CAS No. :	455-37-8
Formula :	C₇H₆FNO
M.W :	139.13
SMILES Code :	O=C(N)C1=CC=CC(F)=C1
MDL No. :	MFCD00007983
InChI Key :	YPIGHNIIXYSPKF-UHFFFAOYSA-N
Pubchem ID :	68000

Safety of m-Fluorobenzamide

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of m-Fluorobenzamide

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 455-37-8 ]

[ 455-37-8 ] Synthesis Path-Downstream 1~54

1
[ 455-37-8 ]
[ 2757-23-5 ]
[ 52059-64-0 ]

References: [1]ChemistryOpen,2015,vol. 4,p. 342 - 362.
[2]Acta Chemica Scandinavica (1947),1973,vol. 27,p. 2161 - 2170.

2
[ 50-00-0 ]
[ 455-37-8 ]
[ 141409-15-6 ]
3-(3'-fluorobenzamidomethyl)-6-methylthio-2-(4'-tolyl)imidazo<1,2-b>pyridazine [ No CAS ]

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 609 - 622.

3
[ 50-00-0 ]
[ 455-37-8 ]
[ 156146-50-8 ]
6-fluoro-3-(3'-fluorobenzamidomethyl)-2-(3'',4''-methylenedioxyphenyl)imidazo<1,2-b>pyridazine [ No CAS ]

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 609 - 622.

4
[ 50-00-0 ]
[ 455-37-8 ]
[ 141409-81-6 ]

References: [1]Australian Journal of Chemistry,1992,vol. 45,p. 731 - 749.

5
[ 455-37-8 ]
[ 455-38-9 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 4443 - 4448.

6
[ 455-37-8 ]
1-methyl-5-(3-fluorophenyl)tetrazole [ No CAS ]

References: [1]Journal of the American Chemical Society,1980,vol. 102,p. 2968 - 2979.

7
[ 455-37-8 ]
N-chloro-3-fluorobenzamide [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 5348 - 5351.
[2]Journal of the Chemical Society. Perkin transactions II,1993,p. 1787 - 1790.

8
[ 67-56-1 ]
[ 455-37-8 ]
[ 455-68-5 ]

References: [1]European Journal of Organic Chemistry,2007,p. 1026 - 1030.

9
[ 88229-23-6 ]
[ 455-37-8 ]

References: [1]Chemistry - A European Journal,2007,vol. 13,p. 6590 - 6594.

10
N,N-diallyl-3-fluorobenzamide [ No CAS ]
[ 455-37-8 ]

References: [1]Chemistry - A European Journal,2007,vol. 13,p. 6590 - 6594.

11
[ 455-37-8 ]
[ 851181-30-1 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 237 - 245.

12
[ 455-37-8 ]
[ 1027058-38-3 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 237 - 245.

13
[ 455-37-8 ]
6-fluoro-3-(3'-fluorobenzamidomethyl)-2-phenylimidazo<1,2-b>pyridazine [ No CAS ]

References: [1]Australian Journal of Chemistry,1992,vol. 45,p. 731 - 749.

14
[ 455-37-8 ]
6-chloro-3-(3'-fluorobenzamidomethyl)-2-phenylimidazo<1,2-b>pyridazine [ No CAS ]

References: [1]Australian Journal of Chemistry,1992,vol. 45,p. 731 - 749.

15
[ 455-37-8 ]
6-fluoro-3-(3'-fluorobenzamidomethyl)-2-(4''-tolyl)imidazo<1,2-b>pyridazine [ No CAS ]

References: [1]Australian Journal of Chemistry,1992,vol. 45,p. 731 - 749.

16
[ 455-37-8 ]
6-chloro-3-(3'-fluorobenzamidomethyl)-2-(4''-tolyl)imidazo<1,2-b>pyridazine [ No CAS ]

References: [1]Australian Journal of Chemistry,1992,vol. 45,p. 731 - 749.

17
[ 455-37-8 ]
[ 52023-00-4 ]

References: [1]Acta Chemica Scandinavica (1947),1973,vol. 27,p. 2161 - 2170.

18
[ 455-38-9 ]
[ 455-37-8 ]

References: [1]Journal of the American Chemical Society,1963,vol. 85,p. 709 - 724.
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2544 - 2546.
[3]Patent: WO2009/127815,2009,A1 .

19
paraformaldehyde [ No CAS ]
3-methyl-1',2',3',6'-tetrahydro-2,4'-bipyridine trifluoroacetate salt [ No CAS ]
[ 455-37-8 ]
3-fluoro-N-[(3-methyl-3',6'-dihydro-2,4'-bipyridin-1'(2'H)-yl)methyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; In ethanol;Heating / reflux;	[1643] A mixture of the product from Example 143B (trifluoroacetic acid salt, 29 mg, 0.1 mmol), paraformaldehyde (30 mg, 1 mmol), <strong>[455-37-8]3-fluorobenzamide</strong> (70 mg, 0.5 mmol, Aldrich), and 42 mg of potassium carbonate (0.3 mmol) in 2.5 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure under reduced pressure. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 24 mg (74%) pure compound. 1H NMR (500 MHz, DMSO-d6) delta2.30 (s, 3H), 2.47 (m, 2H), 2.76 (m, 2H), 3.25 (m, 2H), 4.28 (d, J=6 Hz, 2H), 5.80 (m, 1H), 7.14 (m, 1H), 7.39 (t, J=6 Hz, 1H), 7.55 (m, 2H), 7.69 (d, J=6 Hz, 1H), 7.76 (d, J=6 Hz, 1H), 8.34 (d, J=6 Hz, 1H), 8.91 (t, J=6 Hz, 1H); MS (ESI APCI-) m/e 324 (M-H)+.

References: [1]Patent: US2003/229094,2003,A1 .Location in patent: Page 100.

20
[ 630118-73-9 ]
[ 455-37-8 ]
3-fluoro-N-[(3-methyl-3',6'-dihydro-2,4'-bipyridin-1'(2'H)-yl)methyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24 mg (74%)	With potassium carbonate; paraformaldehyde; In ethanol;	EXAMPLE 212 3-fluoro-N-[(3-methyl-3',6'-dihydro-2,4'-bipyridin-1'(2'H)-yl)methyl]benzamide A mixture of the product from Example 143B (trifluoroacetic acid salt, 29 mg, 0.1 mmol), paraformaldehyde (30 mg, 1 mmol), <strong>[455-37-8]3-fluorobenzamide</strong> (70 mg, 0.5 mmol, Aldrich), and 42 mg of potassium carbonate (0.3 mmol) in 2.5 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure under reduced pressure. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 24 mg (74%) pure compound. 1H NMR (500 MHz, DMSO-d6) delta2.30 (s, 3H), 2.47 (m, 2H), 2.76 (m, 2H), 3.25 (m, 2H), 4.28 (d, J=6 Hz, 2H), 5.80 (m, 1H), 7.14 (m, 1H), 7.39 (t, J=6 Hz, 1H), 7.55 (m, 2H), 7.69 (d, J=6 Hz, 1H), 7.76 (d, J=6 Hz, 1H), 8.34 (d, J=6 Hz, 1H), 8.91 (t, J=6 Hz, 1H); MS (ESI APCI-) m/e 324 (M-H)+.

References: [1]Patent: US2004/29887,2004,A1 .

21
[ 455-37-8 ]
[ 1092101-15-9 ]
[ 1092101-19-3 ]
[ 1092101-28-4 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 463 - 465.

22
[ 403-54-3 ]
[ 455-37-8 ]

References: [1]Applied Organometallic Chemistry,2014,vol. 28,p. 900 - 907.
[2]Journal of Organic Chemistry,2015,vol. 80,p. 4148 - 4151.
[3]Catalysis science and technology,2015,vol. 5,p. 1606 - 1622.
[4]Green Chemistry,2013,vol. 15,p. 2447 - 2456.
[5]Organometallics,2011,vol. 30,p. 5442 - 5451.
[6]Advanced Synthesis and Catalysis,2016,vol. 358,p. 2889 - 2894.
[7]Chemistry - A European Journal,2008,vol. 14,p. 6601 - 6605.
[8]Inorganic Chemistry Communications,2020,vol. 112.

23
[ 67-56-1 ]
[ 455-37-8 ]
[ 72755-13-6 ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 3868 - 3876.
[2]Tetrahedron Letters,2009,vol. 50,p. 3287 - 3289.

24
[ 455-37-8 ]
[ 3556-52-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sulfuric acid; nitric acid; at 10℃;	Amide 18 (20 g, 144 mmol) was dissolved in cone, nitric acid (40 mL) and added dropwise to a mixture of cone, sulphuric acid (70 mL) and cone, nitric acid (10 mL) while <n="39"/>keeping the temperature <10 0C. The mixture was partitioned between water (1 L) and ethylacetate (IL) and the organic phase separated, dried (MgSO4) and evaporated to an oil. This was suspended in ethylacetate (100 mL) and heated. Hexane (100 mL) was added and the mixture was cooled to -20C overnight. The resulting crystalline solid was collected by filtration and washed with hexane to give nitroamide 19 as white crystals (11.5 g, 44%): m.p. 129-130 C.

References: [1]Patent: WO2009/127815,2009,A1 .Location in patent: Page/Page column 37-38.

25
[ 456-47-3 ]
[ 455-37-8 ]
[ 369-83-5 ]

References: [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2588 - 2598.

26
[ 455-37-8 ]
C₃₁H₃₅ClN₄O₄ [ No CAS ]
C₃₈H₄₀FN₅O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 613 - 618.

27
[ 455-37-8 ]
C₃₁H₃₅ClN₄O₄ [ No CAS ]
C₃₈H₄₀FN₅O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 613 - 618.

28
[ 455-37-8 ]
[ 1354531-79-5 ]
C₂₇H₂₈FN₅O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 613 - 618.

29
[ 455-37-8 ]
[ 1314082-90-0 ]

References: [1]ChemMedChem,2011,vol. 6,p. 1300 - 1309.

30
[ 455-37-8 ]
[ 1314082-92-2 ]

References: [1]ChemMedChem,2011,vol. 6,p. 1300 - 1309.

31
[ 455-37-8 ]
[ 72505-20-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With Lawessons reagent; In tetrahydrofuran; at 60℃;	Synthesis of 3-fluorobenzenecarbothioamide (Intermediate a)A 100 mL round-bottomed flask equipped with condenser and magnetic stirrer was charged with <strong>[455-37-8]3-fluorobenzoamide</strong> (2.0 g, 14.4 mmol), which was dissolved in 30 mL of THF, then Lawesson's reagent was added to the solution (3.5 g, 8.64 mmol). The mixture was heated to 60C and stirred overnight; the transformation was monitored by TLC (Eluent: n-hexane/EtOAc 7:3). The solution was cooled at room temperature and the solvent removed by vacuum distillation.The crude was purified by flash chromatography (Eluent: n-hexane/EtOAc 7:3) from which 3- fluorobenzenecarbothioamide was obtained as a yellow solid (2.0 g, 12.9 mmol, Y = 89 %).1H-NMR (CDCl3): delta 7.80-7.55 (bs, 1H, NH2), 7.66-7.60 (m, 2H), 7.44-7.37 (m, 1H), 7.27-7.20 (m, 1H), 7.30-7.00 (bs, 1H, NH2).MS (ES1+) m/z; 156.11 [M+H]+.
89%	With Lawessons reagent; In tetrahydrofuran; at 60℃;	Synthesis of 3-fluorobenzenecarbothioamide (Intermediate a) A 100 mL round-bottomed flask equipped with condenser and magnetic stirrer was charged with <strong>[455-37-8]3-fluorobenzoamide</strong> (2.0 g, 14.4 mmol), which was dissolved in 30 mL of THF, then Lawesson's reagent was added to the solution (3.5 g, 8.64 mmol). The mixture was heated to 60 C and stirred overnight; the transformation was monitored by TLC (Eluent: n-hexane /EtOAc 7:3). The solution was cooled at room temperature and the solvent removed by vacuum distillation. The crude was purified by flash chromatography (Eluent: n-hexane / EtOAc 7:3) from which 3-fluorobenzenecarbothioamide was obtained as a yellow solid (2.0 g, 12.9 mmol, Y = 89 %). 1H-NMR (CDCl3): delta 7.80-7.55 (bs, 1H, NH2), 7.66-7.60 (m, 2H), 7.44-7.37 (m, 1H), 7.27-7.20 (m, 1H), 7.30-7.00 (bs, 1H, NH2). MS (ES1+) m/z: 156.11 [M+H]+.
	With Lawessons reagent; In tetrahydrofuran; for 4h;Reflux;	General procedure: To a solution of benzamide 11a-u (1 equiv) in THF (30mL) was added Lawesson?s reagent (0.6 equiv), and the mixture was heated to reflux for 4 hrs. The reaction mixture was concentrated invacuo,then diluted with ethyl acetate (30 ml), and washed with 1N NaHCO3 (3× 20 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate,filtered and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using a mixture of dichloromethane/methanol(100:1, v/v) as eluent to afford a yellow solid product.A solution of the obtained solid 12a-u (1 equiv) and ethyl 2-chloroacetoacetate (1.2 equiv) in ethanol (25 ml) was heated to reflux for 6 h, then the mixture was allowed to stand at 0 C for 10 hrs, and a white needle crystal was precipitate out.The reaction mixture was filtered and the filter cake was washed with 10 mL of ethanol, dried in vacuum to give the desired product.

References: [1]Patent: WO2015/197640,2015,A1 .Location in patent: Page/Page column 9.
[2]Patent: EP3184524,2017,A1 .Location in patent: Page/Page column 0074-0077.
[3]ChemMedChem,2011,vol. 6,p. 1300 - 1309.
[4]Crystal Growth and Design,2014,vol. 14,p. 2753 - 2762.
[5]European Journal of Medicinal Chemistry,2016,vol. 113,p. 246 - 257.

32
[ 455-37-8 ]
[ 1380333-86-7 ]
[ 1380333-96-9 ]

References: [1]European Journal of Organic Chemistry,2012,p. 2889 - 2893.

33
[ 455-37-8 ]
[ 1415749-93-7 ]

References: [1]Acta Crystallographica, Section C: Crystal Structure Communications,2012,vol. 68,p. o399-o404.

34
[ 455-37-8 ]
[ 777-01-5 ]

References: [1]Acta Crystallographica, Section C: Crystal Structure Communications,2012,vol. 68,p. o399-o404.

35
[ 591-50-4 ]
[ 455-37-8 ]
[ 1629-09-0 ]

References: [1]Organic and biomolecular chemistry,2014,vol. 12,p. 7478 - 7481.
[2]European Journal of Organic Chemistry,2013,p. 515 - 524.

36
[ 455-37-8 ]
[ 696-62-8 ]
[ 58955-03-6 ]

References: [1]European Journal of Organic Chemistry,2013,p. 515 - 524.

37
[ 637-87-6 ]
[ 455-37-8 ]
[ 1978-87-6 ]

References: [1]European Journal of Organic Chemistry,2013,p. 515 - 524.

38
[ 456-48-4 ]
[ 403-54-3 ]
[ 455-37-8 ]

References: [1]RSC Advances,2013,vol. 3,p. 5889 - 5894.

39
[ 456-47-3 ]
[ 455-37-8 ]

References: [1]Green Chemistry,2013,vol. 15,p. 1956 - 1961.

40
C₇H₆BF₃NO^(1-)*K⁽¹⁺⁾ [ No CAS ]
[ 824-75-9 ]
[ 455-37-8 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 14012 - 14015.

41
[ 455-37-8 ]
[ 324-57-2 ]

References: [1]Synlett,2013,vol. 24,p. 2119 - 2123.

42
[ 455-37-8 ]
(E)-3-fluoro-N-styrylbenzamide [ No CAS ]

References: [1]Synlett,2013,vol. 24,p. 2119 - 2123.

43
[ 95-14-7 ]
[ 455-37-8 ]
[ 122-78-1 ]
C₂₁H₁₇FN₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene; for 24h;Reflux;	General procedure: The enamides were prepared according to a modified procedure reported by Lang and coworkers1:A mixture of the appropriate benzamide (1 equiv.), phenylacetaldehyde (1 equiv.),benzotriazole (1 equiv.) and p-TsOH (0.1 equiv.) in toluene was heated to reflux for 24 h.Water formed during the reaction was removed azeotropically by a Dean-Stark apparatus. Thesolvent was removed under reduced pressure and the residue was submitted to a short filtercolumn to remove unreacted starting material. The obtained crude product was dissolved indry THF, cooled to 0 C and NaH (60% in mineral oil, 1.5 eq) was added portionwise. Thereaction mixture was stirred at room temperature until full consumption of the startingmaterial. Then Et2O was added, washed with K2CO3 and the aqueous phase was extractedthree times with Et2O. The combined organic layers were dried over Na2SO4 and the solventwas removed under reduced pressure. The crude product was purified by flashchromatography using cyclohexane and EtOAc (+1% v/v NEt3) to obtain both isomers

References: [1]Synlett,2013,vol. 24,p. 2119 - 2123.

44
[ 455-37-8 ]
[ 615-43-0 ]
[ 324-15-2 ]

References: [1]Chinese Journal of Chemistry,2013,vol. 31,p. 1247 - 1249.

45
[ 331-25-9 ]
[ 455-37-8 ]

References: [1]Organic Letters,2014,vol. 16,p. 624 - 627.

46
[ 32222-47-2 ]
[ 455-37-8 ]

References: [1]Organic Letters,2014,vol. 16,p. 624 - 627.

47
[ 4858-85-9 ]
[ 455-37-8 ]
2-(3-fluorophenyl)oxazolo[4,5-b]pyrazine [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1047 - 1055.

48
[ 201230-82-2 ]
[ 1121-86-4 ]
[ 455-37-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 1,4-diaza-bicyclo[2.2.2]octane; N-methoxylamine hydrochloride; sodium iodide; palladium dichloride; In acetonitrile; at 90℃; under 3800.26 Torr; for 8h;Autoclave; Inert atmosphere;	General procedure: To an autoclave (100 mL capacity), were added an arylhalide (1 mmol), methoxylamine hydrochloride (1.2 equiv),DABCO (2 equiv), PdCl2 (10 mol%), NaI (0.2 mmol) and MeCN (15 mL), under an inert atm. The autoclave was flushed three times with CO and then pressurized to 5 atm of CO. The mixture was stirred with a mechanical stirrer (550rpm) at 90 C for 8 h. The reactor was cooled to r.t., degassed carefully, opened and the reaction mixture removed. The reactor vessel was washed with EtOAc (2 × 5 mL) to remove residual product. The mixture was filtered and the filtrate washed with brine (2 × 4 mL), dried over Na2SO4, filtered and the solvent evaporated under vacuum. Purification of the residue was carried out by column chromatography (silicagel, 100-200 mesh, PE-EtOAc) to afford the corresponding product in good to excellent yield.

References: [1]Synlett,2014,vol. 25,p. 85 - 88.
[2]RSC Advances,2015,vol. 5,p. 76122 - 76127.

49
[ 455-37-8 ]
[ 534-07-6 ]
[ 303224-30-8 ]

Yield	Reaction Conditions	Operation in experiment
39%	In toluene; at 100℃; for 5h;	1,3-Dichloroacetone (3.65 g, 28.75 mmol) was added to a solution of <strong>[455-37-8]3-fluorobenzamide</strong> (2 g, 14.37 mmol) in dry toluene (20 mL). The resulting reaction mixture was stirred at 100 C for 5 h. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether) to afford 4-(chloromethyl)-2-(3-fluorophenyl)oxazole (1.2 g, yield 39%) as a yellow liquid. 1H NMR (300 MHz, CDCl3) delta 7.85 - 7.83 (m, 1 H), 7.77 - 7.73 (m, 2H), 7.48 - 7.41 (m, 1 H), 7.20 - 7.14 (m, 1 H), 4.58 (d, J = 0.9 Hz, 2H).

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3213 - 3222.
[2]Patent: EP2533783,2015,B1 .Location in patent: Paragraph 0629-0630.

50
[ 455-37-8 ]
[ 1589081-06-0 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3213 - 3222.

51
[ 455-37-8 ]
[ 1589081-27-5 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3213 - 3222.

52
[ 292638-84-7 ]
[ 455-37-8 ]
[ 1650579-79-5 ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 937 - 942.

53
[ 455-37-8 ]
[ 2042-37-7 ]
[ 138867-17-1 ]

References: [1]RSC Advances,2014,vol. 4,p. 44811 - 44814.

54
[ 456-48-4 ]
[ 455-37-8 ]

Yield	Reaction Conditions	Operation in experiment
21%		General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde(7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.
21%		General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde (7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.

References: [1]RSC Advances,2019,vol. 10,p. 724 - 728.
[2]RSC Advances,2016,vol. 6,p. 37093 - 37098.
[3]Synlett,2014,vol. 25.
[4]Synlett,2015,vol. 26,p. 84 - 86.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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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

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CAS No.: 455-37-8

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CAS No.: 455-37-8

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