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[ CAS No. 4442-53-9 ]

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Chemical Structure| 4442-53-9
Chemical Structure| 4442-53-9
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CAS No. :4442-53-9 MDL No. :MFCD00239415
Formula : C9H8O4 Boiling Point : 334.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :180.16 g/mol Pubchem ID :78184
Synonyms :

Safety of [ 4442-53-9 ]

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 [ 4442-53-9 ]

  • Upstream synthesis route of [ 4442-53-9 ]
  • Downstream synthetic route of [ 4442-53-9 ]

[ 4442-53-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 29668-43-7 ]
  • [ 4442-53-9 ]
YieldReaction ConditionsOperation in experiment
0.332 g
Stage #1: With aminosulfonic acid In water; acetone at 0 - 5℃; for 0.333333 h;
Stage #2: With sodium chlorite In water; acetone at 22 - 26℃; for 18 h;
A solution of 2,3-dihydrobenzo[b][l,4]dioxine-5-carbaldehyde (0.500 g, 3.04 mmol) in acetone (10 mL) was stirred at 0-5°C and aqueous solution of sulphamic acid (0.455 g, 4.5 mmol) was added. The reaction mass was stirred for 20 min. Then aqueous solution of sodium chlorite (0.421 g, 4.5 mmol) was added and the reaction was further continued at RT for 18 h. After completion of reaction, reaction mixture was concentrated under reduced pressure and reaction mass was quenched with water. Solid obtained was filtered off and vacuum dried to afford 0.332 g of desired product. 1H NMR (DMSO-de): δ 4.27 (s, 4H), 6.84 (t, J = 7.2 Hz, 1H), 7.02 (d, J = 7.8 Hz, 1H), 7.20 (d, J= 7.5 Hz, 1H), 12.5 (bs, 1H); MS [M+H]+: 181.12.
Reference: [1] Patent: WO2013/153535, 2013, A1, . Location in patent: Page/Page column 63
  • 2
  • [ 303-38-8 ]
  • [ 106-93-4 ]
  • [ 4442-53-9 ]
Reference: [1] Journal of Organic Chemistry, 1948, vol. 13, p. 489,493
[2] Patent: US5919814, 1999, A,
  • 3
  • [ 2411-83-8 ]
  • [ 4442-53-9 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 11, p. 2947 - 2954
[3] Patent: CN106905335, 2017, A,
  • 4
  • [ 303-38-8 ]
  • [ 4442-53-9 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 11, p. 2947 - 2954
[3] Patent: CN106905335, 2017, A,
  • 5
  • [ 24677-78-9 ]
  • [ 4442-53-9 ]
Reference: [1] Patent: WO2013/153535, 2013, A1,
  • 6
  • [ 493-09-4 ]
  • [ 124-38-9 ]
  • [ 4442-53-9 ]
  • [ 4442-54-0 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 92, p. 14360 - 14363
  • 7
  • [ 493-09-4 ]
  • [ 124-38-9 ]
  • [ 4442-53-9 ]
  • [ 4442-54-0 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 92, p. 14360 - 14363
  • 8
  • [ 4442-53-9 ]
  • [ 214894-89-0 ]
Reference: [1] Patent: WO2017/155909, 2017, A1,
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
  • 9
  • [ 4442-53-9 ]
  • [ 274910-19-9 ]
YieldReaction ConditionsOperation in experiment
99% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18 h; To a solution of 2,3-dihydrobenzo[£][l,4]dioxine-5-carboxylic acid (5.00 g, 28.0 mmol) in THF (150 mL) at 0 °C was added lithium aluminium hydride (2.13 g, 56.0 mmol) in small portions. The reaction mixture was stirred at 0 °C for 10 min and stirred for a further 18 h at r.t. Water (150 mL) was added to the reaction mixture which was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 20 as yellow oil (3.22 g, 99percent). 1H NMR (CDC13) δ 6.87-6.79 (m, 3H), 4.66 (s, 2H), 4.32-4.30 (m, 2H), 4.28-4.25 (m, 2H), 2.19 (bs, 1H). Found: [M+H-18]=149.5
99% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18 h; 4.1.1.1. 6-Bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methyl)-2-methoxyquinoline (VI: Y = 2,3-O(CH2)2O–). To a solution of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid (5.00 g, 28.0 mmol)in THF (150 mL) at 0 C was added lithium aluminium hydride(2.13 g, 56.0 mmol) in small portions. The reaction mixture wasstirred at 0 C for 10 min and stirred for a further 18 h at 20 C.Water (150 mL) was added to the reaction mixture which wasextracted with EtOAc (2 100 mL). The combined organic layerswere washed with brine (100 mL), dried over Na2SO4, filteredand concentrated under reduced pressure to obtain (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol as a yellow oil (3.22 g,99percent). 1H NMR (CDCl3, 400 MHz) d 6.87–6.79 (m, 3H), 4.66 (s, 2H),4.32–4.30 (m, 2H), 4.28–4.25 (m, 2H), 2.19 (bs, 1H). Found: [M+H-18] = 149.5.
Reference: [1] Patent: WO2017/155909, 2017, A1, . Location in patent: Paragraph 0075
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
  • 10
  • [ 4442-53-9 ]
  • [ 64-17-5 ]
  • [ 261767-10-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 11, p. 1110 - 1118
[2] Patent: CN103664910, 2017, B, . Location in patent: Paragraph 011
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