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[ CAS No. 24673-56-1 ]

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Product Details of [ 24673-56-1 ]

CAS No. :	24673-56-1	MDL No. :	MFCD00060511
Formula :	C₁₀H₈O₃	Boiling Point :	328.7°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	176.17 g/mol	Pubchem ID :	600591
Synonyms :

Safety of [ 24673-56-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 24673-56-1 ]

Upstream synthesis route of [ 24673-56-1 ]
Downstream synthetic route of [ 24673-56-1 ]

[ 24673-56-1 ] Synthesis Path-Upstream 1~10

1
[ 118-93-4 ]
[ 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

2
[ 63815-27-0 ]
[ 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
[ 1878-62-2 ]
[ 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

4
[ 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

5
[ 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

6
[ 4687-23-4 ]
[ 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

7
[ 67713-99-9 ]
[ 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

8
[ 1023290-69-8 ]
[ 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

9
[ 441055-15-8 ]
[ 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

10
[ 24673-56-1 ]
[ 620175-39-5 ]

Reference： [1] Patent: WO2008/98374, 2008, A1,

[ 24673-56-1 ] Synthesis Path-Downstream 1~15

1
[ 2076-42-8 ]
[ 24673-56-1 ]

Reference： [1]Helvetica Chimica Acta,1948,vol. 31,p. 78,80

2
[ 67-56-1 ]
[ 24673-56-1 ]
[ 2076-36-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With acetyl chloride; for 17h;Heating / reflux;	i-Methyl-benzofuran-l-carboxylic acid methyl esterAcetylchloride (6.7 mL, 91 mmol) was added dropwise to 750 mL dry methanol cooled on an ice-bath under N2 atmosphere. After completion of the addition, the solution was stirred at RT for 30min. Subsequently, 16.0 g (90 mmol) 3-methyl benzo[b]furan-2-carboxylic acid was added andthe solution was refluxed for 17 h under N2 atmosphere. The solution was cooled on an ice-bathto 0 0C and 500 mL ice-cold water was added. The resulting white precipitate was collected byfiltration and washed with cold methanol. Yield: 16.1 g (94%) of a white solid. 1H-NMR (200MHz, CDCl3): delta 7.72 (d, J= 8 Hz, IH), 7.60 (t, J= 8 Hz, IH), 7.53 (t, J= 8 Hz, IH), 7.41 (d, J=8 Hz, IH), 4.08 (s, 3H), 2.73 (s, 3H) ppm.
		To a solution of <strong>[24673-56-1]3-methyl-benzofuran-2-carboxylic acid</strong> (0.98 g, 5.6 mmol) and catalytic amount of DMF (5 drops) in THF (25 ml) was added oxalyl chloride (0.53 ml, 6.1 mmol). After stirring the solution for 1 h at room temperature, methanol (20 ml) and TEA (7.0 ml) were added. The reaction mixture was stirred overnight at room temperature, then concentrated and dissolved in ethyl acetate (100 ml) and washed with aqueous sodium bicarbonate solution (100 ml). The organic layer was dried over sodium sulfate and concentrated to provide crude methyl 3-methylbenzofuran-2-carboxylate (1.0 g, 5.3 mmol) as a tan solid, which was used without further purification.

Reference： [1]Patent: WO2006/10008,2006,A1 .Location in patent: Page/Page column 167
[2]Patent: US2680732,1950,
[3]Patent: WO2005/19174,2005,A1 .Location in patent: Page/Page column 43

3
[ 24673-56-1 ]
[ 21535-97-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With acetic acid; In N,N-dimethyl-formamide; at 95 - 100℃; for 8h;Green chemistry;	35.9 g (0.2 mol, 98%, Belling Technology Co., Ltd.) 3-methylbenzofuran-2-carboxylic acid was dissolved in 100.0 g of N,N-dimethylformamide and 0.32 g of acetic acid (0.002 mol, 37%) ), Heating at 95 to 100 C, stirring the reaction for 8 hours,The solvent was distilled off under reduced pressure to give 3-methylbenzofuran; The NMR data was consistent with the reported compound with a yield of 94% and a purity of 98%.
	With quinoline; copper;Heating;	3-Methylbenzofuran-2-carboxylic acid (commercially available) was heated withcopper metal in quinoline to give compound 5. Colorlessoil, 1H-NMR (500 MHz, CDCl3) delta: 2.22 (3H, d, J=1.2 Hz),7.18-7.26 (2H,m), 7.38 (1H, dd, J=1.2, 8.0 Hz), 7.48 (1H, m),7.51 (1H, dd, J=1.2, 8.0 Hz). 13C-NMR (125 MHz, CDCl3)delta: 6.4, 110.6, 115.2, 119.0, 121.9, 123.8, 128.4, 141.4, 155.5.Its spectral data are in accordance with previously reported data.

Reference： [1]Patent: CN109694343,2019,A .Location in patent: Paragraph 0032; 0033; 0041
[2]Organic Letters,2009,vol. 11,p. 5710 - 5713
[3]Organic Syntheses, Collective,1963,vol. Vol. IV,p. 590,592
[4]Patent: WO2013/80222,2013,A1 .Location in patent: Page/Page column 43
[5]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 997 - 1001

4
[ 24673-56-1 ]
[ 2256-86-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; for 4h;Heating / reflux;	General procedure for the preparation of 3-Methyl-benzofiotaiotaran-2-carboxylic acid amidesA suspension of the acid (11.4 mmol), thionyl chloride (28.9 mmol) and cat. DMF (1.8 mL) in DCM (100 mL) was heated to reflux for 4h. The reaction solution was concentrated, coevaporated with toluene (2 x 20 mL), dried under HV and redissolved in DCM (50 mL). This solution was added to a solution of the amine (34.2 mmol) and TEA (3.2 mL, 22.8 mmol) in DCM (100 mL) at 0 0C. After stirring for 16h at RT, the reaction mixture was washed with IM HCl (3 x 50 mL), brine (100 mL), dried over MgSO4 and concentrated.
	With oxalyl dichloride;N,N-dimethyl-formamide; In tetrahydrofuran; at 20℃; for 1h;	Example 17; Synthesis of a compound of Formula (I) where R¹, R3, R6, and R8 are OMe, R2, R7, and R10 are Me, R4 and R5 are OH, R9 is H, R¹¹ is CN, Y is CH2, and R¹2 is 3- dimethylaminomethylbenzofuran-2-ylcarbonylamino (compound 47); Step 1; To a solution of <strong>[24673-56-1]3-methyl-benzofuran-2-carboxylic acid</strong> (0.98 g, 5.6 mmol) and catalytic amount ofDMF (5 drops) in THF (25 mL) was added oxalyl chloride (0.53 mL, 6.1 mmol). After stirring the solution for 1 hr at room temperature, MeOH (20 mL) and TEA (7.0 mL) were added. The reaction mixture was stirred overnight at room temperature, then concentrated, redissolved in EtOAc (100 mL) and washed with sat. NaHCO3 (aq) mL). The organic layer was dried over Na2S04 and concentrated to provide crude methyl 3-methyl- benzofuran-2-carboxylate (1.0 g, 5.3 mmol) as a tan solid, which was used without further purification.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 2 - 20℃;Heating / reflux;	A. N,3-dimethylbenzofuran-2-carboxamide[0218] A mixture of 3-methylbenzofuran-2-carboxylic acid (1.0 kg, 5.676mol) in methylene chloride (5.8L) and DMF (5mL) was chilled to ~ 2 0C. A solution of oxalyl chloride (864g, 6.81 mol) was added to the reaction mixture keeping the temperature below 10 0C, over a period of 2 hrs. A vigorous evolution of a gas was observed. The reaction mixture was stirred overnight under nitrogen at room temperature and then refluxed for 3 hrs. All of the solids were dissolved to give a brown color solution. HPLC analysis of an aliquot indicated that the reaction was complete. The mixture was concentrated on a rotary evaporator and the residual oxalyl chloride was chased with DCM (2L). The solid product was re-dissolved in DCM (6L) in a round bottom flask (1 OL) and chilled to ~ - 50C. A solution of methyl amine (40% in water, 1.7L, 3.5 eq, 19.86 mol) was carefully added to the acid chloride solution while keeping the temperature below 8 0C then stirred overnight at room temperature. Analysis of an aliquot indicated that the reaction was complete. Water (8.0L) was added to the reaction mixture, the layers were separated, the aqueous layer was back extracted with DCM (2x3 L), the combined organic layer was washed with water (4L) and dried over Na2SO4. The organic layer was filtered, the filtrate was concentrated and traces of DCM were co evaporated with heptanes (2L). The heptanes slurry was filtered and the cake was washed with heptanes (2x2L). All the brown color was removed in the heptane filtrate. The solid product was dried under high vacuum overnight to a constant weight. Yield of the title compound was 1.015 kg (94.5%. 1H NMR (CDCl3) : delta (ppm) 8.45 (s,lH), 7.61 (d, IH), 7.41 (m, 2 H), 7.30 (m, 1 H), 3.03 (d, 2 H), 2.63 (s, 3 H). HPLC: 99.0 area% (Rtau = 7.91 min)

Reference： [1]Acta Poloniae Pharmaceutica,1956,vol. 13,p. 11,19
Chem.Abstr.,1956,p. 16671
[2]Journal of Pharmaceutical Sciences,1978,vol. 67,p. 125 - 127
[3]Patent: WO2006/10008,2006,A1 .Location in patent: Page/Page column 172-173
[4]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4726 - 4733
[5]Patent: WO2005/118584,2005,A2 .Location in patent: Page/Page column 80-81
[6]Journal of Organic Chemistry,2017,vol. 82,p. 7123 - 7150
[7]Patent: WO2008/98374,2008,A1 .Location in patent: Page/Page column 50; 24
[8]Journal of the American Chemical Society,2018,vol. 140,p. 13945 - 13951

5
[ 106-88-7 ]
[ 24673-56-1 ]
[ 84993-62-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 2839 - 2843
[2]Tetrahedron Letters,1982,vol. 23,p. 4127 - 4130

6
2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid <i>tert</i>-butyl ester [ No CAS ]
[ 24673-56-1 ]
[ 857080-06-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4961 - 4966

7
[ 24673-56-1 ]
[ 870190-53-7 ]
[ 938442-96-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4961 - 4966

8
[ 854372-00-2 ]
[ 24673-56-1 ]
[ 854372-23-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 3.5h;	Step 13A: A mixture of D-2-(4'-Hydroxy-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl ester (305 mg, 0.75 mmol, 1 eq), <strong>[24673-56-1]3-Methyl-benzofuran-2-carboxylic acid</strong> (131 mg, 0.74 mmol, 1 eq), 4-dimethylaminopyridine (DMAP, 95 mg, 0.77 mol, 1 eq), and 1,3-Dicyclohexylcarbodiimide (DCC, 240 mg, 1.17 mmol, 1.6 eq) dissolved in 5 mL of dichloromethane under nitrogen atmosphere was allowed to react at room temperature for 3.5 hrs. Regular work-up and column chromatography (10% EtOAc in hexane) to give D-<strong>[24673-56-1]3-Methyl-benzofuran-2-carboxylic acid</strong> 4'-(1-tert-butoxycarbonyl-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester (300 mg) in 71% yield. NMR: G8475-101. 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 0.9 (d, J=7.1 Hz, 3 H) 1.0 (d, J=6.8 Hz, 3 H) 1.2 (s, 9 H) 2.1 (m, 1 H) 2.7 (s, 3 H) 3.7 (dd, J=10.0, 4.4 Hz, 1 H) 5.1 (d, J=9.9 Hz, 1 H) 7.4 (m, 3 H) 7.5 (m, 1 H) 7.6 (t, J=8.0 Hz, 3 H) 7.7 (m, 3 H) 7.9 (d, J=8.3 Hz, 2 H).

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6629 - 6644
[2]Patent: US2005/130973,2005,A1 .Location in patent: Page/Page column 44
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 311 - 316

9
[ 24673-56-1 ]
[ 214360-73-3 ]
[ 857080-05-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6629 - 6644

10
[ 108-86-1 ]
[ 24673-56-1 ]
[ 4521-08-8 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 11350 - 11351

11
[ 24673-56-1 ]
[ 696-62-8 ]
2-(4-methoxyphenyl)-3-methylbenzo[b]furan [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1781 - 1783

12
[ 24673-56-1 ]
D-3-methyl-2-{4'-[(3-methylbenzofuran-2-carbonyl)amino]biphenyl-4-sulfonylamino}butyric acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6629 - 6644
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4961 - 4966

13
[ 24673-56-1 ]
[ 857080-06-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6629 - 6644

14
[ 24673-56-1 ]
D-3-methyl-benzofuran-2-carboxylic acid 4'-(1-carboxy-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6629 - 6644

15
[ 24673-56-1 ]
[ 62058-03-1 ]
C₂₀H₂₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example B .6 Preparation of compound 7; 1 -Hydroxy- lH-benzotriazo Ie (0.001 mol) was added to a stirred mixture of 3-methylbenzofurancarboxylic acid [24673-56-1] (0.0009 mol) in dichloromethane (5 ml) and DMF (5 ml). The mixture was stirred for 10 minutes and iV-(ethyl- carbonimidoyl)-iV,iV-dimethyl-l,3-propanediamine, monohydrochloride [25952-53-8] (0.001 mol) was added. The resulting mixture was stirred for 1 hour before (lalpha,3alpha,4alpha,5beta,7alpha)-4-aminotricyclo[3.3.1.13'7]decan-l-ol [62058-03-1] (0.001 mol) was added. The reaction mixture was stirred at room temperature overnight and then (Polystyrylmethyl)-trimethylammonium bicarbonate (I g; Novabiochem Cat. No.: 01-64-0419) and Methylisocyanate polystyrene (I g; Novabiochem Cat. No.: 01-64-0169) were added. The resulting mixture was shaken for 1 hour and filtered. The filtrate was evaporated and the obtained residue was purified by flash column chromatography (eluent: CH2CyCH3OH 90/10). The product fractions were collected and the solvent was evaporated, yielding 0.144 g of compound 7.

Reference： [1]Patent: WO2006/24627,2006,A2 .Location in patent: Page/Page column 46; 55

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Ghs Precautionary Statements

Precautionary Statements-General
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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

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