m-Fluorobenzamide | Fluorinated Building Blocks

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Quality Control of m-Fluorobenzamide Purity: 99% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of m-Fluorobenzamide

CAS No. :	455-37-8
Formula :	C₇H₆FNO
M.W :	139.13
SMILES Code :	O=C(N)C1=CC=CC(F)=C1
Synonyms :	m-Fluorobenzamide
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 1~35

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.

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

Precautionary Statements-General
Code	Phrase
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P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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Code	Phrase
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P321
P322
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P378
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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Storage
Code	Phrase
P401
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H242	Heating may cause a fire
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Code	Phrase
H300	Fatal if swallowed
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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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