[ CAS No. 4265-16-1 ]

Name: Benzo[b]furan-2-carboxaldehyde
Brand: Ambeed
SKU: A207838
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Quality Control of [ 4265-16-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4265-16-1 ]

SDS

Product Details of [ 4265-16-1 ]

CAS No. :	4265-16-1	MDL No. :	MFCD00015463
Formula :	C₉H₆O₂	Boiling Point :	251.5°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	146.14	Pubchem ID :	61341
Synonyms :

Computed Properties of [ 4265-16-1 ]

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

Safety of [ 4265-16-1 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4265-16-1 ]

Upstream synthesis route of [ 4265-16-1 ]

[ 4265-16-1 ] Synthesis Path-Upstream 1~23

1
[ 271-89-6 ]
[ 68-12-2 ]
[ 4265-16-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 80℃;	POCl₃ (4.73 mL, 50.79 mmol) was slowly added to a solution of DMF (6.56 mL, 84.75 mmol) while the temperature was maintained below 40 °C. Then, benzofuran 1 (2.00 g,16.93 mol) was added dropwise to this reaction mixture below 40 °C, over a period of 15 min. The mixture was heated at 80 °C for 24 h. The reaction mixture was then poured into ice-water and carefully quenched with a solution of sodium hydroxide. The organic material was separated, and the aqueous layer was extracted with ethyl acetate. It was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated, and was purified on silica gel column (petroleum ether: EtOAc = 10:1) to give product 2 (2.27 g, 90percent) as brown oil. ¹H NMR (400 MHz,CDCl₃): δ 9.83 (1H, s, COH), 7.75-7.70 (1H, m, H-4), 7.56-7.54 (2H, m, H-6,7), 7.46 (1H, s, H-3), 7.32-7.28 (1H, m, H-5). ¹³C NMR (100 MHz, CDCl₃): δ 179.63 (COH), 156.03 (C-7a), 152.52 (C-2), 129.07 (C-3a), 126.51 (C-6), 124.05 (C-5), 123.58 (C-4), 117.93 (C-3), 112.44 (C-7).
80%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.00 h; Stage #2: at 20℃;	1. To a solution of benzofuran (1.5 g, 12.69 mmol) in 60 mL of THF, was added 5.08 mL(12.69 mmol) of n-BuLi solution in hexanes (2.5 M) at -78 °C. After 1 hr at -78 °C, the reaction mixture was added DMF (3.43 mL). After overnight at RT, the reaction was quenched with saturated ammonium chloride, and extracted with EtOAc (x3). The combined organic extracts were dried (MgS0₄), filtered, and concentrated. Flash chromatography (10 percentEtOAc/Hexanes) gave benzofuran-2-carbaldehyde (1.48 g, 80percent). *H NMR (400 MHz, CDC1₃) δ ppm: 9.88 (s, IH), 7.76 (d, J=8.4 Hz, IH), 7.62 (d, J=8.4 Hz, IH), 7.57 (s, IH), 7.52 (td, J=7.2, 1.2 Hz IH), 7.35 (td, J=7.2, 1.2 Hz, IH).
61%	Stage #1: With n-butyllithium; ammonium chloride In tetrahydrofuran; hexane at -78℃; for 0.50 h; Inert atmosphere Stage #2: at -78℃; for 1.00 h;	Step 1: benzofuran-2-carbaldehyde To a solution of benzofuran (10 g, 84.7 mmol) in dry THF was added n-BuLi (2.5 M solution in hexane, 33.9 mL, 84.7 mmol) dropwise at -78° C. under nitrogen, the mixture was stirred at -78° C. for 0.5 h, and then added DMF (19.6 mL, 254 mmol). The resulted mixture was kept at -78° C. and stirred for 1 h. The reaction was quenched by addition of saturated NH₄Cl aqueous solution (20 mL), and then added ethyl acetate (300 mL) and H₂O (100 mL), the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layer was washed with water and brine, dried over sodium sulfate and concentrated under vacuum, the residue was purified by column chromatography on silica gel (ethyl acetate:petroleum ether=10:1) to afford benzofuran-2-carbaldehyde (7.5 g, yield: 61percent) as yellow oil. ¹H NMR (400 MHz, CDCl₃): δ 9.90 (s, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.59 (s, 1H), 7.53-7.57 (m, 1H), 7.35-7.39 (m, 1H).

40%

at 80℃;

Preparation of 2,3-Benzofuran-5-carboxaldehyde 39[0201] To a DMF (0.580 mL) solution of 2,3-benzofuran 38 (0.331 mL, 3.0 mmol) was added phosphorous oxychloride (0.302 mL, 3.3 mmol). The reaction mixture was stirred overnight at 80 °C, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2 X 20 mL). The organic layer was dried with brine and MgSC>4, then concentrated in vacuo. Flash column chromatography on silica gel (n-hexanes : ethyl acetate = 50:1) of the residue afforded the desired product 39 in 40percent yield (172 mg, yellow oil). ^LH NMR (400 MHz, CDC1₃): 9.88 (s, 1H), 7.76 (d, J= 7.2 Hz, 2H), 7.62 (dd, J= 8.4, 0.8 Hz, 1H), 7.54 (d, J= 0.8 Hz, 1H), 7.53 (td, J= 12, 1.2 Hz, 1H), 7.35 (td, J= 7.2, 0.8 Hz, 1H).

Reference： [1] Chemical Communications, 2017, vol. 53, # 54, p. 7545 - 7548
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[12] Journal of the Chemical Society, 1955, p. 3688,3692
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[15] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 1, p. 136 - 143
[16] Journal of Organic Chemistry, 2018,

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Reference： [1] Green Chemistry, 2012, vol. 14, # 5, p. 1493 - 1501
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 7, p. 1157 - 1163
[3] Journal of the American Chemical Society, 2008, vol. 130, # 10, p. 2898 - 2899
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 14, p. 4241 - 4245
[5] European Journal of Organic Chemistry, 2015, vol. 2015, # 19, p. 4071 - 4076
[6] Chemische Berichte, 1988, vol. 121, p. 2259 - 2262
[7] Patent: US6420375, 2002, B1
[8] European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 772 - 780
[9] European Journal of Organic Chemistry, 2014, vol. 2014, # 4, p. 772 - 780
[10] Synlett, 2016, vol. 27, # 16, p. 2372 - 2377
[11] Organic Letters, 2017, vol. 19, # 11, p. 2865 - 2868

3
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Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1530 - 1536
[2] Journal of the Indian Chemical Society, 1980, vol. 57, # 6, p. 633 - 636
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 14, p. 4241 - 4245
[4] European Journal of Organic Chemistry, 2015, vol. 2015, # 19, p. 4071 - 4076
[5] Advanced Synthesis and Catalysis, 2016, vol. 358, # 7, p. 1157 - 1163

4
[ 27064-03-5 ]
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Reference： [1] Organic Letters, 2017, vol. 19, # 7, p. 1646 - 1649

5
[ 271-89-6 ]
[ 4265-16-1 ]

Reference： [1] Patent: US5037853, 1991, A
[2] Patent: US5120752, 1992, A

6
[ 90-02-8 ]
[ 4265-16-1 ]

Reference： [1] European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 353 - 358
[2] Organic Letters, 2012, vol. 14, # 5, p. 1298 - 1301
[3] Chemistry - A European Journal, 2013, vol. 19, # 13, p. 4335 - 4343
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 14, p. 4241 - 4245
[5] European Journal of Organic Chemistry, 2015, vol. 2015, # 19, p. 4071 - 4076
[6] Medicinal Chemistry Research, 2016, vol. 25, # 3, p. 494 - 500
[7] Pharmaceutical Chemistry Journal, 2018, vol. 51, # 10, p. 893 - 901
[8] Advanced Synthesis and Catalysis, 2016, vol. 358, # 7, p. 1157 - 1163
[9] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1530 - 1536
[10] Journal of Molecular Structure, 2018, vol. 1153, p. 119 - 127

7
[ 90-02-8 ]
[ 2032-35-1 ]
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Reference： [1] Patent: US4528282, 1985, A

8
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Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 43, p. 11303 - 11307[2] Angew. Chem., 2013, vol. 125, # 43, p. 11513 - 11517,5

9
[ 119116-94-8 ]
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Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6972 - 6977

10
[ 108-95-2 ]
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Reference： [1] Medicinal Chemistry Research, 2016, vol. 25, # 3, p. 494 - 500
[2] Journal of Molecular Structure, 2018, vol. 1153, p. 119 - 127
[3] Pharmaceutical Chemistry Journal, 2018, vol. 51, # 10, p. 893 - 901

11
[ 108-98-5 ]
[ 4265-16-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 7, p. 1646 - 1649

12
[ 533-58-4 ]
[ 4265-16-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 11, p. 2865 - 2868

13
[ 74401-08-4 ]
[ 4265-16-1 ]

Reference： [1] Chemische Berichte, 1985, vol. 118, # 12, p. 4674 - 4681
[2] European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 353 - 358

14
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Reference： [1] Journal of the Indian Chemical Society, 1980, vol. 57, # 6, p. 633 - 636

15
[ 50635-12-6 ]
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Reference： [1] Nippon Kagaku Zasshi, 1953, vol. 74, p. 636[2] Chem. Zentralbl., 1954, vol. 125, p. 12071

16
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Reference： [1] Journal of the Indian Chemical Society, 1980, vol. 57, # 6, p. 633 - 636

17
[ 496-41-3 ]
[ 4265-16-1 ]

Reference： [1] Helvetica Chimica Acta, 1930, vol. 13, p. 1275,1280
[2] Helvetica Chimica Acta, 1930, vol. 13, p. 1275,1280
[3] Helvetica Chimica Acta, 1930, vol. 13, p. 1275,1280

18
[ 41717-28-6 ]
[ 4265-16-1 ]

Reference： [1] Helvetica Chimica Acta, 1930, vol. 13, p. 1275,1280
[2] Helvetica Chimica Acta, 1930, vol. 13, p. 1275,1280
[3] Helvetica Chimica Acta, 1930, vol. 13, p. 1275,1280

19
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Reference： [1] Helvetica Chimica Acta, 1930, vol. 13, p. 1275,1280

20
[ 4265-25-2 ]
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Reference： [1] Bulletin de la Societe Chimique de France, 1945, vol. <5> 12, p. 609,615

21
[ 7252-83-7 ]
[ 90-02-8 ]
[ 4265-16-1 ]

Reference： [1] Russian Chemical Bulletin, 2007, vol. 56, # 2, p. 325 - 329

22
[ 7446-08-4 ]
[ 64-17-5 ]
[ 4265-25-2 ]
[ 4265-16-1 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1944, vol. 218, p. 683[2] Bulletin de la Societe Chimique de France, 1945, vol. <5> 12, p. 609,612

23
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[ 68-12-2 ]
[ 10025-87-3 ]
[ 4265-16-1 ]

Reference： [1] Journal of the Chemical Society, 1955, p. 3688,3692

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Ghs Precautionary Statements

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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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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. 4265-16-1 ]

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[ 4265-16-1 ] Synthesis Path-Upstream 1~23

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Aldehydes

Related Parent Nucleus of [ 4265-16-1 ]

Benzofurans

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[ 4265-16-1 ]

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[ 4265-16-1 ]