[ CAS No. 51688-75-6 ] {[proInfo.proName]}

Name: 51688-75-6|4-Amino-3-ethylbenzoic acid|98%
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SKU: A241328
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Quality Control of [ 51688-75-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 51688-75-6 ]

Product Details of [ 51688-75-6 ]

CAS No. :	51688-75-6	MDL No. :	MFCD04114098
Formula :	C₉H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MFTBLGQBZWFKHP-UHFFFAOYSA-N
M.W :	165.19	Pubchem ID :	2762776
Synonyms :

Calculated chemistry of [ 51688-75-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	47.58
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) :	-6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.24
Log Po/w (XLOGP3) :	1.8
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	0.53
Log Po/w (SILICOS-IT) :	1.29
Consensus Log Po/w :	1.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	0.959 mg/ml ; 0.00581 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.295 mg/ml ; 0.00178 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	1.05 mg/ml ; 0.00638 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.23

Safety of [ 51688-75-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 51688-75-6 ]

* 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.

Upstream synthesis route of [ 51688-75-6 ]
Downstream synthetic route of [ 51688-75-6 ]

[ 51688-75-6 ] Synthesis Path-Upstream 1~5

1
[ 34921-76-1 ]
[ 51688-75-6 ]

Yield	Reaction Conditions	Operation in experiment
84.5%	Stage #1: for 22 h; Reflux; Inert atmosphere Stage #2: With hydrogenchloride In water	Preparation of 4-amino-3-ethylbenzoic AcidA suspension of 4-cyano-2-ethylacetanilide (10.1 g, 53.66 mmol) in 20percent aqueous sodium hydroxide (38 mL, 188 mmol) was stirred at reflux, under nitrogen atmosphere for 22 hours. The dark solution was cooled to room temperature, diluted with water (200 mL) and washed with ethyl acetate (2.x.50 mL). The aqueous phase was acidified with concentrated hydrochloric acid to pH 5 and extracted with ethyl acetate (2.x.100 mL). After further acidifying to pH 4 the aqueous phase was further extracted with ethyl acetate (2.x.50 mL) and the combined extracts was washed with brine (50 mL), dried (magnesium sulfate) and evaporated in vacuo. The residual solid was triturated with petroleum ether, removed by filtration, washed with petroleum ether and dried in vacuo. The beige solid (7.49 g, 84.5percent) was 4-amino-3-ethylbenzoic acid of good purity.

Reference： [1] Patent: US2011/190267, 2011, A1, . Location in patent: Page/Page column 55-56

2
[ 103796-17-4 ]
[ 51688-75-6 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 2733,2736

3
[ 33098-65-6 ]
[ 51688-75-6 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 2733,2736

4
[ 105902-59-8 ]
[ 51688-75-6 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 2733,2736

5
[ 51688-73-4 ]
[ 51688-75-6 ]

Reference： [1] Patent: US2011/190267, 2011, A1,

[ 51688-75-6 ] Synthesis Path-Downstream 1~40

1
[ 51688-75-6 ]
[ 103027-53-8 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 2733,2736

2
[ 103796-17-4 ]
[ 51688-75-6 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 2733,2736

3
[ 51688-75-6 ]
(2R,4S)-2-Amino-4-fluoro-pentanedioic acid diisopropyl ester; hydrochloride [ No CAS ]
[ 194809-17-1 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3280 - 3291

4
[ 51688-75-6 ]
(2S,4S)-2-Amino-4-fluoro-pentanedioic acid diisopropyl ester; hydrochloride [ No CAS ]
[ 194809-19-3 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3280 - 3291

6
[ 51688-75-6 ]
(2S,4S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-amino]-3-ethyl-benzoylamino}-4-fluoro-pentanedioic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3280 - 3291

7
[ 51688-75-6 ]
(2S,4R)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-amino]-3-ethyl-benzoylamino}-4-fluoro-pentanedioic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3280 - 3291

8
[ 51688-75-6 ]
[ 194809-20-6 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3280 - 3291

9
[ 51688-75-6 ]
[ 194809-18-2 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3280 - 3291

10
[ 33098-65-6 ]
[ 51688-75-6 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 2733,2736

11
[ 51688-75-6 ]
[ 99062-37-0 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 2733,2736

12
[ 105902-59-8 ]
[ 51688-75-6 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 2733,2736

13
[ 1062246-03-0 ]
[ 51688-75-6 ]
[ 1137870-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; water; for 18.0h;Reflux;	Example 194 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-ethyl-benzoic acid (I-194) A mixture of 1.1 g (3.481 mmole) of 2-chloro-9-cyclopentyl-7,7-difluoro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-20), 0.746 g (4.525 mmole) of <strong>[51688-75-6]4-amino-3-ethylbenzoic acid</strong>, 10 mL of ethanol and 40 mL of 1M hydrochloric acid was heated at reflux for 18 hours. The mixture was cooled and the white precipitate was collected by filtratration, washed with cold water and dried in vacuum to give 0.3421 g of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-ethyl-benzoic acid (I-194) as off-white solid.

Reference： [1]Patent: US2009/318408,2009,A1 .Location in patent: Page/Page column 75

14
[ 34921-76-1 ]
[ 51688-75-6 ]

Yield	Reaction Conditions	Operation in experiment
84.5%		Preparation of 4-amino-3-ethylbenzoic AcidA suspension of 4-cyano-2-ethylacetanilide (10.1 g, 53.66 mmol) in 20% aqueous sodium hydroxide (38 mL, 188 mmol) was stirred at reflux, under nitrogen atmosphere for 22 hours. The dark solution was cooled to room temperature, diluted with water (200 mL) and washed with ethyl acetate (2×50 mL). The aqueous phase was acidified with concentrated hydrochloric acid to pH 5 and extracted with ethyl acetate (2×100 mL). After further acidifying to pH 4 the aqueous phase was further extracted with ethyl acetate (2×50 mL) and the combined extracts was washed with brine (50 mL), dried (magnesium sulfate) and evaporated in vacuo. The residual solid was triturated with petroleum ether, removed by filtration, washed with petroleum ether and dried in vacuo. The beige solid (7.49 g, 84.5%) was 4-amino-3-ethylbenzoic acid of good purity.

Reference： [1]Patent: US2011/190267,2011,A1 .Location in patent: Page/Page column 55-56

15
[ 51688-75-6 ]
[ 100-39-0 ]
[ 1314003-64-9 ]

Yield	Reaction Conditions	Operation in experiment
83.7%	With potassium carbonate; In N,N-dimethyl-formamide; at 80.0℃; for 18.0h;Inert atmosphere;	Preparation of Benzyl 4-amino-3-ethylbenzoateA stirred solution of <strong>[51688-75-6]4-amino-3-ethylbenzoic acid</strong> (7.40 g, 44.80 mmol) in anhydrous N,N-dimethylformamide (110 mL) was treated with potassium carbonate (12.38 g, 89.60 mmol) and benzyl bromide (9.20 g, 53.76 mmol) and the mixture heated to 80 C. under nitrogen for 18 hours. A small sample was removed, treated with 10% aqueous citric acid and extracted with ethyl acetate. TLC analysis (CH2Cl2/MeOH, 9:1, UV) of the organic phase showed that complete conversion had occurred to a product at higher Rf (starting material Rf 0.30, product Rf 0.95). The reaction mixture was cooled, poured into water (1100 mL) and extracted with diethyl ether (3×300 mL). The combined extract was washed with water (4×250 mL), dried (magnesium sulfate) and evaporated in vacuo to leave an amber oil (12.15 g). The 1H NMR spectrum was consistent with the structure of benzyl 4-amino-3-ethylbenzoate but showed some impurity peaks. 6.0 g of this impure material was used in an initial examination of the next step. The remaining impure material (6.1 g) was purified by column chromatography on silica gel, eluting with petroleum ether/EtOAc (83:17). Benzyl 4-amino-3-ethylbenzoate was obtained as a pale yellow viscous oil (4.83 g) of good purity by NMR analysis. This mass of pure material correlates to a yield of 83.7% of the theoretical.

Reference： [1]Patent: US2011/190267,2011,A1 .Location in patent: Page/Page column 55-56

16
[ 51688-73-4 ]
[ 51688-75-6 ]

Reference： [1]Patent: US2011/190267,2011,A1

17
[ 51688-75-6 ]
[ 1314003-65-0 ]

Reference： [1]Patent: US2011/190267,2011,A1

18
[ 51688-75-6 ]
[ 1314003-66-1 ]

Reference： [1]Patent: US2011/190267,2011,A1

19
[ 51688-75-6 ]
[ 1314003-19-4 ]

Reference： [1]Patent: US2011/190267,2011,A1

20
[ 51688-75-6 ]
[ 1449669-05-9 ]