[ CAS No. 4687-25-6 ]

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

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2D3D

Structure of 4687-25-6

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Quality Control of [ 4687-25-6 ]

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COA GC NMR CNMR HPLC/UPLC 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 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.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Purity	Size	Price	VIP Price	USA Stock *1-2 Days	Global Stock *3-4 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}^Deals	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Purity	Size	Price	VIP Price	USA Stock *1-2 Days	Global Stock *3-4 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}^Deals	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}^Deals	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals

H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure

H400	Very toxic to aquatic life
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