116668-47-4

Basic information

• Product Name: 6-AMINO-2-NAPHTHOIC ACID
• Synonyms: 6-AMINO-2-NAPHTHOIC ACID;2-Naphthalenecarboxylicacid,6-amino-(9CI);6-AMINO-2-NAPHTHOIC ACID 90%;6-Amino-2-naphthalenecarboxylic acid;6-Amino-2-naphthoic acid, tech;6-Aminonaphthalene-2-carboxylic acid, 6-Amino-2-carboxynaphthalene;6-AMino-2-naphthoic acid, 90% 5GR
• CAS NO: 116668-47-4
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19
• Product Categories: AMINOACID;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 116668-47-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 206-209 °C(lit.)
• Boiling Point: 321.94°C (rough estimate)
• Flash Point: 205.8 °C
• Appearance: Beige-green/Powder
• Density: 1.1963 (rough estimate)
• Vapor Pressure: 1.08E-07mmHg at 25°C
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 4.49±0.30(Predicted)
• CAS DataBase Reference: 6-AMINO-2-NAPHTHOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-2-NAPHTHOIC ACID(116668-47-4)
• EPA Substance Registry System: 6-AMINO-2-NAPHTHOIC ACID(116668-47-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 116668-47-4(Hazardous Substances Data)

Usage

Chemical Properties

beige-greenish to brown powder

InChI:InChI=1/C11H9NO2/c12-10-4-3-7-5-9(11(13)14)2-1-8(7)6-10/h1-6H,12H2,(H,13,14)/p-1

Synthetic route

6-acetylamino-[2]naphthonitrile (71590-34-6) → 6-amino-2-naphthoic acid (116668-47-4)

Conditions	Yield
With sulfuric acid; acetic acid

6-nitro-[2]naphthoic acid (5783-91-5) → 6-amino-2-naphthoic acid (116668-47-4)

Conditions	Yield
With hydrogenchloride; acetic acid; tin(ll) chloride

6-acetylamino-[2]naphthoic acid (46816-16-4) → 6-amino-2-naphthoic acid (116668-47-4)

Conditions	Yield
With hydrogenchloride

N-(6-bromo-[2]naphthyl)-acetamide (71590-32-4) → 6-amino-2-naphthoic acid (116668-47-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuCN; pyridine 2: H2SO4; acetic acid View Scheme

6-nitro-[2]naphthonitrile → 6-amino-2-naphthoic acid (116668-47-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous acetic acid; H2SO4 2: SnCl2+2H2O; HCl; acetic acid View Scheme

N-(6-methyl-[2]naphthyl)-acetamide (83008-10-0) → 6-amino-2-naphthoic acid (116668-47-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: permanganate; aqueous magnesium sulfate 2: diluted hydrochloric acid View Scheme

formaldehyd (50-00-0) + 6-amino-2-naphthoic acid (116668-47-4) → 6-(N,N-dimethylamino)-2-naphthoic acid (5043-05-0)

Conditions	Yield
With sodium cyanoborohydride In methanol; water at 20℃; for 0.5h;	100%
With sodium cyanoborohydride In methanol at 0 - 25℃; for 2.16667h; Inert atmosphere;	95%
With sodium cyanoborohydride; acetic acid In methanol at 0℃; for 2h;	88%
With sodium cyanoborohydride; acetic acid In methanol; water at 20℃; Cooling with ice;	87%

6-amino-2-naphthoic acid (116668-47-4) + methyl iodide (74-88-4) → methyl 6-(dimethylamino)-2-naphthoate (5043-06-1)

Conditions	Yield
Stage #1: 6-amino-2-naphthoic acid; methyl iodide With sodium carbonate In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;	99%

di-tert-butyl dicarbonate (24424-99-5) + 6-amino-2-naphthoic acid (116668-47-4) → 6-[(tert-butoxycarbonyl)-amino]-2-naphthoic acid (516465-99-9)

Conditions	Yield
With sodium hydroxide In water; tert-butyl alcohol at 20℃; for 12h;	98%
With sodium hydroxide In 1,4-dioxane for 16h;	76%
With hydrogenchloride; NaOH In water; tert-butyl alcohol

methanol (67-56-1) + 6-amino-2-naphthoic acid (116668-47-4) → methyl 6-amino-2-naphthoate (5159-59-1)

Conditions	Yield
With sulfuric acid Reflux;	96%
With sulfuric acid for 1.5h; Heating;	95%
With sulfuric acid for 36h; Reflux;	92%

6-amino-2-naphthoic acid (116668-47-4) → (6-amino-2-naphthalenyl)methanol (393522-70-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h;	93%
Multi-step reaction with 2 steps 1: sulfuric acid / 1.5 h / Heating 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 5 °C View Scheme
With D-Glucose; Bacillus subtilis glucose dehydrogenase; Segniliparus rugosus carboxylic acid reductase; nicotinamide adenine dinucleotide phosphate; dimethyl sulfoxide; ATP; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; pH=7.5; Enzymatic reaction;
With D-Glucose; Escherichia coli endogenous alcohol dehydrogenase; Segniliparus rugosus carboxylic acid reductase; dimethyl sulfoxide; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; pH=7.5; Enzymatic reaction;

6-amino-2-naphthoic acid (116668-47-4) + benzyl chloroformate (501-53-1) → 6-(((benzyloxy)carbonyl)amino)-2-naphthoic acid (1313494-75-5)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 17h;	92%

1,3,5-benzene tris(carbonyl chloride) (4422-95-1) + 6-amino-2-naphthoic acid (116668-47-4) → C42H27N3O9 (1431933-38-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	92%

ethanol (64-17-5) + 6-amino-2-naphthoic acid (116668-47-4) → ethyl 6-aminonaphthalene-2-carboxylate

Conditions	Yield
With sulfuric acid for 12h; Reflux; Inert atmosphere;	88%
With sulfuric acid at 80℃; pH=6; Reflux;	86%
Stage #1: ethanol; 6-amino-2-naphthoic acid With thionyl chloride Reflux; Stage #2: In tetrahydrofuran; ethyl acetate	70%
With thionyl chloride for 3h; Heating / reflux;

tetrafluoroboric acid + 6-amino-2-naphthoic acid (116668-47-4) + nitrosonium tetrafluoroborate → 6-carboxynaphthalenediazonium tetrafluoroborate

Conditions	Yield
In diethyl ether; acetonitrile at -40℃; for 0.5h; Inert atmosphere;	85%

6-amino-2-naphthoic acid (116668-47-4) + L-valine benzyl ester hydrochloride (2462-34-2) → C23H24N2O3

Conditions	Yield
Stage #1: L-valine benzyl ester hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 6-amino-2-naphthoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 24h;	83%

methanol (67-56-1) + 6-amino-2-naphthoic acid (116668-47-4) → 6-(N,N-dimethylamino)-2-naphthoic acid (5043-05-0)

Conditions	Yield
With formaldehyd; sodium cyanoborohydride; acetic acid at 20℃; for 3h; Cooling with ice;	80%

6-amino-2-naphthoic acid (116668-47-4) + ethyl iodide (75-03-6) → 6-N,N-diethylamino-2-naphthoic acid ethyl ester

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	80%

C10H22N2O4 + 6-amino-2-naphthoic acid (116668-47-4) → C21H29N3O5

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran; N,N-dimethyl-formamide	78%

pyridine-2-carbaldehyde (1121-60-4) + 6-amino-2-naphthoic acid (116668-47-4) → (2-py)-CH=N-C10H6-COOH

Conditions	Yield
In methanol at 75℃; for 12h; Autoclave;	67%

6-amino-2-naphthoic acid (116668-47-4) + L-cysteine diamide dihydrochloride → C28H28N6O4S2 (1387559-32-1)

Conditions	Yield
Stage #1: 6-amino-2-naphthoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: L-cysteine diamide dihydrochloride With triethylamine In dimethyl sulfoxide at 20℃; for 12h;	61%

1-Adamantanecarboxylic acid (828-51-3) + 6-amino-2-naphthoic acid (116668-47-4) → 6-(1-adamantanecarboxamido)naphthalene-2-carboxylic acid (1268629-39-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	60%

6-amino-2-naphthoic acid (116668-47-4) → 6-amino-5-chloro-2-naphthoic acid

Conditions	Yield
With N-chloro-succinimide In tetrachloromethane for 1h; Reflux;	60%

4-(Diethylamino)salicylaldehyde (17754-90-4) + 6-amino-2-naphthoic acid (116668-47-4) → (E)-6-((4-(diethylamino)-2-hydroxybenzylidene)amino)-2-naphthoic acid

Conditions	Yield
With acetic acid In ethanol for 14h;	58%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 6-amino-2-naphthoic acid (116668-47-4) → 6-amino-N-(2-morpholinoethyl)-2-naphthamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;	54.6%

6-amino-2-naphthoic acid (116668-47-4) + 2-amino-benzenethiol (137-07-5) → C17H12N2S

Conditions	Yield
With potassium carbonate at 220℃; for 6h;	50%

3-azidopropylamine (88192-19-2) + 6-amino-2-naphthoic acid (116668-47-4) → 6-amino-N-(3-azidopropyl)-2-naphthamide (1310048-45-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	48%

6-amino-2-naphthoic acid (116668-47-4) + aniline (62-53-3) → 6-amino-N-phenyl-2-naphthamide (139036-46-7)

Conditions	Yield
Stage #1: 6-amino-2-naphthoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.25h; Stage #2: aniline In N,N-dimethyl-formamide for 24h;	46%

6-amino-2-naphthoic acid (116668-47-4) + sodium 1-amino-4-bromoanthraquinone-2-sulfonate (6258-06-6) → sodium 1-amino-4-(6-carboxy-2-naphthylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (1213268-72-4)

Conditions	Yield
With disodium hydrogenphosphate; sodium dihydrogenphosphate; copper In water at 120℃; under 7500.75 Torr; for 0.0833333h; pH=6 - 7; Ullmann reaction; Microwave irradiation;	45%
With copper In aq. phosphate buffer at 80 - 120℃; pH=6 - 7; Ullmann Condensation; Microwave irradiation;
With copper In aq. phosphate buffer at 80 - 120℃; Sealed tube; Microwave irradiation;

6-amino-2-naphthoic acid (116668-47-4) + acryloyl chloride (814-68-6) → 6-acryloylaminonaphthalene-2-carboxylic acid (1089725-57-4)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	41.5%

3-pyridinecarboxaldehyde (500-22-1) + 6-amino-2-naphthoic acid (116668-47-4) → (3-py)-CH=N-C10H6-COOH

Conditions	Yield
In methanol at 75℃; for 12h; Autoclave;	41%

methyl 4' amino-[1,1'-biphenyl]-3-carboxylate (400747-22-0) + 6-amino-2-naphthoic acid (116668-47-4) → methyl 4'-(6-amino-2-naphthamido)biphenyl-3-carboxylate (1360630-50-7)

Conditions	Yield
Stage #1: 6-amino-2-naphthoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.25h; Stage #2: methyl 4' amino-[1,1'-biphenyl]-3-carboxylate In N,N-dimethyl-formamide for 48h;	40%

methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylidene]amino}-2-thiophenecarboxylate (515141-52-3) + 6-amino-2-naphthoic acid (116668-47-4) → 6-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-naphthalenecarboxylic acid (832102-19-9)

Conditions	Yield
In phenol at 100 - 135℃; for 1.5h;	25%

6-amino-2-naphthoic acid (116668-47-4) + benzyl chloride (100-44-7) → benzyl 6-(benzylamino)-2-naphthoate

Conditions	Yield
With potassium carbonate; sodium iodide In DMF (N,N-dimethyl-formamide) at 80℃;	21%

phosgene (75-44-5) + 6-amino-2-naphthoic acid (116668-47-4) → 6-isocyanato-[2]naphthoyl chloride (100125-22-2)

Conditions	Yield
With nitrobenzene

Upstream product

• 83008-10-0 N-(6-methyl-[2]naphthyl)-acetamide 
• 71590-32-4 N-(6-bromo-[2]naphthyl)-acetamide 
• 46816-16-4 6-acetylamino-[2]naphthoic acid 
• 5783-91-5 6-nitro-[2]naphthoic acid 
• 71590-34-6 6-acetylamino-[2]naphthonitrile 

Downstream Products

• 393522-70-8 (6-amino-2-naphthalenyl)methanol 
• 5159-59-1 methyl 6-amino-2-naphthoate 
• 832102-19-9 6-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-naphthalenecarboxylic acid 
• 5043-05-0 6-(N,N-dimethylamino)-2-naphthoic acid 
• 5043-06-1 methyl 6-(dimethylamino)-2-naphthoate 

Relevant articles and documents

Routes to the synthesis of 6-amino-2-naphthoic acid.

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