1-Methylnaphthalene supplier

Name
1 -Methylnaphthalene
EINECS 201-966-8
CAS No. 90-12-0
Article Data339
CAS DataBase
Density 1.016 g/cm³
Solubility Water: 0.026 g/L (25 °C)
Melting Point -22 °C
Formula C₁₁H₁₀
Boiling Point 242.8 °C at 760 mmHg
Molecular Weight 142.2
Flash Point 82.2 °C
Transport Information UN 3082 9/PG 3
Appearance Colorless liquid
Safety 7-26-36/37/39-61-45-36/37-23-36
Risk Codes 22-36/37/38-42/43-51/53-39/23/24/25-23/24/25-20/21/22
Molecular Structure
Hazard Symbols Xn,N,T
Synonyms 1-Methylnaphthalene;Naphthalene, alpha-methyl-;Methynaph H;NSC 3574;a-Methylnaphthalene;alpha-Methylnaphthalene;AI3-15378;CCRIS 6151;
PSA 0.00000
LogP 3.14820

Synthetic route

: 90-11-9
1-Bromonaphthalene

3CoCH3: 3CoCH3

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
In benzene at 10℃; for 24h;	100%

: 90-11-9
1-Bromonaphthalene

: 544-97-8
dimethyl zinc(II)

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 2h; Heating;	100%
Stage #1: 1-Bromonaphthalene; dimethyl zinc(II) With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.5h; Substitution; Stage #2: With oxovanadium(V) ethoxydichloride In tetrahydrofuran; diethyl ether; hexane at 20℃; for 3h; Oxidation; Alkylation; Further stages.;	73%

: 90-11-9
1-Bromonaphthalene

: (3-dimethylaminopropyl)dimethylgallium

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 15h;	99%

: 86-52-2
1-Chloromethylnaphthalene

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With potassium formate; PdCl22 In benzene at 60℃; for 4h;	98%
With potassium formate; PdCl22 In benzene at 60℃; for 4h; Product distribution; further catalyst, reagent; solid or aqueous solution of reagent;	98%
With sodium tetrahydroborate; water In methanol at 20℃; for 0.333333h;	94%

: 90-11-9
1-Bromonaphthalene

: [3-(dimethylamino)propyl]dimethyl aluminium(III)

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 12h;	98%

: 90-11-9
1-Bromonaphthalene

bis{μ-[2-(dimethylamino)ethanolato-N,O:O]}tetramethyldialuminum: bis{μ-[2-(dimethylamino)ethanolato-N,O:O]}tetramethyldialuminum

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With triphenylphosphine; {MoPdcp[μ-(CO)2][μ3-(CO)](PPh3)}2 In benzene at 78℃; for 2h;	98%

: 90-14-2
1-Iodonaphthalene

: 75-16-1
methylmagnesium bromide

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
Stage #1: 1-Iodonaphthalene With [K{(Me)Ni[N(SiMe3)2,6-diisopropylphenyl]2}] In tetrahydrofuran at -35℃; for 0.333333h; Inert atmosphere; Stage #2: methylmagnesium bromide In tetrahydrofuran at 20℃; for 1.5h; Reagent/catalyst; Inert atmosphere;	98%

: 1351445-39-0
N,N,N-trimethyl-1-naphthalenaminium trifluoromethanesulfonate

: 75-24-1
trimethylaluminum

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 110℃; for 24h; Reagent/catalyst; Solvent; Temperature; Time; Schlenk technique; Inert atmosphere;	98%

: 5254-91-1
α-Naphthylmethylenthioessigsaeureethylester

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With nickel In ethanol for 4h; Heating;	95%
With nickel In ethanol for 4h; Heating;	95%

: 118226-43-0
N,N-dimethyl-N-(1,4-dihydronaphthyl-1-methyl)amine oxide

A: 40476-27-5
1-methylene-1,4-dihydronaphthalene (benzo-p-isotoluene)

B: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
at 85 - 105℃; under 0.5 Torr;	A 95% B 5%

: 90-11-9
1-Bromonaphthalene

A: 91-20-3
naphthalene

B: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With Me3Co(CN)2Li3 In tetrahydrofuran for 18h; Product distribution; for -78 deg C to r.t., variation of reagent;	A 4% B 95%

: 90-11-9
1-Bromonaphthalene

: [(CH3)2Ga(μ-O-CH2CH2-OCH3)]2

A: 91-20-3
naphthalene

B: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 17h;	A 3% B 95%

...Expand

: C9H22InN

: 90-13-1
1-Chloronaphthalene

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
bis(triphenylphosphine)nickel(II) chloride In benzene at 80℃; for 5h; Substitution;	95%

: 85924-73-8
C11H7Li

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 1034.3 Torr; for 2h;	94%

: 90-14-2
1-Iodonaphthalene

: 917-54-4
methyllithium

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
Stage #1: methyllithium With indium(III) chloride In tetrahydrofuran Stage #2: 1-Iodonaphthalene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Heating;	94%
bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; diethyl ether at 20℃; for 24h;	113 mg

: 13061-96-6
dihydroxy-methyl-borane

: 86-57-7
1-Nitronaphthalene

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With bis(acetylacetonato)palladium(II); 18-crown-6 ether; potassium phosphate tribasic trihydrate; 2-(2,6-dimethylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride In 1,4-dioxane at 130℃; for 48h; Suzuki Coupling; Sealed tube; Inert atmosphere;	94%
With potassium phosphate tribasic trihydrate; Tris(3,6-dioxaheptyl)amine; 2-(2,6-dimethylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride; palladium(II) acetylacetonate In 1,4-dioxane at 20 - 130℃; for 48.5h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;	87%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; palladium diacetate; caesium carbonate In toluene at 150℃; for 24h; Inert atmosphere;	55%

: 321-38-0
1-Fluoronaphthalene

: 75-16-1
methylmagnesium bromide

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
bis(tricyclohexylphosphine)nickel(II) dichloride In diethyl ether; toluene at 80℃; for 0.333333h;	93%
With C30H36NiOP2 In tetrahydrofuran at 25℃; for 16h; Inert atmosphere; Schlenk technique;	78%

: 823-96-1
Trimethylboroxine

: naphthalen-1-yl 2,3,4,5,6-pentafluorobenzenesulfonate

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With potassium phosphate monohydrate; palladium diacetate; XPhos In tert-butyl alcohol at 50℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube;	93%

: 512-56-1
trimethyl phosphite

: 68716-52-9
1-naphthylboronic acid pinacol ester

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With copper(l) iodide; lithium iodide; lithium tert-butoxide at 50℃; for 16h; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; Inert atmosphere;	93%

: 3163-27-7
2-(bromomethyl)naphthalene

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With sodium tetrahydroborate; water In methanol at 20℃; for 0.25h;	92%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;	89%
With TETRAHYDROPYRANE; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride for 2h; Heating;	82%
With phosphonic Acid; iodine In 1,2-dichloro-ethane at 120℃; for 36h; Inert atmosphere;	78%
With ethanol; platinum Hydrogenolyse;

: 1-(2-ethynylphenyl)-1-methylethylene

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With TpRu(PPh3)(CH3CN)2PF6 In toluene at 110℃; for 6h;	92%
tungsten pentacarbonyl tetrahydrofuran In tetrahydrofuran at 20℃; for 24h; Cyclization;	83%

: 75-16-1
methylmagnesium bromide

: 2216-69-5
1-Methoxynaphthalene

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
bis(tricyclohexylphosphine)nickel(II) dichloride In diethyl ether; toluene at 80℃; for 0.333333h;	92%
With tricyclohexylphosphine In toluene at 40℃; for 2h; Inert atmosphere;	93 %Chromat.

: 90-11-9
1-Bromonaphthalene

: 5158-46-3
methylzinc chloride

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With palladium; triphenylphosphine In tetrahydrofuran at 70℃; for 12h; Catalytic behavior; Negishi Coupling; Inert atmosphere; Green chemistry;	92%

: 66-77-3
1-naphthaldehyde

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With ethoxyethoxyethanol; hydrazine hydrate; potassium hydroxide at 220℃; under 10343.2 Torr; Wolff-Kishner Reduction; Sonication;	91%
With W-7 Raney-Nickel In ethanol for 2h; Heating;	89%
With sodium hydroxide; water; hydrazine hydrate In ethylene glycol for 3h; Reduction; Heating;	54%
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane

: 90-11-9
1-Bromonaphthalene

: 60228-61-7
bis{bis(trimethylsilyl)amido}(methyl)(iodo)tin(IV)

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 101℃; for 4h; Stille reaction;	91%

: 90-11-9
1-Bromonaphthalene

: 917-54-4
methyllithium

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
Stage #1: 1-Bromonaphthalene With bis(tri-t-butylphosphine)palladium(0); oxygen In toluene at 20℃; for 0.0166667h; Schlenk technique; Stage #2: methyllithium In toluene at 20℃; for 0.0333333h; Catalytic behavior; Reagent/catalyst; Schlenk technique;	91%
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In diethyl ether at 20℃; for 0.00555556h; pH=6; Schlenk technique;	85%

: 63171-65-3
4-Hydro-1-methylnaphtalene-1-carboxylic acid

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With chlorosulfonic acid In dichloromethane at 0℃; for 0.166667h;	90%

: 137203-34-0
bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct

: 90-14-2
1-Iodonaphthalene

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); dicyclohexyl(2',6'-diisopropyl-4'-sulfobiphenyl-2-yl)phosphonium hydrogen sulfate In tetrahydrofuran at 65℃; for 2h; Inert atmosphere; Ionic liquid; chemoselective reaction;	90%

: 87306-73-8
2-Methyl-2-[(naphthalen-1-ylmethyl)-amino]-propan-1-ol

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 2585.7 Torr; for 8h; Ambient temperature;	88%

: 68211-49-4
1-naphthyl tosylate

: 75-16-1
methylmagnesium bromide

: 90-12-0
1-Methylnaphthalene

Conditions

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 65℃; for 24h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;	87%
With cobalt (III) fluoride; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran at 80℃; for 5h;	82%
With iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 23℃; for 1h;

: 98-88-4
benzoyl chloride

: 90-12-0
1-Methylnaphthalene

: 116672-26-5
(4-methylnaphthalen-1-yl)(phenyl)methanone

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane for 1h; Friedel-Crafts Acylation;	100%
With sulfated zirconia In chlorobenzene at 130℃; for 20h;	53%
With carbon disulfide; aluminium trichloride at 0 - 10℃;
With carbon disulfide; aluminium trichloride

: 90-12-0
1-Methylnaphthalene

: 6627-78-7
1-bromo-4-methylnaphthalene

Conditions

Conditions	Yield
With aluminum oxide; copper(ll) bromide In tetrachloromethane at 50℃; for 2h;	100%
With benzyltrimethylazanium tribroman-2-uide; zinc(II) chloride In acetic acid for 3h; Ambient temperature;	99%
With N-Bromosuccinimide In acetonitrile at 30 - 40℃; for 12h;	98%

: 90-12-0
1-Methylnaphthalene

: 17075-39-7
4-chloro-1-methyl-naphthalene

Conditions

Conditions	Yield
With aluminum oxide; copper dichloride In chlorobenzene at 130℃; for 2h;	100%
With lead(IV) acetate; tin(IV) chloride In dichloromethane for 0.25h;	85%
With benzyltrimethylazanium tetrachloro-λ3-iodanuide In acetic acid at 70℃; for 18h;	73%

: 90-12-0
1-Methylnaphthalene

: 3278-84-0
1-methyl-2,4-dibromonaphthalene

Conditions

Conditions	Yield
With aluminum oxide; copper(ll) bromide In tetrachloromethane at 80℃; for 16h;	100%

: 124-38-9
carbon dioxide

: 90-12-0
1-Methylnaphthalene

: 4488-40-8
4-Methyl-1-naphthoic acid

Conditions

Conditions	Yield
With aluminum tri-bromide; Triphenylsilyl chloride In chlorobenzene at 20℃; under 22502.3 Torr; for 3h; Autoclave; regioselective reaction;	99%
With aluminum tri-bromide In benzene at 40℃; under 22501.8 Torr; for 24h;	33%

: 90-12-0
1-Methylnaphthalene

: 73453-32-4, 73453-33-5, 19224-41-0
4,4'-dimethyl-1,1'-binaphthalene

Conditions

Conditions	Yield
With air; trifluorormethanesulfonic acid; sodium nitrite In acetonitrile at 0℃; for 1h; Product distribution; Mechanism; effect of further reagents;	97%
With air; trifluorormethanesulfonic acid; sodium nitrite In acetonitrile at 0℃; for 1h;	97%
With boron trifluoride diethyl etherate; thallium(III) trifluoroacetate In tetrachloromethane Ambient temperature;	93%

: 100-52-7
benzaldehyde

: 90-12-0
1-Methylnaphthalene

: 1024594-36-2
C29H24

Conditions

Conditions	Yield
With Acetyl bromide; silica gel; zinc dibromide In benzene at 50℃; for 3h;	97%

: 90-12-0
1-Methylnaphthalene

: 86-53-3
1-Cyanonaphthalene

Conditions

Conditions	Yield
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 70℃; for 24h; Inert atmosphere; Sealed tube;	97%
With tert.-butylhydroperoxide; ammonium fluoride; iodine; oxygen In water; dimethyl sulfoxide at 70℃; for 48h; Reagent/catalyst; Solvent; Time; Schlenk technique; Sealed tube;	80%
Stage #1: 1-Methylnaphthalene With hydrogen bromide; dihydrogen peroxide In tetrachloromethane; water at 20℃; for 1h; Irradiation; Stage #2: With ammonia; iodine In tetrachloromethane; water; acetonitrile at 20 - 60℃; for 4h;	73%

: 90-12-0
1-Methylnaphthalene

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane	96%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 80℃; for 2.5h; Inert atmosphere;	95%
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; dibenzoyl peroxide In ethyl acetate for 4.5h; Reflux;	90%

: 64-19-7
acetic acid

: 90-12-0
1-Methylnaphthalene

A: 13098-88-9
naphthalen-1-ylmethyl acetate

B: 66-77-3
1-naphthaldehyde

Conditions

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

...Expand

: 90-12-0
1-Methylnaphthalene

A: 13098-88-9
naphthalen-1-ylmethyl acetate

B: 66-77-3
1-naphthaldehyde

Conditions

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%

: 90-12-0
1-Methylnaphthalene

: 20601-22-3
2-bromo-1-methylnaphthalene

Conditions

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide In water at 20℃; for 24h; Darkness;	94%
With hydrogen bromide; dihydrogen peroxide In water at 20℃; for 64h; Darkness;	81%

1-Methylnaphthalene Consensus Reports

Reported in EPA TSCA Inventory.

1-Methylnaphthalene Specification

The 1-Methylnaphthalene with CAS registry number of 90-12-0 is also known as Naphthalene, alpha-methyl-. The IUPAC name and product name are the same. It belongs to product categories of Alpha Sort; Chemical Class; Hydrocarbons; M; MAlphabetic; Meta-methAnalytical Standards; NaphthalenesChemical Class; Neats; Volatiles/ Semivolatiles; Arenes; Building Blocks; Organic Building Blocks; Alphabetical Listings; Flavors and Fragrances; M-N; Naphthalenes. Its EINECS registry number is 201-966-8. In addition, the formula is C₁₁H₁₀ and the molecular weight is 142.20. This chemical is a colorless liquid and should be stored in ventilated and dry room below 30 °C.1-Methylnaphthalene is sensitive to heat. Reacts with strong oxidizing agents. Incompatible with oxygen and peroxides .

Physical properties about 1-Methylnaphthalene are:
(1)ACD/LogP: 3.91; (2)ACD/LogD (pH 5.5): 3.91; (3)ACD/LogD (pH 7.4): 3.91; (4)ACD/BCF (pH 5.5): 550.66; (5)ACD/BCF (pH 7.4): 550.66; (6)ACD/KOC (pH 5.5): 3188.07; (7)ACD/KOC (pH 7.4): 3188.07; (8)Index of Refraction: 1.616; (9)Molar Refractivity: 48.92 cm³; (10)Molar Volume: 139.8 cm³; (11)Surface Tension: 38.7 dyne/cm; (12)Density: 1.016 g/cm³; (13)Flash Point: 82.2 °C; (14)Enthalpy of Vaporization: 46.03 kJ/mol; (15)Boiling Point: 242.8 °C at 760 mmHg; (16)Vapour Pressure: 0.0518 mmHg at 25 °C.

Preparation of 1-Methylnaphthalene:
It is exist in high temperature tar about 0.8%-1.2%. Phenol and pyridine base are removed from the fraction of 230-300 °C. Then the fraction is distillated to collect fraction at 240-245 °C. At last, the fraction is cooled to obtain the product.

Uses of 1-Methylnaphthalene:
It is used as raw material of surfactant, water reducer, dispersant, drugs and other organic synthesis. It is used to produce 1-methylnaphthalene-d10. The reaction occurs with reagents deuterium oxide, sodium deuteroxide and other condition of supercritical pressure at 420-430 °C for 24 hours. The yield is about 75%.
1-Methylnaphthalene is used to produce 1-methylnaphthalene-d10.

Safety information of 1-Methylnaphthalene:
When you are using 1-Methylnaphthalene, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It is harmful by inhalation, in contact with skin and if swallowed. What's more, may cause sensitisation by inhalation and skin contact. It also is toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep container tightly closed and avoid release to the environment. Do not breathe gas/fumes/vapour/spray. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If accident happens or you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1=CC=CC2=CC=CC=C12
2. InChI: InChI=1S/C11H10/c1-9-5-4-7-10-6-2-3-8-11(9)10/h2-8H,1H3
3. InChIKey: QPUYECUOLPXSFR-UHFFFAOYSA-N

The toxicity data of 1-Methylnaphthalene is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LDLo	skin	7500mg/kg (7500mg/kg)		National Technical Information Service. Vol. OTS0556357,
rat	LD50	oral	1840mg/kg (1840mg/kg)		"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 85, 1982.

Product Name

1 -Methylnaphthalene

Synthetic route

1-Methylnaphthalene Consensus Reports

1-Methylnaphthalene Specification

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