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[ CAS No. 635-22-3 ]

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Inaccessible (Haz class 6.1), Domestic USD 41.00
Inaccessible (Haz class 6.1), International USD 64.00
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2D
Chemical Structure| 635-22-3
Chemical Structure| 635-22-3
Structure of 635-22-3 *Storage: {[proInfo.prStorage]}

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Product Details of [ 635-22-3 ]

CAS No. :635-22-3MDL No. :MFCD00007844
Formula : C6H5ClN2O2 Boiling Point : 344.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :172.57Pubchem ID :-
Synonyms :

Computed Properties of [ 635-22-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 635-22-3 ]

Signal Word:DangerClass:6.1
Precautionary Statements:P260-P262-P264-P270-P271-P273-P280-P284-P301+P310+P330-P302+P352+P310+P361+P364-P304+P340+P310-P305+P351+P338+P337+P313-P314-P391-P403+P233-P405-P501UN#:2237
Hazard Statements:H300+H310+H330-H315-H319-H373-H411Packing Group:
GHS Pictogram:

Application In Synthesis of [ 635-22-3 ]

  • Upstream synthesis route of [ 635-22-3 ]
  • Downstream synthetic route of [ 635-22-3 ]

[ 635-22-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 635-22-3 ]
  • [ 341010-40-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 49, p. 365
  • 2
  • [ 635-22-3 ]
  • [ 121-17-5 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With hydrogenchloride In water at 0℃; for 0.0833333 h; Schlenk technique
Stage #2: With tert.-butylnitrite In water at -196 - 20℃; Schlenk technique; Inert atmosphere
Stage #3: at -78 - 20℃; for 5 h; Schlenk technique; Inert atmosphere
General procedure: An oven-dried Schlenk tube (A) equipped with a magnetic stir bar was charged with AgF (132.2 mg, 1.05 mmol, 3.5 equiv), sealed with a septum, and degassed by alternating vacuum evacuation and nitrogen backfill (three times) before freshly distilled EtCN (3 mL)was added. To the resulting suspension, which was precooled to –78 °C (dry ice–acetone bath), was added TMSCF3 (149.3 mg, 1.05 mmol, 3.5 equiv) by microsyringe. The mixture was allowed towarm to r.t. and stirring was continued for an additional 15 min. In due course, AgF solid dissolved and a gray, dark solution of [Ag-CF3] formed. Another Schlenk tube (B) equipped with a magnetic stir bar was charged with the aniline (ArNH2; 0.30 mmol, 1.0 equiv) in freshly distilled EtCN (1.5 mL). To the resulting solution, which was precooled to 0 °C (ice bath), aq HCl (12 M; 50.0 μL, 0.60mmol, 2.0 equiv) was added; precipitate formed immediately. After 5 min stirring, t-BuONO (37.7 mg, 0.33 mmol, 1.1 equiv) was added by microsyringe, and the mixture was allowed to stir at 0 °C for 15 min. The resulting suspension in Schlenk tube (B) was degassed by alternating vacuum evacuation at –196 °C (liquid nitrogen), then the solution was allowed to warm to r.t. under a nitrogen atmosphere (three times), and finally cooled to –78 °C (dry ice–acetone bath). The gray, dark solution of [AgCF3] in Schlenk tube (A), which was precooled to –78 °C (dry ice–acetone bath), was added to Schlenk tube (B) (ArN2+Cl–) by syringe at –78 °C (dry ice–acetone bath) over a period of 1 h. After the addition was complete, the reaction mixture was stirred for 3 h at –78 °C (dry ice–acetone bath), allowed to warm to r.t., and stirring was continued for an additional 1 h. An off-white precipitate was observed, and the reaction mixture was diluted with EtOAc (3 mL) and filtered through a short silica gel column. The solvent was removed under reduced pressure with a rotatory evaporator, and the crude residue was purified by silica gel column chromatography to give the desired trifluoromethylation product 3. The yields of products 3a, 3f, 3g, 3l, 3o, 3r, 3x, and 3zb are based on the 19F NMR spectra with 4-F3COC6H4OMe as internal standard. Analytical data for the representative product ethyl 4-(trifluoromethyl)benzoate (3i) are provided below. Data for other products can be found in the literature.
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 28, p. 10330 - 10333
[2] Synthesis (Germany), 2014, vol. 46, # 16, p. 2143 - 2148
  • 3
  • [ 635-22-3 ]
  • [ 16588-24-2 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃;
Stage #2: With copper(I) bromide In water for 1 h;
To a solution of 4-chloro-3-nitro-phenylamine (17.2 g, 0.1 mol) in 260 mL HBr (48percent) at 0°C was added dropwise NaN02 (13.8 g, 0.2 mol) in water. The reaction mixture was stirred for 1 h at 0°C then CuBr (24 g, 0.17 mol) was added in portions to the mixture and stirred for an additional 1 h. Water was added, the mixture allowed to warm to room temperature and was then extracted with EtOAc. The crude product was purified by silica gel column chromatography to give the title compound (13 g, 55percent). 1H NMR CDCI3400 MHz δ 8.03-8.02 (m, 1 H), 7.66-7.63 (m, 1 H), 7.45-7.42 (m, 1 H).
55%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃; for 1 h;
Stage #2: With copper(I) bromide In water at 0℃; for 1 h;
To a solution of 4-chloro-3-nitro-phenylamine (17.2 g, 0.1 mol) in 260 mL HBr (48percent) at 0° C. was added dropwise NaNO2 (13.8 g, 0.2 mol) in water. The reaction mixture was stirred for 1 h at 0° C. then CuBr (24 g, 0.17 mol) was added in portions to the mixture and stirred for an additional 1 h. Water was added, the mixture allowed to warm to room temperature and was then extracted with EtOAc. The crude product was purified by silica gel column chromatography to give the title compound (13 g, 55percent). 1H NMR CDCl3400 MHz δ 8.03-8.02 (m, 1H), 7.66-7.63 (m, 1H), 7.45-7.42 (m, 1H).
Reference: [1] Patent: WO2013/117522, 2013, A1, . Location in patent: Page/Page column 40
[2] Patent: US2015/18367, 2015, A1, . Location in patent: Paragraph 0177; 0178
[3] Journal of the American Chemical Society, 1962, vol. 84, p. 1026 - 1032
[4] Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1795 - 1799[5] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843
  • 4
  • [ 635-22-3 ]
  • [ 41252-95-3 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1930, vol. 49, p. 1082,1087
[2] Journal of the American Chemical Society, 1962, vol. 84, p. 1026 - 1032
  • 5
  • [ 635-22-3 ]
  • [ 126811-30-1 ]
Reference: [1] Patent: WO2013/117522, 2013, A1,
[2] Patent: US2015/18367, 2015, A1,
  • 6
  • [ 635-22-3 ]
  • [ 1421373-66-1 ]
Reference: [1] Patent: CN107915724, 2018, A,
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