35418-07-6|Methyl 3-(4-aminophenyl)propanoate| Ambeed

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Quality Control of [ 35418-07-6 ] Purity: 96% SDS Specification

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Product Details of [ 35418-07-6 ]

CAS No. :	35418-07-6
Formula :	C₁₀H₁₃NO₂
M.W :	179.22
SMILES Code :	O=C(OC)CCC1=CC=C(N)C=C1
MDL No. :	MFCD00546554
InChI Key :	LXHNQRGWWMORLQ-UHFFFAOYSA-N
Pubchem ID :	417374

Safety of [ 35418-07-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 35418-07-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	51.52
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.93
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.64
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.38
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.67
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.66

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.06
Solubility	1.55 mg/ml ; 0.00867 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.35
Solubility	0.797 mg/ml ; 0.00445 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.92
Solubility	0.214 mg/ml ; 0.00119 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.23 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	1.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.1

Application In Synthesis of [ 35418-07-6 ]

* 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 [ 35418-07-6 ]

[ 35418-07-6 ] Synthesis Path-Downstream 1~35

1
[ 637-57-0 ]
[ 35418-07-6 ]

References: [1]Bulletin de la Societe Royale des Sciences de Liege,1956,vol. 25,p. 79,84.

2
[ 2393-17-1 ]
[ 35418-07-6 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 4639,4641.

3
[ 35418-07-6 ]
[ 1138-80-3 ]
[ 79-22-1 ]
[ 102182-02-5 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 4639,4641.

4
[ 186581-53-3 ]
[ 2393-17-1 ]
[ 35418-07-6 ]

References: [1]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1980,vol. 35,p. 934 - 936.

5
[ 67-56-1 ]
[ 2393-17-1 ]
[ 35418-07-6 ]

Yield	Reaction Conditions	Operation in experiment
99%		Under ice-cooling, thionyl chloride (15 mL, 206 mmol) was added dropwise to methanol (60 mL), and the mixture was stirred for 10 min. 3-(4-Aminophenyl)propanoic acid (10.1 g, 61.1 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 18 hr. The solvent and excess thionyl chloride were evaporated under reduced pressure, and water and saturated aqueous sodium hydrogencarbonate were added. 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 obtained solid was washed with hexane to give the title compound (10.9 g, yield 99%) as pale-brown prism crystals. MS m/z 180 (MH+).
98%		Thionyl chloride (Aldrich, 4.08 g, 2.5 ml, 34.3 mmol) was added dropwise to anhydrous MeOH (10mL) in ice-water-salt bath. After 20 min, 3-(4-aminophenyl)propionic acid (Trans World Chemicals, 1.7 g, 10.3 mmol) was added and the reaction mixture was allowed to stir at rt overnight. The resulting reaction mixture was concentrated in vacuo and the residue was diluted with EtOAc, washed with sat. aqueous NaHCO3, water, and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to give methyl 3-(4-aminophenyl)propanoate (1.80 g, 98%).
78%	With thionyl chloride; at 0 - 20℃; for 12h;	[1114] Preparation Example 67: 3-(4-amino-phenyl)-propionic acid methyl ester[1115] SOCl2 (1.5 mL) was added slowly to MeOH (6 mL) at 0 ~ 5, and the mixture was stirredfor 10 minutes. 3-(4-Amino-phenyl)-propionic acid (1 g, 6.05 mmol) was addedthereto at the same temperature. After the temperature was elevated to roomtemperature, the mixture was stirred for 12 hours. After the termination of thereaction, the reactant was concentrated under reduced pressure, added withsaturated sodium bicarbonate aqueous solution, and extracted with EtOAc. Theorganic layer was added with NaCl aqueous solution, extracted again, and thenfiltered by using celite. The filtrate was concentrated under reduced pressure.The residue was added with n-Hex, and then concentrated under reduced pressureagain. n-Hex (20 mL) was added to the obtained solid, and the mixture wasstirred under reflux for 1 hour, and then stirred at room temperature for 2hours. The mixture was filtered to obtain the title compound (0.85 g, 78%).[1116] 1H NMR (500 MHz, CDCl3)delta 6.98(d, 2H), 6.61(d, 2H), 3.65(s, 3H), 2.83(t, 2H), 2.56(t, 2H)

74%

With sulfuric acid; for 24h;Reflux;

General procedure: After dissolving the carboxylic acid in the alcohol, three drops of H2SO4 95% were added to the solution and the mixture was refluxed for 24 h. The solvent was evaporated under reduced pressure and water was added to the crude mixture. The pH of the aqueous layer was adjusted to 7 adding drops of a saturated solution of NaHCO3 and brine was added in the mixture. The aqueous layer was extracted three times with ethyl acetate; the organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure yielding the final compound. Further purification step was made when it was necessary.

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1365 - 1378.
[2]Patent: EP1726580,2006,A1 .Location in patent: Page/Page column 36.
[3]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6463 - 6480.
[4]Patent: US2011/130398,2011,A1 .Location in patent: Page/Page column 87.
[5]Patent: WO2014/69963,2014,A1 .Location in patent: Paragraph 1114-1116.
[6]European Journal of Medicinal Chemistry,2015,vol. 90,p. 351 - 359.
[7]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1784 - 1789.
[8]Journal of Medicinal Chemistry,1989,vol. 32,p. 256 - 264.
[9]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.
[10]Journal of Medicinal Chemistry,2001,vol. 44,p. 4696 - 4703.
[11]Organic Letters,2010,vol. 12,p. 4932 - 4935.
[12]Molecular Informatics,2018,vol. 37.

6
[ 596-43-0 ]
[ 35418-07-6 ]
[ 117625-23-7 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 256 - 264.

7
[ 109-87-5 ]
[ 35418-07-6 ]
2,8-bis(2-methoxycarbonylethyl)-6H,12H-5,11-methano-dibenzo<b,f><1,5>diazocine [ No CAS ]

References: [1]Synthetic Communications,1995,vol. 25,p. 1849 - 1856.

8
[ 54405-42-4 ]
[ 35418-07-6 ]

Yield	Reaction Conditions	Operation in experiment
95.7%		The intermediate W-9 (1.00 g, 4.78 mmol) was dissolved in a mixed solution of MeOH (10 mL) and ethyl acetate (1 mL), After stirring for 10 min, palladium-carbon (10%, 0.2 g) was added and reacted under a hydrogen atmosphere at room temperature for 4 h. The catalyst was filtered out and the filtrate was concentrated under vacuum to give product W-10 (white solid, 0.82 g, 95.7%). Methyl 3-(4-aminophenyl)propanoate1(W-10), H NMR (400 MHz, DMSO-d6) delta 6.84 (d, J = 8.3 Hz, 2H), 6.47 (d, J = 8.4 Hz, 2H), 4.84 (s, 2H), 3.56 (s, 3H), 2.66 (t, J = 7.6 Hz, 2H), 2.51 (t, J = 5.5 Hz, 3H).
91%	With 5%-palladium/activated carbon; hydrogen; In methanol; under 1810.07 Torr; for 0.5h;	Methyl 3-(4-nitrophenyl)propanoate (450 mg, 2.151 mmol) was dissolved in MeOH (10 ml) and then Pd/C 5% (458 mg, 0.215 mmol) was added. The solution was shaken under hydrogen atmosphere at 35 psi for 30 minutes on a Parr apparatus. The catalyst was filtered off and the solvent removed under vacuum to give methyl 3-(4-aminophenyl)propanoate (350 mg, 1.953 mmol, 91% yield).
91%	With 5%-palladium/activated carbon; hydrogen; In methanol; under 1810.07 Torr; for 0.5h;	Methyl 3-(4-nitrophenyl)propanoate (450 mg, 2.151 mmol) was dissolved in MeOH (10 ml) and then Pd/C 5% (458 mg, 0.215 mmol) was added. The solution was shaken under hydrogen atmosphere at 35 psi for 30 min. on a Parr apparatus. The catalyst was filtered off and the solvent removed under vacuum to give methyl 3-(4-aminophenyl)propanoate (350 mg, 1.953 mmol, 91% yield).

0.76 g

With 5%-palladium/activated carbon; hydrogen; at 20℃; under 760.051 Torr; for 24h;

To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

References: [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29.
[2]Patent: US2013/79313,2013,A1 .Location in patent: Paragraph 0956.
[3]Patent: WO2013/45280,2013,A1 .Location in patent: Page/Page column 241; 242.
[4]Synthetic Communications,1995,vol. 25,p. 1849 - 1856.
[5]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S951 - S953.
[6]Chemistry - A European Journal,2015,vol. 21,p. 16517 - 16524.
[7]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 2445 - 2450.

10
[ 35418-07-6 ]
[ 84102-75-0 ]
[ 174774-61-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1999,vol. 47,p. 1694 - 1712.

11
[ 66417-26-3 ]
[ 35418-07-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1999,vol. 47,p. 1694 - 1712.
[2]Journal of Chemical Ecology,2008,vol. 34,p. 339 - 352.

12
[ 35418-07-6 ]
[ 330955-07-2 ]
3-{4-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-phenyl}-propionic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 151 - 155.

13
[ 35418-07-6 ]
[ 860638-06-8 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S951 - S953.

14
[ 13139-15-6 ]
[ 35418-07-6 ]
[ 391610-79-0 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 4696 - 4703.

15
[ 103-82-2 ]
[ 35418-07-6 ]
3-(4-phenylacetylamino-phenyl)-propionic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

16
[ 99-66-1 ]
[ 35418-07-6 ]
[ 1026819-81-7 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

17
[ 35418-07-6 ]
[ 1821-12-1 ]
3-[4-(4-phenyl-butyrylamino)-phenyl]-propionic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

18
[ 35418-07-6 ]
[ 107-92-6 ]
3-(4-butyrylamino-phenyl)-propionic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

19
[ 637-57-0 ]
[ 35418-07-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; methanol; at 25℃; for 10h;	Methyl 3-(4-aminophenyl)propanoate (S32). A solution of methyl (E)-3-(4-nitrophenyl)acrylate (S31, 4.10 g, 19.8 mmol) in MeOH (30 mL) and THF (30 mL) was treated with 10% Pd/C (400 mg). The reaction mixture was purged with H2 and was stirred at 25 C for 10 h. The suspension was filtered through diatomaceous earth and concentrated to afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) 6.99 (d, 2H, J= 8.2 Hz), 6.63 (d, 2H, J= 8.4 Hz), 3.60 (s, <n="33"/>3H), 2.85 (t, 2H, J= 7.7 Hz), 2.58 (t, 2H, J= 7.7 Hz); 13C NMR (CDCl3, 125 MHz) 173.5, 144.6, 130.5, 129.1 , 115.3, 51.5, 36.1, 30.1.
82.5%	With hydrogen;palladium 10% on activated carbon; In 1,4-dioxane; at 20℃; under 3102.97 Torr; for 20h;	To a solution of methyl 4-nitrocinnamate obtained in preparation 15 (1.5 g, 7.25 mmol) in dioxane (25 mL) 10% Pd-C (0.6 g) was added and hydrogenated at room temperature at 60 psi for 20 h. The reaction mixture was filtered through celite and concentrated under reduced pressure. The crude residue was purified by column chromatography using 50% EtOAc-pet ether to give pure title compound (1.07 g, 82.5%) as off white solid. [0258] Mp: 142-144 C. [0259] 1H NMR (200 MHz, CDCl3): delta 2.57 (t, J=7.5 Hz, 2H); 2.85 (t, J=7.8 Hz, 2H); 3.66 (s, 3H); 6.64 (d, J=8.3 Hz, 2H); 7.00 (d, J=8.3 Hz, 2H). [0260] Mass m/z (CI): 180 [M+1].
	With hydrogen;palladium; In ethyl acetate;	b Methyl 3-(4-aminophenyl)propionate 50 g (0.241 mol) of methyl 4-nitrocinnamate are exhaustively hydrogenated at room temperature and 50 psi hydrogen pressure over 5 g of palladium on carbon (10% strength) at catalyst in 1000 ml of ethyl acetate. The catalyst is filtered off and the filtrate is concentrated to dryness in vacuo. The residue is crystallized from ether/petroleum ether. Yield: 40.5 g (94% of theory), Melting point: 52-54 C. Rf: 0.75 (silica gel; methylene chloride/methanol=9.5:0.5)

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.
[2]Patent: WO2008/147553,2008,A1 .Location in patent: Page/Page column 31-32.
[3]Patent: US2003/229083,2003,A1 .Location in patent: Page 23.
[4]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 9365 - 9372.
[5]Patent: US5994356,1999,A .

20
[ 35418-07-6 ]
[ 98-80-6 ]
[ 525589-19-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,6-dimethylpyridine;copper diacetate; n-tetradecanoic acid; In toluene; at 25℃; for 24h;	Methyl 3-(4-(phenylamino)phenyl)propanoate (S33). A solution of PhB(OH)2 (550 mg, 4.51 mmol, 1.5 equiv), Cu(OAc)2 (1 10 mg, 0.61 mmol, 0.2 equiv) and myristic acid (137 mg, 0.60 mmol, 0.2 equiv) in anhydrous toluene (6 mL) was treated with 2,6-lutidine (0.35 mL, 3.0 mmol, 1 equiv) and methyl 3-(4- aminophenyl)propanoate (S32, 537 mg, 3.0 mmol, 1 equiv). The reaction mixture was stirred for 24 h at 25 0C and was concentrated. Column chromatography (SiO2, 4 x 5 cm, 20% EtOAc-hexanes) afforded S33 (660 mg, 2.59 mmol, 87%) as a yellow oil: 1H NMR (CDCl3, 500 MHz) 7.28-7.25 (m, 2H), 7.12 (d, 2H, J= 8.4 Hz),7.05 (dd, 2H, J= 7.7, 1.1 Hz), 7.03 (d, 2H, J= 8.4 Hz), 6.95-6.90 (m, IH), 3.70 (s, 3H), 2.92 (t, 2H, J= 7.7 Hz), 2.66 (t, 2H, J= 7.7 Hz); 13C NMR (CDCl3, 125 MHz) 173.5, 143.9, 141.2, 133.2, 129.3, 129.1, 120.6, 118.3, 117.2, 51.6, 35.9, 30.2.

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.
[2]Patent: WO2008/147553,2008,A1 .Location in patent: Page/Page column 32.

21
[ 463-71-8 ]
[ 35418-07-6 ]
methyl 3-(4-isothiocyanatophenyl)propanoate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5863 - 5867.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 14 - 19.

22
[ 35418-07-6 ]
[ 945414-29-9 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.
[2]Patent: WO2008/147553,2008,A1 .

23
[ 35418-07-6 ]
[ 945414-30-2 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.
[2]Patent: WO2008/147553,2008,A1 .

24
[ 35418-07-6 ]
C₂₀H₂₂NO₃Cl [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.

25
[ 35418-07-6 ]
[ 945414-31-3 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.

26
[ 35418-07-6 ]
1-oxo-1-[5-(2-pyridyl)oxazol-2-yl]-3-(4-(phenylamino)phenyl)-propane [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.

27
[ 882-06-4 ]
[ 35418-07-6 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368.
[2]Patent: WO2008/147553,2008,A1 .

28
[ 35418-07-6 ]
[ 1017671-57-6 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

29
[ 35418-07-6 ]
N-[4-(2-hydroxycarbamoyl-ethyl)phenyl]butyramide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

30
[ 35418-07-6 ]
[ 925102-43-8 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

31
[ 35418-07-6 ]
[ 1027486-50-5 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

32
[ 35418-07-6 ]
N-hydroxy-3-(4-phenylacetylamino-phenyl)propionamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

33
[ 35418-07-6 ]
3-[4-(4-phenyl-butyrylamino)-phenyl]-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

34
[ 35418-07-6 ]
2-propyl-pentanoic acid [4-(2-(hydroxycarbamoyl)ethyl)phenyl]amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

35
[ 35418-07-6 ]
N-[4-(2-hydroxycarbamoyl-ethyl)phenyl]-4-phenyl-butyramide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 467 - 474.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 35418-07-6 ]

Aryls

A147561 [20637-09-6]

Methyl 4-(4-aminophenyl)butanoate

Similarity: 1.00

A310505 [91012-19-0]

Methyl 3-(4-aminophenyl)propanoate hydrochloride

Similarity: 0.98

A527304 [850449-93-3]

Methyl 2-(5-amino-2-methylphenyl)acetate

Similarity: 0.96

A186904 [52913-11-8]

Methyl 2-(3-aminophenyl)acetate

Similarity: 0.91

A263499 [35613-44-6]

Methyl 2-(2-aminophenyl)acetate

Similarity: 0.89

Esters

A147561 [20637-09-6]

Methyl 4-(4-aminophenyl)butanoate

Similarity: 1.00

A310505 [91012-19-0]

Methyl 3-(4-aminophenyl)propanoate hydrochloride

Similarity: 0.98

A527304 [850449-93-3]

Methyl 2-(5-amino-2-methylphenyl)acetate

Similarity: 0.96

A186904 [52913-11-8]

Methyl 2-(3-aminophenyl)acetate

Similarity: 0.91

A263499 [35613-44-6]

Methyl 2-(2-aminophenyl)acetate

Similarity: 0.89

Amines

A147561 [20637-09-6]

Methyl 4-(4-aminophenyl)butanoate

Similarity: 1.00

A310505 [91012-19-0]

Methyl 3-(4-aminophenyl)propanoate hydrochloride

Similarity: 0.98

A527304 [850449-93-3]

Methyl 2-(5-amino-2-methylphenyl)acetate

Similarity: 0.96

A186904 [52913-11-8]

Methyl 2-(3-aminophenyl)acetate

Similarity: 0.91

A263499 [35613-44-6]

Methyl 2-(2-aminophenyl)acetate

Similarity: 0.89

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
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

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.: 35418-07-6

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