Home Cart 0 Sign in  

[ CAS No. 5326-38-5 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 5326-38-5
Chemical Structure| 5326-38-5
Structure of 5326-38-5 * Storage: {[proInfo.prStorage]}

Quality Control of [ 5326-38-5 ]

Related Doc. of [ 5326-38-5 ]

SDS
Alternatived Products of [ 5326-38-5 ]
Alternatived Products of [ 5326-38-5 ]

Product Details of [ 5326-38-5 ]

CAS No. :5326-38-5 MDL No. :MFCD00051517
Formula : C7H6INO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :263.03 g/mol Pubchem ID :79225
Synonyms :

Safety of [ 5326-38-5 ]

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

Application In Synthesis of [ 5326-38-5 ]

  • Upstream synthesis route of [ 5326-38-5 ]
  • Downstream synthetic route of [ 5326-38-5 ]

[ 5326-38-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 615-37-2 ]
  • [ 7745-92-8 ]
  • [ 5326-38-5 ]
  • [ 6277-17-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1281 - 1286
  • 2
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 5326-38-5 ]
  • [ 62621-09-4 ]
Reference: [1] Patent: WO2006/7542, 2006, A1, . Location in patent: Page/Page column 24
  • 3
  • [ 99-52-5 ]
  • [ 5326-38-5 ]
YieldReaction ConditionsOperation in experiment
94% With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In water; acetonitrile at 20℃; for 4 h; Step 1: To a stirred solution of No.246   2-methyl-4-nitroaniline (500 mg, 3.286 mmol) in No.71   acetonitrile and No.37   water were added No.61   p-toluenesulfonic acid monohydrate (1.875 g, 9.858 mmol), No.229   sodium nitrite (453 mg, 6.572 mmol) and No.230   potassium iodide (1.363 g, 8.215 mmol). The reaction mixture was stirred for 4 h at room temperature. The mixture dissolved in No.43   ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give No.247   1-iodo-2-methyl-4-nitrobenzene (812 mg, 94percent).[0500]Step 2: To a stirred solution of No.247   1-iodo-2-methyl-4-nitrobenzene (812 mg, 3.087 mmol) in No.56   dimethylformamide were added No.201   zinc cyanide (544 mg, 4.63 mmol) and No.202   tetrakis(triphenylphosphine) palladium (713 mg, 0.6174 mmol). The reaction mixture was stirred for 24 h at 120° C., then cooled to room temperature and diluted with ethyl acetate. The mixture was filtered using celite pad. The filtrate dissolved in No.43   ethyl acetate and extracted with NaHCO3. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give No.249   2-methyl-4-nitrobenzonitrile (407 mg, 81percent).[0501]Step 3: To a stirred solution of No.249   2-methyl-4-nitrobenzonitrile (407 mg, 2.510 mmol) in No.27   tetrahydrofuran was added 2M No.251   BH3.SMe2 in tetrahydrofuran (2.1 mL). The reaction mixture was stirred for 15 h at 70° C. The mixture was cooled to room temperature, then quenched by water. The mixture dissolved in No.43   ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give No.252   (2-methyl-4-nitrophenyl)methanamine (178 mg, 43percent).[0502]Step 4: To a stirred solution of No.252   (2-methyl-4-nitrophenyl)methanamine (178 mg, 1.071 mmol) in No.64   pyridine, cooled to 0° C., were added No.47   methane sulfonylchloride (0.16 mL, 2.0349 mmol). The resulting reaction mixture was stirred for 2 h. The mixture dissolved in No.46   dichloromethane and washed with 1N HCl. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to obtain No.254   N-(2-methyl-4-nitrobenzyl)methanesulfonamide (100 mg, 38percent).[0503]Step 5: To a stirred solution of No.254   N-(2-methyl-4-nitrobenzyl)methanesulfonamide (100 mg, 0.409 mmol) in No.27   tetrahydrofuran and ethanol as co-solvent were added 10percent No.68   Pd/C (40 mg). The mixture was charged with H2 (gas) balloon. The resulting mixture was stirred for 24 h, then filtered using celite. The filtrate removed in vacuo. The crude was purified by column chromatography. No.256   N-(4-Amino-2-methylbenzyl)methanesulfonamide (61 mg) was obtained as 70percent yield.[0504]Step 6: To a stirred solution of No.256   N-(4-amino-2-methylbenzyl)methanesulfonamide (61 mg, 0.285 mmol) in No.27   tetrahydrofuran and acetonitrile as co-solvent were added No.72   phenylchloroformate (0.04 mL, 0.299 mmol) and No.64   pyridine (0.03 mL, 0.342 mmol). The reaction mixture was stirred for 3 h at room temperature. The mixture dissolved in No.43   ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give No.258   phenyl 3-methyl-4-(methylsulfonamidomethyl)phenylcarbamate (93 mg, 98percent).[0505]Step 7: To a stirred solution of No.258   phenyl 3-methyl-4-(methylsulfonamidomethyl)-phenylcarbamate (46 mg, 0.137 mmol) and No.36   (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (36 mg, 0.137 mmol) in No.71   acetonitrile were added No.191   4-dimethylaminopyridine (17 mg, 0.137 mmol). The reaction mixture was stirred for 15 h at 50° C. The mixture dissolved in No.43   ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. No.260   N-(2-Methyl-4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 81) (61 mg) was obtained as 88percent yield.[0506]1H NMR (300 MHz, DMSO) 8.66 (s, 1H), 8.07 (d, 1H, J=8.43 Hz, Ar), 7.91 (d, 1H, J=8.07 Hz, Ar), 7.27 (m, 8H, Ar), 6.75 (t, 1H, NH), 4.37 (d, 2H, CH2), 4.03 (d, 2H, CH2), 2.83 (s, 3H, mesyl), 2.40 (s, 3H, methyl), 2.23 (s, 3H, methyl).
94% With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In water; acetonitrile at 20℃; for 4 h; Step 1 : To a stirred solution of 2-methyl-4-nitroaniline (500 mg, 3.286 mmol) in acetonitrile and water were added p-toluenesulfonic acid monohydrate (1 .875 g, 9.858 mmol), sodium nitrite (453 mg, 6.572 mmol) and potassium iodide (1.363 g, 8.215 mmol). The reaction mixture was stirred for 4 h at room temperature. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give 1 -iodo-2-methyl-4-nitrobenzene (812 mg, 94 percent).
94% With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In water; acetonitrile at 23℃; for 4 h; Step 1: To a stirred solution of 2-methyl-4-nitroaniline (500 mg, 3.286 mmol) in acetonitrile and water were added p-TsOH.H2O (1.875 g, 9.858 mmol), sodium nitrite (453 mg, 6.572 mmol) and potassium iodide (1.363 g, 8.215 mmol).
The reaction mixture was stirred for 4 h at room temperature.
The mixture dissolved in ethyl acetate and washed with water and brine.
The organic layer was dried over magnesium sulfate and filtered.
The filtrate removed in vacuo.
The crude was purified by column chromatography. 1-lodo-2-methyl-4-nitrobenzene (812 mg) was obtained as 94percent yield.
94% With p-toluenesulfonic acid monohydrate; potassium iodide; sodium nitrite In water; acetonitrile at 20℃; for 4 h; Step 1 : To a stirred solution of 2-methyl-4-nitroaniline (500 mg, 3.286 mmol) in acetonitrile and water were added p-TsOH-H20 (1 .875 g, 9.858 mmol), sodium nitrite (453 mg, 6.572 mmol) and potassium iodide (1 .363 g, 8.215 mmol). The reaction mixture was stirred for 4 h at room temperature. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 1 -lodo-2-methyl-4- nitrobenzene (812 mg) was obtained as 94 percent yield.
63%
Stage #1: With sulfuric acid; sodium nitrite In water; acetone at 0 - 5℃; for 1 h;
Stage #2: With potassium iodide In water; acetone at 0 - 20℃; for 2 h;
To 2-methyi-4-nitroaniline (20.0 g, 131 .45 mmol, 1.00 equiv) in H20/acetone (80/50 mL) al 0-5 °C was added cone. H.2SO4 (27.1 g, 276,53 mmol, 2.10 equiv) followed by the drop-wise addition of a solution of NaN(>> (10.0 g, 144.93 mmol, 1 .10 equiv) in water (20 ml.) and the resulting solution was stirred for 1 h. To this was added drop- wise a solution of KI (30.6 g, 184.34 mmol, 1.40 equiv) in water (20 mL) and the reaction allowed to warm to RT and then stirred for an additional 2 h. The mixture was diluted with 500 mL of ethyl acetate, washed with 2 x 200 mL of water, 3 x 200 mL of aqueous Na2S()3, dried over anhydrous sodium sulfate and concentrated. The residue was purified via silica gel chromatography (ethyl acetate/petroleum ether, 1 :1000) to afford 21.7 g (63percent) of intermediate 164a as a white solid.

Reference: [1] Patent: US2013/79377, 2013, A1, . Location in patent: Paragraph 0498; 0499
[2] Patent: WO2013/45447, 2013, A1, . Location in patent: Page/Page column 66; 67
[3] Patent: US2013/79320, 2013, A1, . Location in patent: Paragraph 0584; 0585; 0593; 0594
[4] Patent: WO2013/45451, 2013, A1, . Location in patent: Page/Page column 80
[5] Patent: WO2013/96771, 2013, A1, . Location in patent: Page/Page column 221
[6] Chemische Berichte, 1897, vol. 30, p. 3000
[7] Magnetic Resonance in Chemistry, 1987, vol. 25, p. 824 - 828
[8] Journal of Medicinal Chemistry, 1996, vol. 39, # 23, p. 4608 - 4621
[9] Journal of Medicinal Chemistry, 2009, vol. 52, # 15, p. 4869 - 4882
  • 4
  • [ 615-37-2 ]
  • [ 7745-92-8 ]
  • [ 5326-38-5 ]
  • [ 6277-17-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1281 - 1286
  • 5
  • [ 615-37-2 ]
  • [ 5326-38-5 ]
Reference: [1] Chemische Berichte, 1897, vol. 30, p. 3000
[2] Justus Liebigs Annalen der Chemie, 1871, vol. 158, p. 347
[3] Chemische Berichte, 1897, vol. 30, p. 3000
[4] Journal of the Chemical Society, 1929, p. 2742
[5] Journal of the American Chemical Society, 1919, vol. 41, p. 2041
  • 6
  • [ 615-37-2 ]
  • [ 7664-93-9 ]
  • [ 5326-38-5 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 2742
[2] Journal of the American Chemical Society, 1919, vol. 41, p. 2041
  • 7
  • [ 615-37-2 ]
  • [ 7745-92-8 ]
  • [ 5326-38-5 ]
  • [ 6277-17-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1281 - 1286
  • 8
  • [ 5326-38-5 ]
  • [ 84-67-3 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 1997,1999
Historical Records

Related Functional Groups of
[ 5326-38-5 ]

Nitroes

Chemical Structure| 41252-98-6

[ 41252-98-6 ]

1-Iodo-2-methyl-3-nitrobenzene

Similarity: 0.89

Chemical Structure| 5326-39-6

[ 5326-39-6 ]

1-Iodo-4-methyl-2-nitrobenzene

Similarity: 0.89

Chemical Structure| 7745-92-8

[ 7745-92-8 ]

2-Iodo-1-methyl-4-nitrobenzene

Similarity: 0.89

Chemical Structure| 4102-38-9

[ 4102-38-9 ]

1-Iodo-2,4-dimethyl-5-nitrobenzene

Similarity: 0.88

Chemical Structure| 41252-97-5

[ 41252-97-5 ]

4-Iodo-2-nitrotoluene

Similarity: 0.88

Aryls

Chemical Structure| 41252-98-6

[ 41252-98-6 ]

1-Iodo-2-methyl-3-nitrobenzene

Similarity: 0.89

Chemical Structure| 5326-39-6

[ 5326-39-6 ]

1-Iodo-4-methyl-2-nitrobenzene

Similarity: 0.89

Chemical Structure| 7745-92-8

[ 7745-92-8 ]

2-Iodo-1-methyl-4-nitrobenzene

Similarity: 0.89

Chemical Structure| 4102-38-9

[ 4102-38-9 ]

1-Iodo-2,4-dimethyl-5-nitrobenzene

Similarity: 0.88

Chemical Structure| 41252-97-5

[ 41252-97-5 ]

4-Iodo-2-nitrotoluene

Similarity: 0.88