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Chemical Structure| 88990-57-2 Chemical Structure| 88990-57-2

Structure of 88990-57-2

Chemical Structure| 88990-57-2

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Product Details of [ 88990-57-2 ]

CAS No. :88990-57-2
Formula : C8H11NO
M.W : 137.18
SMILES Code : OCC1=CC=C(N)C(C)=C1
MDL No. :MFCD04038446

Safety of [ 88990-57-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335-H412
Precautionary Statements:P261-P273-P305+P351+P338

Application In Synthesis of [ 88990-57-2 ]

* 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 [ 88990-57-2 ]

[ 88990-57-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 80866-75-7 ]
  • [ 88990-57-2 ]
YieldReaction ConditionsOperation in experiment
99% palladium-carbon; In ethanol; Example 79 Preparation of 4-(hydroxymethyl)-2-methylaniline (105) (Literature reference for making this compound see: Sun, J.-H.; Teleha, C. A.; Yan, J.-S.; Rodgers, J. D.; Nugiel, D. A. J. Org. Chem. 1997, 62, 5627-5629). A solution of <strong>[80866-75-7]3-methyl-4-nitrobenzyl alcohol</strong> (compound 104, 8.5 g, 50.9 mmol) in ethanol (100 mL) was stirred at room temperature, while 10% Pd/C (1.0 g) was added in one portion. The resulting suspension was hydrogenated (10 psi) in a Parr apparatus at room temperature for 1.5 hours. The catalyst was removed by filtration, and solvent was evaporated under vacuum to give the title compound (105, 6.9 g, 99%). MS (electrospray) 138 (M+1); 1H N MR (CDCl3) δ 2.16 (s, 3H), 2.72 (br s, 3H), 4.52 (s, 2H), 6.64 (d, 1H, J=8.0 Hz), 7.02 (d, 1H, J=8.0 Hz), 7.05 (s, 1H). Use of high pressure (30 Psi) of hydrogen and a long reaction time (8 hours) resulted a hydrogenolysis product. The same starting material (104) (21.05 g, 126 mmol) yielded 2,4-dimethylaniline (15.20 g, 100%) under such conditions. MS (electrospray) 122 (M+1); 1H N MR (CDCl3) δ 2.14 (s, 3H), 2.23 (s, 3H), 3.72 (br s, 1H), 6.58 (d, 1H, J=8.0 Hz), 6.84 (d, 1H, J=8.0 Hz), 6.87 (s, 1H).
99% palladium-carbon; In ethanol; Example 68 Preparation of 4-(hydroxymethyl)-2-methylaniline (90) (Literature reference for making this compound see: Sun, J.-H.; Teleha, C. A.; Yan, J.-S.; Rodgers, J. D.; Nugiel, D. A. J. Org. Chem. 1997, 62, 5627-5629). A solution of <strong>[80866-75-7]3-methyl-4-nitrobenzyl alcohol</strong> (compound 89, 8.5 g, 50.9 mmol) in ethanol (100 mL) was stirred at room temperature, while 10% Pd/C (1.0 g) was added in one portion. The resulting suspension was hydrogenated (10 psi) in a Parr apparatus at room temperature for 1.5 hours. The catalyst was removed by filtration, and solvent was evaporated under vacuum to give the title compound (90, 6.9 g, 99%). MS (electrospray) 138 (M+1); 1H N MR (CDCl3) δ2.16 (s, 3H), 2.72 (br s, 3H), 4.52 (s, 2H), 6.64 (d, 1H, J=8.0 Hz), 7.02 (d, 1H, J=8.0 Hz), 7.05 (s, 1H). Use of high pressure (30 Psi) of hydrogen and a long reaction time (8 hours) resulted a hydrogenolysis product. The same starting material (89) (21.05 g, 126 mmol) yielded 2,4-dimethylaniline (15.20 g, 100%) under such conditions. MS (electrospray) 122 (M+1); 1H N MR (CDCl3) δ2.14 (s, 3H), 2.23 (s, 3H), 3.72 (br s, 1H), 6.58 (d, 1H, J=8.0 Hz), 6.84 (d, 1H, J=8.0 Hz), 6.87 (s, 1H).
97% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; Example 4F1-(Tetrahydro-pyran-2-yl-1 H-indazo-5-yl}-methylamine: synthesized as described in the reference. JOC, 62, 5627(1997).268 269 270Part A:A mixture of 3-methyl -4-nitro benzyl alcohol 264 (2.10 g, 12.6 mmol) and 10% Palladium on carbon (0.2 g) in 25 mL of EtOH was hydrogenated at room temperature. After completion of the reaction, the catalyst was removed by filtration. <n="143"/>The solvent was evaporated and residue dried in a vacuum to give title compound as yellow solid 1.7 g, 97% ), 1H NMR (CDCI3), δ 7.06(s,1 H),7.03(d, J=8.0 Hz, 1 H), 6.66 (d, J=7.7 Hz, 1 H), 4.53 (s, 1 H), 3.62(br, 2H), 2.17 (s, 3H); mass calculated for compound 265 is 137.17, observed LCMS m/z 138.2 (M+H).
91.4% With hydrogen;palladium 10% on activated carbon; In methanol; at 25℃; A solution of <strong>[80866-75-7]3-methyl-4-nitrobenzyl alcohol</strong> (Aldrich; 2.000 g; 12.0 mmol) in MeOH (90 ml) is passed through the H-Cube flow hydrogenator fitted with a 10 mol% Pd/C catalyst cartridge (30 x 4 mm) heated to 25 0C with the full hydrogen option enabled. The flow rate is set at 1 mL/min. Solvent was removed to give the title compound (1.50 g, 91.4 %) without further purification. MS (ESI+): 138.1. HPLC (Condition A): Rt 1.41 min (HPLC purity 53.8 %).

  • 2
  • [ 80866-75-7 ]
  • [ 88990-57-2 ]
  • [ 95-68-1 ]
YieldReaction ConditionsOperation in experiment
palladium-carbon; In ethanol; Example 100 Preparation of 4-(Hydroxymethyl)-2-methylaniline (12-2) (Literature reference for making this compound see: Sun, J. -H.; Teleha, C. A.; Yan, J. -S.; Rodgers, J. D.; Nugiel, D. A. J. Org. Chem. 1997, 62, 5627-5629). A solution of <strong>[80866-75-7]3-methyl-4-nitrobenzyl alcohol</strong> (compound 12-1, 8.5 g, 50.9 mmol) in ethanol (100 mL) was stirred at room temperature, while 10% Pd/C (1.0 g) was added in one portion. The resulting suspension was hydrogenated (10 psi) in a Parr apparatus at room temperature for 1.5 hours. The catalyst was removed by filtration, and solvent was evaporated under vacuum to give the title compound (12-2, 6.9 g, 99%). MS (electrospray) 138 (M+1); 1H N MR (CDCl3) δ 2.16 (s, 3H), 2.72 (br s, 3H), 4.52 (s, 2H), 6.64 (d, 1H, J=8.0 Hz), 7.02 (d, 1H, J=8.0 Hz), 7.05 (s, 1H). Use of high pressure (30 Psi) of hydrogen and a long reaction time (8 hours) resulted a hydrogenolysis product. The same starting material (12-14 1) (21.05 g, 126 mmol) yielded 2,4-dimethylaniline (12-16p) (15.20 g, 100%) under such conditions. MS (electrospray) 122 (M+1); 1H N MR (CDCl3) δ 2.14 (s, 3H), 2.23 (s, 3H), 3.72 (br s, 1H), 6.58 (d, 1H, J=8.0 Hz), 6.84 (d, 1H, J=38.0 Hz), 6.87 (s, 1H).
 

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