[ CAS No. 2486-75-1 ] {[proInfo.proName]}

Name: 2486-75-1|4-Amino-2-methylbenzoic acid|97%
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Quality Control of [ 2486-75-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2486-75-1 ]

SDS Specification

Alternatived Products of [ 2486-75-1 ]

Product Details of [ 2486-75-1 ]

CAS No. :	2486-75-1	MDL No. :	MFCD06656133
Formula :	C₈H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XRSQZFJLEPBPOZ-UHFFFAOYSA-N
M.W :	151.16	Pubchem ID :	241632
Synonyms :

Calculated chemistry of [ 2486-75-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.77
TPSA :	63.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.0
Log Po/w (XLOGP3) :	1.14
Log Po/w (WLOGP) :	1.28
Log Po/w (MLOGP) :	0.21
Log Po/w (SILICOS-IT) :	0.95
Consensus Log Po/w :	0.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.83
Solubility :	2.22 mg/ml ; 0.0147 mol/l
Class :	Very soluble
Log S (Ali) :	-2.06
Solubility :	1.3 mg/ml ; 0.00863 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.78
Solubility :	2.5 mg/ml ; 0.0166 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 2486-75-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2486-75-1 ]

* 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 [ 2486-75-1 ]
Downstream synthetic route of [ 2486-75-1 ]

[ 2486-75-1 ] Synthesis Path-Upstream 1~7

1
[ 2486-75-1 ]
[ 1975-51-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 47, p. 8016 - 8018

2
[ 2486-75-1 ]
[ 578-39-2 ]

Reference： [1] Chemische Berichte, 1884, vol. 17, p. 161

3
[ 2486-75-1 ]
[ 7782-77-6 ]
[ 578-39-2 ]

Reference： [1] Chemische Berichte, 1884, vol. 17, p. 161

4
[ 67-56-1 ]
[ 2486-75-1 ]
[ 6933-47-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride In waterReflux	Step 1. Synthesis of methyl 4-amino-2-methylbenzoate To a solution of 4-amino-2-methylbenzoic acid (1.00 g, 6.60 mmol) in 18 mL of methanol was treated concentrated HCl (2.30 mL, 27.6 mmol) in one portion at r.t. The reaction mixture was refluxed overnight then directly concentrated to give a crude product, which was partitioned between ethyl acetate (50 mL) and saturated NaHCO_3(aq) (20 mL). The organic layer was washed with brine (10 mL), dried over MgSO₄ and concentrated to give the desired product (930 mg, 85percent). ¹H NMR (CDCl₃, 400 MHz) δ 7.83-7.80 (m, 1H), 6.51-6.48 (m, 2H), 4.15 (br s, 2H), 3.83 (s, 3H), 2.55 (s, 3H).

Reference： [1] Patent: US2017/253569, 2017, A1, . Location in patent: Paragraph 0175-0176

5
[ 1975-51-5 ]
[ 2486-75-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 5%-palladium/activated carbon; hydrogen In ethanolFlow reactor	General procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.

Reference： [1] Tetrahedron, 2018, vol. 74, # 47, p. 6795 - 6803
[2] Chemische Berichte, 1884, vol. 17, p. 161
[3] Patent: US2012/46467, 2012, A1, . Location in patent: Page/Page column 26

6
[ 67081-02-1 ]
[ 2486-75-1 ]

Reference： [1] Chemische Berichte, 1885, vol. 18, p. 3452

7
[ 7647-01-0 ]
[ 103204-69-9 ]
[ 2486-75-1 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1926, vol. 264, p. 447
[2] Chem. Zentralbl., 1912, vol. 83, # I, p. 136

[ 2486-75-1 ] Synthesis Path-Downstream 1~40

1
[ 67081-02-1 ]
[ 2486-75-1 ]

Reference： [1]Chemische Berichte,1885,vol. 18,p. 3452

2
[ 1975-51-5 ]
[ 2486-75-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 5%-palladium/activated carbon; hydrogen; In ethanol; under 12001.2 Torr;Flow reactor;	General procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.
	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 16h;	2-Methyl-4-nitrobenzoic acid (741 g, 5 mmol) was dissolved in methanol (20 mL), 10% palladium-carbon (100 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 16 hours. The reaction solution was filtered through celite and, thereafter, the filtrate was concentrated under reduced pressure to obtain 4-amino-2-methylbenzoic acid as a crude material. In accordance with Reference Example 23 and Reference Example 14, from 4-amino-2-methylbenzoic acid obtained, there was obtained 4-[(tert- butyldimethylsilano yloxy)methyl]-3-methylaniline (0.33 g). LC/MS: M+1=252.2

Reference： [1]Tetrahedron,2018,vol. 74,p. 6795 - 6803
[2]Chemische Berichte,1884,vol. 17,p. 161
[3]Patent: US2012/46467,2012,A1 .Location in patent: Page/Page column 26

3
[ 2486-75-1 ]
[ 578-39-2 ]

Reference： [1]Chemische Berichte,1884,vol. 17,p. 161

4
[ 2486-75-1 ]
[ 15719-64-9 ]
[ 108-44-1 ]

Reference： [1]Chemische Berichte,1884,vol. 17,p. 161

5
[ 2486-75-1 ]
[ 108-24-7 ]
[ 103204-69-9 ]

Reference： [1]Bulletin de la Societe Scientifique de Bretagne,1956,vol. 31,p. Sonderheft S.9,41

6
[ 2486-75-1 ]
[ 159005-71-7 ]
4-Amino-N-{(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-2-methyl-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 445 - 450

9
[ 2486-75-1 ]
[ 7782-77-6 ]
[ 578-39-2 ]

Reference： [1]Chemische Berichte,1884,vol. 17,p. 161

11
[ 7647-01-0 ]
[ 1975-51-5 ]
tin [ No CAS ]
[ 2486-75-1 ]

Reference： [1]Chemische Berichte,1884,vol. 17,p. 161

12
[ 7647-01-0 ]
[ 103204-69-9 ]
[ 2486-75-1 ]

Reference： [1]Archiv der Pharmazie,1926,vol. 264,p. 447

13
[ 2486-75-1 ]
[ 1975-51-5 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 8016 - 8018

14
[ 840537-53-3 ]
[ 2486-75-1 ]
C₂₀H₁₈N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine; In DMF (N,N-dimethyl-formamide); at 60℃; for 20h;	A mixture of intermediate 23 (prepared according to A2a. d) (0. 0002 mol), 4-amino-2- methylbenzoic acid (0. 0004 mol) and 2, 6-dimethylpyridine (0. 0006 mol) in DMF, p. a. (2 ml) was stirred for 20 hours at 60C and the solvent was evaporated. The residue was purified by high-performance liquid chromatography and then the desired fractions were collected. The solvent was evaporated and the residue was crystallised from H2O, then the resulting precipitate was filtered off and dried. Yield : 0. 011 G of compound 249.

Reference： [1]Patent: WO2005/12307,2005,A1 .Location in patent: Page/Page column 64

15
[ 2486-75-1 ]
[ 137-07-5 ]
4-(benzo[d]thiazol-2-yl)-3-methylaniline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6728 - 6737
[2]Journal of Enzyme Inhibition and Medicinal Chemistry,2012,vol. 27,p. 515 - 520

16
[ 1124212-41-4 ]
[ 2486-75-1 ]
[ 1124213-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 20℃;	4-Amino-2-methylbenzoic acid (1 g, 6.62 mmol) and triethylamine (4 mL) were stirred in dichloromethane. 1-Propanephosphonic acid cyclic anhydride (8 mL 50% solution in ethyl acetate) was added dropwise and the reaction stirred at room temperature for 2 hours. The reaction was concentrated under reduced pressure and the residue taken up in ethyl acetate. The organic solution was washed with saturated sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated under vacuum to afford the title compound (902 mg). MS (ESI) m/z 409.7 [M+H]+
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 20℃; for 2h;	4-Amino-2-methylbenzoic acid (1g, 6.62mmol) and triethylamine (4ml_) were stirred in dichloromethane. 1-Propanephosphonic acid cyclic anhydride (8mL, 50% solution in ethyl acetate) was added dropwise and the reaction stirred at room temperature for 2 hours. The reaction was concentrated under reduced pressure and the residue taken up in ethyl acetate. The organic solution was washed with saturated sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated under vacuum to afford the title compound (902mg). MS (ESI) m/z 409.7 [M+H]+

Reference： [1]Patent: US2009/264416,2009,A1 .Location in patent: Page/Page column 21
[2]Patent: WO2009/24550,2009,A1 .Location in patent: Page/Page column 37

17
[ 2486-75-1 ]
[ 100-39-0 ]
4-Amino-2-methyl-benzoesaeure-benzylester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	Preparation of 2The aniline (1, 10 g, 66.16 mmol) was dissolved in DMF (100 mL) and triethyl amine (10.11 mL, 72.77 mmol) at RT. Benzyl bromide (7.86 mL, 66.16 mmol) was then added and the resulting clear brown solution was stirred at RT for 24 h. After pouring into saturated aqueous sodium bicarbonate solution (300 mL) the solution was extracted with EtOAc (2×200 mL). The combined organics were washed with brine (200 mL), dried over MgSO4, filtered, and concentrated in vacuo to yield the crude product which was purified by flash column chromatography (250 g of SiO2, elution with 10% EtOAc/Petrol) to obtain the clean product in 19% yield. (Rf=0.64 in 50% EtOAc/Petrol, visualised by KMnC4 and UV)

Reference： [1]Patent: US2011/190267,2011,A1 .Location in patent: Page/Page column 50

18
[ 2486-75-1 ]
[ 1314003-50-3 ]