[ CAS No. 4687-25-6 ]

Name: Benzofuran-3-carbaldehyde
Brand: Ambeed
SKU: A187646
Rating: 95 (27 reviews)

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2D3D

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Quality Control of [ 4687-25-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4687-25-6 ]

SDS

Product Details of [ 4687-25-6 ]

CAS No. :	4687-25-6	MDL No. :	MFCD03412541
Formula :	C₉H₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	146.14	Pubchem ID :	12394139
Synonyms :

Computed Properties of [ 4687-25-6 ]

TPSA :Topological Polar Surface Area	30.2	H-Bond Acceptor Count :	2
XLogP3 :	1.8	H-Bond Donor Count :	0
SP3 :	0.00	Rotatable Bond Count :	1

Safety of [ 4687-25-6 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4687-25-6 ]

Upstream synthesis route of [ 4687-25-6 ]
Downstream synthetic route of [ 4687-25-6 ]

[ 4687-25-6 ] Synthesis Path-Upstream 1~12

1
[ 21535-97-7 ]
[ 4687-25-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With selenium(IV) oxide In 1,4-dioxane for 24.00 h; Reflux	3 -methyl benzofuran (200 mg, 0.19 ml, 1.5 mmol) and Se0₂ (200 mg, 1.8 mmol, 1.2 eq.) weresuspended in 1,4-dioxane (3 ml) and heated to reflux for 24 hours. The reaction mixture was allowed to cool, then diluted with EtOAc/hexane (2:1 v/v, 10 ml) and filtered through a short plug of silica to remove selenium residues. The silica plug was washed with EtOAc (2 x 3 ml) and the combined organic filtrate was evaporated to dryness and purified by silica gel column chromatography (hexane/EtOAc 96:4) to afford a yellow oil (162 mg, 1.1 mmol, 74 percent yield) . ^XH NMR (300 MHz, CDC1₃) δ 10.18 (s, 1H) , 8.26 (s, 1H) , 8.19 (m, 1H) , 7.54 (m, 1H) , 7.41 (m, 2H) ; ESI m/z = 147.0 (MH)⁺, calc . for C₉H₇0₂ = 147.04.

Reference： [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 2, p. 296 - 307
[2] Heterocycles, 2001, vol. 55, # 3, p. 569 - 577
[3] Tetrahedron Asymmetry, 2008, vol. 19, # 4, p. 500 - 511
[4] Patent: WO2012/110833, 2012, A2. Location in patent: Page/Page column 123
[5] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[6] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4
[7] Chemistry - A European Journal, 2006, vol. 12, # 10, p. 2739 - 2744
[8] Patent: WO2009/85256, 2009, A1. Location in patent: Page/Page column 39-40; 50
[9] Journal of Medicinal Chemistry, 2008, vol. 51, # 19, p. 6095 - 6109
[10] Molecules, 2011, vol. 16, # 7, p. 5527 - 5537
[11] Journal of the American Chemical Society, 2016, vol. 138, # 1, p. 458 - 458

2
[ 21535-97-7 ]
[ 4687-23-4 ]
[ 4687-25-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 17, p. 5981 - 5996
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6261 - 6276

3
[ 4687-23-4 ]
[ 4687-25-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 1, p. 95 - 103

4
[ 64175-51-5 ]
[ 4687-25-6 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 526 - 528
[2] Journal of Organic Chemistry, 2009, vol. 74, # 3, p. 1237 - 1246

5
[ 136229-42-0 ]
[ 4687-25-6 ]

Reference： [1] Australian Journal of Chemistry, 1991, vol. 44, # 7, p. 907 - 917

6
[ 63815-27-0 ]
[ 4687-25-6 ]

Reference： [1] Chemistry - A European Journal, 2006, vol. 12, # 10, p. 2739 - 2744
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[3] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

7
[ 1878-62-2 ]
[ 4687-25-6 ]

8
[ 118-93-4 ]
[ 4687-25-6 ]

9
[ 26537-68-8 ]
[ 4687-25-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 1, p. 95 - 103

10
[ 38281-60-6 ]
[ 4687-25-6 ]

Reference： [1] Australian Journal of Chemistry, 1991, vol. 44, # 7, p. 907 - 917

11
[ 7169-34-8 ]
[ 4687-25-6 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 526 - 528

12
[ 82156-58-9 ]
[ 4687-25-6 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 526 - 528

[ 4687-25-6 ] Synthesis Path-Downstream 1~10

1
[ 110-85-0 ]
[ 4687-25-6 ]
[ 586-89-0 ]
2-(3-aminopropyl)-4-pentenoic acid lithium salt [ No CAS ]
N-methylisatin2-(2-fluorophenyl)glycine [ No CAS ]
C₃₈H₃₃FN₄O₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 3677 - 3680

2
[ 21535-97-7 ]
[ 4687-25-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With selenium(IV) oxide; In 1,4-dioxane; for 24h;Reflux;	3 -methyl benzofuran (200 mg, 0.19 ml, 1.5 mmol) and Se02 (200 mg, 1.8 mmol, 1.2 eq.) weresuspended in 1,4-dioxane (3 ml) and heated to reflux for 24 hours. The reaction mixture was allowed to cool, then diluted with EtOAc/hexane (2:1 v/v, 10 ml) and filtered through a short plug of silica to remove selenium residues. The silica plug was washed with EtOAc (2 x 3 ml) and the combined organic filtrate was evaporated to dryness and purified by silica gel column chromatography (hexane/EtOAc 96:4) to afford a yellow oil (162 mg, 1.1 mmol, 74 % yield) . XH NMR (300 MHz, CDC13) delta 10.18 (s, 1H) , 8.26 (s, 1H) , 8.19 (m, 1H) , 7.54 (m, 1H) , 7.41 (m, 2H) ; ESI m/z = 147.0 (MH)+, calc . for C9H702 = 147.04.
41%	With selenium(IV) oxide; In 1,4-dioxane; for 16h;Reflux;	Compound E-3 (16 g, 121 mmol) was dissolved in 1,4-dioxane solution (100 mL), and then add selenium dioxide (17.5g, 157mmol), then, the mixture was stirred and refluxed for 16 hours. The reaction was cooled to room temperature, and the mixture was diluted with ethyl acetate /hexane (2:1, 100 mL). After stirring for 10 min, the insoluble material was removed by filtration and washed with ethyl acetate. The combined filtrates were concentrated under reduced pressure and purified by silica gel column chromatographyThe product was obtained as a yellow solid 7.3 g, yield 41%
	With selenium(IV) oxide; In 1,4-dioxane; for 48h;Heating / reflux;	3-Methylbenzofuran 3 (5.08 g, 38.5 mmol) is treated with SeO2 (5.10 g, 46.2 mmol) in accordance with Method D affording the title compound (3.08 g) after column chromatography (silica gel, 5% EtOAc in heptanes) as a light yellow wax: 1H NMR (360 MHz, CDCl3, deltaH) 10.19 (IH, s), 8.28 (IH, s), 8.20 (IH, dd), 7.57 (IH, dd), 7.43 (IH, app td), 7.40 (IH, app td).; Method D[00102] In accordance with the procedure of Zaidlewicz et al. (Heterocycles, 2001, 55,569-577), a suspension of the 3-methylbenzofuran (1 equiv) and SeO2 (1.2 equiv) in 1,4- dioxane (6 vol) is warmed to reflux and stirred 24 h. At this juncture, reaction progress is <n="41"/>assessed by TLC or LC/MS. If the reaction is incomplete, a further portion of SeO2 (1.2 equiv) is added and stirring continued at reflux for a further 24 h. On completion the reaction mixture is allowed to cool to rt and filtered through Celite 521. The filter cake is washed with EtOAc (12 vol), the filtrate coned in vacuo, and the residue purified by column chromatography (silica gel, 5-40% EtOAc in heptanes) affording the desired product.

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 296 - 307
[2]Heterocycles,2001,vol. 55,p. 569 - 577
[3]Tetrahedron Asymmetry,2008,vol. 19,p. 500 - 511
[4]Patent: WO2012/110833,2012,A2.Location in patent: Page/Page column 123
[5]Angewandte Chemie - International Edition,2015,vol. 54,p. 9021 - 9024
Angew. Chem.,2015,vol. 127,p. 9149 - 9152,4
[6]Patent: CN110156820,2019,A.Location in patent: Paragraph 0090; 0091; 0096; 0097
[7]Journal of Medicinal Chemistry,2019,vol. 62,p. 7160 - 7184
[8]Chemistry - A European Journal,2006,vol. 12,p. 2739 - 2744
[9]Patent: WO2009/85256,2009,A1.Location in patent: Page/Page column 39-40; 50
[10]Journal of Medicinal Chemistry,2008,vol. 51,p. 6095 - 6109
[11]Molecules,2011,vol. 16,p. 5527 - 5537
[12]Journal of the American Chemical Society,2016,vol. 138,p. 458 - 458

3
[ 4687-25-6 ]
[ 57740-67-7 ]
6-[1-Benzofuran-3-yl-meth-(Z)-ylidene]-3-hydroxy-4-phenyl-pyran-2,5-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3487 - 3494

6
[ 4687-23-4 ]
[ 4687-25-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 95 - 103

7
[ 7209-38-3 ]
[ 4687-25-6 ]
[1-Benzofuran-3-yl-meth-(Z)-ylidene]-{3-[4-(3-{[1-benzofuran-3-yl-meth-(Z)-ylidene]-amino}-propyl)-piperazin-1-yl]-propyl}-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 95 - 103

8
[ 4687-25-6 ]
[ 98977-77-6 ]

Reference： [1]Patent: EP3546454,2019,A1

9
[ 4687-25-6 ]
(E)-N-ethyl-N-[(benzofuran-3-yl)methylene]-3-(4-trifluoromethylphenyl)prop-2-en-1-amine [ No CAS ]

Reference： [1]Patent: EP3546454,2019,A1

10
[ 4687-25-6 ]
(E)-N-[(benzofuran-3-yl)methylene]-3-(4-trifluoromethylphenyl)prop-2-en-1-amine [ No CAS ]

Reference： [1]Patent: EP3546454,2019,A1

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[ 4687-25-6 ]

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
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Environmental hazards
Code	Phrase
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H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 4687-25-6 ]

Quality Control of [ 4687-25-6 ]

Related Doc. of [ 4687-25-6 ]

Product Details of [ 4687-25-6 ]

Computed Properties of [ 4687-25-6 ]

Safety of [ 4687-25-6 ]

Application In Synthesis of [ 4687-25-6 ]

[ 4687-25-6 ] Synthesis Path-Upstream 1~12

[ 4687-25-6 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 4687-25-6 ]

Aldehydes

Related Parent Nucleus of [ 4687-25-6 ]

Benzofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 4687-25-6 ]

Related Parent Nucleus of
[ 4687-25-6 ]