[ CAS No. 62784-66-1 ] {[proInfo.proName]}

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Quality Control of [ 62784-66-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 62784-66-1 ]

SDS Specification

Alternatived Products of [ 62784-66-1 ]

Product Details of [ 62784-66-1 ]

CAS No. :	62784-66-1	MDL No. :	MFCD11096937
Formula :	C₂₁H₁₆O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	NHIXQVYVFRYTOB-UHFFFAOYSA-N
M.W :	284.35	Pubchem ID :	593473
Synonyms :

Safety of [ 62784-66-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H312-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 62784-66-1 ]

* 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.

Upstream synthesis route of [ 62784-66-1 ]
Downstream synthetic route of [ 62784-66-1 ]

[ 62784-66-1 ] Synthesis Path-Upstream 1~2

1
[ 94942-89-9 ]
[ 62784-66-1 ]
[ 1187670-07-0 ]
[ 3333-15-1 ]
[ 17040-62-9 ]

Yield	Reaction Conditions	Operation in experiment
73 % ee	With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6 h; Resolution of racemate	Experimental Example 3Production of Optically Active Ester and Optically Active Carboxylic Acid Using 1,1-di(1-naphthyl)methanol As shown in the above reaction equation, an optically active ester and optically active carboxylic acid were obtained by reacting 1,1-di(1-naphthyl)methanol and various racemic carboxylic acids. The results are shown in Table 3.; Entry 26di(1-naphthyl)methyl (R)-2,3-diphenylpropanoateHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=0.75 mL/min); t_R=12.3 min (13.5percent), t_R=23.1 min (86.5percent);IR (neat): 3033, 1736, 1600, 1511, 780, 678 cm^-1;¹H NMR (CDCl₃): δ8.15 (s, 1H, 1'-H), 7.78-7.56 (m, 5H, Ph), 7.49 (t, J=8.3 Hz, 1H, Ph), 7.38-7.14 (m, 11H, Ph), 7.13-6.94 (m, 5H, Ph), 6.76 (dd, J=7.5 Hz, 1H, Ph), 7.06 (d, J=10.5, 7.0 Hz, 1H, Ph), 3.94 (dd, J=10.0, 5.5 Hz, 1H, 2-H), 3.40 (dd, J=13.7, 10.0 Hz, 1H, 3-H), 2.92 (dd, J=13.7, 5.5 Hz, 1H, 3-H);¹³C NMR (CDCl₃): δ172.4, 139.0, 138.2, 134.35, 134.30, 133.7, 133.6, 131.0, 130.8, 129.0, 128.9, 128.68, 128.63, 128.57, 128.4, 128.3, 128.1, 127.5, 126.7, 126.33, 126.31, 126.0, 125.7, 125.6, 125.20, 124.97, 123.4, 123.3, 71.4, 53.6, 39.2;HR MS: calculated for C₃₆H₂₈O₂Na (M+Na⁺)=515.1982, found 515.1963.(S)-2,3-diphenylpropionic acidHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/10/0.01, flow rate=0.75 mL/min); t_R=12.5 min (21.9percent), t_R=15.5 min (78.1percent);¹H NMR (CDCl₃): δ10.35 (br s, 1H, COOH), 7.28-6.98 (m, 10H, Ph), 3.78 (dd, J=8.2, 7.0 Hz, 1H, 2-H), 3.33 (dd, J=13.8, 8.2 Hz, 1H, 3-H), 2.96 (dd, J=13.8, 7.0 Hz, 1H, 3-H).

Reference： [1] Patent: US2010/234610, 2010, A1, . Location in patent: Page/Page column 7
[2] Tetrahedron Letters, 2010, vol. 51, # 43, p. 5666 - 5669

2
[ 58048-38-7 ]
[ 62784-66-1 ]
[ 1213744-25-2 ]
[ 120-36-5 ]
[ 15165-67-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 14-15, p. 2301 - 2304

[ 62784-66-1 ] Synthesis Path-Downstream 1~9

1
[ 15687-27-1 ]
[ 62784-66-1 ]
[ 1116086-46-4 ]
[ 51146-56-6 ]
[ 51146-57-7 ]

Yield	Reaction Conditions	Operation in experiment
39%	With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate;	Entry 44To a dichloromethane solution (1.0 mL) containing p-methoxybenzoic anhydride (68.9 mg, 0.241 mmol) and racemic ibuprofen (41.2 mg, 0.200 mmol); diisopropylethylamine (62.7 muL, 0.360 mmol), benzotetramisole (2.5 mg, 0.010 mmol), and 1,1-di(1-naphthyl)methanol (28.4 mg, 0.100 mmol) were added in order at room temperature. After stirring the reaction mixture solution at room temperature for 12 hr, the reaction was stopped with saturated ammonium chloride water. After fractionating the organic layer, the aqueous layer was extracted 4 times with diethylether. After combining the organic layers, they were dried with anhydrous sodium sulfate. After filtering the solution, it was vacuum concentrated, and the obtained mixture was fractionated by thin layer silica gel chromatography to obtain the corresponding optically active ibuprofen ester (36.9 mg, 39percent, 92percent ee) and the unreacted optically active ibuprofen (13.6 mg, 33percent, 36percent ee).(R)-ibuprofen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/ml): tR=6.1 min (4.1percent), tR=10.7 min (95.9percent);IR (neat): 3036, 1735, 1599, 1512, 782, 679 cm-1;1H NMR (CDCl3): delta8.29 (s, 1H, 1-H), 8.02-7.93 (m, 1H, Ph), 7.85-7.60 (m, 5H, Ph), 7.47-7.26 (m, 3H, Ph), 7.24-7.02 (m, 6H, Ph), 7.00-6.88 (m, 3H, Ph), 3.74 (q, J=7.1 Hz, 1H, 2-H), 2.38 (d, J=7.1 Hz, 2H, 1'-H), 1.78 (qq, J=6.6, 6.6 Hz, 1H, 2'-H), 1.43 (d, J=7.1 Hz, 3H, 3-H), 0.84 (d, J=6.6 Hz, 6H, 3'-H);13C NMR (CDCl3): delta173.7, 140.6, 137.2, 134.9, 134.7, 133.8, 133.7, 131.2, 130.9, 129.3, 129.1, 128.8, 128.7, 128.6, 127.5, 126.7, 126.3, 125.8, 125.6, 125.2, 125.0, 123.5, 123.4, 70.9, 45.3, 45.0, 30.2, 22.4, 18.1;HR MS: calculated for C34H32O2Na (M+Na+)=495.2295; found 495.2276.(S)-ibuprofenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/100/0.1, flow rate=1.0 mL/min); tR=26.3 min (77.5percent), tR=28.5 min (22.5percent);1H NMR (CDCl3): delta10.30 (br s, 1H, COOH), 7.14 (d, J=7.9 Hz, 2H, Ph), 7.02 (d, J=7.9 Hz, 2H, Ph), 3.63 (q, J=7.3 Hz, 1H, 2-H), 2.37 (q, J=7.3 Hz, 2H, 1'-H), 1.77 (qq, J=6.5, 6.5 Hz, 1H, 2'-H), 1.42 (d, J=7.3 Hz, 2H, 3-H), 0.82 (d, J=6.5 Hz, 6H, 3'-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 11-12

2
[ 58048-38-7 ]
[ 62784-66-1 ]
[ 1213744-25-2 ]
[ 120-36-5 ]
[ 15165-67-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304

3
[ 62784-66-1 ]
[ 446878-78-0 ]
[ 1213744-22-9 ]
[ 1129-46-0 ]
[ 1912-23-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304

4
[ 62784-66-1 ]
2-(4-isobutylphenyl)propionic anhydride [ No CAS ]
[ 1116086-46-4 ]
[ 51146-56-6 ]
[ 51146-57-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304

5
[ 15687-27-1 ]
[ 62784-66-1 ]
[ 1224446-49-4 ]
[ 51146-56-6 ]
[ 51146-57-7 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641

6
[ 62784-66-1 ]
[ 137144-15-1 ]
[ 1239016-21-7 ]
[ 144789-13-9 ]
(R)-2-(2-methylphenyl)propanoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641

7
[ 15687-27-1 ]
[ 62784-66-1 ]
[ 1116086-46-4 ]
[ 1224446-49-4 ]
[ 51146-56-6 ]
[ 51146-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate;	Experimental Example 6Production of Optically Active Ester and Optically Active Carboxylic Acid Using Ibuprofen (Optical Resolution of Ibuprofen) As shown by the above reaction equation, an optically active ester and optically active carboxylic acid are obtained by reacting 1,1-di(1-naphthyl)methanol or 1,1-di(9-phenanthryl)methanol and racemic ibuprofen. The results are shown in Table 6.; R)-ibuprofen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/ml): tR=6.1 min (4.1percent), tR=10.7 min (95.9percent);IR (neat): 3036, 1735, 1599, 1512, 782, 679 cm-1;1H NMR (CDCl3): delta8.29 (s, 1H, 1-H), 8.02-7.93 (m, 1H, Ph), 7.85-7.60 (m, 5H, Ph), 7.47-7.26 (m, 3H, Ph), 7.24-7.02 (m, 6H, Ph), 7.00-6.88 (m, 3H, Ph), 3.74 (q, J=7.1 Hz, 1H, 2-H), 2.38 (d, J=7.1 Hz, 2H, 1'-H), 1.78 (qq, J=6.6, 6.6 Hz, 1H, 2'-H), 1.43 (d, J=7.1 Hz, 3H, 3-H), 0.84 (d, J=6.6 Hz, 6H, 3'-H);13C NMR (CDCl3): delta173.7, 140.6, 137.2, 134.9, 134.7, 133.8, 133.7, 131.2, 130.9, 129.3, 129.1, 128.8, 128.7, 128.6, 127.5, 126.7, 126.3, 125.8, 125.6, 125.2, 125.0, 123.5, 123.4, 70.9, 45.3, 45.0, 30.2, 22.4, 18.1;HR MS: calculated for C34H32O2Na (M+Na+)=495.2295; found 495.2276.(S)-ibuprofenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/100/0.1, flow rate=1.0 mL/min); tR=26.3 min (77.5percent), tR=28.5 min (22.5percent);1H NMR (CDCl3): delta10.30 (br s, 1H, COOH), 7.14 (d, J=7.9 Hz, 2H, Ph), 7.02 (d, J=7.9 Hz, 2H, Ph), 3.63 (q, J=7.3 Hz, 1H, 2-H), 2.37 (q, J=7.3 Hz, 2H, 1'-H), 1.77 (qq, J=6.5, 6.5 Hz, 1H, 2'-H), 1.42 (d, J=7.3 Hz, 2H, 3-H), 0.82 (d, J=6.5 Hz, 6H, 3'-H).

Reference： [1]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 11-12

8
[ 940-31-8 ]
[ 62784-66-1 ]
[ 1213744-22-9 ]
[ 1345458-52-7 ]
[ 1129-46-0 ]
[ 1912-23-8 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 11296 - 11304
[2]Heterocycles,2012,vol. 86,p. 1227 - 1252

9
[ 62784-66-1 ]
[ 120-36-5 ]
[ 1213744-25-2 ]
[ 120-36-5 ]

Reference： [1]Heterocycles,2012,vol. 86,p. 1227 - 1252

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Isomers

Technical Information

? Appel Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Friedel-Crafts Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Preparation of Alcohols ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Swern Oxidation ? Vilsmeier-Haack Reaction

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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. 62784-66-1 ] {[proInfo.proName]}

Quality Control of [ 62784-66-1 ]

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Safety of [ 62784-66-1 ]

Application In Synthesis of [ 62784-66-1 ]

[ 62784-66-1 ] Synthesis Path-Upstream 1~2

[ 62784-66-1 ] Synthesis Path-Downstream 1~9

Technical Information

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Aryls

Alcohols

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Physical hazards

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[ 62784-66-1 ]