Conditions | Yield |
---|---|
Stage #1: 1,8-Naphthalic anhydride With sodium hydroxide In water at 100℃; for 0.0166667h; microwave irradiation; Stage #2: With mercury(II) diacetate In water at 200℃; for 0.25h; Pesci reaction; microwave irradiation; Stage #3: With hydrogenchloride In water at 120℃; for 0.25h; microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide; cobalt(II) acetate In ethanol at 65℃; under 1520 Torr; for 4h; Irradiation; | 99.3% |
With sodium hydroxide; tetrabutylammomium bromide; dicobalt octacarbonyl In water; benzene at 65℃; under 760 Torr; for 5h; Irradiation; | 96% |
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 4.5h; Irradiation; | 95% |
With tributyl-amine; water; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 110 - 130℃; under 3 Torr; for 24h; | 48% |
With water; sodium acetate; triethylamine; Pd-bis(1-methylbenzothiazole-2-carbene) In N,N-dimethyl acetamide at 130℃; for 7h; | 55 % Chromat. |
Conditions | Yield |
---|---|
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube; | 99% |
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry; | 99% |
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃; | 98% |
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: (1-nosyl-5-nitroindol-3-yl)methyl 1-naphthoate With 2-(N,N-dimethylamino)ethylthiol hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water; acetonitrile Inert atmosphere; | 99% |
benzyl 1-naphthoate
toluene
A
1-naphthalenecarboxylic acid
B
1-methyl-3-(phenylmethyl)-benzene
C
1-methyl-4-(phenylmethyl)benzene
D
2-benzyltoluene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction; | A 99% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 60℃; for 17.25h; Inert atmosphere; Stage #2: sodium methyl carbonate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-Fluoronaphthalene With C78H70Al2Cl4N6P4Rh2; magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 22h; Inert atmosphere; Glovebox; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; under 760.051 Torr; for 0.5h; Reagent/catalyst; Temperature; | 99% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; oxygen In acetonitrile at 20℃; for 10h; Irradiation; | 97% |
With periodic acid; pyridinium chlorochromate In acetonitrile | 96% |
With tert.-butylhydroperoxide; manganese(II) acetate; trifluoroacetic acid In acetonitrile at 80℃; under 15001.5 Torr; for 13h; Mechanism; chemoselective reaction; | 95% |
dicobalt octacarbonyl
1-naphthyl triflate
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 97% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Sealed tube; | 97% |
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube; | 75% |
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 3h; | 97% |
Conditions | Yield |
---|---|
With potassium; potassium iodide; magnesium chloride In tetrahydrofuran 1.) reflux, 1 h, 2.) -3 deg C, 4.5 h; | 96% |
With C26H30B10Cl2P2Pd In toluene at 50℃; under 760.051 Torr; for 10h; | 91% |
With diethylzinc; palladium diacetate; tert-butyl XPhos In hexanes; N,N-dimethyl acetamide at 40℃; under 7600.51 Torr; Automated synthesizer; | 69% |
With manganese; 2.9-dimethyl-1,10-phenanthroline; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique; | 68% |
With 6,6'-dimethyl-2,2'-bipyridine; lithium chloride; cobalt(II) iodide; zinc In N,N-dimethyl-formamide; acetonitrile at 40℃; under 760.051 Torr; for 14h; Sealed tube; | 46% |
dicobalt octacarbonyl
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 96% |
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 2.5h; | 92% |
With potassium hydroxide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride In water for 72h; Heating; | 10300 % Turnov. |
With dicobalt octacarbonyl; potassium carbonate; benzyl chloride at 60℃; under 760 Torr; for 0.5h; carbonylation of aryl bromides, relative reactivity, effect of cocatalysts; |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation; | 92% |
With iodine; dimethyl sulfoxide at 120℃; for 26h; Sealed tube; Green chemistry; | 88% |
1-(4-methoxyphenyl)-2-(naphthalen-1-yl)ethan-1-one
A
1-naphthalenecarboxylic acid
B
4-methoxybenzoic acid
Conditions | Yield |
---|---|
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction; | A 92% B 92% |
Conditions | Yield |
---|---|
With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In dimethyl sulfoxide at 60℃; for 3h; | 90% |
Conditions | Yield |
---|---|
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; bis-triphenylphosphine-palladium(II) chloride; water; sodium carbonate In water at 100℃; under 7600.51 Torr; for 24h; Catalytic behavior; Autoclave; | 90% |
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 5h; | 87% |
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h; | 87% |
With water; palladium diacetate; triethylamine; triphenylphosphine In 1,4-dioxane at 110℃; under 11251.1 Torr; for 2h; Flow reactor; | 43% |
carbon monoxide
1-Bromonaphthalene
A
1-naphthalenecarboxylic acid
B
1-naphthylglycolic acid
C
1-naphthylglyoxylic acid
Conditions | Yield |
---|---|
With methyl iodide; sodium sulfide In water; isopropyl alcohol at 20℃; for 20h; | A 6% B 3% C 89% |
With methyl iodide; sodium sulfide In water; isopropyl alcohol at 60℃; for 20h; | A 60% B 17% C 20% |
With sodium sulfide; CoCl2 In 1,4-dioxane; water at 20℃; for 20h; Product distribution; other reag.; other solvent; | A 4 % Chromat. B 9 % Chromat. C 86 % Chromat. |
Conditions | Yield |
---|---|
With acetic anhydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal In N,N-dimethyl-formamide at 100℃; for 10h; | 89% |
Stage #1: lithium formate With acetic anhydride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Iodonaphthalene With tris(dibenzylideneacetone)dipalladium (0); lithium chloride In N,N-dimethyl-formamide at 80℃; for 6h; | 82% |
(±)-1,2-di(naphthalen-1-yl)ethane-1,2-diol
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With sodium hypochlorite In acetonitrile at 20℃; for 18h; | 89% |
Conditions | Yield |
---|---|
In Petroleum ether -100 deg C to 0 deg C; | 88% |
1H-cyclobutanaphthalen-1-one
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide for 3.5h; further reagents; | 88% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 35℃; for 1h; | 87% |
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 83.3℃; Rate constant; substituents polar effects; |
Conditions | Yield |
---|---|
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h; | 87% |
With copper(l) iodide; diethylzinc; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 70℃; under 760.051 Torr; | 68% |
thiophenol
A
3-<(phenylthio)methyl>-1H-indole
B
1-naphthalenecarboxylic acid
C
2-nitrophenyl phenyl sulfide
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile Inert atmosphere; | A 84% B 82% C 86% |
Conditions | Yield |
---|---|
With potassium hydroxide In 1,2-dimethoxyethane | A 70% B 85% |
Conditions | Yield |
---|---|
With sodium hypochlorite In acetonitrile at 20℃; for 1.5h; | 85% |
With 2-(3-thiazolium)-1-phenylethanone bromide; triethylamine In dimethyl sulfoxide; acetonitrile at 37℃; Acidic conditions; |
1-(1-naphthyl)ethanol
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With sodium nitrate; water; oxygen In dimethyl sulfoxide at 130℃; for 36h; | 85% |
Conditions | Yield |
---|---|
With thionyl chloride In toluene for 2h; Reflux; | 100% |
With thionyl chloride for 2h; Heating / reflux; | 98% |
With thionyl chloride for 2h; Heating; | 98% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile for 1.5h; Heating; | 100% |
With caesium carbonate In acetonitrile at 20℃; for 1.5h; Reflux; Inert atmosphere; | 79% |
With caesium carbonate In acetonitrile at 20℃; for 90h; Reflux; Inert atmosphere; | 79% |
With 18-crown-6 ether; potassium carbonate In tetrahydrofuran for 21h; Inert atmosphere; Reflux; |
1-naphthalenecarboxylic acid
[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol
((1R,3S)-5-iodo-6,8-dimethoxy-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl 1-naphthoate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 100% |
1-naphthalenecarboxylic acid
cis-cis-decahydro-1-naphthoic acid
Conditions | Yield |
---|---|
With platinum(IV) oxide; hydrogen In acetic acid under 3000.3 Torr; | 100% |
1-naphthalenecarboxylic acid
1-[(1,1-dimethylethoxy)carbonyl]-2(S)-(2-methoxyethyl)piperazine
1-[(1,1-dimethylethoxy)carbonyl]-2(S)-(2-methoxyethyl)-4-(1-naphthalenylcarbonyl)piperazine
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Acylation; | 99% |
piperidine
1-naphthalenecarboxylic acid
(naphthalen-1-yl)(piperidin-1-yl)methanone
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 99% |
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 21h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 3h; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-naphthalenecarboxylic acid; N,0-dimethylhydroxylamine In toluene at 0℃; for 0.166667h; Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5h; | 99% |
1-naphthalenecarboxylic acid
carbonic acid dimethyl ester
methyl 1-naphthoate
Conditions | Yield |
---|---|
With 25 wt percent zeolite NaY-Bf at 200℃; for 5h; Autoclave; Green chemistry; | 99% |
With dimanganese decacarbonyl at 180℃; for 1h; Sealed tube; | 97% |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 40℃; for 1h; | 98.5% |
With oxone at 65℃; for 30h; | 92% |
With sulfuric acid at 65℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h; | 98.1% |
Conditions | Yield |
---|---|
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 1.66667h; | 98% |
In various solvent(s) at 80℃; for 1.66667h; | 98% |
In toluene at 110℃; for 24h; | 89% |
Conditions | Yield |
---|---|
With pyridine; ammonium bicarbonate; di-tert-butyl dicarbonate In 1,4-dioxane at 20℃; | 98% |
Stage #1: 1-naphthalenecarboxylic acid With 1,3,5-trichloro-2,4,6-triazine; potassium carbonate In tetrahydrofuran for 0.0166667h; Milling; Stage #2: With ammonium thiocyanate In tetrahydrofuran for 0.0833333h; Milling; | 90% |
With ammonium carbonate; ortho-tungstic acid; silver(l) oxide In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 8h; | 82.4% |
1-naphthalenecarboxylic acid
2-phenyl-1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; oxygen; palladium diacetate; p-benzoquinone In tert-butyl alcohol at 100℃; under 22801.5 Torr; for 24h; | 98% |
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 21h; Inert atmosphere; | 98% |
1-naphthalenecarboxylic acid
isopropyl bromide
1-isopropyl-1,4-dihydronaphthalene-1-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 1-naphthalenecarboxylic acid With ammonia; lithium In water at -60℃; for 0.5h; Birch reduction; Stage #2: isopropyl bromide With tert-butyl alcohol In water regioselective reaction; | 98% |
Stage #1: 1-naphthalenecarboxylic acid With ammonia; lithium at -78℃; for 1h; Stage #2: isopropyl bromide at -78℃; for 0.25h; | |
With ammonia; lithium at -78℃; for 1.25h; Birch Reduction; |
1-naphthalenecarboxylic acid
N-methoxylamine hydrochloride
N-methoxynaphthalene-1-carboxamide
Conditions | Yield |
---|---|
Stage #1: 1-naphthalenecarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 4h; Under an atmosphere of argon; Stage #2: N-methoxylamine hydrochloride With potassium carbonate In water; ethyl acetate at 0 - 20℃; for 4h; | 98% |
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; | 75% |
Stage #1: 1-naphthalenecarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3.5h; Stage #2: N-methoxylamine hydrochloride With potassium carbonate In water; ethyl acetate at 20℃; for 20h; |
1-naphthalenecarboxylic acid
cyclohexene
cyclohex-2-en-1-yl 1-naphthoate
Conditions | Yield |
---|---|
With di-tert-butyl peroxide; C11H23N2(1+)*Br4Fe(1-) In ethyl acetate at 110℃; for 24h; | 98% |
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In benzene at 80℃; for 8h; | 77% |
1-naphthalenecarboxylic acid
4-((tert-butyldimethylsilyloxy)methyl)phenol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 98% |
1-naphthalenecarboxylic acid
Conditions | Yield |
---|---|
With copper diacetate; sodium carbonate; (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) In dichloromethane; water at 30℃; for 12h; enantioselective reaction; | 98% |
1-naphthalenecarboxylic acid
2-phenylethynylphenol
Conditions | Yield |
---|---|
Stage #1: 1-naphthalenecarboxylic acid; 2-phenylethynylphenol With bis(1,5-cyclooctadiene)diiridium(I) dichloride In dichloromethane at 20℃; for 1h; Stage #2: With silica gel regioselective reaction; | 98% |
1-naphthalenecarboxylic acid
tert-butyl 2-aminobenzylcarbamate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; | 98% |
Reported in EPA TSCA Inventory.
1-Naphthoic acid, with the CAS NO.86-55-5, is also named as 1-Naphthalenecarboxylic acid, 1-Carboxynaphthalene, alpha-Naphthoic acid, naphthalene-1-carboxylic acid, NAPHTHOIC ACID. It belongs to the ProductCategories of Aromatic Compounds; Naphthalene derivatives; Organic acids. 1-Naphthoic acid can be used in organic synthesis.
Physical properties about 1-Naphthoic acid are: (1)ACD/LogP: 3.13±0.21; (2)ACD/LogD (pH 5.5): 1.14; (3)ACD/LogD (pH 7.4): 0.05; (4)ACD/BCF (pH 5.5): 1.45; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 12.40; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.673; (12)Molar Refractivity: 51.0±0.3 cm3; (13)Molar Volume: 136.1±3.0 cm3; (14)Polarizability: 20.2±0.5 10-24cm3; (15)Surface Tension: 56.6±3.0 dyne/cm; (16)Density: 1.3±0.1 g/cm3; (17)Flash Point: 164.6±13.9 °C; (18)Enthalpy of Vaporization: 57.0±3.0 kJ/mol; (19)Boiling Point: 299.999 °C at 760 mmHg; (20)Vapour Pressure: 0.0±0.6 mmHg at 25°C
When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Avoid contact with skin and eyes;
4. Wear suitable gloves;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C11H8O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H,12,13);
(2)InChIKey=LNETULKMXZVUST-UHFFFAOYSA-N;
(3)Smilesc12c(cccc1C(O)=O)cccc2;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 2370mg/kg (2370mg/kg) | National Technical Information Service. Vol. PB85-143766, |
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