[ CAS No. 13623-25-1 ]

{[proInfo.proName]}

Quality Control

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc.

SDS

Product Details

CAS No. :13623-25-1MDL No. :MFCD00021232
Formula :C10H10O2InChI Key :UJGDLLGKMWVCPT-UHFFFAOYSA-N
M.W :162.19Pubchem ID :334036
Boiling Point :291.7°C at 760 mmHg
Synonyms :

Computed Properties

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : 1.6 H-Bond Donor Count : 0
SP3 : 0.30 Rotatable Bond Count : 1

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 13623-25-1 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 1929-29-9 ]
  • [ 13623-25-1 ]
YieldReaction ConditionsOperation in experiment
100% With trifluorormethanesulfonic acid In dichloromethane at 0 - 80℃; for 1.00 h; High pressure; Inert atmosphere; Green chemistry General procedure: Trifluoromethane sulfonic acid (3 eq.) was gently added to a cooled (0 °C) solution of a 3-Phenylpropionic acid (0.5 mmol) in dry CH2Cl2 (1.0 mL) in a 12 mL Q-tube™ pressure tube, furnished by QLabtech. The temperature was raised to room temperature. A Teflon septum was placed on the top of the tube and the appropriate cap and pressure adapter were used. The mixture was heated in an oil bath at 80 °C. The reaction was monitored by TLC and GC/MS until the reactant disappeared. The mixture was poured into ice and extracted three times with CH2Cl2. The organic phase collected was dried on Na2SO4, filtered and concentrated under vacuum. The desired pure product was separated from the crude by flash chromatography.
88% With thionyl chloride In dichloromethane (a)
To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0.279 mol) in 500 ml of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 ml (0.418 mol) of thionyl chloride, the mixture was stirred 10 h, at room temperature and the solvent was removed in vacuo.
The residue was dissolved in 1000 ml of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was sitrred at room temperature for 1 h.
The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 ml).
The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone.
88% With thionyl chloride In dichloromethane (a)
To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0,279 mol) in 500 mL of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 mL (0.418 mol) of thionyl chloride, the mixture was stirred 10 h at room temperature and the solvent was removed in vacuo.
The residue was dissolved in 1000 mL of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was stirred at room temperature for 1 h.
The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 mL).
The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone.
Reference: [1] Molecules, 2014, vol. 19, # 5, p. 5599 - 5610
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 5, p. 470 - 475
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
[4] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[5] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1741 - 1745
[6] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[7] Journal of the American Chemical Society, 1945, vol. 67, p. 1853
[8] Journal of the American Chemical Society, 1949, vol. 71, p. 1092,1095
[9] Yakugaku Zasshi, 1956, vol. 76, p. 163,165, 166[10] Chem.Abstr., 1956, p. 13850
[11] Angewandte Chemie, 1954, vol. 66, p. 435
[12] Monatshefte fuer Chemie, 1978, vol. 109, p. 405 - 419
[13] Chemische Berichte, 1969, vol. 102, p. 3656 - 3665
[14] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 4, p. 687 - 695
[15] Heterocycles, 1988, vol. 27, # 9, p. 2213 - 2217
[16] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 407 - 412
[17] Patent: US5569655, 1996, A
[18] European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 25 - 37
[19] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[20] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5788 - 5793
[21] Patent: US5554620, 1996, A
  • 2
  • [ 557775-38-9 ]
  • [ 13623-25-1 ]
YieldReaction ConditionsOperation in experiment
75% With trifluorormethanesulfonic acid In chloroform at 50℃; General procedure: The 4-nitrophenylamides (10-16) also underwent very efficient intramolecular reactions (Table 1). For example, amide 10 (R═H) provided 1-indanone (17) in 90percent yield upon reaction with CF3SO3H in CHCl3. The 4-nitroaniline by-product may be isolated with up to 90percent recovery. Other acids were studied in this conversion (H2SO4, CF3CO2H, AlCl3, HY-zeolite, Sc(OTf)3), but none successfully converted 10 to the indanone 17. Amides 11-13 also gave the corresponding substituted 1-indanones (18-20) in good yields. The amide 10′ (below), also gave the corresponding substituted 1-indanone 17′ (below), in 68percent yield (other isomers were also obtained).
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5788 - 5793
[2] Patent: US2013/267712, 2013, A1. Location in patent: Paragraph 0038-0039
  • 3
  • [ 201230-82-2 ]
  • [ 3989-14-8 ]
  • [ 13623-25-1 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 20, p. 5386 - 5392
  • 4
  • [ 5111-69-3 ]
  • [ 13623-25-1 ]
  • [ 5111-70-6 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 11, p. 1385 - 1388
[2] Synthesis, 1994, # 9, p. 915 - 916
[3] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8767 - 8772
[4] European Journal of Organic Chemistry, 2003, # 3, p. 578 - 586
[5] ChemCatChem, 2013, vol. 5, # 1, p. 126 - 129
  • 5
  • [ 62803-47-8 ]
  • [ 74-88-4 ]
  • [ 13623-25-1 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 1, p. 452 - 458
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2436 - 2441
  • 6
  • [ 123-11-5 ]
  • [ 13623-25-1 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[3] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[4] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
  • 7
  • [ 1929-29-9 ]
  • [ 13623-25-1 ]
  • [ 146301-02-2 ]
  • [ 13577-08-7 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
[2] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
[3] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
  • 8
  • [ 3469-09-8 ]
  • [ 13623-25-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 5875 - 5880
  • 9
  • [ 15893-42-2 ]
  • [ 13623-25-1 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 14, p. 2517 - 2520
[2] Journal of Organic Chemistry, 1970, vol. 35, p. 647 - 651
[3] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
  • 10
  • [ 943-89-5 ]
  • [ 13623-25-1 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
  • 11
  • [ 3901-07-3 ]
  • [ 13623-25-1 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
  • 12
  • [ 439660-64-7 ]
  • [ 13623-25-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 387 - 390
  • 13
  • [ 15823-04-8 ]
  • [ 13623-25-1 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
  • 14
  • [ 180915-76-8 ]
  • [ 13623-25-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 387 - 390
  • 15
  • [ 830-09-1 ]
  • [ 13623-25-1 ]
Reference: [1] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
  • 16
  • [ 54125-02-9 ]
  • [ 77970-18-4 ]
  • [ 13623-25-1 ]
  • [ 5111-70-6 ]
Reference: [1] Tetrahedron Letters, 1981, vol. 22, p. 603 - 606
Related Products
Historical Records

Related Functional Groups

Aryls

Chemical Structure| 5111-70-6

[ 5111-70-6 ]

5-Methoxy-1-indanone

Similarity: 1.00

Chemical Structure| 28596-75-0

[ 28596-75-0 ]

6-Methoxy-7-methyl-2,3-dihydro-1H-inden-1-one

Similarity: 0.98

Chemical Structure| 6836-19-7

[ 6836-19-7 ]

7-Methoxy-1-tetralone

Similarity: 0.96

Chemical Structure| 1078-19-9

[ 1078-19-9 ]

6-Methoxy-3,4-dihydronaphthalen-1(2H)-one

Similarity: 0.96

Chemical Structure| 1023-17-2

[ 1023-17-2 ]

1-(4-Methoxyphenyl)-2-phenylethanone

Similarity: 0.95

Ketones

Chemical Structure| 5111-70-6

[ 5111-70-6 ]

5-Methoxy-1-indanone

Similarity: 1.00

Chemical Structure| 28596-75-0

[ 28596-75-0 ]

6-Methoxy-7-methyl-2,3-dihydro-1H-inden-1-one

Similarity: 0.98

Chemical Structure| 6836-19-7

[ 6836-19-7 ]

7-Methoxy-1-tetralone

Similarity: 0.96

Chemical Structure| 1078-19-9

[ 1078-19-9 ]

6-Methoxy-3,4-dihydronaphthalen-1(2H)-one

Similarity: 0.96

Chemical Structure| 6500-65-8

[ 6500-65-8 ]

2-Methoxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one

Similarity: 0.95

Ethers

Chemical Structure| 5111-70-6

[ 5111-70-6 ]

5-Methoxy-1-indanone

Similarity: 1.00

Chemical Structure| 28596-75-0

[ 28596-75-0 ]

6-Methoxy-7-methyl-2,3-dihydro-1H-inden-1-one

Similarity: 0.98

Chemical Structure| 6836-19-7

[ 6836-19-7 ]

7-Methoxy-1-tetralone

Similarity: 0.96

Chemical Structure| 1078-19-9

[ 1078-19-9 ]

6-Methoxy-3,4-dihydronaphthalen-1(2H)-one

Similarity: 0.96

Chemical Structure| 6500-65-8

[ 6500-65-8 ]

2-Methoxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one

Similarity: 0.95