[ CAS No. 35700-40-4 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 35700-40-4
Chemical Structure| 35700-40-4
Structure of 35700-40-4

Quality Control of [ 35700-40-4 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 35700-40-4 ]

SDS

Product Details of [ 35700-40-4 ]

CAS No. :35700-40-4MDL No. :MFCD00671526
Formula :C9H8O3Boiling Point :330.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :UHXBMSNEECJPSX-UHFFFAOYSA-N
M.W :164.16Pubchem ID :2795014
Synonyms :

Computed Properties of [ 35700-40-4 ]

TPSA : 46.5 H-Bond Acceptor Count : 3
XLogP3 : 1.5 H-Bond Donor Count : 1
SP3 : 0.22 Rotatable Bond Count : 1

Safety of [ 35700-40-4 ]

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

Application In Synthesis of [ 35700-40-4 ]

  • Upstream synthesis route of [ 35700-40-4 ]
  • Downstream synthetic route of [ 35700-40-4 ]

[ 35700-40-4 ] Synthesis Path-Upstream   1~17

  • 1
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  • [ 35700-40-4 ]
YieldReaction ConditionsOperation in experiment
54.7% With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane a.
Preparation of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a)
To a solution of n-BuLi (1.7 M, 123 ml, 0.21 mol) in 400 ml of hexane at room temperature was added 24.3 g (0.21 mol) of N,N,N',N'-tetramethylethylenediamine (TMEDA), followed by a hexane (40 ml) solution of 2,3-dihydrobenzo[b]furan (14) (12.56 g, 0.11 mol).
The mixture was stirred under argon at room temperature for 4 hours, and then poured into dry ice (pre-washing with anhydrous ether).
After stirring at ambient temperature overnight, the mixture was diluted with water (300 ml), and the layers separated.
The aqueous layer was acidified with conc. HCl to pH 1, cooled and the precipitate collected on a filter.
This was recrystallized from CH2 Cl2 to give 15a (9.43 g, 54.7percent) as a white solid, mp 167°-169.5° C.
54.7% With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane a.
Preparation of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a)
To a solution of n-BuLi (1.7 M, 123 ml, 0.21 mol) in 400 ml of hexane at room temperature was added 24.3 g (0.21 mol) of N,N,N',N'-tetramethylethylenediamine (TMEDA), followed by a hexane (40 ml) solution of 2,3-dihydrobenzo[b]furan (14) (12.56 g, 0.11 mol).
The mixture was stirred under argon at room temperature for 4 hours, and then poured into dry ice (pre-washing with anhydrous ether).
After stirring at ambient temperature overnight, the mixture was diluted with water (300 ml), and the layers separated.
The aqueous layer was acidified with conc. HCl to pH 1, cooled and the precipitate collected on a filter.
This was recrystallized from CH2Cl2 to give 15a (9.43 g, 54.7percent) as a white solid, mp 167-169.5°C.
18% With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; carbon dioxide In tetrahydrofuran; sodium hydroxide EXAMPLE 21
7-Carboxy-2,3-dihydrobenzofuran(22)
To a stirred solution of 2,3-dihydrobenzofuran (1 g, 0.0083 mol) and dry TMEDA (1 eq.) in dry tetrahydrofuran (30 mL) at -10° C. under argon, was added n-BuLi (1.6 M hexane solution) (5 mL, 0.008 mol).
The reaction mixture was maintained at this temperature for 20 min and then carbon dioxide was bubbled through the reaction mixture as it warmed to room temperature.
The reaction mixture was concentrated in vacuo to afford a yellow oil.
The oil was dissolved in 10percent sodium hydroxide (100 mL), washed with methylene chloride (2*25 mL), and acidified with HCl.
The white solid product was filtered, washed with water and air-dried to afford the carboxylic acid (22) (0.22 g, 18percent).
1 H NMR (CDCl3) δ 7.35(1H,d), 7.11(1H,d), 6.59(1H,t), 4.37(2H,t), 2.99(2H,t).
Reference: [1] Patent: US4888353, 1989, A
[2] Patent: EP234872, 1991, B1
[3] Patent: US5122361, 1992, A
  • 2
  • [ 496-16-2 ]
  • [ 124-38-9 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 24, p. 5567 - 5573
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999, vol. 54, # 11, p. 1469 - 1473
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 171 - 178
[5] Monatshefte fuer Chemie, 1990, vol. 121, # 11, p. 883 - 891
  • 3
  • [ 496-16-2 ]
  • [ 110-18-9 ]
  • [ 124-38-9 ]
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Reference: [1] Patent: US5519034, 1996, A
  • 4
  • [ 75934-15-5 ]
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 5
  • [ 119-36-8 ]
  • [ 35700-40-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 310 - 319
[2] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
[3] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 6
  • [ 496-16-2 ]
  • [ 110-18-9 ]
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Reference: [1] Patent: US6207678, 2001, B1
  • 7
  • [ 133844-95-8 ]
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Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 310 - 319
  • 8
  • [ 13661-90-0 ]
  • [ 35700-40-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 310 - 319
  • 9
  • [ 75855-24-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 310 - 319
  • 10
  • [ 69-72-7 ]
  • [ 35700-40-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 310 - 319
  • 11
  • [ 6282-42-4 ]
  • [ 35700-40-4 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 12
  • [ 75934-01-9 ]
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 13
  • [ 75934-00-8 ]
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 14
  • [ 75934-02-0 ]
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 15
  • [ 75934-03-1 ]
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 16
  • [ 75934-11-1 ]
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
  • 17
  • [ 31456-98-1 ]
  • [ 35700-40-4 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 4, p. 783 - 788
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