[ CAS No. 4687-25-6 ]

Name: 4687-25-6|Benzofuran-3-carbaldehyde|95%
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Quality Control of [ 4687-25-6 ]

COA NMR CNMR HPLC LC-MS

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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 g/mol	Pubchem ID :	12394139
Synonyms :

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 1~15

1
[ 4687-25-6 ]
[ 26537-68-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, # 9, p. 1479 - 1486
[2] Patent: WO2009/85256, 2009, A1, . Location in patent: Page/Page column 40; 50

2
[ 4687-25-6 ]
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

3
[ 21535-97-7 ]
[ 4687-25-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With selenium(IV) oxide In 1,4-dioxane for 24 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

4
[ 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

5
[ 4687-23-4 ]
[ 4687-25-6 ]

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

6
[ 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

7
[ 136229-42-0 ]
[ 4687-25-6 ]

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

8
[ 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

9
[ 1878-62-2 ]
[ 4687-25-6 ]

10
[ 118-93-4 ]
[ 4687-25-6 ]

11
[ 26537-68-8 ]
[ 4687-25-6 ]

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

12
[ 38281-60-6 ]
[ 4687-25-6 ]

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

13
[ 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

14
[ 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

15
[ 4687-25-6 ]
[ 67713-99-9 ]

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[ 4687-25-6 ]

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[ 4687-25-6 ]

Benzofurans

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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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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.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;Cooling with ice;	A solution of 1 -Benzofuran-3-carbaldehyde (5 g, 34.2 mmol) in methanol (50 ml_) is cooled with ice and sodium borohydride (1 .9 g, 51 .3 mmol) is added portionwise. The reaction mixture is stirred at room temperature for 1 h. The reaction mixture is concentrated and the residue is partitioned between saturated ammonium chloride and ethylacetate. The organic layer is separated, dried over sodium sulfate and concentrated (5.0 g, colourless liquid, 98%). 1H NMR (400 MHz, CDCI3): delta 7.70-7.68 (m, 1 H), 7.62 (s, 1 H), 7.52-7.50 (m, 1 H), 7.36-7.26 (m, 2H), 4.86 (s, 2H).
95%	With methanol; sodium tetrahydroborate; at 20℃; for 1h;	into a 50-mL round-bottom flask, was placed l-benzofuran-3-carbaldehyde (5 g, 34.21 mmol, 1.00 eq.), and methanol (50 mL). This was followed by the addition of aBH (1.96 g, 51.81 mmol, 1.50 eq.) in several batches. The resulting solution was stirred for 1 h at rt. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 100 rnL of DCM. The resulting mixture was washed with 1x50 mL of NH CI. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with PE:EA (60:40). This resulted in 4.8 g (95%) of l-benzofuran-3-ylmethanol as a white solid.
	With sodium tetrahydroborate; In methanol; at 20℃;Cooling with ice;	A solution of 1-Benzofuran-3-carbaldehyde (5g, 34.2 mmol) in methanol (50 ml_) was cooled with ice and sodium borohydride (1.9g, 51.3 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated and the residue was partitioned between saturated ammonium chloride and dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated. The crude (5.0 g, 98%) was taken as such for next step without further purification. 1H NMR (400 MHz, CDCI3): delta 7.68-7.70 (m, 1 H), 7.62 (s, 1 H), 7.50-7.52 (m, 1 H), 7.26-7.36 (m, 2H), 4.86 (s, 2H).

	With methanol; sodium tetrahydroborate; at 20℃; for 1h;Cooling with ice;	A solution of 1-Benzofuran-3-carbaldehyde (5 g, 34.2 mmol) in methanol (50 mL) was cooled with ice and sodium borohydride (1.9 g, 51.3 mmol) was added portionwise. The reaction mixture was stirred at room temperature for I h. Thereaction mixture was concentrated and the residue was partitioned between saturated ammonium chloride and ethylacetate. The organic layer was separated, dried over sodium sulfate and concentrated. The crude product (5.0 g, colourless liquid, 98%) was taken as such for next step without purification. ?H NMR (400 MHz, CDCI3): 6 7.70-7.68 (m, IH), 7.62 (s, 1H), 7.52-7.50 (m, 1H),7.36-7.26 (m, 2H), 4.86 (s, 2H).
	With methanol; sodium tetrahydroborate; at 20℃; for 1h;Cooling with ice;	Step 1 : benzofuran-3-ylmethanol A solution of 1-Benzofuran-3-carbaldehyde (5 g, 34.2 mmol) in methanol (50 mL) was cooled with ice and sodium borohydride (1.9 g, 51.3 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated and the residue was partitioned between saturated ammonium chloride and ethylacetate. The organic layer was separated, dried over sodium sulfate and concentrated. The crude product (5.0 g, colourless liquid, 98%) was taken as such for next step without purification. H NMR (400 MHz, CDCI3): delta 7.70-7.68 (m, 1 H), 7.62 (s, 1 H), 7.52-7.50 (m, 1 H), 7.36- 7.26 (m, 2H), 4.86 (s, 2H).
	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;	A solution of 1-Benzofuran-3-carbaldehyde (5 g, 34.2 mmol) in methanol (50 mL) was cooled with ice and sodium borohydride (1.9 g, 51.3 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated and the residue was partitioned between saturated ammonium chloride and ethylacetate. The organic layer was separated, dried over sodium sulfate and concentrated. The crude product (5.0 g, colourless liquid, 98%) was taken as such for next step without purification. 1H NMR (400 MHz, CDCI3): delta 7.70-7.68 (m, 1 H), 7.62 (s, 1 H), 7.52-7.50 (m, 1H), 7.36- 7.26 (m, 2H), 4.86 (s, 2H).
	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;Cooling with ice;	A solution of benzofuran-3-carbaldehyde (5 g, 33.8 mmol) in methanol (50 mL) was cooled with ice and sodium borohydride (1.9 g, 50.7 mmol) was added portionwise. The reaction mixture was stirred at rt for 1 h. The mixture was concentrated and the residue was partitioned between saturated ammonium chloride and DCM. The organic layer was separated, dried over sodium sulfate and concentrated. The crude benzofuran-3-ylmethanol (4.6 g, 92%) was taken as such for next step without further purification.
	With sodium tetrahydroborate; In methanol; at -10 - 0℃; for 1h;	Compound E-4 (7.3 g, 50 mmol) was dissolved in methanol (100 mL), cooled to -10 C in a low-temperature bath, sodium borohydride (2.3 g, 60 mmol) was added in portions, and the reaction was maintained at -10C Stirring was continued for 1 hour .The reaction solution was concentrated under reduced pressure, and 50 mL of saturated ammonium chloride solution was added thereto, and then extracted with dichloromethane, and the organic layer was combined.Drying with anhydrous sodium sulfate and concentrating under reduced pressure to give crude oil of product.

Physical hazards
Code	Phrase
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
H224	Extremely flammable liquid and vapour
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
Health hazards
Code	Phrase
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
H313	May be harmful in contact with skin
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
Environmental hazards
Code	Phrase
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 ]

Safety of [ 4687-25-6 ]

Application In Synthesis of [ 4687-25-6 ]

[ 4687-25-6 ] Synthesis Path-Upstream 1~15

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

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

Inquiry

Related Functional Groups of
[ 4687-25-6 ]

Related Parent Nucleus of
[ 4687-25-6 ]