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Chemical Structure| 52130-17-3
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Product Details of [ 52130-17-3 ]

CAS No. :52130-17-3 MDL No. :MFCD00075026
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BYHMLZGICSEKIY-UHFFFAOYSA-N
M.W : 151.16 Pubchem ID :2733699
Synonyms :

Calculated chemistry of [ 52130-17-3 ]

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 Ų

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) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.05
Log Po/w (XLOGP3) : 1.13
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 : 2.25 mg/ml ; 0.0149 mol/l
Class : Very soluble
Log S (Ali) : -2.05
Solubility : 1.34 mg/ml ; 0.00884 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 [ 52130-17-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52130-17-3 ]

* 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 [ 52130-17-3 ]
  • Downstream synthetic route of [ 52130-17-3 ]

[ 52130-17-3 ] Synthesis Path-Upstream   1~10

  • 1
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Reference: [1] Patent: EP2226315, 2010, A1, . Location in patent: Page/Page column 17
  • 2
  • [ 52130-17-3 ]
  • [ 55289-05-9 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1741 - 1745
  • 3
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  • [ 52570-33-9 ]
Reference: [1] Patent: WO2006/117669, 2006, A1,
  • 4
  • [ 52130-17-3 ]
  • [ 603-80-5 ]
YieldReaction ConditionsOperation in experiment
69% With sulfuric acid; sodium nitrite In methanol; dichloromethane; water Alternative Preparation for 2-Methyl-3-hydroxybenzoic acid
To a cold (0° C.) suspension of 0.54 g (3.3 mmol) of 2-methyl-3-aminobenzoic acid in 5 mL of water containing 0.65 mL of concentrated sulfuric acid, was added 0.25 g (3.6 mmol) of solid sodium nitrite.
After approximately 15 minutes the reaction mixture was poured into 20 mL of warm water containing 4 mL of concentrated sulfuric acid.
The resultant reaction mixture was heated slowly to 90° C., resulting in gas evolution.
After the gas evolution ceased, the solution was cooled to room temperature and extracted with ethyl acetate.
The organic layers were combined, washed with 0.5N hydrochloric acid, dried and concentrated under reduced pressure.
The crude residue was purified by rapid filtration through silica gel (eluent of 5percent methanol in methylene chloride) to yield 350 mg of a white solid (m.p. 137-138° C.).
Yield: 69percent. 1 H NMR (CDCl3): δ 8.18 (br.s, 1H), 7.42 (d, J=7.7 Hz, 1H), 7.13 (t, J=7.9 Hz, 1H), 6.93 (d, J=7.9 Hz, 1H), 2.46 (s, 3H).
Analysis for C8 H8 O3: Calcd: C, 63.15; H, 5.29; Found: C, 63.32; H, 5.36.
69% With sulfuric acid; sodium nitrite In methanol; dichloromethane; water Alternative Preparation for 2-Methyl-3-hydroxybenzoic acid
To a cold (0° C.) suspension of 0.54 g (3.3 mmol) of 2-methyl-3-aminobenzoic acid in 5 mL of water containing 0.65 mL of concentrated sulfuric acid, was added 0.25 g (3.6 mmol) of solid sodium nitrite.
After approximately 15 minutes the reaction mixture was poured into 20 mL of warm water containing 4 mL of concentrated sulfuric acid.
The resultant reaction mixture was heated slowly to 90° C., resulting in gas evolution.
After the gas evolution ceased, the solution was cooled to room temperature and extracted with ethyl acetate.
The organic layers were combined, washed with 0.5N hydrochloric acid, dried and concentrated under reduced pressure.
The crude residue was purified by rapid filtration through silica gel (eluent of 5percent methanol in methylene chloride) to yield 350 mg of a white solid (m.p. 137°-138° C.).
Yield: 69percent.
1 H NMR (CDCl3): δ8.18 (br.s, 1H), 7.42 (d, J=7.7 Hz, 1H), 7.13 (t, J=7.9 Hz, 1H), 6.93 (d, J=7.9 Hz, 1H), 2.46 (s, 3H).
Analysis for C8 H8 O3: Calcd: C, 63.15; H, 5.29; Found: C, 63.32; H, 5.36.
69% With sulfuric acid; sodium nitrite In methanol; dichloromethane; water PREPARATION 1
2-Methyl-3-hydroxybenzoic acid
To a cold (0° C.) suspension of 0.54 g (3.3 mmol) of 2-methyl-3-aminobenzoic acid in 5 mL of water containing 0.65 mL of concentrated sulfuric acid, was added 0.25 g (3.6 mmol) of solid sodium nitrite.
After approximately 15 minutes the reaction mixture was poured into 20 mL of warm water containing 4 mL of concentrated sulfuric acid.
The resultant reaction mixture was heated slowly to 90° C. resulting in gas evolution After the gas evolution ceased, the solution was cooled to room temperature and extracted with ethyl acetate.
The organic layers were combined, washed with 0.5N hydrochloric acid, dried and concentrated under reduced pressure.
The crude residue was purified by rapid filtration through silica gel (eluent of 5percent methanol in methylene chloride) to yield 350 mg of a white solid (m.p. 137°-138° C.). Yield: 69percent.
1 H NMR (CDCl3): δ8.18 (br.s, 1H), 7.42 (d, J=7.7 Hz, 1H), 7.13 (t, J=7.9 Hz, 1H), 6.93 (d, J=7.9 Hz, 1H), 2.46 (s, 3H).
Analysis for C8 H8 O3: Calcd: C, 63.15; H, 5.29; Found: C, 63.32; H, 5.36.
Reference: [1] Patent: US6335/459, 2002, B1, . Location in patent: Page column 29
[2] Patent: US6335459, 2002, B1, . Location in patent: Page column 29
[3] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1741 - 1745
[4] Patent: US5952343, 1999, A,
[5] Patent: US5484926, 1996, A,
[6] Patent: US5527829, 1996, A,
[7] Bulletin de la Societe Chimique de France, 1973, p. 3427 - 3432
[8] Journal of Medicinal Chemistry, 1997, vol. 40, # 24, p. 3979 - 3985
[9] Steroids, 2000, vol. 65, # 3, p. 117 - 123
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YieldReaction ConditionsOperation in experiment
36% With hydrogenchloride; sulfuric acid; urea; sodium nitrite In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water Part A
Preparation of 3-Hydroxy-2-methylbenzoic Acid
A one-necked 100 mL round-bottomed flask (magnetic stirring) was charged with 1.0 gram (6.6 mM) 3-amino-2-methylbenzoic acid.
A warm mixture of 2.3 mL conc. sulfuric acid in 4.3 mL water was added to the flask, the resulting slurry was cooled below 15° C. in an ice bath, and 6.6 grams of ice was added.
The reaction mixture was treated via subsurface addition with a solution of 0.6 gram (8.6 mM) sodium nitrite in 6.6 mL ice water with the reaction temperature maintained at 0-5° C. during the addition.
After stirring at 0-5° C. for 30 min., a few crystals of urea were added to decompose the excess nitrite.
The reaction mixture was then poured into a room temperature solution of 23.8 grams (102.3 mM) copper (II) nitrate hemipentahydrate in 200 mL water.
With vigorous stirring, the reaction mixture was treated with 0.9 gram (6.0 mM) copper (I) oxide.
The reaction mixture foamed and changed from turquoise blue to dark green in color.
Reaction was left stirring for 30 min.
The reaction mixture was extracted with diethyl ether (3*), and the organic extracts were combined.
The organic extracts were concentrated to approximately one-fourth the original volume, then extracted with 25 mL 1N sodium hydroxide solution.
The layers were separated, and the dark-red aqueous layer was acidified to pH=2 using 1N hydrochloric acid solution.
The acidified aqueous layer was then extracted with diethyl ether (3*), and the ether extracts were combined, dried (MgSO4), and concentrated to yield a reddish-colored oil.
Purification by flash chromatography on silica gel using a gradient of 0-7percent methanol/methylene chloride afforded 0.39 grams (36percent) of a yellow solid.
36% With hydrogenchloride; sulfuric acid; urea; sodium nitrite In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water Part A
Preparation of 3-Hydroxy-2-methylbenzoic Acid
A one-necked 100 mL round-bottomed flask (magnetic stirring) was charged with 1.0 gram (6.6 mM) 3-amino-2-methylbenzoic acid.
A warm mixture of 2.3 mL conc. sulfuric acid in 4.3 mL water was added to the flask, the resulting slurry was cooled below 15° C. in an ice bath, and 6.6 grams of ice was added.
The reaction mixture was treated via subsurface addition with a solution of 0.6 gram (8.6 mM) sodium nitrite in 6.6 mL ice water with the reaction temperature maintained at 0-5° C. during the addition.
After stirring at 0-5° C. for 30 min., a few crystals of urea were added to decompose the excess nitrite.
The reaction mixture was then poured into a room temperature solution of 23.8 grams (102.3 mM) copper (II) nitrate hemipentahydrate in 200 mL water.
With vigorous stirring, the reaction mixture was treated with 0.9 gram (6.0 mM) copper (I) oxide.
The reaction mixture foamed and changed from turquoise blue to dark green in color.
Reaction was left stirring for 30 min.
The reaction mixture was extracted with diethyl ether (3*), and the organic extracts were combined.
The organic extracts were concentrated to approximately one-fourth the original volume, then extracted with 25 mL 1N sodium hydroxide solution.
The layers were separated, and the dark-red aqueous layer was acidified to pH=2 using 1N hydrochloric acid solution.
The acidified aqueous layer was then extracted with diethyl ether (3*), and the ether extracts were combined, dried (MgSO4), and concentrated to yield a reddish-colored oil.
Purification by flash chromatography on silica gel using a gradient of 0-7percent methanol/methylene chloride afforded 0.39 grams (36percent) of a yellow solid.
Reference: [1] Patent: US6046190, 2000, A,
[2] Patent: US5968942, 1999, A,
[3] Patent: US6143747, 2000, A,
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Reference: [1] Patent: EP1744619, 2015, B1, . Location in patent: Paragraph 0273; 0274
  • 7
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  • [ 18583-89-6 ]
YieldReaction ConditionsOperation in experiment
85% With p-toluenesulfonic acid monohydrate; potassium carbonate In methanol; ethyl acetate A.
3-Amino-2-methyl benzoate methyl ester
A solution of 10 g (66.2 mmol) of 3-amino-2-methyl benzoic acid and 20 g of p-toluenesulfonic acid monohydrate in 400 mL of methanol was refluxed overnight and then diluted with a mixture of ethyl acetate and 1M potassium carbonate.
The resulting layers were cooled and then separated.
The organic layer was then washed sequentially with 1M potassium carbonate, and brine, dried over sodium sulfate, filtered and then concentrated to provide 9.23 g of an orange oil.
Yield: 85percent. 1 H NMR (CDCl3): δ 2.34 (s, 3H), 3.73 (br.s 2H), 3.88 (s, 3H), 6.81 (d, J=7.96 Hz, 1H), 7.05 (t, J=7.78 Hz, 1H), 7.19-7.30 (m, 1H). IR(CHCl3): 3406, 3027, 3012, 2978, 2953, 1718, 1621, 1467, 1435, 1315, 1301, 1265, 1196, 1159, 1108, 1066, 1045, 810 cm-1. MS(FD): m/e 165 (M+, 100).
85% With p-toluenesulfonic acid monohydrate; potassium carbonate In methanol; ethyl acetate A.
3-Amino-2-methyl benzoate methyl ester
A solution of 10 g (66.2 mmol) of 3-amino-2-methyl benzoic acid and 20 g of p-toluenesulfonic acid monohydrate in 400 mL of methanol was refluxed overnight and then diluted with a mixture of ethyl acetate and 1M potassium carbonate.
The resulting layers were cooled and then separated.
The organic layer was then washed sequentially with 1M potassium carbonate, and brine, dried over sodium sulfate, filtered and then concentrated to provide 9.23 g of an orange oil.
Yield: 85percent.
1 H NMR (CDCl3): δ2.34 (s, 3H), 3.73 (br.s, 2H), 3.88 (s, 3H), 6.81 (d, J=7.96 Hz, 1H), 7.05 (t, J=7.78 Hz, 1H), 7.19-7.30 (m, 1H).
IR (CHCl3): 3406, 3027, 3012, 2978, 2953, 1718, 1621, 1467, 1435, 1315, 1301, 1265, 1196, 1159, 1108, 1066, 1045, 810 cm-1.
MS(FD): m/e 165 (M+, 100).
85% With p-toluenesulfonic acid monohydrate; potassium carbonate In methanol; ethyl acetate A.
3-Amino-2-methyl benzoate methyl ester
A solution of 10 g (66.2 mmol) of 3-amino-2-methyl benzoic acid and 20 g of p-toluenesulfonic acid monohydrate in 400 mL of methanol was refluxed overnight and then diluted with a mixture of ethyl acetate and 1M potassium carbonate.
The resulting layers were cooled and then separated.
The organic layer was then washed sequentially with 1M potassium carbonate, and brine, dried over sodium sulfate, filtered and then concentrated to provide 9.23 g of an orange oil.
Yield: 85percent.
1 H NMR (CDCl3): δ2.34 (s, 3H), 3.73 (br.s, 2H), 3.88 (s, 3H), 6.81 (d, J=7.96 Hz, 1H), 7.05 (t, J=7.78 Hz, 1H), 7.19-7.30 (m, 1H).
IR (CHCl3): 3406, 3027, 3012, 2978, 2953, 1718, 1621, 1467, 1435, 1315, 1301, 1265, 1196, 1159, 1108, 1066, 1045, 810 cm-1.
MS (FD): m/e 165 (M+, 100).
Reference: [1] Patent: US5952343, 1999, A,
[2] Patent: US5461154, 1995, A,
[3] Patent: US5484926, 1996, A,
[4] Patent: US6555541, 2003, B1,
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YieldReaction ConditionsOperation in experiment
91% at 70℃; for 22 h; -amino-2-methylbenzoate[01 1 62] To stirred solution of methyl 3-amino-2-methylbenzoic acid (5 g, 33.1 mmol) in methanol (50 mL), was added cone. H2S04 (5 mL) at 0 0 C and the mixture was heated at 70 °C for 22 h. On completion, methanol was removed under reduced pressure, and then sat. sodium bicarbonate solution was added and the product extracted with 10 percentMeOH/DCM. Combined organic layers were dried, concentrated to yield methyl 3-amino-2-methylbenzoate (5 g, 91 percent).
90% at 70℃; 3-amino-4-methylbenzoic acid (15.00 g, 0.099 mol) was suspended in MEOH (150 mL) and thionyl chloride (25. 33 mL, 0.347 mol, 3.5 equiv. ) was added dropwise. The mixture was heated overnight at 70 C. After cooling to RT, volatiles were removed under reduced pressure and the residue triturated with ether (150 mL). The solid was filtered off and dried (18.36 g). The solid was suspended in DCM (600 mL) and saturated aqueous NAHC03 (250 mL) was added. After stirring for 15 minutes, the organic layer was separated and washed successively with NAHC03 solution (2 x 250 mL), water (250 mL) and brine (250 ML). The solution was dried (NA2SO4), filtered and evaporated to dryness to give the desired aniline (14. 8 G, 90percent yield).
23% at 70℃; for 22 h; STEP 1 : To 3-amino-2-methylbenzoic acid (500 mg, 3.3 mmol) in methanol (20 ml) was added sulfuric acid (500 μl) and heated to 7O0C for 22 h, at which point the volume was reduced by rotary evaporation. The residue was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The resultant organic layer was dried over sodium sulfate, filtered, and then concentrated to afford a tan oil (125 mg, 23percent) of methyl 3-amino-2-methylbenzoate, which was used without further purification. 1H NMR (400 MHz, DMSOd6): 6.99-6.93 (m, IH), 6.89-6.86 (d, IH), 6.81-6.78 (d, IH), 5.12-5.07 (br. s, 2H), 3.78 (s, 3H), 2.16 (s, 3H). MS (EI) for C9H, ,NO2: 166 (MH+).
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 38, p. 13469 - 13473
[2] Patent: WO2012/142513, 2012, A1, . Location in patent: Page/Page column 297
[3] Patent: WO2004/65367, 2004, A1, . Location in patent: Page 151
[4] Patent: WO2009/55077, 2009, A1, . Location in patent: Page/Page column 398
  • 9
  • [ 1975-50-4 ]
  • [ 52130-17-3 ]
YieldReaction ConditionsOperation in experiment
90% With palladium on activated charcoal; hydrogen In ethyl acetate for 15 h; 2-Methyl-3-nitrobenzoic acid (2 g, 12.12 mmol) was dissolved in ethyl acetate in a two neck round bottom flask to it 5percent Pd-C (0.10 g).
The reaction mixture is stirred for 15 h under balloon pressure filled with hydrogen gas.
On completion of the reaction the crude product was collected by evaporating the solvent under reduced pressure.
The crude product was then purified by column chromatography (silica gel 60-120 mesh, using dichloromethane and ethanol, (v/v, 99.5:0.5) as eluent to give pure white solid. mp: 181 °C. Yield: 1.5 g (90percent). IR νmax in cm-1: 3244 (νN-H), 1724 (νC=O, acid), 1284 (νC-N, aromatic amine).
Elemental analysis calculated for C8H9NO2: C, 63.56percent; H, 6.00percent; N, 9.27percent.; Found: C, 63.13percent; H, 5.87percent; N, 8.99percent.
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1741 - 1745
[2] Journal of Molecular Structure, 2013, vol. 1049, p. 78 - 89
[3] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
[4] Bulletin de la Societe Chimique de France, 1973, p. 3427 - 3432
[5] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8589 - 8592
[6] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4282 - 4299
[7] Patent: US5179125, 1993, A,
[8] Patent: US5210266, 1993, A,
[9] Patent: US5530028, 1996, A,
[10] Soft Matter, 2013, vol. 9, # 4, p. 1066 - 1075
[11] Dyes and Pigments, 2013, vol. 99, # 2, p. 447 - 455
[12] RSC Advances, 2016, vol. 6, # 49, p. 43069 - 43079
[13] Journal of Materials Chemistry C, 2017, vol. 5, # 27, p. 6729 - 6737
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Reference: [1] Patent: EP2096109, 2009, A1, . Location in patent: Page/Page column 22
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