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Basic Information
CAS No.: 66-99-9
Name: 2-Naphthaldehyde
Molecular Structure:
Molecular Structure of 66-99-9 (2-Naphthaldehyde)
Formula: C11H8O
Molecular Weight: 156.184
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;
EINECS: 200-640-2
Density: 1.155 g/cm3
Melting Point: 58-61 °C(lit.)
Boiling Point: 299.5 °C at 760 mmHg
Flash Point: 179.5 °C
Solubility: Soluble in hot water.
Appearance: Pink crystalline
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 36/37/38-22
Safety: 22-24/25-36-26
PSA: 17.07000
LogP: 2.65230
Synthetic route
1592-38-7

2-Naphthalenemethanol

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%
4469-45-8

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

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.
77853-39-5

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

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
64002-54-6

diacetoxy(2-naphthyl)methane

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%
57009-73-1

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

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%
939-26-4

2-bromomethylnaphthyl bromide

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%
2506-41-4

1-chloromethylnaphthalene

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%
77196-31-7

2-(dimethoxymethyl)naphthalene

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;
827-54-3

2-Vinylnaphthalene

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%
1448723-24-7

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

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%
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Chemistry

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°
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)  

Uses

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

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% .

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. 

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

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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