691905-26-7|2',6'-Dimethylbiphenyl-3-carbaldehyde| Ambeed

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Quality Control of [ 691905-26-7 ] Purity: 98% SDS Specification

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Product Details of [ 691905-26-7 ]

CAS No. :	691905-26-7
Formula :	C₁₅H₁₄O
M.W :	210.27
SMILES Code :	O=CC1=CC(C2=C(C)C=CC=C2C)=CC=C1
MDL No. :	MFCD11895278
InChI Key :	SCADEVWRJSJBOM-UHFFFAOYSA-N
Pubchem ID :	23082866

Safety of [ 691905-26-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 691905-26-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 691905-26-7 ]

[ 691905-26-7 ] Synthesis Path-Downstream 1~35

1
[ 691905-26-7 ]
[ 35418-07-6 ]
C₂₅H₂₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20℃; for 55h;molecular sieves;	To a solution of <strong>[35418-07-6]methyl 3-(4-aminophenyl)propanoate</strong> (3.33 g, 18.6 mmol) and 2',6'-dimethylbiphenyl-3-carbaldehyde (3.91 g, 18.6 mmol) in toluene (40 mL) were added molecular sieves (0.4 nm, beads, 7.2 g), and the mixture was stirred at room temperature for 55 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (100 mL). Sodium cyanoborohydride (2.53 g, 40.3 mmol) and acetic acid (2.31 mL, 40.3 mmol) were successively added, and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr. Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane) to give the title compound (4.24 g, yield 61%) as a colorless oil. MS m/z 374 (MH+).

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Patent: EP1726580,2006,A1 .Location in patent: Page/Page column 122.

2
[ 3132-99-8 ]
[ 100379-00-8 ]
[ 691905-26-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 20h;	3-Bromobenzaldehyde (18.5 g, 100 mmol) and 2,6-dimethylphenylboronic acid (21.0 g, 140 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (200 mL), ethanol (100 mL) and toluene (200 mL). The air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (5.78 g, 5.00 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80C for 20 hr. After cooling the reaction mixture, water was added and the mixture was diluted with ethyl acetate. The insoluble material was filtered off through celite. The organic layer in the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-10% ethyl acetate/hexane) to give the title compound (20.4 g, yield 97%) as a colorless oil. MS m/z 211 (MH+).
96%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃;Inert atmosphere;	3-Bromobenzaldehyde (1.8 g, 10 mmol) and (2,6-dimethylphenyl)boronic acid (2.1 g, 14 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (20 mL), EtOH (10 mL), and toluene (20 mL). After argon substitution, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. The reaction mixture was stirred under argon atmosphere at 80 C for 20 h. The reaction mixture was cooled, and water was added to the reaction mixture. The mixture was diluted with AcOEt, and the insoluble material was filtered through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 1, v/v) as eluent to afford the product 7a (2.1 g, 96%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ: 10.06 (s, 1H), 7.86-7.90 (m, 1H), 7.67-7.69 (m, 1H), 7.61 (t, J = 7.6 Hz, 1H), 7.42-7.46 (m, 1H), 7.11-7.23 (m, 3H), 2.02 (s, 6H).
83%	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 22h;Inert atmosphere;	3-bromo-benzaldehyde (370.4 mg, 2.002 mmol), 2,6- dimethyl phenyl boronic acid (420.5 mg, 2.804 mmol), saturated aqueous sodium hydrogen carbonate solution (1M solution, 4 mL, 4.001 mmol) ethanol (2.2 mL) of and in a mixed solution of toluene (4 mL), tetrakis (triphenylphosphine) palladium (0) (114.9 mg, 0.099 mmol) was added, under an argon atmosphere and stirred for 22 hours at 80 C.. The reaction mixture was cooled, water (5 mL) and ethyl acetate (10 mL) was added and filtered over Celite (registered trademark). Was separated into aqueous and organic layers, the aqueous layer was extracted twice with ethyl acetate (20 mL), the combined organic layers were extracted with brine (30 mL), further sedge aqueous layer of ethyl acetate (20 and extracted with mL). The combined organic layers were dried over sodium sulfate, the solvent was evaporated, and the residue was purified by column chromatography to give the title compound (hexane: diethyl ether = 60:: 1 ~ 50 1) (347.8 mg, 1.655 mmol, 83 %, to give a colorless oil).

83%	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; water; toluene; at 80℃; for 22h;Inert atmosphere;	3-bromobenzaldehyde (370.4 mg, 2.002 mmol), 2,6- dimethyl phenyl boronic acid (420.5 mg, 2.804 mmol), saturated aqueous sodium hydrogen carbonate solution (1M solution, 4 mL, 4.001 mmol) ethanol (2.2 mL) of and in a mixed solution of toluene (4 mL), tetrakis (triphenylphosphine) palladium (0) (114.9 mg, 0.099 mmol) was added, under an argon atmosphere and stirred for 22 hours at 80 C.. The reaction mixture was cooled, water (5 mL) and ethyl acetate (10 mL) was added and filtered over Celite (registered trademark). Was separated into aqueous and organic layers, the aqueous layer was extracted twice with ethyl acetate (20 mL), the combined organic layers were extracted with brine (30 mL), further sedge aqueous layer of ethyl acetate (20 and extracted with mL). The combined organic layers were dried over sodium sulfate, the solvent was evaporated, and the residue was purified by column chromatography (hexane: diethyl ether = 60: 1 to 50: 1) toRi purified title compound (347.8 mg, 1.655 mmol, 83%, colorless oil) was obtained.
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 100℃; for 16h;	To a degassed solution of 3-bromobenzaldehyde (500 mg, 2.70 mmol) , (2, 6-dimethylphenyl) boronic acid (608 mg, 4.05 mmol) , and Pd (PPh3) 4 (156 mg, 0.14 mmol) in dioxane (5 mL) was added K2CO3 (2N, 4.05 mL, 8.11 mmol) . The reaction was heated to 100. After 16 h, the mixture was poured into NH4Cl (sat, 25 mL) and extracted with EtOAc (2 x 25 mL) . The combined organic layers were dried over MgSO4 and concentrated. The resulting residue was purified by HPLC (ISCO 40 gram silica gel cartridge, 0 to 40EtOAc/Hex) to give the title compound.

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.
[3]Patent: EP1726580,2006,A1 .Location in patent: Page/Page column 36.
[4]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 2445 - 2450.
[5]Chemical Communications,2014,vol. 50,p. 10409 - 10411.
[6]Patent: JP2016/17036,2016,A .Location in patent: Paragraph 0304; 0306-0308.
[7]Patent: JP2016/17037,2016,A .Location in patent: Paragraph 0260.
[8]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1049 - 1054.
[9]Patent: WO2016/19863,2016,A1 .Location in patent: Page/Page column 88.

3
[ 691905-26-7 ]
[ 691905-27-8 ]

Yield	Reaction Conditions	Operation in experiment
17%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 3.16667h;	To a stirred solution of Compound l-2a in methanol (7.5 g, 35.68mmol), NaBH (4.06g, 107.4mmol) was added portion-wise at 0C over a period of 10 min. The reaction temperature was raised to RT and stirred for additional 3 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution, then distilled out methanol completely and diluted with water and extracted with ethyl acetate for 2 times. The organic layer was washed with sat. NaCl solution, dried over Na2S04 and concentrated to afford the crude product. The crude compound was purified by column chromatography on silica gel (100- 200 mesh) using 8-10% of ethyl acetate in pet ether as an eluent to afford Compound l-2b(1.3g, 17%). NMR (400 MHz, CDC13): d 7.45-7.40 (m, 1H), 7.38-7.32 (m, 1H), 7.18-7.05 (m, 5H), 4.74 (d, 2H), 2.02 (s, 6H), 1.64 (t, 1H)

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.
[3]Patent: WO2021/28810,2021,A1 .Location in patent: Page/Page column 105.

4
[ 691905-26-7 ]
[ 74-89-5 ]
[ 1218910-02-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1049 - 1054.

5
[ 691905-26-7 ]
[ 691902-33-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

6
[ 691905-26-7 ]
methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](methyl)amino]phenyl}propanoate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Patent: EP1726580,2006,A1 .

7
[ 691905-26-7 ]
[ 1269763-57-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

8
[ 691905-26-7 ]
[ 1269763-58-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

9
[ 691905-26-7 ]
[ 1269763-59-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

10
[ 691905-26-7 ]
[ 1269763-60-1 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

11
[ 691905-26-7 ]
[ 691902-31-5 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

12
[ 691905-26-7 ]
[ 691902-35-9 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

13
[ 691905-26-7 ]
[ 691902-74-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

14
[ 691905-26-7 ]
[ 865134-29-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Patent: EP1726580,2006,A1 .

15
[ 691905-26-7 ]
3-(4-[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Patent: EP1726580,2006,A1 .

16
[ 691905-26-7 ]
3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](methyl)amino]phenyl}propanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Patent: EP1726580,2006,A1 .

17
[ 691905-26-7 ]
C₂₅H₂₆O₂S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

18
[ 691905-26-7 ]
C₂₆H₂₇FO₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

19
[ 691905-26-7 ]
C₂₇H₃₀O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

20
[ 691905-26-7 ]
C₂₇H₃₀O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

21
[ 691905-26-7 ]
[ 691902-32-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

22
[ 691905-26-7 ]
[ 691902-30-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

23
[ 691905-26-7 ]
[ 691902-34-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

24
[ 691905-26-7 ]
[ 691902-73-5 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.

25
[ 691905-26-7 ]
[ 805248-55-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

26
[ 691905-26-7 ]
[ 805248-48-0 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

27
[ 691905-26-7 ]
[ 805248-71-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

28
[ 691905-26-7 ]
[ 805248-53-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

29
[ 691905-26-7 ]
[ 805248-47-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

30
[ 691905-26-7 ]
[ 805248-62-8 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

31
[ 691905-26-7 ]
C₂₇H₂₆O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

32
[ 691905-26-7 ]
C₂₇H₂₈O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

33
[ 691905-26-7 ]
[ 805248-49-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

34
[ 691905-26-7 ]
[ 1359669-49-0 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

35
[ 691905-26-7 ]
[ 1359669-51-4 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1538 - 1552.

Historical Records

Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 691905-26-7 ]

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P502	Refer to manufacturer/supplier for information on recovery/recycling

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

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CAS No.: 691905-26-7

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