66-99-9

Basic information

• Product Name: 2-Naphthaldehyde
• Synonyms: naphthalene-2-carbaldehyde;2-Naphthakdehyde;2-naphthaldehyde (beta);Naphthaldehyde,97%;B-NAPHTHALDEHYDE;2-NAPHTHALDEHYDE 98%;2-Naphthaldehyde,98%;2-Naphthaldehyde, 98% 25GR
• CAS NO: 66-99-9
• Molecular Formula: C11H8O
• Molecular Weight: 156.18
• EINECS: 200-640-2
• Product Categories: Naphthalene series;Pyridines
• Mol File: 66-99-9.mol
• Article Data: 364

Chemical Properties

• Melting Point: 58-61 °C(lit.)
• Boiling Point: 160 °C (19 mmHg)
• Flash Point: 160°C/19mm
• Appearance: Off-white to yellow or light beige/Powder or Chunks
• Density: 1.6211
• Vapor Pressure: 0.00119mmHg at 25°C
• Refractive Index: 1.6211 (estimate)
• Storage Temp.: ?20°C
• Solubility: Chloroform, Methanol (Sparingly)
• Water Solubility: Soluble in hot water.
• Sensitive: Air Sensitive
• BRN: 507750
• CAS DataBase Reference: 2-Naphthaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthaldehyde(66-99-9)
• EPA Substance Registry System: 2-Naphthaldehyde(66-99-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-36-26
• RIDADR: UN 3335
• WGK Germany: 3
• RTECS: QJ0190010
• F: 10-23
• Hazardous Substances Data: 66-99-9(Hazardous Substances Data)

Usage

Chemical Properties

Pink crystalline

Uses

Different sources of media describe the Uses of 66-99-9 differently. You can refer to the following data:
1. 2-Naphthaldehyde aids in stereo-selective formation of bicyclo 2-siloxy-2-alkoxyoxetanes. It is also used as catalytic agent and petrochemical additive.
2. 2-Naphthaldehyde can be used as a reactant:In proline catalyzed aldol reaction. In asymmetric three-component Mannich reaction.For the synthesis of Hantzsch 1,4-dihydropyridines.13}Asymmetric benzoin condensation reaction.For the synthesis of pyrazolo[1,2?b]phthalazinediones.For the synthesis C60 by flash vacuum pyrolysis.

Definition

ChEBI: A naphthaldehyde that is naphthalene substituted by a formyl group at position 2.

Synthesis Reference(s)

Synthesis, p. 470, 1996 DOI: 10.1055/s-1996-4246

Purification Methods

Distil 2-naphthaldehyde with steam then crystallise it from water or EtOH. [Beilstein 7 IV 1288.]

InChI:InChI=1/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H

Synthetic route

2-Naphthalenemethanol (1592-38-7) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
With triethylene diamine nickel thiosulfate; water In chloroform at 20℃; for 0.0833333h; Hydrolysis;	96%

(naphthalen-2-ylmethylene)bis(ethylsulfane) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 20℃; for 12h;	95%

carbon monoxide (201230-82-2) + 2-naphthyl triflate (3857-83-8) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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 → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
With triethylsilane; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 60℃; for 12h;	91%

methyl 2-naphthyl ketone (93-08-3) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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-chloronaphthalene (91-58-7) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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) + (E)-2-(2-(naphthalen-2-yl)vinyl)quinoline → 2-(2-(naphthalen-2-yl)ethyl)quinoline (1401882-30-1) + β-naphthaldehyde (66-99-9)

Conditions	Yield
With ruthenium trichloride; potassium tert-butylate In 1,4-dioxane for 24h;	A 81% B 91%

2-naphthaldoxime (51873-98-4, 57207-34-8, 24091-02-9) → β-naphthaldehyde (66-99-9)

Conditions	Yield
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-Naphthalenemethanol (1592-38-7) + β-naphthaldehyde (66-99-9)

Conditions	Yield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 2h; chemoselective reaction;	A 7% B 90%

malonic acid (141-82-2) + β-naphthaldehyde (66-99-9) → (E)-3-(naphthalen-2-yl)acrylic acid (49711-14-0)

Conditions	Yield
With piperidine; pyridine	100%
With piperidine; pyridine at 115℃; for 3h; Knoevenagel Condensation;	93%
With pyridine for 1h; Heating;	82%

β-naphthaldehyde (66-99-9) + acetone (67-64-1) → 4-(2-naphtalenyl)-3-buten-2-one (75032-63-2)

Conditions	Yield
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) → 2-Naphthalenemethanol (1592-38-7)

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

Conditions	Yield
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) + β-naphthaldehyde (66-99-9) → (E)-2-(2-nitroprop-1-en-1-yl)naphthalene (37629-58-6)

Conditions	Yield
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) + β-naphthaldehyde (66-99-9) → 2-(naphthalen-2-yl)-2-[(trimethylsilyl)oxy]acetonitrile (139224-73-0, 83575-58-0)

Conditions	Yield
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) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → 2-methyl-3-naphthalen-2-yl-acrylic acid ethyl ester (100510-32-5)

Conditions	Yield
In benzene for 4.5h; Ambient temperature;	100%
In toluene Reflux;	93%

β-naphthaldehyde (66-99-9) → naphthalen-2-yl formate (1988-18-7)

Conditions	Yield
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) + β-naphthaldehyde (66-99-9) → methyl 2,2-dimethyl-3-(naphthalen-2-yl)-3-(trimethylsilyloxy)propanoate (156541-03-6)

Conditions	Yield
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) + β-naphthaldehyde (66-99-9) → 4-methoxy-N-(naphthalen-2-ylmethylene)aniline (3525-61-9)

Conditions	Yield
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) + 2-hydroxyethanethiol (60-24-2) → 2-(naphthalene-2-yl)-1,3-oxathiolane

Conditions	Yield
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) + β-naphthaldehyde (66-99-9) → (R)-1-(naphthalen-2-yl)but-3-en-1-ol

Conditions	Yield
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) + 1,2,3-Benzotriazole (95-14-7) + β-naphthaldehyde (66-99-9) → [1-(4-morpholino)-1-(2-naphthyl)]methyl-1H-1,2,3-benzotriazole (433232-15-6)

Conditions	Yield
In ethanol at 20℃; for 15h;	100%

β-naphthaldehyde (66-99-9) + diethylzinc → (S)-1-(2-naphthyl)propan-1-ol (112576-12-2, 132154-59-7, 87241-23-4)

Conditions	Yield
With (R)-2-(1-[(S)-2-(diphenylphosphino)ferrocenylethylimino]methyl)phenol In hexane; toluene at 0℃; for 48h;	100%

β-naphthaldehyde (66-99-9) + 3-monochloro-1,2-propanediol (96-24-2) → 4-chloromethyl-2-naphthalen-2-yl[1,3]dioxolane

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	100%

β-naphthaldehyde (66-99-9) + methylamine (74-89-5) → N-methyl-1-(naphthalene-2-yl)methanimine (125660-64-2)

Conditions	Yield
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) + β-naphthaldehyde (66-99-9) → trimethyl-(2,2,2-trifluoro-1-naphthalen-2-yl-ethoxy)-silane

Conditions	Yield
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) + 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone (627546-31-0) → 3-(2-naphthyl)-1-pyrrol-1-yl-2-propen-1-one

Conditions	Yield
In toluene at 100℃; for 48h; Wittig olefination;	100%

β-naphthaldehyde (66-99-9) + 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone (627546-31-0) → (E)-3-(naphthalen-2-yl)-1-(1H-pyrrol-1-yl)prop-2-en-1-one (736140-68-4)

Conditions	Yield
In toluene at 100℃; for 48h; Wittig reaction;	100%

β-naphthaldehyde (66-99-9) + phenylboronic acid (98-80-6) → (S)-naphthalen-2-yl(phenyl)methanol (99412-45-0)

Conditions	Yield
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) → naphthalen-2-ylmethyl 2-naphthoate (135512-98-0)

Conditions	Yield
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) + 1-amino-2-propene (107-11-9) → (E)-N-allyl-1-(naphthalen-2-yl)methanimine (87869-50-9)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 20h;	100%
With magnesium sulfate In dichloromethane for 24h; Inert atmosphere;	100%

pyrrolidine (123-75-1) + β-naphthaldehyde (66-99-9) + phenylacetylene (536-74-3) → 1-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)pyrrolidine

Conditions	Yield
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%

nitromethane (75-52-5) + β-naphthaldehyde (66-99-9) → (1R)-1-(2-naphthyl)-2-nitroethanol

Conditions	Yield
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) + ammonium chloride + β-naphthaldehyde (66-99-9) → 3-hydroxy-3-(naphthalen-2-yl)propanenitrile (144119-14-2, 128104-67-6)

Conditions	Yield
In tetrahydrofuran; acetonitrile	100%

Upstream product

• 14289-45-3 2-(naphthalen-2-yl)-2-oxoacetic acid 
• 110-82-7 cyclohexane 
• 10378-56-0 β-naphthyldiazomethane 
• 64-19-7 acetic acid 
• 91-57-6 2-Methylnaphthalene 
• 2243-83-6 2-naphthaloyl chloride 
• 22013-66-7 5-(2-Naphthoyl)-5H-benzocarbazole 
• 77196-31-7 2-(dimethoxymethyl)naphthalene 
• 1592-38-7 2-Naphthalenemethanol 
• 107-06-2 1,2-dichloro-ethane 
• 20862-03-7 2-naphthyl cyanohydrin 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 3007-91-8 ethyl-2-naphthoate 
• 25308-57-0 isopropyl 2-naphtalenecarboxylate 

Downstream Products

• 37629-37-1 2-(2-nitrovinyl)naphthalene 
• 20884-05-3 (E)-3-(2-naphthyl)-2-propenal 
• 147093-03-6 4-(2-naphthylidene)-2-phenyl-5(4H)oxazolone 
• 211871-51-1 2-(2-amino-2-phenylethyl)naphthalene 
• 49711-14-0 (E)-3-(naphthalen-2-yl)acrylic acid 
• 129042-57-5 3-amino-3-(2-naphthyl)propionic acid 
• 101884-41-7 1-(2,4-dihydroxy-3-nitro-phenyl)-3t-[2]naphthyl-propenone 
• 110876-52-3 (2-methyl-[1]naphthyl)-[2]naphthyl ketone 
• 94307-49-0 3-[2]naphthyl-2-phenyl-acrylic acid 
• 35060-38-9 (2-naphthyl)phenylmethanol 
• 18263-29-1 N-(naphthalen-2-ylmethylene)aniline 
• 42299-50-3 (2E)-1-phenyl-3-(2-naphthyl)-2-propen-1-one 
• 29708-01-8 2-cyano-3-[2]naphthyl-acrylic acid ethyl ester 
• 29708-02-9 (E)-ethyl 2-cyano-3-(naphthalen-2-yl)acrylate 

Relevant articles and documents

Effect of Mo loading on 2-naphthaldehyde formation from vapor phase oxidation of 2-methylnaphthalene with V2O5/TiO2 catalysts

Mo-modified V2O5/TiO2 catalysts were prepared by wetness impregnation method and investigated for the selective oxidation of 2-methylnaphthalene to 2-naphthaldehyde. The catalysts were characterized by XRD, BET, XPS, and Raman to investigate the promotional effect of Mo on catalyst structure, surface property, and catalytic performance. The introduction of molybdenum decreases the amount of KVO3 phase and enhances the dispersion of the vanadium phase. XPS and Raman results indicate that Mo prevents Sn and K to interact with V species and bonds with Ti or V through bridge oxygen. V1Mo1 sample demonstrates a remarkable improvement in conversion and selectivity compared with others.

Selective functionalization of benzylic C-H bonds of two different benzylic ethers by bowl-shaped N -hydroxyimide derivatives as efficient organoradical catalysts

A highly efficient, site-selective benzylic C-H bond amination of two different benzylic ether substrates was described by using bowl-shaped N-hydroxyimide organoradical catalysts with diethyl azodicarboxylate. The synthetic utility of this approach is demonstrated by the subsequent transformation of the amination products into the corresponding aldehydes and alkylhydrazines.

Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride

A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.