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[ CAS No. 72985-23-0 ]

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2D
Chemical Structure| 72985-23-0
Chemical Structure| 72985-23-0
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Product Details of [ 72985-23-0 ]

CAS No. :72985-23-0MDL No. :MFCD12547299
Formula : C9H8O2 Boiling Point : 332.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :148.16Pubchem ID :638756
Synonyms :

Computed Properties of [ 72985-23-0 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.22 Rotatable Bond Count : 0

Safety of [ 72985-23-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 72985-23-0 ]

  • Upstream synthesis route of [ 72985-23-0 ]
  • Downstream synthetic route of [ 72985-23-0 ]

[ 72985-23-0 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 177166-15-3 ]
  • [ 72985-23-0 ]
YieldReaction ConditionsOperation in experiment
96% With calcium hydroxide In methanol Step 4:
6-methylphthalide
A total of 107 g (472 mmol) of 6-bromomethylphthalide was dissolved in 50 mL of methanol (dioxane was also used in different experiment).
The solution was added to a parr bottle with 40 g (540 mmol) of calcium hydroxide and 2 g of 10percent Pd/C.
The suspension was hydrogenated at 40 psi until no more hydrogen uptake was recorded.
All solids were filtered and filtrate was concentrated to a total of 67 g of brown solid in 96percent yield. 1H NMR (CDCl3) (300 MHz) δ 2.53 (s, 3H), 5.30 (s, 2H), 7.49 (s 1H), 7.54 (d, 3JHCCH=7.9 Hz, 1H), 7.47 (d, 3JHCCH=7.9 Hz, 1H)
96% With hydrogen; calcium hydroxide In methanol Step 4:
6-methylphthalide
A total of 107 g (472 mmol) of 6-bromomethylphthalide was dissolved in 50 mL of methanol (dioxane was also used in different experiment).
The solution was added to a parr bottle with 40 g (540 mmol) of calcium hydroxide and 2 g of 10percent Pd/C.
The suspension was hydrogenated at 40 psi until no more hydrogen uptake was recorded.
All solids were filtered and filtrate was concentrated to a total of 67 g of brown solid in 96percent yield. 1H NMR (CDCl3) (300 MHz) δ 2.53 (s, 3H), 5.30 (s, 2H), 7.49 (s 1H), 7.54 (d, 3JHCCH=7.9 Hz, 1H), 7.47 (d, 3JHCCH=7.9 Hz, 1H)
Reference: [1] Patent: US2008/277622, 2008, A1,
[2] Patent: US2011/251395, 2011, A1, . Location in patent: Page/Page column 14
[3] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 201 - 217
  • 2
  • [ 19477-73-7 ]
  • [ 594-27-4 ]
  • [ 72985-23-0 ]
YieldReaction ConditionsOperation in experiment
88% With tris-(o-tolyl)phosphine In N,N,N,N,N,N-hexamethylphosphoric triamide at 50℃; for 2 h; Tris(dibenzylideneacetone)dipalladium (0) (30 mg, 0.033 mmol), tri-o-tolylphosphine (40 mg, 0.13 mmol), and tetramethyltin (600 mg, 3.35 mmol) were dissolved in hexamethylphosphoramide (0.6 ml), and 6-bromo-1(3H)-isobenzofuranone (144 mg, 0.676 mmol) obtained from Example 26-(2) was added thereto, then the mixture was heated at 50°C for 2 hours. After cooling the reaction mixture, the mixture was diluted with ethyl acetate, and washed successively twice with water and twice with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was subjected to chromatography on a silica gel (5 g) column (eluent; hexane : ethyl acetate = 3 : 1). The fractions containing the target compound were concentrated, and the obtained solid was recrystallized to afford the title compound (88.3 mg, 88percent yield) as a crystalline solid. NMR spectrum (400 MHz, CDCl3) δ ppm: 2.472 (3H, s), 5.284 (2H, s), 7.376 (1H, d, J=8 Hz), 7.497 (1H, d, J=8 Hz), 7.721 (1H, s).
Reference: [1] Patent: EP1362856, 2003, A1, . Location in patent: Page/Page column 160
  • 3
  • [ 201230-82-2 ]
  • [ 126156-20-5 ]
  • [ 72985-23-0 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In acetonitrile at 250℃; for 24 h; Autoclave General procedure: A magnetic stirring bar, 2-iodobenzyl alcohol (1a, 116.0 mg, 0.5 mmol), NEt3 (251.6 mg, 2.5 mmol), and MeCN (10 mL) were placed in a stainless steel autoclave equipped with an inserted Pyrex glass liner. The autoclave was closed, purged three times with carbon monoxide, pressurized with 65 atm of CO and then heated at 250 °C by salt bath with stirring for 16 h. After the reaction, excess CO was discharged at room temperature. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (hexane/EtOAc = 3/1) to give 2a (60.4 mg, 91percent) as a white solid.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 15, p. 3015 - 3021
  • 4
  • [ 610-72-0 ]
  • [ 72985-23-0 ]
YieldReaction ConditionsOperation in experiment
52% With ammonium iodide; Oxone; potassium bromide In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 12 h; Green chemistry General procedure: To a mixture of MeCN and CF3CH2OH (6:4) (5.0 mL), carboxylic acid 1 (0.5 mmol), NH4I (0.25mmol), KBr (0.4 mmol) and Oxone○® (0.75 mmol) were added. The resulting solution was stirred at room temperature for 12 h and then solvents were removed under reduced pressure. Water (10mL), sat. aq Na2S2O3 (4 mL) and sat. aq Na2CO3 (4 mL) were added to the residue and the mixture was stirred for another 5 min. The mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative TLC on silica gelusing (hexane-AcOEt 3:1) as eluant to give the pure product of aryl lactone 2.
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 51, p. 12236 - 12239
[2] Helvetica Chimica Acta, 2014, vol. 97, # 6, p. 854 - 860
[3] Synthetic Communications, 2014, vol. 44, # 11, p. 1608 - 1613
[4] Patent: US2011/251395, 2011, A1,
  • 5
  • [ 74-95-3 ]
  • [ 99-04-7 ]
  • [ 72985-23-0 ]
Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, # 33, p. 6097 - 6100[2] Angewandte Chemie, 2009, vol. 121, # 33, p. 6213 - 6216
  • 6
  • [ 848498-20-4 ]
  • [ 72985-23-0 ]
YieldReaction ConditionsOperation in experiment
29.9% With calcium carbonate In 1,4-dioxane; water for 5 h; Reflux 6. 6-Methylisobenzofuran- 1 (3H)-one; A heterogeneous, colorless solution of methyl 2-(bromomethyl)-5- methylbenzoate and regioisomer (27.2 mmol) and calcium carbonate (16.33 g, 163 mmol) in 1,4-dioxane (194 mL) and water (194 mL) was refluxed. After 5 hr, the reaction was cooled to room temperature. The insolubles were filtered, and the filtrate wasconcentrated in vacuo. The residue was extracted with CH2CL2 (2 x 200 mL). The organic layers were combined, dried over MgSO4, and concentrated in vacuo to give an oil which was purified by flash chromatography using an ISCO 220g column eluting with 10-50percent EtOAc/hexanes. Appropriate fractions were collected and concentrated in vacuo to give the desired product (1.205 g, 8.13 mmol, 29.9percent yield) as a white solid.
Reference: [1] Patent: WO2011/159857, 2011, A1, . Location in patent: Page/Page column 126-127
  • 7
  • [ 75-09-2 ]
  • [ 99-04-7 ]
  • [ 72985-23-0 ]
Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, # 33, p. 6097 - 6100[2] Angewandte Chemie, 2009, vol. 121, # 33, p. 6213 - 6216
  • 8
  • [ 72985-22-9 ]
  • [ 72985-23-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 8, p. 1428 - 1435
  • 9
  • [ 124-38-9 ]
  • [ 72985-23-0 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 11, p. 2501 - 2505
  • 10
  • [ 13730-55-7 ]
  • [ 72985-23-0 ]
Reference: [1] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 201 - 217
[2] Patent: US2011/251395, 2011, A1,
[3] Patent: WO2011/159857, 2011, A1,
  • 11
  • [ 74725-06-7 ]
  • [ 72985-23-0 ]
Reference: [1] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 201 - 217
[2] Patent: US2011/251395, 2011, A1,
  • 12
  • [ 610-72-0 ]
  • [ 72985-23-0 ]
  • [ 72985-21-8 ]
  • [ 72985-20-7 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 8, p. 1428 - 1435
[2] Journal of Organic Chemistry, 1980, vol. 45, # 8, p. 1428 - 1435
  • 13
  • [ 90534-49-9 ]
  • [ 54120-64-8 ]
  • [ 72985-23-0 ]
Reference: [1] ChemCatChem, 2014, vol. 6, # 1, p. 109 - 112
[2] ChemCatChem, 2015, vol. 7, # 5, p. 865 - 871
  • 14
  • [ 589-18-4 ]
  • [ 201230-82-2 ]
  • [ 72985-23-0 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 7, p. 1900 - 1907
  • 15
  • [ 72985-20-7 ]
  • [ 72985-23-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 8, p. 1428 - 1435
  • 16
  • [ 19438-61-0 ]
  • [ 54120-64-8 ]
  • [ 72985-23-0 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 21, p. 4796 - 4799
  • 17
  • [ 589-18-4 ]
  • [ 72985-23-0 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 11, p. 2501 - 2505
  • 18
  • [ 4316-23-8 ]
  • [ 54120-64-8 ]
  • [ 72985-23-0 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 5, p. 865 - 871
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