[ CAS No. 89424-83-9 ] {[proInfo.proName]}

Name: 89424-83-9|1,3-Dihydroisobenzofuran-5-carbaldehyde|95%
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SKU: A307286
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Quality Control of [ 89424-83-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 89424-83-9 ]

Product Details of [ 89424-83-9 ]

CAS No. :	89424-83-9	MDL No. :	MFCD09842492
Formula :	C₉H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WAYCQEPIQNTRDJ-UHFFFAOYSA-N
M.W :	148.16	Pubchem ID :	11389470
Synonyms :

Calculated chemistry of [ 89424-83-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.73
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	0.61
Log Po/w (WLOGP) :	1.23
Log Po/w (MLOGP) :	0.78
Log Po/w (SILICOS-IT) :	2.65
Consensus Log Po/w :	1.39

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.48
Solubility :	4.9 mg/ml ; 0.0331 mol/l
Class :	Very soluble
Log S (Ali) :	-0.74
Solubility :	27.2 mg/ml ; 0.183 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.62
Solubility :	0.358 mg/ml ; 0.00242 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 89424-83-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89424-83-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 89424-83-9 ]

[ 89424-83-9 ] Synthesis Path-Downstream 1~56

1
[ 89424-83-9 ]
[ 1450-72-2 ]
[ 90834-17-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 1151 - 1152

2
[ 89424-83-9 ]
C₁₃H₁₉NO₃P^(1-)*Li⁽¹⁺⁾ [ No CAS ]
[ 6974-47-6 ]
[ 598-02-7 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 1263 - 1266

3
[ 89424-83-9 ]
[ 118-93-4 ]
[ 90834-18-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 1151 - 1152

4
[ 75-15-0 ]
[ 89424-83-9 ]
[ 1573-17-7 ]
acetic acid 5-acetoxymethyl-2-(1,3-dihydro-isobenzofuran-5-ylmethylene)-[1,3]dithiol-4-ylmethyl ester [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 152,p. 185 - 190

5
[ 75-15-0 ]
[ 89424-83-9 ]
[ 19519-58-5 ]
[2-(1,3-dihydro-isobenzofuran-5-ylmethylene)-5-(dimethoxy-phosphoryl)-[1,3]dithiol-4-yl]-phosphonic acid dimethyl ester [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 152,p. 185 - 190

6
[ 75-15-0 ]
[ 89424-83-9 ]
[ 16356-02-8 ]
5-(4,5-bis-methoxymethyl-[1,3]dithiol-2-ylidenemethyl)-1,3-dihydro-isobenzofuran [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 152,p. 185 - 190

7
[ 89424-83-9 ]
[ 89424-84-0 ]

Reference： [1]Organic Preparations and Procedures International,2000,vol. 32,p. 596 - 600
[2]Chinese Journal of Chemistry,2011,vol. 29,p. 1180 - 1184

8
[ 89424-83-9 ]
[ 5464-68-6 ]
(E)-3-(1,3-Dihydro-isobenzofuran-5-yl)-acrylamide [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2000,vol. 164,p. 87 - 94

9
[ 89424-83-9 ]
[ 3842-86-2 ]
3-(1,3-dihydro-isobenzofuran-5-yl)-N,N-dimethyl-acrylamide [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2000,vol. 164,p. 87 - 94

10
[ 89424-83-9 ]
[ 89424-84-0 ]
1,2-bis-(1,3-dihydro-isobenzofuran-5-yl)-ethane-1,2-diol [ No CAS ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 547 - 551

11
[ 56-23-5 ]
[ 89424-83-9 ]
(Z)-2-Chloro-1,3-bis-(1,3-dihydro-isobenzofuran-5-yl)-prop-2-en-1-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 2179 - 2181

12
[ 89424-83-9 ]
[ 109-73-9 ]
Butyl-[1-(1,3-dihydro-isobenzofuran-5-yl)-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 842 - 843

13
[ 89424-83-9 ]
[ 62-53-3 ]
[ 49571-72-4 ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 842 - 843

14
[ 89424-83-9 ]
[ 100-46-9 ]
Benzyl-[1-(1,3-dihydro-isobenzofuran-5-yl)-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 842 - 843

15
acetic acid acetoxy-(1,3-dihydro-isobenzofuran-5-yl)-methyl ester [ No CAS ]
[ 89424-83-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 2632 - 2634

16
[ 120-72-9 ]
[ 89424-83-9 ]
C₂₅H₂₀N₂O [ No CAS ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3153 - 3160
[2]Synthetic Communications,2005,vol. 35,p. 2765 - 2769

17
[ 89424-83-9 ]
[ 5586-73-2 ]
N-[(3,4-methylenedioxy)benzylidene]-N-(3,3-diphenylpropyl)amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 492 - 499

18
2-(4-acetylphenylamino)-3-(2-chlorophenyl)-1,8-naphthyridine [ No CAS ]
[ 89424-83-9 ]
C₃₀H₂₀N₃O₃Cl [ No CAS ]

Reference： [1]Heterocyclic Communications,2007,vol. 13,p. 43 - 48

19
[ 89424-83-9 ]
N-(3,3-diphenylpropyl)-N-[(3,4-methylenedioxy)benzyl]amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 492 - 499

20
[ 89424-83-9 ]
N-(3,3-diphenylpropyl)-N-[(3,4-methylenedioxy)benzyl]-N'-phenylurea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 492 - 499

21
[ 89424-83-9 ]
N-(3,3-diphenylpropyl)-N-[3,4-(methylenedioxy)benzyl]-N'-phenylthiourea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 492 - 499

22
[ 89424-83-9 ]
4-[5-(1,3-dihydro-isobenzofuran-5-yl)-4-phenyl-4,5-dihydro-[1,2,4]oxadiazol-3-yl]-benzoic acid methyl ester [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 842 - 843

23
[ 89424-83-9 ]
4-[4-benzyl-5-(1,3-dihydro-isobenzofuran-5-yl)-4,5-dihydro-[1,2,4]oxadiazol-3-yl]-benzoic acid methyl ester [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 842 - 843

24
[ 89424-83-9 ]
4-[5-(1,3-dihydro-isobenzofuran-5-yl)-4-phenyl-4,5-dihydro-[1,2,4]oxadiazol-3-yl]-N-ethyl-benzamide [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 842 - 843

25
[ 89424-83-9 ]
4-[4-benzyl-5-(1,3-dihydro-isobenzofuran-5-yl)-4,5-dihydro-[1,2,4]oxadiazol-3-yl]-N-ethyl-benzamide [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 842 - 843

26
[ 89424-84-0 ]
[ 89424-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; acetone;	EXAMPLES 34-64 Using a similar procedure to that described in Example 33 but replacing benzaldehyde by the appropriate substituted aldehyde of the formula Ra. CHO, the following acids of formula Ib (benzene ring B is unsubstituted, Rb=H) were obtained in yields of 37-92% using either 10% v/v methanol in methylene chloride, 40% v/v acetone in methylene chloride, or 40:10:1 by (volume) toluene/ethyl acetate/acetic acid as the eluant for the flash chromatography. The aldehyde starting material for Example 64 was obtained as follows: To a solution of 1,3-dihydro(5-benzo[c]furyl)methanol (1.265 g.) in dry methylene chloride (10 ml.) was added pyridinium dichromate (3.23 g.) in one portion. The dark mixture was stirred for 90 minutes and diluted with ether (100 ml.). The suspension obtained was separated by filtration through diatomaceous earth. The residue was washed with ether (50 ml.) and the combined filtrate and washings evaporated. The residual oil was purified by flash column chromatography, eluding with 40% v/v ethyl acetate/hexane to give 1,3-dihydro(5-benzo[c]furyl)carboxaldehyde as a semi-solid mass (0.66 g.); NMR: 9.95 (1H,s); 7.7-7.8 (2H,m); 7.3 (1H d,J-8H) and 5.1 (4H,s)ppm.
	With Dess-Martin periodane; In dichloromethane; at 20℃; for 4h;	[(1,] 3-Dihydro-isobenzofuran-5-yl)-methanol (440mg, 2.9mmol) was dissolved in 20 ml of DCM. [1,] 1, [1-TRIACETOXY-1,] [1-DIHYDRO-1,] 2-benziodoxol-3 [(LH)-ONE] (Dess-Martin reagent) (1.3g, 3. [2MMOL)] was added and the reaction was stirred at r. t. for 4h. The reaction mixture was diluted with ether and extracted 2x with [NAOH] [IN,] 2x with [H2O] and dried over [MGS04.] The crude product was sufficiently pure and used without any further purification. HPLC: 2.00 min. [LC-MS] : M/Z ESI: 1.50 min, 149.18 [(M+1).]
	With manganese(IV) oxide; In dichloromethane; for 5h;Reflux;	A N,N-dimethylformamide solution (10 ml) of 5-(bromomethyl)- l,3-dihydro-2-benzofuran (0.7 g) and sodium acetate (0.54 g) was stirred at 700C for 3 hours. The reaction solution was diluted with t-butyl methyl ether, then washed with water and a saturated saline solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure to obtain l,3-dihydro-2-benzofuran-5-ylmethyl acetate as a crude product. The crude product thus obtained was dissolved in methanol (10 ml), sodium methoxide (0.05 g) was added thereto and the mixture was stirred for 1 hour at room temperature. The reaction solution was diluted with t-butyl methyl ether, then washed with water and a saturated saline solution, and the organic layer was dried over magnesium sulfate. The solvent was distilled off under a reduced pressure to obtain l,3-dihydro-2-benzofuran-5-ylmethanol as a crude product. The crude product thus obtained was dissolved in methylene chloride (20 ml), activated manganese (IV) oxide (2.3 g) was added thereto and the mixture was heated and refluxed for 5 hours. The reaction solution was filtered using Celite and the filtered solution was concentrated under a <n="122"/>reduced pressure. The resulting residue was purified with silica gel chromatography to obtain l,3-dihydro-2-benzofuran-5-carbaldehyde (0.35 g).1H-NMR (CDCl3) delta : 5.16 (4H, s), 7.39-7.41 (IH, m), 7.78-7.80 (2H, m), 10.02 (IH, s).

Reference： [1]Patent: US4567197,1986,A
[2]Patent: WO2004/7491,2004,A1 .Location in patent: Page 55
[3]Patent: WO2009/112275,2009,A1 .Location in patent: Page/Page column 120-121

27
[ 89424-83-9 ]
[ 583-60-8 ]
[ 91-59-8 ]
[ 1192269-65-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 587 - 590

28
[ 89424-83-9 ]
[ 1187196-50-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; at 20℃; for 1h;	Ethanol (10 ml) and water (6 ml) solution including 1 ,3-dihydro-2-benzofuran- -5-carbaldehyde (0.4 g), hydroxyamine hydrochloride (0.28 g) and sodium acetate (0.45 g) was stirred at room temperature for 1 hour. The reaction solution was diluted with t-butyl methyl ether, then washed with water and a saturated saline solution, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure to obtain l-(l,3-dihydro-2-benzofuran-5-yl)-N-hydroxymethanimine (0.2 g) as a crude product. The crude product thus obtained was dissolved in N,N-dimethylformamide (10 ml), N-chlorosuccinimide (0.18 g) was added thereto, and the mixture was stirred at room temperature for 2 hours. To the reaction solution, l,3-dichloro-5-[l-(trifluoromethyl)vinyl]benzene (0.2 g) was added. After cooled to 00C, potassium hydrogen carbonate (0.1 g) was added thereto and the mixture was stirred at room temperature for 8 hours. After adding water, extraction was carried out using t-butyl methyl ether. The organic layer was washed with a saturated saline solution, and then dried over magnesium sulfate. The solvent was distilled off under a reduced pressure and the resulting residue was purified with silica gel chromatography to obtain 5-(3,5-dichlorophenyl)- <n="123"/>3-(l ,3-dihydro-2-benzofuran-5-yl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (0.14 g).1H-NMR (CDCl3) delta : 3.72 (IH, d), 4.11 (IH, d), 5.11 (4H, s), 7.27-7.30 (IH, m), 7.41-7.41 (IH, m), 7.51-7.57 (4H, m).

Reference： [1]Patent: WO2009/112275,2009,A1 .Location in patent: Page/Page column 121-122
[2]Journal of Chemical Sciences,2019,vol. 131

29
[ 764-93-2 ]
[ 89424-83-9 ]
C₁₉H₂₈O₂ [ No CAS ]
C₁₉H₂₈O₂ [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 211 - 215

30
[ 89424-83-9 ]
[ 610-99-1 ]
3-(3,4-(methylenedioxy)phenyl)-3-hydroxy-1-(2-hydroxyphenyl)-2-methylpropan-1-one [ No CAS ]
3-(3,4-(methylenedioxy)phenyl)-3-hydroxy-1-(2-hydroxyphenyl)-2-methylpropan-1-one [ No CAS ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 2676 - 2688

31
[ 89424-83-9 ]
2-amino-4-(3,4-methylenedioxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-3-carbonitrile [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 68,p. 291 - 300

32
[ 89424-83-9 ]
[ 1470027-77-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 68,p. 291 - 300

33
[ 89424-83-9 ]
[ 109-77-3 ]
[ 2972-82-9 ]

Yield	Reaction Conditions	Operation in experiment
	With (2-aminomethyl)phenol moiety on the surface of hydroxyapatite encapsulated maghemite (gamma-Fe2O3); In water; for 0.0833333h;Reflux;	General procedure: A stirring mixture of an appropriate aldehyde (1mmol), malononitrile (1.2mmol), magnetic catalytic system (1.5mol %) and water (5mL) were heated under refluxing conditions for a few minutes. To this stirred mixture, 4-hydroxycoumarin (1mmol) was added. The reaction mixture was refluxed for 10-30min. The progress of the reaction was monitored by TLC. After completion of the reaction, it was allowed to cool at room temperature and the reaction mixture was diluted with ethyl acetate and the catalyst was easily separated from the reaction mixture with an external magnet and washed twice with ethyl acetate. The combined organic layers were concentrated in vacuum and the resulting residue was purified by recrystallization from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 68,p. 291 - 300

34
[ 89424-83-9 ]
[ 162011-91-8 ]
[ 1448459-06-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium carbonate; In methanol; at 65℃;	General procedure: Compound 2a or 11a or 11b (0.01 mol) and anhydrous sodium carbonate (0.01 mol) were dissolved in methanol solution, then the corresponding aldehyde or ketone (0.012 mol) was added. The mixture was stirred at 65 C for 3-8 h and the reaction was monitored by TLC until completion. Most of the target product can be precipitated from the reaction system. Filtration and drying was done to give a series of target compounds 12, 13 and 14. When the ketone was acetone the target product cannot be precipitated from reaction system. The reaction solution was evaporated under reduced pressure to steam out of most of the methanol, the reaction mixture was washed with water and ethyl acetate, dried and purified by column chromatography.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 65,p. 323 - 336

35
[ 5344-90-1 ]
[ 89424-83-9 ]
2-(1,3-dihydroisobenzofuran-5-yl)quinazoline [ No CAS ]