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[ CAS No. 15307-93-4 ]

{[proInfo.proName]} (Synonyms:2,6-Dichloro-N-phenylaniline) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 15307-93-4
Chemical Structure| 15307-93-4
Structure of 15307-93-4 * Storage: {[proInfo.prStorage]}

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Product Details of [ 15307-93-4 ]

CAS No. :15307-93-4 MDL No. :MFCD00269648
Formula : C12H9Cl2N Boiling Point : 309.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :238.11 g/mol Pubchem ID :84867
Synonyms :

Safety of [ 15307-93-4 ]

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

Application In Synthesis of [ 15307-93-4 ]

  • Upstream synthesis route of [ 15307-93-4 ]
  • Downstream synthetic route of [ 15307-93-4 ]

[ 15307-93-4 ] Synthesis Path-Upstream   1~13

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Reference: [1] Revue Roumaine de Chimie, 2014, vol. 59, # 11-12, p. 1021 - 1027
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Reference: [1] Revue Roumaine de Chimie, 2014, vol. 59, # 11-12, p. 1021 - 1027
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YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide In water; toluene at 80 - 90℃; for 4 h; The compound II (272 g, 0.92 mol), toluene (800 g, 8.7 mol) was dried in a four-necked flask, heated to 90 ° C, and sodium hydroxide was added three times with stirring, and 14.8 g (0.37 mol) was added.The reaction was refluxed for 3 hours and then cooled to below 80 ° C. 184 mL of distilled water was added to the reaction flask and the temperature was raised to 90 ° C. The mixture was stirred for 1 hour. The reaction solution was transferred to a separatory funnel.To the reaction solution was further added 46 mL of water and 28 mL of hydrochloric acid, and the reaction solution was transferred to a distillation flask, distilled under reduced pressure, and toluene was distilled off to give 203.4 g of a pale yellow solid (Compound III: N- (2,6- Chlorophenyl) aniline), yield 93percent.
Reference: [1] Patent: CN106905178, 2017, A, . Location in patent: Paragraph 0021; 0040; 0041
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YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide In chlorobenzene EXAMPLE 22
A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine obtained in Example 1 and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring.
While keeping the reaction temperature at 100° C., the reaction was continued for 5 hours.
After the reaction was completed, the reaction mixture was cooled to 25° C., and washed with 300 g of a 10percent aqueous solution of sodium hydroxide.
Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of N-phenyl-2,6-dichloroaniline in the state of a black solid (yield: 85percent, mp: 49.5° to 50.7° C.).
The obtained N-phenyl-2,6-dichloroaniline had a purity of 92.1percent measured by means of gas chromatography.
After N-phenyl-2,6-dichloroaniline was purified by recrystallizing from methanol, 1 H-NMR analysis, IR analysis and elementary analysis were conducted.
The results are shown below.
1 H-NMR (solvent: CDCl3, internal standard: TMS): δ ppm: 7.53 to 6.55 (8H, m, benzene ring), 5.83 (1H, S, NH).
IR (KBr tablet): ν NH: 3380 (cm-1).
Reference: [1] Patent: US4908479, 1990, A,
[2] Pharmaceutical Chemistry Journal, 1996, vol. 30, # 1, p. 38 - 40
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YieldReaction ConditionsOperation in experiment
90.75% With sodium hydroxide In water; N,N-dimethyl-formamide; toluene EXAMPLE 1
Preparation of N-phenyl 2,6-dichloroaniline
37.6 g of 2,4,6-trimethyl phenol and 11 g of sodium hydroxide were dissolved in 30 ml of water and mixed with 150 ml of toluene.
The toluene recovered from heating was mixed with 139 ml of N,N-dimethylformamide to obtain a N,N-dimethylformamide solution.
40 g of 2,6-dichlorophenol was dissolved in 130 ml of toluene, followed by the addition of 9.8 g of sodium hydroxide in 20 ml of water, 41.5 g of N-phenyl chloroacetamide and 8.7 ml of N,N-dimethylformamide, and refluxed in a oil bath at 140°-150° C. for 15 h.
The toluene was recovered from the reflux, and mixed with the above N,N-dimethylformamide solution and reacted for 3 h.
Recovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg) resulted in the formation of 53 g of N-phenyl 2,6-dichloroaniline and the product yield was 90.75percent.
Reference: [1] Patent: US5475139, 1995, A,
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Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 23 - 39
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  • [ 10113-35-6 ]
  • [ 6697-95-6 ]
  • [ 39920-37-1 ]
  • [ 13603-93-5 ]
  • [ 608-31-1 ]
Reference: [1] Revue Roumaine de Chimie, 2014, vol. 59, # 11-12, p. 1021 - 1027
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Reference: [1] Pharmaceutical Chemistry Journal, 1996, vol. 30, # 1, p. 38 - 40
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Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 23 - 39
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Reference: [1] Patent: CN106905178, 2017, A,
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Reference: [1] Patent: CN106905178, 2017, A,
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Reference: [1] Pharmaceutical Chemistry Journal, 1996, vol. 30, # 1, p. 38 - 40
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2358 - 2368
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 3, p. 1355 - 1362
[4] Medicinal Chemistry Research, 2013, vol. 22, # 7, p. 3076 - 3084
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 5, p. 1995 - 1997
[2] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 5, p. 1995 - 1997
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2358 - 2368
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2358 - 2368
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