Product Name

  • Name

    2-Naphthaldehyde

  • EINECS 200-640-2
  • CAS No. 66-99-9
  • Article Data331
  • CAS DataBase
  • Density 1.155 g/cm3
  • Solubility Soluble in hot water.
  • Melting Point 58-61 °C(lit.)
  • Formula C11H8O
  • Boiling Point 299.5 °C at 760 mmHg
  • Molecular Weight 156.184
  • Flash Point 179.5 °C
  • Transport Information
  • Appearance Pink crystalline
  • Safety 22-24/25-36-26
  • Risk Codes 36/37/38-22
  • Molecular Structure Molecular Structure of 66-99-9 (2-Naphthaldehyde)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms 2-Naphthaldehyde(8CI);2-Formylnaphthalene;2-Naphthalenealdehyde;2-Naphthylcarboxaldehyde;NCR 1;NCR 1 (aldehyde);NSC 8557;Naphthalene-2-carbaldehyde;b-Formylnaphthalene;b-Naphthaldehyde;b-Naphthylcarboxaldehyde;2-Naphthalenecarboxaldehyde;
  • PSA 17.07000
  • LogP 2.65230

Synthetic route

2-Naphthalenemethanol
1592-38-7

2-Naphthalenemethanol

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With dimethyl selenoxide In benzene for 5h; Heating;100%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In 1,2-dichloro-ethane at 120℃; under 7500.6 Torr; for 9h;100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In tert-butyl alcohol for 1h; Reflux;100%
2-(naphthalen-2-yl)-1,3-dioxolane
4469-45-8

2-(naphthalen-2-yl)-1,3-dioxolane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In methanol; water at 20℃; for 0.166667h; Ring cleavage;100%
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;95%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
With Pyrene-1-carboxylic acid; C33H22NO4(1-)*Na(1+) In dimethylsulfoxide-d6; water-d2 at 85℃; for 6h; Reagent/catalyst;73 %Spectr.
2-(naphthalen-2-yl)-1,3-dithiolane
77853-39-5

2-(naphthalen-2-yl)-1,3-dithiolane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran Ambient temperature;100%
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran Product distribution; Ambient temperature; various 1,3-dithiolanes;100%
With K-10 clay supported copper(II) nitrate trihydrate In dichloromethane for 6h; Ambient temperature; with K-10 clay-supported iron(III) nitrate nonahydrate;99.6%
With K-10 clay supported copper(II) nitrate trihydrate In dichloromethane for 6h; Ambient temperature; K-10 clay supported iron(III) nitrate nonahydrate;99.6%
With indium (III) iodide; dihydrogen peroxide In water; toluene at 20℃; for 15h; Inert atmosphere; Sealed tube;86 mg
diacetoxy(2-naphthyl)methane
64002-54-6

diacetoxy(2-naphthyl)methane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With H6P2W18O62 In toluene at 100℃; for 0.0833333h;100%
With rice husk supported FeCl3 nanoparticles In ethanol at 70℃; for 0.166667h;95%
With ethanol at 50 - 60℃; for 0.166667h;94%
2-(naphthalen-2-yl)-1,3-dithiane
57009-73-1

2-(naphthalen-2-yl)-1,3-dithiane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide; tantalum pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 24h;100%
With iron(III)-acetylacetonate; dihydrogen peroxide; sodium iodide In water; ethyl acetate at 20℃; for 1.3h;98%
Stage #1: 2-(naphthalen-2-yl)-1,3-dithiane With acetyl chloride; sodium nitrite In dichloromethane at 0 - 5℃; for 0.25h;
Stage #2: With water In dichloromethane at 0 - 20℃; for 0.5h;		96%
2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; dimethyl selenoxide In 1,2-dichloro-ethane for 6h; Heating;98%
With pyridine N-oxide; silver(l) oxide In acetonitrile at 25℃;95%
With hexamethylenetetramine; water; sodium dodecyl-sulfate; lanthanum(lll) triflate at 100℃; for 1.5h; Sommelet Aldehyde Synthesis; Green chemistry;94%
1-chloromethylnaphthalene
2506-41-4

1-chloromethylnaphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Potassium benzeneselenite; dibenzo-18-crown-6 In acetonitrile for 5h; Heating;98%
With bismuth(III) nitrate; tetrabutyl ammonium fluoride at 100℃; for 3.5h;90%
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation;90%
2-(dimethoxymethyl)naphthalene
77196-31-7

2-(dimethoxymethyl)naphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With water In acetonitrile for 0.333333h; UV-irradiation;98%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
2-Vinylnaphthalene
827-54-3

2-Vinylnaphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With sodium periodate; C53H44As2N2O3Ru In water; ethyl acetate; acetonitrile at 25℃; for 0.5h;98%
With oxygen; palladium diacetate; toluene-4-sulfonic acid In water at 100℃; under 6080.41 Torr; for 24h; Autoclave;88%
With sodium periodate In water; ethyl acetate; acetonitrile at 0℃; for 3h;87%
N,N-(naphthalene-2-carbonyl)tosylhydrazide
1448723-24-7

N,N-(naphthalene-2-carbonyl)tosylhydrazide

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
Stage #1: N,N-(naphthalene-2-carbonyl)tosylhydrazide With 1-(Trimethylsilyl)imidazole In toluene at 55℃; for 6h; Inert atmosphere;
Stage #2: With citric acid In methanol; toluene at 20℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;		98%
Naphthalene-2-carboxaldehyde N,N-dimethylhydrazone
59670-87-0

Naphthalene-2-carboxaldehyde N,N-dimethylhydrazone

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With triethylene diamine nickel thiosulfate; water In chloroform at 20℃; for 0.0833333h; Hydrolysis;96%
(naphthalen-2-ylmethylene)bis(ethylsulfane)

(naphthalen-2-ylmethylene)bis(ethylsulfane)

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With cetyl(trimethyl)-ammonium tribromide In dichloromethane at 0 - 5℃; for 0.0833333h;95%
With dihydrogen peroxide; vanadia; ammonium bromide In dichloromethane; water at 0 - 5℃; for 1.75h;95%
Stage #1: (naphthalen-2-ylmethylene)bis(ethylsulfane) With acetyl chloride; sodium nitrite In dichloromethane at 0 - 5℃; for 0.25h;
Stage #2: With water In dichloromethane at 0 - 20℃; for 0.75h;		95%
With ammonium heptamolybdate; dihydrogen peroxide; ammonium bromide; perchloric acid In dichloromethane; water at 0 - 5℃; for 0.5h;84%
2-(naphthalene-2-yl)-1,3-dithiane-1-oxide
1064664-57-8

2-(naphthalene-2-yl)-1,3-dithiane-1-oxide

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile at 20℃; for 12h;95%
carbon monoxide
201230-82-2

carbon monoxide

2-naphthyl triflate
3857-83-8

2-naphthyl triflate

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With palladium diacetate; (C8H17)3SiH; 1,3-bis-(diphenylphosphino)propane; triethylamine In N,N-dimethyl-formamide at 70℃; for 3.5h;94%
With pyridine; hydrogen; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In N,N-dimethyl-formamide at 80℃; under 15001.5 Torr; for 24h;69%
2-(mercaptomethyl)naphthalene
1076-67-1

2-(mercaptomethyl)naphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate; tetrakis(pyridine)silver(II) peroxodisulfate; oxygen In N,N-dimethyl-formamide at 23℃; under 760.051 Torr; Irradiation;94%
2-naphthylacetic acid
581-96-4

2-naphthylacetic acid

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube;93%
With sodium azide; [bis(acetoxy)iodo]benzene In acetonitrile at 0 - 20℃; for 0.333333h;87%
With iron(III) chloride; oxygen In N,N-dimethyl-formamide at 110℃;83%
tert-butyldimethyl(2,2,2-trichloro-1-naphthylen-2-ylethoxy)silane
1027382-25-7

tert-butyldimethyl(2,2,2-trichloro-1-naphthylen-2-ylethoxy)silane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 50℃;93%
(+/-)-1-(2-naphthalenyl)-ethane-1,2-diol
43210-74-8, 49801-14-1, 13603-65-1

(+/-)-1-(2-naphthalenyl)-ethane-1,2-diol

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With oxygen; palladium diacetate; toluene-4-sulfonic acid In water at 100℃; under 6080.41 Torr; for 24h;93%
With oxygen; sodium carbonate In water at 20℃; for 5h; Irradiation; Green chemistry;80%
With oxygen; copper diacetate; palladium dichloride In N,N-dimethyl acetamide at 140℃; under 760.051 Torr; for 48h;10%
N,N-dimethyl-2-naphthylcarboxamide
13577-85-0

N,N-dimethyl-2-naphthylcarboxamide

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; for 10h; Reagent/catalyst; Temperature; chemoselective reaction;93%
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; for 10h;93%
With lithium diisobutylmorpholinoaluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.5h;99 %Chromat.
With C11H25AlNO4(1-)*Na(1+) In tetrahydrofuran; toluene at 0 - 20℃; for 0.5h;> 99 %Chromat.
With benzoic acid ethyl ester; copper diisobutyl-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;99 %Chromat.
[2]naphthaldehyde-semicarbazone
120445-69-4, 3745-94-6

[2]naphthaldehyde-semicarbazone

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With tribromo-isocyanuric acid In acetonitrile at 20℃; for 3.5h;92%
With cetyltrimethylammonium bromate In 1,4-dioxane for 5h; Heating;66%
2-azidomethylnaphthalene
164269-42-5

2-azidomethylnaphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With MoO2(S2CNEt2)2; oxygen In water for 15h; Heating;92%
With di[(2,4-bis-tert-butyl-1-methoxy-3-neopentylcyclopentadienyl)dichlororuthenium(III)]; water In acetonitrile at 75℃; for 7h; Inert atmosphere;74 %Chromat.
2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 2h; Irradiation; Green chemistry;91%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 80℃; for 20h;90%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 80℃; for 20h;90%
2-(naphthalene-2-yl)-1,3-oxathiolane

2-(naphthalene-2-yl)-1,3-oxathiolane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With perchloric acid; dihydrogen peroxide; ammonium bromide; molybdic acid In dichloromethane at 0 - 5℃; for 4h;91%
With ammonium bromide; dihydrogen peroxide; vanadia In dichloromethane at 0 - 5℃; for 0.75h;90%
Stage #1: 2-(naphthalene-2-yl)-1,3-oxathiolane With acetyl chloride; sodium nitrite In dichloromethane at 0 - 5℃; for 0.25h;
Stage #2: With water In dichloromethane at 0 - 20℃; for 0.166667h;		84%
With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Irradiation;80%
2-naphthalenecarboxylic acid 2-pyridinylmethyl ester
760191-94-4

2-naphthalenecarboxylic acid 2-pyridinylmethyl ester

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With triethylsilane; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 60℃; for 12h;91%
methyl 2-naphthyl ketone
93-08-3

methyl 2-naphthyl ketone

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 27h; chemoselective reaction;91%
Multi-step reaction with 2 steps
1: pyridine; potassium permanganate; aqueous KOH-solution
2: N,N-dimethyl-p-toluidine
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C
2: palladium dichloride; copper(l) chloride; oxygen / dimethyl sulfoxide / 10 h / 120 °C / 760.05 Torr
View Scheme
2-(tert-butoxymethyl)naphthalene
42101-90-6

2-(tert-butoxymethyl)naphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With water; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 20℃; for 8h;91%
2,2-diethoxy acetic acid
20461-86-3

2,2-diethoxy acetic acid

2-chloronaphthalene
91-58-7

2-chloronaphthalene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With nickel(II) chloride hexahydrate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; for 0.6h; Schlenk technique; Inert atmosphere; Flow reactor;91%
2-Naphthalenemethanol
1592-38-7

2-Naphthalenemethanol

(E)-2-(2-(naphthalen-2-yl)vinyl)quinoline

(E)-2-(2-(naphthalen-2-yl)vinyl)quinoline

A

2-(2-(naphthalen-2-yl)ethyl)quinoline
1401882-30-1

2-(2-(naphthalen-2-yl)ethyl)quinoline

B

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With ruthenium trichloride; potassium tert-butylate In 1,4-dioxane for 24h;A 81%
B 91%
...Expand
2-naphthaldoxime
51873-98-4, 57207-34-8, 24091-02-9

2-naphthaldoxime

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With zinc dichromate(VI) In dichloromethane for 3h; Ambient temperature;90%
With zinc(II) nitrate; silica gel for 0.0666667h; deoxymation; Irradiation;87%
With benzeneseleninic anhydride In tetrahydrofuran at 40 - 50℃; for 0.333333h;81%
2-(naphthalen-2-yl)-1,3-dioxolane
4469-45-8

2-(naphthalen-2-yl)-1,3-dioxolane

A

2-Naphthalenemethanol
1592-38-7

2-Naphthalenemethanol

B

β-naphthaldehyde
66-99-9

β-naphthaldehyde

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 2h; chemoselective reaction;A 7%
B 90%
malonic acid
141-82-2

malonic acid

β-naphthaldehyde
66-99-9

β-naphthaldehyde

(E)-3-(naphthalen-2-yl)acrylic acid
49711-14-0

(E)-3-(naphthalen-2-yl)acrylic acid

Conditions
ConditionsYield
With piperidine; pyridine100%
With piperidine; pyridine at 115℃; for 3h; Knoevenagel Condensation;93%
With pyridine for 1h; Heating;82%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

acetone
67-64-1

acetone

4-(2-naphtalenyl)-3-buten-2-one
75032-63-2

4-(2-naphtalenyl)-3-buten-2-one

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 20℃; for 0.5h;100%
With boehmite at 55℃; for 24h; Aldol Condensation; Green chemistry;55%
With sodium hydroxide
β-naphthaldehyde
66-99-9

β-naphthaldehyde

2-Naphthalenemethanol
1592-38-7

2-Naphthalenemethanol

Conditions
ConditionsYield
With borohydride Ultra resin In methanol at 20℃; for 2h;100%
With {2,3-bis(diisopropylamino)cycloprop-2-en-1-ylium-1-yl}trihydroborate; silica gel In dichloromethane for 1h;99%
With formaldehyd; triethylamine In 1,2-dimethoxyethane at 80℃; for 26h; Reagent/catalyst; Schlenk technique; Inert atmosphere; chemoselective reaction;99%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

2-napthaldehyde N-[-(2-napthyl)methylidene]hydrazone
2144-02-7

2-napthaldehyde N-[-(2-napthyl)methylidene]hydrazone

Conditions
ConditionsYield
With hydrazine dihydrochloride for 0.25h; Grinding; Neat (no solvent);100%
With bismuth(III) chloride; hydrazine In water at 20℃; for 0.0333333h; Sonication; Green chemistry;98%
With carbazic acid at 60℃; for 5h; Neat (no solvent);97%
Nitroethane
79-24-3

Nitroethane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

(E)-2-(2-nitroprop-1-en-1-yl)naphthalene
37629-58-6

(E)-2-(2-nitroprop-1-en-1-yl)naphthalene

Conditions
ConditionsYield
With ammonium acetate for 6h; Henry reaction; Reflux;100%
With ammonium acetate at 125℃; for 2h; Inert atmosphere;82%
Stage #1: Nitroethane; β-naphthaldehyde With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 0 - 20℃; for 12h; Inert atmosphere;
Stage #2: With trifluoroacetic anhydride In dichloromethane at -10℃; for 0.5h; Inert atmosphere;
Stage #3: With triethylamine In dichloromethane at -10℃; for 0.5h; Inert atmosphere;		75%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

β-naphthaldehyde
66-99-9

β-naphthaldehyde

2-(naphthalen-2-yl)-2-[(trimethylsilyl)oxy]acetonitrile
139224-73-0, 83575-58-0

2-(naphthalen-2-yl)-2-[(trimethylsilyl)oxy]acetonitrile

Conditions
ConditionsYield
Stage #1: β-naphthaldehyde With scandium tris(trifluoromethanesulfonate); 1-n-butyl-3-methylimidazolium hexafluoroantimonate at 20℃; for 0.166667h;
Stage #2: trimethylsilyl cyanide at 20℃; for 0.0833333h; Inert atmosphere;		100%
With <1,3-Dibenzylimidazolidinium>-carbodithioat In dichloromethane at 20℃; for 15h;99%
With lithium chloride In tetrahydrofuran at 22℃; for 0.4h;96%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

(carbethoxyethylidene)triphenylphosphorane
21382-82-1

(carbethoxyethylidene)triphenylphosphorane

2-methyl-3-naphthalen-2-yl-acrylic acid ethyl ester
100510-32-5

2-methyl-3-naphthalen-2-yl-acrylic acid ethyl ester

Conditions
ConditionsYield
In benzene for 4.5h; Ambient temperature;100%
In toluene Reflux;93%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

naphthalen-2-yl formate
1988-18-7

naphthalen-2-yl formate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; for 0.0833333h;100%
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 3h; Baeyer-Villiger oxidation;90%
With dihydrogen peroxide; bis(2,4-dinitrophenyl) diselenide In dichloromethane for 80h; Ambient temperature;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Ambient temperature;
With 2,4-bis (2-methylphenyl)-6-hydroperoxy-1,3,5-triazine for 18h; Baeyer-Villiger Ketone Oxidation;18 %Spectr.
1-methoxy-2-methyl-1-trimethylsiloxy-1-propene
31469-15-5

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

β-naphthaldehyde
66-99-9

β-naphthaldehyde

methyl 2,2-dimethyl-3-(naphthalen-2-yl)-3-(trimethylsilyloxy)propanoate
156541-03-6

methyl 2,2-dimethyl-3-(naphthalen-2-yl)-3-(trimethylsilyloxy)propanoate

Conditions
ConditionsYield
In acetonitrile for 1.5h; Irradiation;100%
With mesoporous aluminosilicate Al-MCM-41 In dichloromethane at 0℃; for 0.25h; Mukaiyama Aldol Addition; Inert atmosphere;99%
With polymer-supported phosphine In N,N-dimethyl-formamide at 20℃; for 4h; Mukaiyama Aldol Addition; Inert atmosphere;95%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

β-naphthaldehyde
66-99-9

β-naphthaldehyde

4-methoxy-N-(naphthalen-2-ylmethylene)aniline
3525-61-9

4-methoxy-N-(naphthalen-2-ylmethylene)aniline

Conditions
ConditionsYield
In ethanol for 1h; Sonication;100%
With acetic acid In ethanol for 3h; Reflux;88%
With magnesium sulfate In dichloromethane at 20℃;60%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-(naphthalene-2-yl)-1,3-oxathiolane

2-(naphthalene-2-yl)-1,3-oxathiolane

Conditions
ConditionsYield
With PPA; silica gel In 1,2-dichloro-ethane at 20℃; for 0.5h;100%
With iodine In dichloromethane at 20℃; for 0.333333h;90%
With lithium tetrafluoroborate In acetonitrile at 20℃; for 2.5h;88%
allyldiethylaluminium
18760-02-6

allyldiethylaluminium

β-naphthaldehyde
66-99-9

β-naphthaldehyde

(R)-1-(naphthalen-2-yl)but-3-en-1-ol

(R)-1-(naphthalen-2-yl)but-3-en-1-ol

Conditions
ConditionsYield
With titanium(IV) isopropylate; (R,S)-2-OH-3,5-Cl2-C6H2-SO2-NH-CH(CH2Ph)-CH(Ph)OH In tetrahydrofuran at 0℃; for 12h;100%
morpholine
110-91-8

morpholine

1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

β-naphthaldehyde
66-99-9

β-naphthaldehyde

[1-(4-morpholino)-1-(2-naphthyl)]methyl-1H-1,2,3-benzotriazole
433232-15-6

[1-(4-morpholino)-1-(2-naphthyl)]methyl-1H-1,2,3-benzotriazole

Conditions
ConditionsYield
In ethanol at 20℃; for 15h;100%
...Expand
β-naphthaldehyde
66-99-9

β-naphthaldehyde

diethylzinc

diethylzinc

(S)-1-(2-naphthyl)propan-1-ol
112576-12-2, 132154-59-7, 87241-23-4

(S)-1-(2-naphthyl)propan-1-ol

Conditions
ConditionsYield
With (R)-2-(1-[(S)-2-(diphenylphosphino)ferrocenylethylimino]methyl)phenol In hexane; toluene at 0℃; for 48h;100%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

4-chloromethyl-2-naphthalen-2-yl[1,3]dioxolane

4-chloromethyl-2-naphthalen-2-yl[1,3]dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;100%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

methylamine
74-89-5

methylamine

N-methyl-1-(naphthalene-2-yl)methanimine
125660-64-2

N-methyl-1-(naphthalene-2-yl)methanimine

Conditions
ConditionsYield
at 20℃; for 12h;100%
With sulfuric acid In ethanol at 80 - 90℃;95%
In tetrahydrofuran; methanol
In ethanol; water
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

trimethyl-(2,2,2-trifluoro-1-naphthalen-2-yl-ethoxy)-silane

trimethyl-(2,2,2-trifluoro-1-naphthalen-2-yl-ethoxy)-silane

Conditions
ConditionsYield
With potassium fluoride; (4R,4'R,5R,5'R)-α,α,α',α',α",α",α‴,α‴-octaphenyl-2,2'-(benzene-1,4-diyl)bis(1,3-dioxolane-4,5-dimethanol) In acetonitrile at 20℃; Inert atmosphere;100%
With tri-tert-butyl phosphine In N,N-dimethyl-formamide at 20℃; for 0.5h;99%
With copper diacetate; 1,2-bis-(diphenylphosphino)ethane In toluene at 20℃;99%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone
627546-31-0

1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone

3-(2-naphthyl)-1-pyrrol-1-yl-2-propen-1-one

3-(2-naphthyl)-1-pyrrol-1-yl-2-propen-1-one

Conditions
ConditionsYield
In toluene at 100℃; for 48h; Wittig olefination;100%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone
627546-31-0

1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone

(E)-3-(naphthalen-2-yl)-1-(1H-pyrrol-1-yl)prop-2-en-1-one
736140-68-4

(E)-3-(naphthalen-2-yl)-1-(1H-pyrrol-1-yl)prop-2-en-1-one

Conditions
ConditionsYield
In toluene at 100℃; for 48h; Wittig reaction;100%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

phenylboronic acid
98-80-6

phenylboronic acid

(S)-naphthalen-2-yl(phenyl)methanol
99412-45-0

(S)-naphthalen-2-yl(phenyl)methanol

Conditions
ConditionsYield
Stage #1: phenylboronic acid With diethylzinc In toluene at 60℃; for 12h;
Stage #2: N,N,N',N'-tetra-n-butyl-BINOL-3,3-dicarboxamide In toluene at 0℃; for 0.25h;
Stage #3: β-naphthaldehyde In toluene at 0℃; for 2.5h;		100%
Stage #1: phenylboronic acid With diethylzinc In hexane; toluene at 20 - 60℃; for 12h; Inert atmosphere;
Stage #2: With diphenyl[(2S)-1-[(2,4,6-trimethylphenyl)methyl]pyrrolidin-2-yl]methanol In hexane; toluene at 20℃; for 0.25h; Inert atmosphere;
Stage #3: β-naphthaldehyde In hexane; toluene at -20℃; for 1h; Inert atmosphere; enantioselective reaction;		99%
Stage #1: phenylboronic acid With diethylzinc In toluene at 60℃; for 12h;
Stage #2: With (S)-diphenyl(1-methylpyrrolidin-2-yl)methanol In toluene at 20℃; for 0.166667h;
Stage #3: β-naphthaldehyde In toluene at 20℃; for 12h; enantioselective reaction;		97%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

naphthalen-2-ylmethyl 2-naphthoate
135512-98-0

naphthalen-2-ylmethyl 2-naphthoate

Conditions
ConditionsYield
With C18BF16(1-)*C34H53F2NiOP2(1+) In toluene at 20℃; for 1h; Glovebox; Inert atmosphere;100%
With triethylamine; lithium bromide at 20℃; for 48h; Tishchenko reaction;92%
With sodium hydride for 16h; Tishchenko reaction; Neat (no solvent); High speed ball milling;91%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

1-amino-2-propene
107-11-9

1-amino-2-propene

(E)-N-allyl-1-(naphthalen-2-yl)methanimine
87869-50-9

(E)-N-allyl-1-(naphthalen-2-yl)methanimine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 20h;100%
With magnesium sulfate In dichloromethane for 24h; Inert atmosphere;100%
pyrrolidine
123-75-1

pyrrolidine

β-naphthaldehyde
66-99-9

β-naphthaldehyde

phenylacetylene
536-74-3

phenylacetylene

1-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)pyrrolidine

1-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)pyrrolidine

Conditions
ConditionsYield
With N,N'-ethylenebis(salicylideneiminato)copper(II) In neat (no solvent) at 80℃; for 0.75h;100%
With zinc diacetate In toluene for 7h; Heating;90%
With [Ag(4,5-bis-(phenylthiomethyl)acridine)(NO3)] In dichloromethane at 60℃; for 5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;88%
...Expand
nitromethane
75-52-5

nitromethane

β-naphthaldehyde
66-99-9

β-naphthaldehyde

(1R)-1-(2-naphthyl)-2-nitroethanol

(1R)-1-(2-naphthyl)-2-nitroethanol

Conditions
ConditionsYield
Stage #1: nitromethane; β-naphthaldehyde With diethyl-tert-butylamine; N,N'-bis[2-(2,4,6-trimethylbenzoyl)-3-oxobutylidene]-(1S,2S)-bis(3,5-dimethylphenyl)ethylene-1,2-diaminato cobalt (II) In dichloromethane at -40℃; for 45h;
Stage #2: With water In tetrahydrofuran; dichloromethane Product distribution / selectivity;		100%
Stage #1: nitromethane; β-naphthaldehyde With 1,2,2,6,6-pentamethylpiperidine; N,N'-bis[2-(2,4,6-trimethylbenzoyl)-3-oxobutylidene]-(1S,2S)-bis(3,5-dimethylphenyl)ethylene-1,2-diaminato cobalt (II) In dichloromethane at -40℃; for 20h;
Stage #2: With water In tetrahydrofuran; dichloromethane Product distribution / selectivity;		96%
With C24H26N2O2; dimethyl zinc(II) In n-heptane; toluene at -50 - -15℃; Henry asymmetric reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;95%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

ammonium chloride

ammonium chloride

β-naphthaldehyde
66-99-9

β-naphthaldehyde

3-hydroxy-3-(naphthalen-2-yl)propanenitrile
144119-14-2, 128104-67-6

3-hydroxy-3-(naphthalen-2-yl)propanenitrile

Conditions
ConditionsYield
In tetrahydrofuran; acetonitrile100%
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2-naphthaldehyde Chemical Properties

The Molecular Structure of 2-naphthaldehyde (CAS NO.66-99-9):

Empirical Formula: C11H8O
Molecular Weight: 156.1806
Density:1.155 g/cm3
Melting point: 58-61 °C(lit.)   
Boiling point: 299.5 °C at 760 mmHg
Flash point: 179.5 °C
FreezingPoint: 1.0755
Sensitive: Air Sensitive
Index of Refraction: 1.675  
Molar Refractivity: 50.84 cm3   
Surface Tension: 48.1 dyne/cm   
Enthalpy of Vaporization: 53.95 kJ/mol
Vapour Pressure: 0.00119 mmHg at 25°C 
Appearance: Pink crystalline
IUPAC: naphthalene-2-carbaldehyde  
Synonyms: 2-Naphthaldehyde ; 2-Formylnaphthalene ; 2-Naphthalenecarboxaldehyde ; 4-07-00-01288 (Beilstein Handbook Reference) ; BRN 0507750 ; EINECS 200-640-2 ; beta-Formylnaphthalene ; beta-Naphthaldehyde ; beta-Naphthylaldehyde ; beta-Naphthylcarboxaldehyde ; 2-Naphthalenecarboxaldehyde ; 2-Naphthalenecarboxaldehyde (9CI)  

2-naphthaldehyde Uses

 2-naphthaldehyde (CAS NO.66-99-9) can be used in organic synthesis.

2-naphthaldehyde Production

Which leads to the dry anhydrous hydrogen chloride, and anhydrous tin dichloride, a mixture of ether, to saturation, after adding 2 - naphthyl nitrile solution of ethyl ether, and then pass into the hydrogen chloride to saturation, and aldimine generated yellow tin tetrachloride network adduct. The complex with the steam distillation, from the distillate filter out the white solid product, namely, crude 2 - naphthalene formaldehyde, after vacuum distillation, was pure, the yield of about 70% .

2-naphthaldehyde Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 unreported 1500mg/kg (1500mg/kg)   Farmaco, Edizione Scientifica. Vol. 19, Pg. 964, 1964.
 
LD50/LC50: RTECS: Not available. 
Carcinogenicity: 2-Naphthaldehyde - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. 

2-naphthaldehyde Safety Profile

Hazard Codes: HarmfulXnIrritantXi
Risk Statements: 36/37/38-22 
R36/37/38: Irritating to eyes, respiratory system and skin
R22: Harmful if swallowed
Safety Statements: 22-24/25-36-26 
S22: Do not breathe dust
S24/25: Avoid contact with skin and eyes
S36: Wear suitable protective clothing
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 3
RTECS: QJ0190010
F: 10-23
HS Code: 29122900

2-naphthaldehyde Specification

It's stable under normal temperatures and pressures. 
Conditions to Avoid: Incompatible materials. 
Incompatibilities with Other Materials: Strong oxidizing agents, strong bases. 
Hazardous Decomposition Products: Carbon monoxide, carbon dioxide. 
Hazardous Polymerization: Has not been reported. 

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