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[ CAS No. 1075-26-9 ]

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2D
Chemical Structure| 1075-26-9
Chemical Structure| 1075-26-9
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Product Details of [ 1075-26-9 ]

CAS No. :1075-26-9MDL No. :MFCD02179595
Formula : C9H9NO Boiling Point : 360.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :147.17Pubchem ID :-
Synonyms :

Computed Properties of [ 1075-26-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 1075-26-9 ]

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

Application In Synthesis of [ 1075-26-9 ]

  • Upstream synthesis route of [ 1075-26-9 ]
  • Downstream synthetic route of [ 1075-26-9 ]

[ 1075-26-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1075-26-9 ]
  • [ 21005-45-8 ]
YieldReaction ConditionsOperation in experiment
24%
Stage #1: With Dess-Martin periodane In dichloromethane for 1 h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5 h;
a) 1 -Methyl- lH-indole-6-carbaldehyde; Dess-Martin periodane (2.56 g, 6.04 mmol) was dissolved into anhydrous CH2Cl2 (25 ml). (lH-Indol-6-yl)-methanol (883 mg, 6.04 mmol) in anhydrous CH2Cl2 (20 ml) was added and the mixture was stirred for 1 h. Aqueous sodium hydroxide (12 ml of IN solution) was added and the reaction was stirred for 30 min. The organic layer was separated and washed with water (10 ml), brine (10 ml), dried over MgSO4, filtered and concentrated to a thick brown oil. Purification by column chromatography (silica gel, gradient elution of 2percent MeOH/CH2Cl2 to 5percent MeOH/CH2Cl2) gave lH-indole-6-carbaldehyde (212 mg, 24percent) as a brown solid: 1H NMR (300 MHz, DMSO-d6) δ 11.67 (bs, IH), 9.99 (s, IH), 7.97 (s, IH), 7.70-7.65 (m, 2H), 7.54-7.50 (m, IH), 6.59-5.54 (m, IH).
Reference: [1] Patent: WO2007/53131, 2007, A2, . Location in patent: Page/Page column 157
  • 2
  • [ 1075-26-9 ]
  • [ 1196-70-9 ]
YieldReaction ConditionsOperation in experiment
82% With manganese dioxide In dichloromethane b.
6-Formylindole
Manganese dioxide (240 g) was added to a mechanically stirred solution of 6-hydroxymethylindole (40.7 g) in methylene chloride (1.6 liter).
The mixture was stirred for 18 hr, filtered through a pad of diatomaceous earth, the filter cake washed with methylene chloride and chloroform, and the filtrate evaporated to give 6-formylindole (30.55 g) as a yellow solid.
The filter cake was washed with tetrahydrofuran and the washings evaporated to give a further crop of 6-formylindole (2.35 g, 82percent combined yield); partial NMR (250 MHz, DMSO-d6): 6.58(m, 1H, H3 -indole), 10.00(s, 1H, CHO), 11.71(br s, 1H, NH).
56%
Stage #1: With Dess-Martin periodane In dichloromethane for 1 h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.25 h;
Dess-Martin periodinane (1.53 g, 2.6 mmol) was dissolved into methylene chloride (15 mL). Indol-6-yl-methanol (500 mg, 3.4 mmol) in methylene chloride (12 mL) was added and the mixture was stirred for 1 hr. Sodium hydroxide (5 mL of 1 N solution) was added and the reaction was stirred for 15 min. The organic layer was separated and washed with H20 (5 mL), brine (5 mL), dried over MGS04 and concentrated to afford the title compound as a brown solid (275 mg, 56percent). TH NMR (300 MHz, DMSO-D6) 8 11.7 (s, 1H), 9.98 (s, 1H), 7.97 (s, 1H), 7.70-7. 65 (m, 2H), 7.52 (dd, J= 8.2, 1.4 Hz, 1H), 6.57-6. 5 (m, 1H).
Reference: [1] Patent: US4894386, 1990, A,
[2] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115
[3] Patent: WO2004/52890, 2004, A1, . Location in patent: Page 46-47; 93-94
[4] Patent: US5281593, 1994, A,
[5] Patent: EP469833, 1992, A1,
  • 3
  • [ 32989-68-7 ]
  • [ 1196-70-9 ]
  • [ 1075-26-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115
  • 4
  • [ 32989-68-7 ]
  • [ 1196-70-9 ]
  • [ 1075-26-9 ]
  • [ 111596-29-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115
[2] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115
  • 5
  • [ 31680-07-6 ]
  • [ 1196-70-9 ]
  • [ 1075-26-9 ]
  • [ 111596-29-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115
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