66-77-3

Basic information

• Product Name: 1-Naphthaldehyde
• Synonyms: alpha-Naphthal;alpha-Naphthylaldehyde;alpha-Naphthylcarboxaldehyde;-Naphthaldehdye;naphthalene-1-carbaldehyde;Naphthalene-1-carboxaldehyde;ALPHA-NAPHTHALDEHYDE;AKOS BBS-00003152
• CAS NO: 66-77-3
• Molecular Formula: C11H8O
• Molecular Weight: 156.18
• EINECS: 200-633-4
• Product Categories: Naphthalene series
• Mol File: 66-77-3.mol
• Article Data: 294

Chemical Properties

• Melting Point: 1-2 °C(lit.)
• Boiling Point: 160-161 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to dark yellow-brown/Liquid
• Density: 1.15 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 0.00188mmHg at 25°C
• Refractive Index: n20/D 1.652(lit.)
• Storage Temp.: 2-8°C
• Solubility: <1g/l
• Water Solubility: Soluble in ethanol, ether, acetone, benzene. Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 386082
• CAS DataBase Reference: 1-Naphthaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthaldehyde(66-77-3)
• EPA Substance Registry System: 1-Naphthaldehyde(66-77-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 37/39-26-24/25-36/37-23-36-16
• RIDADR: 3082
• WGK Germany: 3
• RTECS: QJ0190000
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 66-77-3(Hazardous Substances Data)

Usage

Applications

1-Naphthaldehyde is used as a reagent in the synthesis of phosphors without rare-earth elements for eco-energy lighting based LEDs. It is also used in the synthesis of 1-Naphthoic Acid and 1-Naphthalenemethanol.

Appearance

Clear Colorless to Pale Yellow Oil

Chemical Properties

Yellow liquid

Uses

Different sources of media describe the Uses of 66-77-3 differently. You can refer to the following data:
1. 1-Naphthaldehyde is used in the synthesis of single-crystalline homochiral porous metal-organic frameworks (MOFs). It is also a starting material for the Canizzaro reaction to produce 1-Naphthoic acid and 1-Naphthalenemethanol.
2. 1-Naphthaldehyde can be used to synthesize:(S)-1-α-naphthyl-1-ethanolN-(4-aryl)-N-(α-naphthyliden)aminesN-aryl-N-[1-(1-naphthyl)but-3-enyl]aminesnaphthalene-1-carboxylic acid methyl ester

Definition

ChEBI: A naphthaldehyde with a formyl group at position 1.

Synthesis Reference(s)

Tetrahedron, 41, p. 5703, 1985 DOI: 10.1016/S0040-4020(01)91375-4

Purification Methods

Distil 1-naphthaldehyde with steam, extract the distillate into Et2O, dry (Na2SO4), filter, evaporate the filtrate and distil the residue in a vacuum. [Beilstein 7 IV 1286.]

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

Synthetic route

1-naphthalene methanol (4780-79-4) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 1h; Oxidation;	100%
With C23H35N3O3(1+)*Br(1-); copper In chlorobenzene at 80℃; for 15h;	99%
With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2h; Green chemistry; chemoselective reaction;	99%

2,2-dimethyl-5-(naphthalen-1-ylmethylene)-1,3-dioxane-4,6-dione (75804-52-3) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With copper(II) acetate dihydrate; manganese(III) triacetate dihydrate In acetic acid at 50℃; for 24h; Inert atmosphere;	100%

diacetoxy(1-naphthyl)methane (64002-53-5) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With bismuth(III) chloride In chloroform for 0.333333h; deprotection; Heating;	99%
With tin(ll) chloride In acetonitrile at 25℃; for 0.0333333h; Hydrolysis;	99%
With H6P2W18O62 In toluene at 100℃; for 0.0833333h;	99%

1-Chloromethylnaphthalene (86-52-2) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h;	97%
With 4-methylmorpholine N-oxide; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; potassium iodide at 100℃; for 0.0333333h; Microwave irradiation; Ionic liquid;	91%
With sodium nitrate; acetic acid In water for 3h; Reflux;	87%

naphthalene-1-carbonic acid chloride (879-18-5) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene for 0.166667h; Ambient temperature;	97%
With tri-n-butyl-tin hydride In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;	90%
With polymethylhydrosiloxane; trifuran-2-yl-phosphane; tetrabutyl ammonium fluoride; potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water at 20℃; for 1h;	86%

1-naphtylaldehyde oxime (13504-46-6, 51873-97-3, 57207-33-7) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With molybdenum(V) chloride; zinc In acetonitrile at 20℃; for 0.116667h;	97%
With ammonium peroxydisulfate; Montmorillonite K10; silver nitrate In hexane at 50℃; for 2.5h;	95%
With iodine In acetonitrile for 4h; deoximation; Heating;	93%

2-(bromomethyl)naphthalene (3163-27-7) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With dihydrogen peroxide In ethanol for 4h; Reflux; Green chemistry;	96%
With sodium periodate In dichloromethane at 40 - 50℃; Ionic liquid;	82%
With sodium periodate In N,N-dimethyl-formamide at 150℃; for 0.583333h;	80%

2-(naphth-1-yl)-1,3-dioxolane (26963-79-1) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With lithium tetrafluoroborate In acetonitrile for 48h; Ambient temperature;	96%
With ammonium cerium(IV) nitrate In methanol; water at 20℃; for 0.166667h; Ring cleavage;	95%
With polyaniline-sulfate salt; water for 2h; Heating;	90%
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 3h; Reflux; chemoselective reaction;	86%
With Pyrene-1-carboxylic acid; C33H22NO4(1-)*Na(1+) In dimethylsulfoxide-d6; water-d2 at 85℃; for 6h; Reagent/catalyst;	23 %Spectr.

1-naphthalenecarboxylic acid (86-55-5) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With Bis(N-methylpiperazinyl) aluminum hydride In tetrahydrofuran for 24h; Heating;	95%
With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 6h; Ambient temperature;	80%
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 6 h; Yield given. Multistep reaction;
With ThxBHO-s-Bu In tetrahydrofuran at 25℃; for 96h; Yield given;
Multi-step reaction with 2 steps 1.1: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 4 h / Reflux 1.2: 12 h / 20 °C 2.1: sodium hydride; sodium iodide / mineral oil; tetrahydrofuran / 85 °C / Inert atmosphere; Sealed tube View Scheme

acetic acid (64-19-7) + 1-Methylnaphthalene (90-12-0) → naphthalen-1-ylmethyl acetate (13098-88-9) + 1-naphthaldehyde (66-77-3)

Conditions	Yield
With ammonium cerium(IV) nitrate In water at 85℃; for 2h;	A 3% B 95%

1-Methylnaphthalene (90-12-0) → naphthalen-1-ylmethyl acetate (13098-88-9) + 1-naphthaldehyde (66-77-3)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetic acid at 85℃; for 2h;	A 3% B 95%
With *5H2O; lithium chloride In acetic acid at 100℃; for 27h;	A 35% B 39%

1-[bis(N,N-diethyldithiocarbamato)methyl]naphthalene (1391998-52-9) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With nitric acid In water at 20℃;	95%

N-Formylpiperidine (2591-86-8) + 1-naphthylmagnesiumbromide (703-55-9) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
In diethyl ether for 0.25h; Ambient temperature;	94%

N,N-dimethyl-1-naphthamide (3815-24-5) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; chemoselective reaction;	93%
With sodium hydride; sodium iodide In tetrahydrofuran; mineral oil at 85℃; Inert atmosphere; Sealed tube;	88%
With lithium diethoxyaluminum hydride

naphth-1-yl acetic acid (86-87-3) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With 1H-imidazole; sodium periodate In water; acetonitrile at 20℃; for 30h;	93%
With 1H-imidazole; sodium periodate; [Mn(III)-salophen]Cl In water; acetonitrile at 20℃; for 0.25h;	90%
With 1H-imidazole; sodium periodate; {Mn(III)[5,10,15,20-tetrakis(4-H2N-Ph)porphyrin]}polystyrene In acetonitrile at 20℃; for 6h;	89%

1-(naphthalen-1-ylmethylene)-2-phenylhydrazine (24090-98-0) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With caro's acid; silica gel for 0.0416667h; Oxidation; Irradiation;	93%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 1-naphthyl triflate (99747-74-7) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 25℃; for 16h; Schlenk technique; Inert atmosphere;	93%

1-Methylnaphthalene (90-12-0) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 2h; Irradiation; Green chemistry;	92%
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;	89%
With air; titanium(IV) oxide; silver sulfate In acetonitrile for 5h; Ambient temperature; Irradiation;	26%

4-morpholinecarboxaldehyde (4394-85-8) + 1-naphthylmagnesiumbromide (703-55-9) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
In diethyl ether for 0.5h; Ambient temperature;	92%

1-naphthaldehyde semicarbazone (120445-68-3, 7510-44-3) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With magnesium hydrogen sulfate; water; silica gel In hexane at 20℃; for 0.5h;	92%
With tetrachlorosilane; silica gel In hexane; water for 2h; Heating;	92%
With ammonium dichromate(VI); water; silica gel; zirconium(IV) chloride at 80℃; for 1.08333h;	85%
With potassium permanganate; silica gel In water at 20℃; for 0.25h;	78%
With sulfuric acid; silica gel In hexane for 0.166667h;

1'-naphthacetophenone (941-98-0) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 15h; Reagent/catalyst; Solvent; chemoselective reaction;	92%
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

(naphtalen-1-yl)methyl iodide (24471-54-3) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With 1‑dodecyl‑3‑methylimidazolium iron chloride; periodic acid at 50℃; for 4h; Reagent/catalyst; Green chemistry;	92%

N-(1-naphthoyl)-4-methylbenzenesulfonohydrazide → 1-naphthaldehyde (66-77-3)

Conditions	Yield
Stage #1: N-(1-naphthoyl)-4-methylbenzenesulfonohydrazide With 1H-imidazole; 1-(Trimethylsilyl)imidazole In toluene at 55℃; for 4.5h; Inert atmosphere; Stage #2: With citric acid In toluene at 23℃; for 2.5h; Inert atmosphere;	92%

(naphth-1-yl)methylamine (118-31-0) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;	91%
With dihydrogen peroxide; vanadia In water at 50℃; for 12h;	70%
With water; indole-2,3-dione
With oxalic acid; dimethyl sulfoxide; O-phenyl phosphorodichloridate; triethylamine 1.) -10 deg C, 15 min, CH2Cl2, 2.) -10 deg C to 20 deg C, 45 min, 3.) 20 deg C, 30 min; Yield given. Multistep reaction;

1-Cyanonaphthalene (86-53-3) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;	91%
With sodium hydride; zinc(II) chloride In tetrahydrofuran; mineral oil at 40℃; for 8h; Inert atmosphere; Sealed tube;	82%
With calcium bis(hypophosphite); calcium acetate; nickel(II) acetate tetrahydrate In ethanol; water at 100℃; for 21h; Sealed tube;	80%

2-(2-naphthalen-1-yl)-1,3-dithiolane (86201-62-9) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With iodosylbenzene In dichloromethane at 20℃; for 0.5h;	90%
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h; Yield given;
With indium (III) iodide; dihydrogen peroxide In water; toluene at 20℃; for 15h; Inert atmosphere; Sealed tube;	108 mg

[1]naphthylmethylen-aniline (890-50-6) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With hydrogenchloride; water at 20℃; for 1h;	90%

N,N-diethyl-1-naphthamide (5454-10-4) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.5h;	90%
With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In methyl cyclohexane at 20℃; for 24h; Inert atmosphere;	75%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 1-Iodonaphthalene (90-14-2) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 25℃; for 16h; Schlenk technique; Inert atmosphere;	90%

N-cyclohexyl-N-(1-naphthylmethyl)-4-nitrobenzenesulfinamide (78804-11-2) → 1-naphthaldehyde (66-77-3)

Conditions	Yield
With potassium carbonate In o-xylene for 6h; Heating;	89%

1-naphthaldehyde (66-77-3) + aniline (62-53-3) → [1]naphthylmethylen-aniline (890-50-6)

Conditions	Yield
In chloroform Ambient temperature;	100%
In benzene Heating;	74%
In water at 20℃; for 2h;	69%

1-naphthaldehyde (66-77-3) + malononitrile (109-77-3) → (1-naphthylmethylidene)malononitrile (2972-83-0)

Conditions	Yield
With aluminum oxide Inert atmosphere; Neat (no solvent);	100%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 0.05h; Knoevenagel Condensation; Green chemistry;	100%
With polystyrene-supported DABCO In methanol at 25℃; for 0.8h; Knoevenagel Condensation; Green chemistry;	99%

1-naphthaldehyde (66-77-3) → 1-naphtylaldehyde oxime (13504-46-6, 51873-97-3, 57207-33-7)

Conditions	Yield
With hydroxylamine hydrochloride; sodium carbonate In ethanol at 20℃;	100%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃; for 2h;	99%
With pyridine; hydroxylamine In ethanol	99%

1-naphthaldehyde (66-77-3) → 1-naphthalene methanol (4780-79-4)

Conditions	Yield
With methyltriphenylphosphonium tetrahydroborate In dichloromethane Reduction;	100%
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran at 20℃; Reduction;	100%
With Zn(BH4)2(bpy) In acetonitrile at 20℃; for 0.133333h;	99%

diethylzinc (557-20-0) + 1-naphthaldehyde (66-77-3) → (R)-1-(1-naphthyl)propanol (56620-47-4, 77495-17-1, 135818-31-4, 114091-67-7)

Conditions	Yield
(1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol In toluene at 0℃; for 12h;	100%
Stage #1: diethylzinc; 1-naphthaldehyde With diphenyl-((R)-1-((S)-1-phenylethyl)aziridin-2-yl)-methanol In hexane; toluene at 0 - 25℃; for 48.5h; Inert atmosphere; Stage #2: With ammonium chloride In hexane; water; toluene Saturated solution; optical yield given as %ee; enantioselective reaction;	99%
Stage #1: diethylzinc With (1R,3S)-1-benzyl-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol In hexane; toluene at 0℃; for 0.0833333h; Stage #2: 1-naphthaldehyde In hexane; toluene at 0℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; enantioselective reaction;	99%

1-naphthaldehyde (66-77-3) + 4-methoxy-aniline (104-94-9) → (E)-4-methoxy-N-(naphthalene-1-ylmethylene)phenylamine (3525-60-8)

Conditions	Yield
In ethanol at 20℃; Inert atmosphere;	100%
In ethanol for 1h; Heating;	96%
In benzene Heating;
In benzene Heating;
In ethanol at 25℃; for 12h;

1-naphthaldehyde (66-77-3) + toluene-4-sulfonic acid hydrazide (1576-35-8) → (Z)-4-methyl-N'-(naphthalen-1-ylmethylene) benzenesulfonohydrazide (19350-73-3)

Conditions	Yield
In diethyl ether for 1h; Ambient temperature;	100%
In methanol	85%
In methanol at 60℃;

1-naphthaldehyde (66-77-3) → 1-Cyanonaphthalene (86-53-3)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride at 100℃; for 0.25h; Condensation; microwave irradiation;	100%
With oxygen; copper; ammonium chloride In pyridine at 60℃; for 24h;	99%
With hydroxylamine hydrochloride In 1-methyl-pyrrolidin-2-one for 0.0833333h; Heating;	98%

Methyltriphenylphosphonium bromide (1779-49-3) + 1-naphthaldehyde (66-77-3) → 1-vinylnaphthalene (826-74-4)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In toluene at 0 - 20℃; for 4.5h; Stage #2: 1-naphthaldehyde In toluene at 0 - 20℃;	100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In toluene at 0 - 20℃; for 4.5h; Stage #2: 1-naphthaldehyde In toluene at 0 - 20℃;	100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In toluene at 0 - 20℃; for 4.5h; Stage #2: 1-naphthaldehyde In toluene at 0 - 20℃;	100%

1-naphthaldehyde (66-77-3) + methylamine (74-89-5) → (±)-(2S,3R)-ethyl 1,3-dimethyl-2-(naphthalen-1-yl)-4-oxoazetidine-3-carboxylate (41004-67-5, 41004-71-1, 100062-83-7)

Conditions	Yield
at 20℃; for 12h;	100%
In water for 1h; Ambient temperature;
In tetrahydrofuran; methanol

1-naphthaldehyde (66-77-3) + phosphonic acid diethyl ester (762-04-9) → diethyl hydroxy(naphth-1-yl)methylphosphonate (1090-21-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 20℃; for 17h;	100%
With N-ethyl-N,N-diisopropylamine at 20℃; for 18h;	100%
With (2,6-iPr2PhNH)5SmLi2(THF)2 In hexane at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;	99%

diethyl 1-cyanomethylphosphonate (2537-48-6) + 1-naphthaldehyde (66-77-3) → 3-(1-naphthyl)acrylonitrile (111686-30-7)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Wadsworth-Emmons reaction;	100%
With potassium carbonate for 0.25h; Ambient temperature;

1-naphthaldehyde (66-77-3) + allyl bromide (106-95-6) → 1-naphthalen-1-yl-but-3-en-1-ol (72551-06-5)

Conditions	Yield
With hydrogenchloride; antimony In water for 16h;	100%
With tin(ll) chloride; zinc In water for 2h;	99%
With potassium fluoride; antimony In water for 16h; allylation;	96%

ethyl acetoacetate (141-97-9) + 1-naphthaldehyde (66-77-3) + urea (57-13-6) → 6-methyl-4-naphthalen-1-yl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (219814-93-4, 1032574-17-6)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In ethanol at 100℃; for 1h; Biginelli reaction; Microwave irradiation; Inert atmosphere;	100%
With copper doped mesoporous silica MCM-41 supported dual acidic ionic liquid-HSO4 In ethanol at 80℃; for 1h; Biginelli Pyrimidone Synthesis;	97%
Stage #1: 1-naphthaldehyde; urea With hydrogenchloride In tetrahydrofuran; water at 67℃; for 1h; Biginelli Pyrimidone Synthesis; Green chemistry; Stage #2: ethyl acetoacetate With N,N′-(cyclohexane-1,2-diyl)bis(3,6-dichloropicolinamide) In tetrahydrofuran; water at 67℃; for 5h; Biginelli Pyrimidone Synthesis; Green chemistry;	95%

1-naphthaldehyde (66-77-3) + trimethylsilylacetylene (1066-54-2) → 1-(naphthalen-1-yl)-3-(trimethylsilyl)prop-2-yn-1-ol (405064-45-1)

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-naphthaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere;	100%
Stage #1: trimethylsilylacetylene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: 1-naphthaldehyde In diethyl ether; hexane at -78 - -10℃; Further stages.;	64%
Stage #1: trimethylsilylacetylene With n-butyllithium In diethyl ether at -78℃; Stage #2: 1-naphthaldehyde In diethyl ether at -78 - -10℃;	63%

1-naphthaldehyde (66-77-3) + diethylzinc → 1-(1-naphthyl)-1-propanol (56620-47-4)

Conditions	Yield
With titanium(IV) isopropylate; (R,R)-1,1'-bis[N(1-ferrocenylethyl)-4-Me-benzenesulfonamide] In hexane; toluene at 20℃; for 48h;	100%

1-naphthaldehyde (66-77-3) + 2-hydroxyethanethiol (60-24-2) → 2-(naphthalene-1-yl)-1,3-oxathiolane

Conditions	Yield
With PPA; silica gel In 1,2-dichloro-ethane at 20℃; for 0.5h;	100%
Fe(CF3SO3)3 In acetonitrile at 20℃; for 0.25h;	93%
With eosin y In 1,4-dioxane at 20℃; for 12h; Irradiation; Inert atmosphere; Schlenk technique;	91%
With tantalum pentachloride In dichloromethane at 20℃; for 1.5h;	87%
With ammonium cerium(IV) nitrate In acetonitrile at 30℃; for 10h;	85%

1-naphthaldehyde (66-77-3) + phenylacetylene (536-74-3) → 1-(1-naphthyl)-3-phenylprop-2-yn-1-ol (672959-14-7, 439595-18-3)

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In hexanes; diethyl ether at 0℃; for 1h; Stage #2: 1-naphthaldehyde In hexanes; diethyl ether at 0 - 20℃; for 0.5h;	100%
Stage #1: phenylacetylene With titanium(IV) isopropylate; C16H15NO; dimethyl zinc(II) In tetrahydrofuran; toluene at 20℃; for 1.5h; Inert atmosphere; Stage #2: 1-naphthaldehyde In tetrahydrofuran; toluene at 0 - 20℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	96%
With dimethyl zinc(II); (1R,2S)-cis-1-amino-2-indenol-derived oxazolidine In n-heptane; toluene at -4℃; for 48h;	91%

carbon tetrabromide (558-13-4) + 1-naphthaldehyde (66-77-3) → 1-(2,2-dibromovinyl)naphthalene (77295-63-7)

Conditions	Yield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-naphthaldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%
With triphenylphosphine In dichloromethane at 0℃; for 2h; Inert atmosphere;	88%
With triphenylphosphine In dichloromethane at 0℃; Inert atmosphere;	75%

1H-indene-1,3(2H)-dione (606-23-5) + 1-naphthaldehyde (66-77-3) + (E)-benzalacetone (1896-62-4) → 2-(naphthalen-1-yl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions	Yield
Stage #1: 1H-indene-1,3(2H)-dione; 1-naphthaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;	100%

1-naphthaldehyde (66-77-3) + (trifluoromethyl)trimethylsilane (81290-20-2) → trimethyl(2,2,2-trifluoro-1-(naphthalen-1-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 potassium fluoride; tetrabutylammomium bromide In toluene at 0℃; for 1h;	99%
With tri-tert-butyl phosphine In N,N-dimethyl-formamide at 20℃;	95%

1-naphthaldehyde (66-77-3) + 1-amino-2-propene (107-11-9) → (E)-N-allyl-1-(naphthalen-1-yl)methanimine (87869-49-6)

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

1-naphthaldehyde (66-77-3) + hex-1-yne (693-02-7) → 1-(naphthalen-1-yl)hept-2-yn-1-ol (862776-51-0)

Conditions	Yield
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere; Stage #2: 1-naphthaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane	100%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 1-naphthaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 0.583333h; Inert atmosphere;	80%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: 1-naphthaldehyde In tetrahydrofuran at -78 - 20℃; Further stages.;

(4-nitro-1H-benzimidazol-2-yl)-piperidin-4-ylmethyl-amine (616223-98-4) + 1-naphthaldehyde (66-77-3) → (1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(4-nitro-1H-benzimidazol-2-yl)-amine (616223-99-5)

Conditions	Yield
With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); acetic acid at 20℃;	100%

1-naphthaldehyde (66-77-3) + methyl 2-cyanoacetate (105-34-0) → methyl (E)-2-cyano-3-(naphthen-1-yl)acrylate

Conditions	Yield
ytterbium(III) triflate In ethanol at 20℃; for 5h;	100%
With piperidine; acetic acid In benzene for 2.5h; Knoevenagel Condensation; Dean-Stark; Reflux;	93%
piperidine In methanol at 50 - 60℃; for 0.5 - 10h; Product distribution / selectivity;	92.5%
In methanol at 20℃; for 24h; Product distribution / selectivity;
With C112H128N32Pd4(12+) at 50℃; for 9h;

Nitroethane (79-24-3) + 1-naphthaldehyde (66-77-3) → (E)-1-(2-nitroprop-1-en-1-yl)naphthalene (131981-73-2)

Conditions	Yield
With ammonium acetate for 6h; Henry reaction; Reflux;	100%
With N-butylamine In ethanol	97%
With cyclohexylamine at 120℃; Microwave irradiation;	55%
With ammonium acetate In acetic acid	8.5 g (33%)
With ammonium acetate for 2h; Henry Nitro Aldol Condensation; Inert atmosphere; Reflux;

2-thioxo-4-thiazolidinone (141-84-4) + 1-naphthaldehyde (66-77-3) → (Z)-5-(naphthalen-1'-ylmethylene)-2-thioxothiazolidin-4-one (181765-58-2)

Conditions	Yield
With acetic acid; triethylamine In ethyl acetate at 85℃; for 3h;	100%
With sodium acetate; acetic acid for 16h; Reflux;	82%
With sodium acetate In acetic acid Reflux;	76%
With piperidine In ethanol at 70℃; for 16h; Knoevenagel Condensation;	59%

1-naphthaldehyde (66-77-3) + ethylamine (75-04-7) → N-Ethylaldinium (52135-91-8)

Conditions	Yield
at 20℃; for 12h;	100%

(R)-1-phenyl-ethyl-amine (3886-69-9) + 1-naphthaldehyde (66-77-3) → (R)-N-(naphthalen-1-ylmethylene)-1-phenylethanamine (208539-59-7)

Conditions	Yield
In toluene at 100℃; for 2h; Inert atmosphere;	100%
With magnesium sulfate In dichloromethane at 20℃; for 12h;

Upstream product

• 100-97-0 hexamethylenetetramine 
• 64-19-7 acetic acid 
• 86-52-2 1-Chloromethylnaphthalene 
• 64-17-5 ethanol 
• 3163-27-7 2-(bromomethyl)naphthalene 
• 113061-21-5 [1]naphthaldehyde-[N-(4-dimethylamino-phenyl)-oxime ] 
• 109-94-4 formic acid ethyl ester 
• 108-31-6 maleic anhydride 
• 73354-52-6 1-Phenyl-3-(1-naphthyl)-2,3-epoxy-1-propanone 
• 13504-46-6 1-naphtylaldehyde oxime 
• 35787-71-4 thianthrene cation radical perchlorate 
• 30365-88-9 1-naphthaldehyde - picric acid complex 
• 99845-94-0 1-naphthylmethyl hydrogen peroxide 
• 90-12-0 1-Methylnaphthalene 

Downstream Products

• 13026-12-5 (E)-3-(naphthalen-1-yl)acrylic acid 
• 92887-61-1 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-[1]naphthylmethanediyl-bis-pyrazol-3-one 
• 61442-33-9 5-naphthalen-1-ylmethylene-2-thioxo-3-p-tolyl-imidazolidin-4-one 
• 27869-54-1 β-naphthylmethyl-α-phenylacrylonitrile 
• 23854-03-7 1-(α-naphthyl)-2-nitro-1-propene 
• 4735-49-3 1-[(E)-2-nitroethenyl]naphthalene 
• 15727-65-8 1-ethynylnaphthalene 
• 73044-21-0 5-naphthalen-1-yl-4-nitro-3-pentafluorophenyl-4,5-dihydro-isoxazole 
• 31400-21-2 N--N'-diphenylmethylen-hydrazin 
• 70976-43-1 5t-naphthalen-1-yl-4r-nitro-3-phenyl-4,5-dihydro-isoxazole 
• 98722-31-7 phenyl-thioacetic acid-([1]naphthylmethylene-hydrazide) 
• 52364-39-3 4-(α-Naphthyl)-2,3,3-triphenyl-1,2λ⁵-oxaphosphetan-2-on 
• 57439-09-5 4-(α-Naphthylethyl)benzoesaeure 
• 23833-69-4 1-[(Z)-2-(4-Methoxy-phenyl)-vinyl]-naphthalene 

Relevant articles and documents

Control of C-C and C-N bond cleavage of 2H-azirine by means of the excitation wavelength: Studies in matrices and in solutions

The remarkable wavelengh-dependent photoreactions of 3-methyl-2-(1-naphthyl)-2H-azirine (1) were observed in matrices at 10 K and in solutions at room temperature. Irradiation of 1 with the long-wavelength light (366 nm) exclusively gave the products form

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