide In tetrahydrofuran; ethanol at 20℃; for 2h;

Reference： [1]Kim, Hyungwoo; Chang, Ji Young [Langmuir, 2014, vol. 30, # 45, p. 13673 - 13679]

48
[ 132-75-2 ]
[ 151903-52-5 ]
NA-HBA [ No CAS ]

Reference： [1]Langmuir,2014,vol. 30,p. 13673 - 13679

49
[ 132-75-2 ]
[ 100-51-6 ]
2-(naphthalen-1-yl)-3-phenylpropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide; at 130℃; for 2h;Microwave irradiation; Green chemistry;	A solution of 1-naphthaleneacetonitrile (167 mg, 1 mmol)Benzyl alcohol (119 mg, 1.1 mmol),[Rh (cod) Cl] 2 (4.9 mg, 0.01 mmol, 1 mol%),Triphenylphosphine (26.2 mg, 0.1 mmol, 10 mol%),Potassium hydroxide (22 mg, 0.4 mmol, 40 mol%) were sequentially added to a 10 ml microwave reaction tube.The mixture was reacted at 130 C for 2 hours,Cool to room temperature. The solvent was removed by rotary evaporation and then the title compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether) in 82% yield.

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1405 - 1415
[2]Patent: CN105985256,2016,A .Location in patent: Paragraph 0131; 0132; 0133; 0134; 0135

50
[ 132-75-2 ]
[ 2412-58-0 ]
1-(1-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)-2-(naphth-1-yl)ethanone [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2478 - 2481

51
[ 13922-41-3 ]
[ 107-14-2 ]
[ 132-75-2 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 50 - 53

52
2-(3,4-dihydronaphthalen-1-yl)acetonitrile [ No CAS ]
[ 132-75-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; at 100℃; for 24h;	Step 4): 2-(Naphthalen-1 -yl)acetonitrile[00192] To 30 mL of 1 ,2-dichloroethane were added 2-(3 ,4-dihydronaphthalen- 1 -yl)acetonitrile (1.69 g, 10.0 mmol) and DDQ (2.986 g, 13.16 mmol). The mixture was reacted at an oil bath temperature of 100 C for 24 hours. The reaction mixture was cooled to 25 C and diluted with 60 mL of ethyl acetate, then filtered. The filtrate was washed with saturarted aqueous sodium bicarbonate (40 mL) and saturated brine (40 mL) in turn. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concerntrated in vacuo and the residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 60/1) to give the title compound as a pale white solid (1.5 g, 90%). The compound was characterized by the following spectroscopic data: ?H NIVIR (400 IVIFIz, CDC13) (ppm): 7.94 - 7.90 (m, 1H), 7.87 (s, 1H), 7.85 (s, 1H), 7.64 - 7.54 (m, 3H), 7.50 - 7.45 (m, 1H), 4.10 (s, 2H).
90%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; at 100℃; for 24h;	2-(3,4-Dihydronaphthalen-1-yl)acetonitrile (1.69 g, 10.0 mmol) And DDQ (2.986g, 13.16mmol) Add to 1,2-dichloroethane (30mL), Reaction in a 100 C oil bath for 24 h, The reaction was quenched, cooled to 25 C, diluted with ethyl acetate (60 mL), filtered, and filtered, washed with saturated sodium hydrogen carbonate (40 mL) and brine (40 mL). . Filtered, the filtrate was dried under reduced pressure, The crude product was purified by silica gel column chromatography (EtOAc/EtOAc The title compound was obtained as a pale white solid (1. 5 g, 90%).

Reference： [1]Patent: WO2015/158313,2015,A1 .Location in patent: Paragraph 00192
[2]Patent: CN104725249,2019,B .Location in patent: Paragraph 0288; 0294-0296

53
[ 132-75-2 ]
[ 106-93-4 ]
[ 56477-59-9 ]

Yield	Reaction Conditions	Operation in experiment
60%		Step 1): 1 -(Naphthalen- 1 -yl)cyclopropanecarbonitrile[00249] To 10 mL of anhydrous DMF were added 2-(naphthalen-1-yl)acetonitrile (1.67 g, 10.0mmol) and sodium hydride (60% dispersion in mineral oil, 1.2 g, 30.0 mmol) at -30 C. The mixture was stirred for 1 hour, then a solution of 1,2-dibromoethane (1.75 mL, 20.0 mmol) in DMF (10 mL) was added dropwise slowly. The resulting mixture was warmed slowly to 25 C, and stirred at 25 C for 30 minutes. The reaction mixture was quenched with saturated aqueous sodium chloride (30 mL), and extracted with ethyl acetate (30 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 50/1) to give the title compound as a white solid (1.16 g, 60%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 194.1 [M+H] and ?H NMR (600 MHz, CDC13) (ppm): 8.40 (d, J = 8.4 Hz, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.66 (t, J = 7.2 Hz, 1H), 7.57 (t, J = 7.2 Hz, 1H), 7.49 (d, J = 7.2 Hz, 1H), 7.43 (t, J = 7.2 Hz, 1H), 1.86 (q, J= 4.8 Hz, 2H), 1.45 (q, J= 4.8 Hz, 2H).
60%		At -30 C, 2-(Naphthalen-1-yl)acetonitrile (1.67 g, 10. Ommol) And sodium hydride (60% dispersed in mineral oil, 1.2g, 30 . Ommol ) added to anhydrous DMF (10 mL), After stirring for 1 h, Slow drop 1,2-dibromoethane (1.75 mL, 20.0 mmol, dissolved in 10 mL of DMF). The temperature was slowly raised to 25 C and the reaction was carried out for 30 minutes. The reaction was stopped and quenched by the addition of saturated brine (30 mL). It was extracted with ethyl acetate (30 mL EtOAc). Filtration, the filtrate was dried under reduced pressure, and the crude material was applied to silica gel column ( petroleum ether / ethyl acetate (v/V) = 50/1) The title compound was obtained as a white solid (1.16 g, 60%)
56.2%		At -30 C, 2-(Naphthalen-1-yl) acetonitrile (500mg, 2.99mmol) and sodium hydride (60%, 598mg, 14.95mmol) added into 10mL of anhydrous DMF, After stirring for 1h, added the drops of 1,2-Dibromoethane (0.52mL, 5.98mmol, dissolved in 10mL DMF), slowly raise the temperature at 25 C and react for 1hour. Stop the reaction and then quench it by adding 30mL of saturated brine, extract with ethyl acetate (30mL X 3), and the combined organic phases were dried over anhydrous sodium sulfate. Filtered, the filtrate was dried under reduced pressure, purified by column chromatography (petroleum ether / ethyl acetate (nu / nu) = 50/1), and then obtained the title compound as a white solid (325mg, 56.2%).

Reference： [1]Patent: WO2015/158313,2015,A1 .Location in patent: Paragraph 00249
[2]Patent: CN104725249,2019,B .Location in patent: Paragraph 0627; 0629-0632
[3]Patent: CN104292126,2016,B .Location in patent: Paragraph 0219; 0221; 0222
[4]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4306 - 4311

54
[ 132-75-2 ]
[ 613-84-3 ]
5-methyl-2-(naphthalen-1-yl)benzofuran-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With sodium methylate; copper diacetate; In dimethyl sulfoxide; at 100℃;	Room temperature (20-35 deg.] C) under the reaction flask were sequentially added 5-methyl-salicylaldehyde (0.5mmol), Cu (OAc) 2 (0.1mmol), 1- naphthylacetonitrile (0.75mmol), sodium methoxide (2mmol) and DMSO (2ml), then stirred and heated to 100 deg.] C until the reaction of 5-methyl salicylaldehyde reaction was complete. After completion of the reaction, the reaction solution was cooled to room temperature and 20ml of water was added, extracted with methylene chloride three times with dichloromethane 10ml, separated on silica gel column, evaporated under reduced pressure, yield 13%

Reference： [1]Organic Letters,2016,vol. 18,p. 728 - 731
[2]Patent: CN105399710,2016,A .Location in patent: Paragraph 0034; 0035

55
[ 132-75-2 ]
[ 1174638-52-8 ]
C₄₆H₄₃N₃O₄S₂ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3390 - 3393

56
[ 132-75-2 ]
[ 107-04-0 ]
[ 56477-59-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃;

Reference： [1]Lee, Taegyo; Hartwig, John F. [Angewandte Chemie - International Edition, 2016, vol. 55, # 30, p. 8723 - 8727][Angew. Chem., 2016, vol. 128, # 30, p. 8865 - 8869,5]

57
[ 132-75-2 ]
[ 67843-74-7 ]
[ 923982-65-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hexamethyldisilazane; In tetrahydrofuran; at 10℃; for 18.23h;Inert atmosphere; Large scale;	2-naphthylacetonitrile (50 Kg) is dissolved in THF (250 L), 32 kg of (S)-(+)- epichlorohydrin is added and the solution cooled to -10 C. A 2.0 M solution of sodium hexamethyldisilylazane in THF (299 L) is then added keeping the internal temperature below -10 C. This addition requires 14 hrs., 14 minutes to complete. The reaction mixture is then stirred an additional four hours at approximately -10 C, after which a sample of the reaction mixture is analyzed by HPLC. While keeping the internal temperature less than 0 C, borane dimethylsulfide (71 kg) is added over four hours and 33 minutes. After completion of the borane addition the reaction mixture is slowly heated to 60 C to reduce the nitrile to the amine. During this heat-up, an exotherm is noted, which initiates at 45 C. After heating at 60 C for 14 hours and 46 minutes, a sample of the reaction mixture is analyzed by HPLC. [00245] The reaction mixture is then cooled to 24 C and transferred to a solution of 2M HCl over 2 hours and 28 minutes and the reactor is rinsed with THF (22.3 Kg) and transferred to the HCl containing reaction mixture. The two phase mixture is heated to 45 C to 55 C and stirred for 1 hour 48 minutes at this temperature followed by cooling to 30 C. The pH of the quenched reaction mixture is measured and found to be 1. Reaction workup continues by addition of IP Ac, stir, and separate the layers. Charge 1 M HCl solution to the organic layer, stir, separate the layers, and discard the organic layer. Aqueous ammonia is added to the combined aqueous layer and the pH measured which shows a pH of 9. Workup then continues by extraction with two extractions of the aqueous layer with IP Ac. The combined organic extracts are then washed with 5% sodium chloride solution. The resulting organic layer is partially concentrated to azeotropically dry and co-evaporation with methylene chloride four times and followed by dilution with methylene chloride and transfer of the reaction mixture via in-line filter to clean, dry reactor and diluting with IP Ac. p-Toluenesulfonic acid hydrate (54 Kg) is then added in portions to precipitate the desired product as its pTsOH salt and the reaction suspension is stirred over three hours at 10 C to 15 C and the product is isolated by filtration. The filter cake is washed with 2-methyltetrahydrofuran and followed by IP Ac then pull dried over two hours. The crude product is purified by stirring with 2-methyltetrahydrofuran over 11 hours 36 minutes at 10 C to 15 C and the product is isolated by filtration. The filtered solid is washed with 2-methyltetrahydrofuran and then dried to a constant weight to give 73.8 Kg of the desired product as a white solid. Yield = 73.8 Kg (62%). HPLC = 96.8%.

Reference： [1]Patent: WO2016/205762,2016,A1 .Location in patent: Paragraph 00244-00245

58
[ 132-75-2 ]
[ 2243-81-4 ]

Yield	Reaction Conditions	Operation in experiment
46%	With oxygen; copper(II) sulfate; urea; In 1,2-dichloro-ethane; at 120℃;Sealed tube;	In the reaction vessel was added 5mol% CuSO4, the reaction tube was evacuated, filled with oxygen,In an oxygen atmosphere, 0.2 mmol of 1-naphthaleneacetonitrile was added,0.5 mmol urea, 2 ml 1,2-dichloroethane, the reaction vessel was sealed, reacted at 120 C,After the reaction was completed, it was washed with water, extracted with chloroform, dried and evaporated to remove the solvent by distillation under reduced pressure. The crude product was separated by column chromatography to obtain the target product in a yield of 46%.

Reference： [1]RSC Advances,2017,vol. 7,p. 18588 - 18591
[2]Patent: CN106478442,2017,A .Location in patent: Paragraph 0046; 0047; 0048

59
[ 132-75-2 ]
[ 5228-51-3 ]
3-ethyl-3H-benzo[a]pyrazolo[3,4-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-alkyl-5-nitro-1H-indazoles 1a-d (10 mmol) and <strong>[132-75-2]1-naphthylacetonitrile</strong> (2) (13 mmol) were added with stirring to a solution of KOH(20 g, 357 mmol) in methanol (40 mL). The mixture was stirred at r.t. for 48 h. After concentration at reduced pressure, the precipitate wascollected by filtration, washed with water, followed by cold EtOH and acetone, and then air dried to give the crude products 3a-d. Further purification was achieved by crystallisation from a suitable solvent such as EtOH or acetone.

Reference： [1]Journal of Chemical Research,2017,vol. 41,p. 371 - 375

60
[ 132-75-2 ]
[ 1046454-17-4 ]
3-propyl-3H-benzo[a]pyrazolo[3,4-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-alkyl-5-nitro-1H-indazoles 1a-d (10 mmol) and <strong>[132-75-2]1-naphthylacetonitrile</strong> (2) (13 mmol) were added with stirring to a solution of KOH(20 g, 357 mmol) in methanol (40 mL). The mixture was stirred at r.t. for 48 h. After concentration at reduced pressure, the precipitate wascollected by filtration, washed with water, followed by cold EtOH and acetone, and then air dried to give the crude products 3a-d. Further purification was achieved by crystallisation from a suitable solvent such as EtOH or acetone.

Reference： [1]Journal of Chemical Research,2017,vol. 41,p. 371 - 375

61
[ 132-75-2 ]
1-butyl-5-nitro-1H-indazole [ No CAS ]
3-butyl-3H-benzo[a]pyrazolo[3,4-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-alkyl-5-nitro-1H-indazoles 1a-d (10 mmol) and <strong>[132-75-2]1-naphthylacetonitrile</strong> (2) (13 mmol) were added with stirring to a solution of KOH(20 g, 357 mmol) in methanol (40 mL). The mixture was stirred at r.t. for 48 h. After concentration at reduced pressure, the precipitate wascollected by filtration, washed with water, followed by cold EtOH and acetone, and then air dried to give the crude products 3a-d. Further purification was achieved by crystallisation from a suitable solvent such as EtOH or acetone.

Reference： [1]Journal of Chemical Research,2017,vol. 41,p. 371 - 375

62
[ 132-75-2 ]
[ 5228-49-9 ]
3-methyl-3H-benzo[a]pyrazolo[3,4-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-alkyl-5-nitro-1H-indazoles 1a-d (10 mmol) and 1-naphthylacetonitrile (2) (13 mmol) were added with stirring to a solution of KOH(20 g, 357 mmol) in methanol (40 mL). The mixture was stirred at r.t. for 48 h. After concentration at reduced pressure, the precipitate wascollected by filtration, washed with water, followed by cold EtOH and acetone, and then air dried to give the crude products 3a-d. Further purification was achieved by crystallisation from a suitable solvent such as EtOH or acetone. 3-Methyl-3H-benzo[a]pyrazolo[3,4-j]acridine-13-carbonitrile(3a): Shiny yellow needles (acetone); m.p. 320-322 C; yield 73%;IR (KBr) (numax cm-1): 2223 (CN); 1H NMR (300 MHz, CDCl3): delta 4.17(3H, s, NCH3), 7.78-7.99 (7H, m, ArH), 8.09 (1H, d, J = 9.3 Hz, ArH),9.42 (1H, s, ArH), 9.98 (1H, d, J = 7.5 Hz, ArH); 13C NMR (75 MHz,CDCl3): delta 36.2, 107.3, 115.3, 116.4, 120.5, 123.2, 124.1, 126.0, 127.5,128.1, 128.3, 129.0, 129.3, 129.3, 132.5, 133.4, 135.5, 137.4, 145.7,147.6; MS (m/z) 308 [M]+ found: C, 78.05; H, 3.94; N, 17.90; calcd forC20H12N4 (308.3): C, 77.91; H, 3.92; N, 18.17%.

Reference： [1]Journal of Chemical Research,2017,vol. 41,p. 371 - 375

63
[ 67-56-1 ]
[ 132-75-2 ]
[ 24168-42-1 ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 5483 - 5490

64
[ 132-75-2 ]
[ 69015-43-6 ]
3-butyl-3H-benzo[a]imidazo[4,5-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole 1a-1d (10 mmol) and 2 (13 mmol) were added with stirring to a solution of potassium hydroxide (20 g,357 mmol) in methanol (40 mL). The mixture was stirred at room temperature for 48 h and concentrated under reduced pressure, and the precipitate was collected by filtration, washed in succession with water,cold ethanol, and acetone, and dried in air. Crude compounds 3a-3d were purified by recrystallization from appropriate solvent.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 1586 - 1592
Zh. Org. Khim.,2017,vol. 53,p. 1586 - 1592,7

65
[ 132-75-2 ]
C₁₁H₁₃N₃O₂ [ No CAS ]
3-isobutyl-3H-benzo[a]imidazo[4,5-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole 1a-1d (10 mmol) and 2 (13 mmol) were added with stirring to a solution of potassium hydroxide (20 g,357 mmol) in methanol (40 mL). The mixture was stirred at room temperature for 48 h and concentrated under reduced pressure, and the precipitate was collected by filtration, washed in succession with water,cold ethanol, and acetone, and dried in air. Crude compounds 3a-3d were purified by recrystallization from appropriate solvent.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 1586 - 1592
Zh. Org. Khim.,2017,vol. 53,p. 1586 - 1592,7

66
[ 132-75-2 ]
[ 90349-15-8 ]
3-ethyl-3H-benzo[a]imidazo[4,5-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole 1a-1d (10 mmol) and 2 (13 mmol) were added with stirring to a solution of potassium hydroxide (20 g,357 mmol) in methanol (40 mL). The mixture was stirred at room temperature for 48 h and concentrated under reduced pressure, and the precipitate was collected by filtration, washed in succession with water,cold ethanol, and acetone, and dried in air. Crude compounds 3a-3d were purified by recrystallization from appropriate solvent.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 1586 - 1592
Zh. Org. Khim.,2017,vol. 53,p. 1586 - 1592,7

67
[ 132-75-2 ]
[ 90840-34-9 ]
3-propyl-3H-benzo[a]imidazo[4,5-j]acridine-13-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium hydroxide; In methanol; at 20℃; for 48h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole 1a-1d (10 mmol) and 2 (13 mmol) were added with stirring to a solution of potassium hydroxide (20 g,357 mmol) in methanol (40 mL). The mixture was stirred at room temperature for 48 h and concentrated under reduced pressure, and the precipitate was collected by filtration, washed in succession with water,cold ethanol, and acetone, and dried in air. Crude compounds 3a-3d were purified by recrystallization from appropriate solvent.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 1586 - 1592
Zh. Org. Khim.,2017,vol. 53,p. 1586 - 1592,7

68
[ 132-75-2 ]
methyl 7-azidothieno[2,3-b]pyrazine-6-carboxylate [ No CAS ]
3-(naphthalen-1-yl)pyrazino[2',3':4,5]thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidin-5(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 20℃; for 3h;Inert atmosphere;	General procedure: To a mixture of DBU (20 mol%) in DMSO (4 mL) were added 2 (1.5 equiv) and benzyl cyanide (50 mg, 1 equiv). The reaction mixture was stirred at r.t. for 3 h. Then, aq NH4Cl was added dropwise. H2O and EtOAc were added and the phases were separated. The aqueous layer was extracted with EtOAc. The organic phase was dried (MgSO4) and filtered. The solvent was evaporated under reduced pressure to give an oil, which was purified by column chromatography. The solvent polarity was increased via a gradient from neat petroleum ether (PE) to a mixture of EtOAc/PE (Table 1).

Reference： [1]Synthesis,2018,vol. 50,p. 1159 - 1165

69
[ 132-75-2 ]
[ 108-93-0 ]
C₁₈H₁₇N [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 2473 - 2478

70
[ 132-75-2 ]
diphenyl(vinyl)sulfonium trifluoromethanesulfonate [ No CAS ]
[ 56477-59-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 21℃; for 12h;	General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetonitriles 1 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.), and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture DBU (456 mg, 3 mmol, 3.0 equiv.) was added. The mixture was stirred for 12 hours at room temperature, and then to the mixture was added saturated ammonium chloride solution (25 mL). The resulting mixture was extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 2 was purified using silica gel column chromatography using an appropriate eluent.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1443 - 1445

71
[ 132-75-2 ]
[ 105-13-5 ]
C₂₀H₁₇NO [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 9226 - 9231

72
[ 132-75-2 ]
[ 4926-45-8 ]
(Z)-2-((Z)-3-(hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-ylidene)-2-(naphthalen-1-yl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium hydroxide; In methanol;Reflux;	Compound 1 (2.45 g, 15 mmol) and 2 (2.84 g, 17 mmol) were added with stirring to a solution of KOH (22.4 g, 400 mmol) in MeOH (70 mL). The mixture was refluxed with stirring for 3 h and then poured into water (300 mL). After neutralization with HCl solution (6 M), the precipitate was collected by filtration, washed with water and then air dried to give crude 3. Recrystallization from acetone gave pure product 3. (Z)-2-((Z)-3-(hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-ylidene)-2-(naphthalen-1-yl)acetonitrile (3) was obtained as a dark red powder, yield (84%), mp 200-202C; 1H NMR (CDCl3) delta 6.49 (1H, t, J = 6.9 Hz), 6.82 (1H, d, J = 9.0 Hz), 7.45 (1H, t, J = 6.9 Hz), 7.51-7.65 (4H, m), 7.95-8.02 (3H, m), 8.96 (1H, d, J = 6.9 Hz), 13.47 (1H, brs); 13C NMR (CDCl3): delta 114.3, 118.3, 119.0, 123.7, 124.1, 124.6, 126.3, 126.7, 127.2, 127.5, 128.2, 128.6, 131.7, 133.4, 135.2, 142.7, 144.8, 148.9, 152.5; MS (m/z) 312 (M+). IR (KBr): 3448/cm (OH), 2210/cm (CN); Anal. Calcd for C19H12N4O (312.3): C, 73.07; H, 3.87; N, 17.94, Found: C, 73.39; H, 3.90; N, 17.74.

Reference： [1]Indian Journal of Heterocyclic Chemistry,2018,vol. 28,p. 313 - 319

73
[ 132-75-2 ]
[ 124276-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 1.2: 18 h 2.1: lithium hydroxide / water / 18 h / Reflux

Reference： [1]Gieuw, Matthew H.; Leung, Vincent Ming-Yau; Ke, Zhihai; Yeung, Ying-Yeung [Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311]

74
[ 132-75-2 ]
[ 107-15-3 ]
[ 835-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon disulfide at 110℃; for 2h;	1.A; 2.A; 3.A; 4.A; 1.A; 2.A; 3-4 (A) 1000 g (6.0 mol) of naphthylacetonitrile was added to the reaction vessel.Add 5000 ml of ethylenediamine and add CS245.7 g (0.6 mol).Raise to 110 ° C, stir for 2 h;At room temperature, 10 L of water was added dropwise, and the dropping rate was 1 L/min, and a solid was precipitated.That is filtered to give free base naphazoline.
	With 3-mercaptopropionic acid at 40℃; for 9h;	1-6 Synthesis of naphazoline nitrate 1-naphthaleneacetonitrile (334g, 2.0mol, 1.0eq) was weighed and added to a 1L four-necked flask, then the catalyst 3-mercaptopropionic acid (6.6g) was added, and then ethylenediamine (144g) was added dropwise at a temperature of 40°C. , 2.4mol, 1.2eq), added dropwise for 1h, dripping was completed, the reaction was incubated for 8h, TLC monitored the disappearance of raw materials (VPE/EA=5:1), stopped the reaction, cooled to room temperature, a large amount of solid was precipitated, and then 95% ethanol was added (900 mL), stirring and dissolving the crude product 4,5-dihydro-2-(1-naphthylmethyl)-1H-imidazole, cooling the reaction solution to 510°C, then adding 65% concentrated nitric acid dropwise, adjusting pH=2.5, Until a large amount of pale yellow solid is precipitated, filtration to obtain 427 g of crude naphazoline nitrate, the yield is 78.2%, and the HPLC purity is 96.3%.

Reference： [1]Current Patent Assignee: GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD. - CN110041261, 2019, A Location in patent: Paragraph 0040-0042; 0045-0047; 0050-0052; 0055-0057
[2]Current Patent Assignee: CHANGZHOU TIANHUA PHARMACEUTICAL - CN113912545, 2022, A Location in patent: Paragraph 0012; 0024-0026; 0029-0031; 0034-0036; 0039;...

75
[ 132-75-2 ]
[ 693-13-0 ]
C₁₉H₂₃N₃ [ No CAS ]

Reference： [1]RSC Advances,2020,vol. 10,p. 6576 - 6583

76
[ 132-75-2 ]
C₂₄H₁₈N₂ [ No CAS ]

Reference： [1]RSC Advances,2020,vol. 10,p. 6576 - 6583

77
[ 109-04-6 ]
[ 132-75-2 ]
[1]naphthyl-[2]pyridyl-acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Appropriate starting arylacetonitrile (1 eq.) was added to a stirredsuspension of KOH (5 eq.) in DMSO (200 mL per 1 mol of KOH). Themixture was brought to 60 C. Bromopyridine (1.5 eq.) was then addeddropwise, at 60-70 C, followed by further stirring at this temperaturefor 4 h. The reaction mixture was cooled and poured onto water(500 mL) and the resulting cloudy solution was extracted with AcOEt(2 × 150 mL), washed with water (100 mL) and brine (100 mL). Theorganic extract was dried over anhydrous MgSO4, filtered and concentratedunder reduced pressure. The residue was dissolved in AcOH(100 mL) and concentrated H2SO4 (35 mL). The solution was heated at100 C until TLC showed complete reaction (1-3 h). The solution wascooled and poured onto excess of ice-25% aqueous ammonia. The resultingmixture was extracted with CH2Cl2 (3 × 75 mL). The combinedorganic extracts were washed with water (2 × 75 mL), brine (75 mL),dried over anhydrous Na2SO4, filtered and evaporated. The title compoundswere purified by recrystallization or by FC.

Reference： [1]Bioorganic Chemistry,2020,vol. 98

78
[ 99-75-2 ]
[ 132-75-2 ]
methyl 4-(2-cyano-2-(naphthalen-1-yl)ethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With copper(I) oxide; [2,2]bipyridinyl; di-tert-butyl peroxide In chlorobenzene at 130℃; for 13h;	4.2 Typical procedure for preparation of targeted molecules General procedure: Under N2, a mixture of arylacetonitrile 2 (0.4mmol), 1 (4.0mL), Cu2O (10mmol%), Bpy (20mmol%) and DTBP (3.0 equiv.) in PhCl (2.0mL) was stirred at 130°C for indicated time. After the mixture was cooled down to the room temperature, the mixture was passed through a short silica gel column with EtOAc as eluent. The filtrate was concentrated under reduced pressure and the residue was further purified by column chromatography on silica gel to obtain the product 3.

Reference： [1]Guo, Fengzhe; Li, Fangshao; Li, Qiang; Tang, Zi-Long; Wu, Xiaofang; Xiao, Jing; Zhong, Ting [Tetrahedron, 2020, vol. 76, # 48]

79
[ 132-75-2 ]
[ 5144-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 3-mercaptopropionic acid / 9 h / 40 °C 2: HNO₃ / lithium hydroxide monohydrate / 5 - 10 °C / pH 2.5

Reference： [1]Current Patent Assignee: CHANGZHOU TIANHUA PHARMACEUTICAL - CN113912545, 2022, A

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	132-75-2	MDL No. :	MFCD00004041
Formula :	C₁₂H₉N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OQRMWUNUKVUHQO-UHFFFAOYSA-N
M.W :	167.21	Pubchem ID :	8596
Synonyms :

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.08
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.47
TPSA :	23.79 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.25 cm/s

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	2.91
Log Po/w (WLOGP) :	2.91
Log Po/w (MLOGP) :	2.76
Log Po/w (SILICOS-IT) :	3.31
Consensus Log Po/w :	2.75

[ CAS No. 132-75-2 ] {[proInfo.proName]}

Quality Control of [ 132-75-2 ]

Related Doc. of [ 132-75-2 ]

Product Details of [ 132-75-2 ]

Calculated chemistry of [ 132-75-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 132-75-2 ]

Application In Synthesis of [ 132-75-2 ]

[ 132-75-2 ] Synthesis Path-Upstream 1~2

[ 132-75-2 ] Synthesis Path-Downstream 1~79

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.21
Solubility :	0.102 mg/ml ; 0.000612 mol/l
Class :	Soluble
Log S (Ali) :	-3.07
Solubility :	0.142 mg/ml ; 0.00085 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.56
Solubility :	0.00465 mg/ml ; 0.0000278 mol/l
Class :	Moderately soluble

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

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
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
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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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.
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P270	Do not eat, drink or smoke when using this product.
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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.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P333	If skin irritation or rash occurs:
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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.
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P411
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P413
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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