Home Cart 0 Sign in  

[ CAS No. 5312-97-0 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 5312-97-0
Chemical Structure| 5312-97-0
Structure of 5312-97-0 * Storage: {[proInfo.prStorage]}

Quality Control of [ 5312-97-0 ]

Related Doc. of [ 5312-97-0 ]

SDS
Alternatived Products of [ 5312-97-0 ]
Alternatived Products of [ 5312-97-0 ]

Product Details of [ 5312-97-0 ]

CAS No. :5312-97-0 MDL No. :MFCD00016375
Formula : C9H9NO2 Boiling Point : 638°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :163.17 g/mol Pubchem ID :79200
Synonyms :

Safety of [ 5312-97-0 ]

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 [ 5312-97-0 ]

  • Upstream synthesis route of [ 5312-97-0 ]
  • Downstream synthetic route of [ 5312-97-0 ]

[ 5312-97-0 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 5312-97-0 ]
  • [ 4640-29-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 24, p. 7032 - 7043
[2] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 7, p. 866 - 872
[3] Tetrahedron, 1965, vol. 21, p. 2231 - 2237
  • 2
  • [ 68-12-2 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2 h;
Stage #2: at 0℃; for 2 h;
Stage #3: With ammonia; iodine In tetrahydrofuran; hexane; water at 0 - 20℃; for 2 h;
General procedure: n-Butyllithium (1.67 M solution in hexane, 2.9 mL, 4.8 mmol) was added dropwise into a solution of 1,3-dimethoxybenzene (0.55 g, 4.0 mmol) in THF (5 mL) at 0 °C and the mixture was stirred for 2 h at the same temperature. Then, DMF (0.34 mL, 4.4 mmol) was added to the mixture and the obtained mixture was stirred at 0 °C. After 2 h at the same temperature, aq NH3 (8 mL, 120 mmol) and I2 (1.12 g, 4.4 mmol) were added and stirred for 2 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (15 mL) and was extracted with Et2O (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide 2,6-dimethoxybenzonitrile in over 80percent purity. The product was purified by a short column chromatography on silica gel (Hexane/EtOAc=3:1) to give pure 2,6-dimethoxybenzonitrile in 91percent yield as a colorless solid.
Reference: [1] Synlett, 2010, # 10, p. 1562 - 1566
[2] Tetrahedron, 2011, vol. 67, # 5, p. 958 - 964
  • 3
  • [ 93-61-8 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: at 0℃; for 0.5 h;
Stage #2: at 100℃; for 10 h;
Stage #3: With ammonia; iodine In tetrahydrofuran; water; N,N-dimethyl-formamide at 20℃; for 3 h;
General procedure: To an ice cooled solution of N-methylformanilide (2.2 mmol) was added dropwise diphosphoryl chloride (2.2 mmol). The solution was stirred for 30 min at 0 °C, and then 1,2-dimethoxybenzene (276.3 mg, 2 mmol) in DMF (1.0 mL) was added dropwise. After being stirred for 10 h at 100 °C, I2 (1015.2 mg, 4 mmol), aq NH3 (4 mL, 28-30percent) and THF (1 mL) were added to the reaction mixture. The obtained mixture was stirred for 3 h at rt. After the reaction, the mixture was poured into aq satd Na2SO3 solution and extracted with CHCl3 (3.x.20 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The product was purified by flash short column chromatography (Hexane:AcOEt=3:1) to afford 3,4-dimethoxybenzonitrile as a white solid in 92percent yield.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4588 - 4595
  • 4
  • [ 67184-41-2 ]
  • [ 5312-97-0 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With Bromotrichloromethane; triphenylphosphine In dichloromethane for 0.416667 h; Reflux
Stage #2: With triethylamine In dichloromethane for 8 h; Reflux
General procedure: BrCCl3 (940 mg, 4.8 mmol) was added to PPh3 (1.26 g, 4.8 mmol) in dry CH2Cl2 (14 mL). The resulting mixture was stirred at room temperature for 20 min, during which time the solution turned from yellow to red–brownish in colour. Thereafter,3,4-dimethoxybenzaldoxime (4i, 800 mg, 4.4 mmol) was added. The reaction mixture was heated under reflux for 25 min. Then, dry Et3N (485 mg, 4.8 mmol) was added dropwise with a syringe over 1 min. The reaction mixture was heated under reflux for 8 h. Thereafter, it was cooled to room temperature and added to cold water (50 mL). The mixture was extracted with dichloromethane (2 × 30 mL) and chloroform (30 mL). The combined organic phases were dried over anhydrous MgSO4, concentrated under reduced pressure and subjected to column chromatography on silica gel (CH2Cl2/hexane 4 : 1) to give 3,4-dimethoxybenzonitrile (2q, 665 mg, 92percent) as a colourless solid.
Reference: [1] Synlett, 2004, # 11, p. 2019 - 2021
[2] Journal of Chemical Research, 2014, vol. 38, # 2, p. 80 - 84
[3] Synthetic Communications, 1998, vol. 28, # 24, p. 4629 - 4637
  • 5
  • [ 93-02-7 ]
  • [ 5312-97-0 ]
Reference: [1] Synthesis, 1989, # 6, p. 451 - 452
[2] Journal of Organic Chemistry, 1985, vol. 50, # 8, p. 1182 - 1186
[3] Synthetic Communications, 1998, vol. 28, # 24, p. 4629 - 4637
[4] Tetrahedron Letters, 2013, vol. 54, # 17, p. 2177 - 2179
[5] Angewandte Chemie - International Edition, 2015, vol. 54, # 14, p. 4241 - 4245
  • 6
  • [ 5285-87-0 ]
  • [ 107099-99-0 ]
  • [ 5312-97-0 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 19, p. 4331 - 4333
  • 7
  • [ 3012-37-1 ]
  • [ 107099-99-0 ]
  • [ 5312-97-0 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 19, p. 4331 - 4333
  • 8
  • [ 2137-92-0 ]
  • [ 107099-99-0 ]
  • [ 5312-97-0 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 19, p. 4331 - 4333
  • 9
  • [ 542-90-5 ]
  • [ 107099-99-0 ]
  • [ 5312-97-0 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 19, p. 4331 - 4333
  • 10
  • [ 1758-25-4 ]
  • [ 5312-97-0 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 5, p. 914 - 918
  • 11
  • [ 3275-95-4 ]
  • [ 5312-97-0 ]
Reference: [1] Journal of Chemical Research - Part S, 1999, # 12, p. 726 - 727
  • 12
  • [ 2785-98-0 ]
  • [ 5312-97-0 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 6, p. 1115 - 1118
  • 13
  • [ 25245-35-6 ]
  • [ 544-92-3 ]
  • [ 5312-97-0 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 7, p. 866 - 872
[2] Tetrahedron, 1965, vol. 21, p. 2231 - 2237
  • 14
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 7, p. 866 - 872
[2] Justus Liebigs Annalen der Chemie, 1906, vol. 344, p. 46[3] Chemische Berichte, 1905, vol. 38, p. 796
  • 15
  • [ 186581-53-3 ]
  • [ 4640-29-3 ]
  • [ 5312-97-0 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 10, p. 1471 - 1476
  • 16
  • [ 42020-21-3 ]
  • [ 5312-97-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1906, vol. 344, p. 46[2] Chemische Berichte, 1905, vol. 38, p. 796
  • 17
  • [ 506-68-3 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
Reference: [1] Helvetica Chimica Acta, 1920, vol. 3, p. 266
  • 18
  • [ 143-33-9 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
  • [ 874-90-8 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1989, # 2, p. 156 - 167
Historical Records

Related Functional Groups of
[ 5312-97-0 ]

Nitriles

Chemical Structure| 6609-56-9

[ 6609-56-9 ]

2-Methoxybenzonitrile

Similarity: 0.98

Chemical Structure| 53078-69-6

[ 53078-69-6 ]

2-Methoxy-4-methylbenzonitrile

Similarity: 0.98

Chemical Structure| 4107-65-7

[ 4107-65-7 ]

2,4-Dimethoxybenzonitrile

Similarity: 0.95

Chemical Structure| 3556-60-3

[ 3556-60-3 ]

3-Methoxy-4-methylbenzonitrile

Similarity: 0.95

Chemical Structure| 473923-98-7

[ 473923-98-7 ]

3-Methoxy-5-methylbenzonitrile

Similarity: 0.95

Aryls

Chemical Structure| 6609-56-9

[ 6609-56-9 ]

2-Methoxybenzonitrile

Similarity: 0.98

Chemical Structure| 53078-69-6

[ 53078-69-6 ]

2-Methoxy-4-methylbenzonitrile

Similarity: 0.98

Chemical Structure| 4107-65-7

[ 4107-65-7 ]

2,4-Dimethoxybenzonitrile

Similarity: 0.95

Chemical Structure| 3556-60-3

[ 3556-60-3 ]

3-Methoxy-4-methylbenzonitrile

Similarity: 0.95

Chemical Structure| 473923-98-7

[ 473923-98-7 ]

3-Methoxy-5-methylbenzonitrile

Similarity: 0.95

Ethers

Chemical Structure| 6609-56-9

[ 6609-56-9 ]

2-Methoxybenzonitrile

Similarity: 0.98

Chemical Structure| 53078-69-6

[ 53078-69-6 ]

2-Methoxy-4-methylbenzonitrile

Similarity: 0.98

Chemical Structure| 4107-65-7

[ 4107-65-7 ]

2,4-Dimethoxybenzonitrile

Similarity: 0.95

Chemical Structure| 3556-60-3

[ 3556-60-3 ]

3-Methoxy-4-methylbenzonitrile

Similarity: 0.95

Chemical Structure| 473923-98-7

[ 473923-98-7 ]

3-Methoxy-5-methylbenzonitrile

Similarity: 0.95