2-Naphthalenecarboxylicacid, 6-amino- supplier

Name
6-AMINO-2-NAPHTHOIC ACID
EINECS
CAS No. 116668-47-4
Article Data3
CAS DataBase
Density 1.352 g/cm³
Solubility
Melting Point 206-209 °C(lit.)
Formula C₁₁H₉NO₂
Boiling Point 416.7 °C at 760 mmHg
Molecular Weight 187.198
Flash Point 205.8 °C
Transport Information
Appearance beige-greenish to brown powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 6-Amino-2-naphthoic Acid;
PSA 63.32000
LogP 2.70140

Synthetic route

: 71590-34-6
6-acetylamino-[2]naphthonitrile

: 116668-47-4
6-amino-2-naphthoic acid

Conditions

Conditions	Yield
With sulfuric acid; acetic acid

: 5783-91-5
6-nitro-[2]naphthoic acid

: 116668-47-4
6-amino-2-naphthoic acid

Conditions

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

: 46816-16-4
6-acetylamino-[2]naphthoic acid

: 116668-47-4
6-amino-2-naphthoic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 71590-32-4
N-(6-bromo-[2]naphthyl)-acetamide

: 116668-47-4
6-amino-2-naphthoic acid

Conditions

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

: 6-nitro-[2]naphthonitrile

: 116668-47-4
6-amino-2-naphthoic acid

Conditions

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

: 83008-10-0
N-(6-methyl-[2]naphthyl)-acetamide

: 116668-47-4
6-amino-2-naphthoic acid

Conditions

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

: 50-00-0
formaldehyd

: 116668-47-4
6-amino-2-naphthoic acid

: 5043-05-0
6-(N,N-dimethylamino)-2-naphthoic acid

Conditions

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%

: 116668-47-4
6-amino-2-naphthoic acid

: 74-88-4
methyl iodide

: 5043-06-1
methyl 6-(dimethylamino)-2-naphthoate

Conditions

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%

: 24424-99-5
di-tert-butyl dicarbonate

: 116668-47-4
6-amino-2-naphthoic acid

: 516465-99-9
6-[(tert-butoxycarbonyl)-amino]-2-naphthoic acid

Conditions

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

: 67-56-1
methanol

: 116668-47-4
6-amino-2-naphthoic acid

: 5159-59-1
methyl 6-amino-2-naphthoate

Conditions

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

: 116668-47-4
6-amino-2-naphthoic acid

: 393522-70-8
(6-amino-2-naphthalenyl)methanol

Conditions

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;

: 116668-47-4
6-amino-2-naphthoic acid

: 501-53-1
benzyl chloroformate

: 1313494-75-5
6-(((benzyloxy)carbonyl)amino)-2-naphthoic acid

Conditions

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

: 4422-95-1
1,3,5-benzene tris(carbonyl chloride)

: 116668-47-4
6-amino-2-naphthoic acid

: 1431933-38-8
C42H27N3O9

Conditions

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

: 64-17-5
ethanol

: 116668-47-4
6-amino-2-naphthoic acid

: ethyl 6-aminonaphthalene-2-carboxylate

Conditions

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

: 116668-47-4
6-amino-2-naphthoic acid

: nitrosonium tetrafluoroborate

: 6-carboxynaphthalenediazonium tetrafluoroborate

Conditions

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

...Expand

: 116668-47-4
6-amino-2-naphthoic acid

: 2462-34-2
L-valine benzyl ester hydrochloride

: C23H24N2O3

Conditions

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%

: 67-56-1
methanol

: 116668-47-4
6-amino-2-naphthoic acid

: 5043-05-0
6-(N,N-dimethylamino)-2-naphthoic acid

Conditions

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

: 116668-47-4
6-amino-2-naphthoic acid

: 75-03-6
ethyl iodide

: 6-N,N-diethylamino-2-naphthoic acid ethyl ester

Conditions

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

: C10H22N2O4

: 116668-47-4
6-amino-2-naphthoic acid

: C21H29N3O5

Conditions

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

: 1121-60-4
pyridine-2-carbaldehyde

: 116668-47-4
6-amino-2-naphthoic acid

: (2-py)-CH=N-C10H6-COOH

Conditions

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

: 116668-47-4
6-amino-2-naphthoic acid

: L-cysteine diamide dihydrochloride

: 1387559-32-1
C28H28N6O4S2

Conditions

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%

: 828-51-3
1-Adamantanecarboxylic acid

: 116668-47-4
6-amino-2-naphthoic acid

: 1268629-39-5
6-(1-adamantanecarboxamido)naphthalene-2-carboxylic acid

Conditions

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

: 116668-47-4
6-amino-2-naphthoic acid

: 6-amino-5-chloro-2-naphthoic acid

Conditions

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

: 17754-90-4
4-(Diethylamino)salicylaldehyde

: 116668-47-4
6-amino-2-naphthoic acid

: (E)-6-((4-(diethylamino)-2-hydroxybenzylidene)amino)-2-naphthoic acid

Conditions

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

: 2038-03-1
4-(2-AMINOETHYL)MORPHOLINE

: 116668-47-4
6-amino-2-naphthoic acid

: 6-amino-N-(2-morpholinoethyl)-2-naphthamide

Conditions

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%

: 116668-47-4
6-amino-2-naphthoic acid

: 137-07-5
2-amino-benzenethiol

: C17H12N2S

Conditions

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

: 88192-19-2
3-azidopropylamine

: 116668-47-4
6-amino-2-naphthoic acid

: 1310048-45-3
6-amino-N-(3-azidopropyl)-2-naphthamide

Conditions

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%

: 116668-47-4
6-amino-2-naphthoic acid

: 62-53-3
aniline

: 139036-46-7
6-amino-N-phenyl-2-naphthamide

Conditions

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%

: 116668-47-4
6-amino-2-naphthoic acid

: 6258-06-6
sodium 1-amino-4-bromoanthraquinone-2-sulfonate

: 1213268-72-4
sodium 1-amino-4-(6-carboxy-2-naphthylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate

Conditions

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;

: 116668-47-4
6-amino-2-naphthoic acid

: 814-68-6
acryloyl chloride

: 1089725-57-4
6-acryloylaminonaphthalene-2-carboxylic acid

Conditions

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

: 500-22-1
3-pyridinecarboxaldehyde

: 116668-47-4
6-amino-2-naphthoic acid

: (3-py)-CH=N-C10H6-COOH

Conditions

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

: 400747-22-0
methyl 4' amino-[1,1'-biphenyl]-3-carboxylate

: 116668-47-4
6-amino-2-naphthoic acid

: 1360630-50-7
methyl 4'-(6-amino-2-naphthamido)biphenyl-3-carboxylate

Conditions

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%

: 515141-52-3
methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylidene]amino}-2-thiophenecarboxylate

: 116668-47-4
6-amino-2-naphthoic acid

: 832102-19-9
6-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-naphthalenecarboxylic acid

Conditions

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

: 116668-47-4
6-amino-2-naphthoic acid

: 100-44-7
benzyl chloride

: benzyl 6-(benzylamino)-2-naphthoate

Conditions

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

: 75-44-5
phosgene

: 116668-47-4
6-amino-2-naphthoic acid

: 100125-22-2
6-isocyanato-[2]naphthoyl chloride

Conditions

Conditions	Yield
With nitrobenzene

2-Naphthalenecarboxylicacid, 6-amino- Specification

The 2-Naphthalenecarboxylicacid, 6-amino-, with the CAS registry number of 116668-47-4, is also known as 6-Amino-2-naphthoic Acid. It belongs to the product categories of Aminoacid; Aromatic Amino Acids; Peptide Synthesis; Unnatural Amino Acid Derivatives. Its molecular formula is C₁₁H₉NO₂ and molecular weight is 187.19. What's more, its IUPAC name is 6-Aminonaphthalene-2-carboxylic acid. In addition, it must be stored in airtight containers and placed in a dry, cool place. Besides, you should ensure the work place is well-ventilated.

Physical properties about the 2-Naphthalenecarboxylicacid, 6-amino- are: (1)ACD/LogP: 1.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.81; (4)ACD/LogD (pH 7.4): -0.85; (5)ACD/BCF (pH 5.5): 1.36; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.02; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.73; (14)Molar Refractivity: 55.26 cm³; (15)Molar Volume: 138.3 cm³; (16)Surface Tension: 69.2 dyne/cm; (17)Density: 1.352 g/cm³; (18)Flash Point: 205.8 °C; (19)Enthalpy of Vaporization: 70.64 kJ/mol; (20)Boiling Point: 416.7 °C at 760 mmHg; (21)Vapour Pressure: 1.08E-07 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In addition, during using it, wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)c1ccc2c(c1)ccc(N)c2
(2) 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)
(3) InChIKey: NZTPZUIIYNYZKT-UHFFFAOYAN

Product Name

6-AMINO-2-NAPHTHOIC ACID

Synthetic route

2-Naphthalenecarboxylicacid, 6-amino- Specification

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