Cas no 86-56-6 (N,N-Dimethyl-1-naphthylamine)

N,N-Dimethyl-1-naphthylamine structure
N,N-Dimethyl-1-naphthylamine structure
Product Name:N,N-Dimethyl-1-naphthylamine
CAS No:86-56-6
MF:C12H13N
MW:171.238322973251
MDL:MFCD00003919
CID:34384
PubChem ID:6848
Update Time:2024-10-26

N,N-Dimethyl-1-naphthylamine Chemical and Physical Properties

Names and Identifiers

    • N,N-Dimethyl-1-naphthylamine
    • 1-Dimethylaminoaphthalene
    • 1-Dimethylaminonaphthalene
    • N,N-DIMETHYL-A-NAPHTYLAMINE
    • N,N-dimethylnaphthalen-1-amine
    • N.N-Dimethyl-1-naphthylamine
    • 1-DiMe- thylaMinonaphthalene
    • N,N-DiMethyl-1-naphthalenaMine
    • N,N-DiMethyl-α-naphthylaMine
    • N-DiMe thyl-1-naphthylaMine
    • 1-Naphthalenamine, N,N-dimethyl-
    • N,N-Dimethyl-1-napthylamine
    • Dimethyl(1-naphthyl)amine
    • alpha-Dimethylaminonaphthalene
    • 1-Naphthylamine, N,N-dimethyl-
    • n-methyl-1-naphthalene methylamine
    • N,N-Dimethyl-1-naftylamin
    • Dimethyl-alpha-naphthylamine
    • N,N-Dimethyl-alpha-naphthylamine
    • N,N-Dimethyl-1-naftylamin [Czech]
    • 1
    • FT-0631407
    • Naphthalenamine, N,N-dimethyl-
    • DIMETHYL(NAPHTH-1-YL)AMINE
    • EN300-18113
    • N,N-dimethyl-naphthalen-1-yl-amine
    • SCHEMBL2349
    • N,N-DIMETHYL-1-NAPHTHYLAMINE [MI]
    • Z57169438
    • 86-56-6
    • 1-Naphthalenamine,N-dimethyl-
    • HY-D0222
    • 1-Naphthylamine,N-dimethyl-
    • N,N-Dimethyl-1-naphthylamine, 99%
    • Dimethyl-.alpha.-naphthylamine
    • dimethylaminonaphtalene
    • .alpha.-Dimethylaminonaphthalene
    • LS-95727
    • Q6951323
    • W-104062
    • N,N-Dimethyl-.alpha.-naphthylamine
    • 020063I9Y0
    • NSC-8713
    • D0755
    • MFCD00003919
    • InChI=1/C12H13N/c1-13(2)12-9-5-7-10-6-3-4-8-11(10)12/h3-9H,1-2H
    • dimethylaminonaphthalene
    • A841719
    • 1-(Dimethylamino)naphthalene
    • WLN: L66J BN1&1
    • CHEMBL2358331
    • .alpha.-Dimethylnaphthylamine
    • FS-1057
    • DTXSID9058941
    • 28109-57-1
    • BRN 1424075
    • N,N-dimethyl naphthalen-1-amine
    • N,N-Dimethyl-1-naphthylamine, >=98.0% (GC)
    • NSC 8713
    • NCGC00188093-01
    • dimethyl(1-naphthyl)amin
    • CS-0010134
    • D89713
    • AKOS000119550
    • UNII-020063I9Y0
    • EINECS 201-682-4
    • NSC8713
    • 1-Naphthylamine, N,N-dimethyl- (6CI, 7CI, 8CI)
    • N,N-Dimethyl-1-naphthalenamine (ACI)
    • Dimethyl-α-naphthylamine
    • α-Dimethylaminonaphthalene
    • SY048186
    • DB-056937
    • NS00022847
    • N,?N-?Dimethyl-?1-?naphthylamine
    • naphthalene, 1-dimethylamino-
    • MDL： MFCD00003919
    • Inchi： 1S/C12H13N/c1-13(2)12-9-5-7-10-6-3-4-8-11(10)12/h3-9H,1-2H3
    • InChI Key： AJUXDFHPVZQOGF-UHFFFAOYSA-N
    • SMILES： C1C=C2C=CC=C(C2=CC=1)N(C)C
    • BRN： 1424075

Computed Properties

  • Exact Mass: 171.10500
  • Monoisotopic Mass: 171.104799
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 165
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 3.5
  • Topological Polar Surface Area: 3.2

Experimental Properties

  • Color/Form: Colorless or brown oily liquid, with aromatic smell, sensitive to light and weak purple fluorescence
  • Density: 1.042?g/mL?at 25?°C(lit.)
  • Boiling Point: 274°C(lit.)
  • Flash Point: Degrees Fahrenheit:235.4°F
    Degrees Celsius:113°C
  • Refractive Index: n20/D 1.622(lit.)
  • Water Partition Coefficient: Insoluble
  • Stability/Shelf Life: Stable. Incompatible with strong oxidizing agents.
  • PSA: 3.24000
  • LogP: 2.90580
  • Merck: 3252
  • pka: 4.83(at 25℃)
  • Solubility: Soluble in ethanol \ ether and dilute inorganic acids, insoluble in water

N,N-Dimethyl-1-naphthylamine Security Information

N,N-Dimethyl-1-naphthylamine Customs Data

  • HS CODE：2921450090
  • Customs Data：

    China Customs Code:

    2921450090

    Overview:

    2921450090. 1-Naphthylamine and2-Derivatives and salts of naphthylamine(include1-Naphthylamine). VAT:17.0%. Tax refund rate:9.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2921450090 1-naphthylamine (Ah-naphthylamine), 2-naphthylamine (b-naphthylamine) and their derivatives; salts thereof.Supervision conditions:None.VAT:17.0%.Tax rebate rate:9.0%.MFN tariff:6.5%.General tariff:30.0%

N,N-Dimethyl-1-naphthylamine Pricemore >>

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N,N-Dimethyl-1-naphthylamine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Disodium phosphate Solvents: Dimethylformamide ;  overnight, rt
Reference
Chromo-Orthogonal Deprotection of Carboxylic Acids by Aminonaphthalene and Aminoaniline Photocages
Lovrincevic, Vilma; et al, Journal of Organic Chemistry, 2022, 87(5), 2489-2500

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Dimethyl sulfoxide ;  rt; 50 °C
1.2 Reagents: Water
Reference
Cu(II)-catalyzed C-H (SP3) oxidation and C-N cleavage: base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source
Zhang, Lei; et al, Chemical Communications (Cambridge, 2012, 48(47), 5928-5930

Production Method 3

Reaction Conditions
1.1 Reagents: Hydrazine hydrate (1:1) Catalysts: Tris(2,2′-bipyridyl)ruthenium(II) chloride Solvents: Dimethyl sulfoxide ;  21 h, rt
Reference
Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides
Kim, Kyu Dong; et al, Organic Letters, 2018, 20(23), 7712-7716

Production Method 4

Reaction Conditions
1.1 Reagents: Phenylboronic acid Solvents: Dichloromethane ;  10 min, rt
Reference
Deoxygenation of tertiary amine N-oxides under metal free condition using phenylboronic acid
Gupta, Surabhi; et al, Tetrahedron Letters, 2017, 58(10), 909-913

Production Method 5

Reaction Conditions
1.1 Catalysts: Zinc oxide (ZnO) ,  Iridium Solvents: Methanol ;  12 h, 150 °C
Reference
Additive-free N-methylation of amines with methanol over supported iridium catalyst
Wang, Jing; et al, Catalysis Science & Technology, 2021, 11(10), 3364-3375

Production Method 6

Reaction Conditions
1.1 Catalysts: Potassium carbonate ,  Iridium(2+), diammine(1,3-dihydro-1,3-dimethyl-2H-imidazol-2-ylidene)[(1,2,3,4,5… ;  17 h, 120 °C
Reference
Efficient and Versatile Catalytic Systems for the N -Methylation of Primary Amines with Methanol Catalyzed by N -Heterocyclic Carbene Complexes of Iridium
Toyooka, Genki; et al, Synthesis, 2018, 50(23), 4617-4626

Production Method 7

Reaction Conditions
1.1 Reagents: Zinc chloride ,  Sodium cyanoborohydride Solvents: Methanol ;  overnight, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
Reference
Deoxygenation of tertiary amine N-oxides under metal free condition using phenylboronic acid
Gupta, Surabhi; et al, Tetrahedron Letters, 2017, 58(10), 909-913

Production Method 8

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Sodium borohydride
Reference
N-Permethylation of primary and secondary aromatic amines
Giumanini, Angelo G.; et al, Synthesis, 1980, (9), 743-6

Production Method 9

Reaction Conditions
1.1 Reagents: Sodium carbonate Solvents: Water ;  1 h, rt
1.2 Reagents: Potassium hydroxide Solvents: Water ;  pH 11 - 13, rt
Reference
A simple and effective procedure for the N-permethylation of amino-substituted naphthalenes
Sorokin, Vladimir I.; et al, European Journal of Organic Chemistry, 2003, (3), 496-498

Production Method 10

Reaction Conditions
1.1 Solvents: Pyridine ,  Water
Reference
Employment of pyridine as catalyst in production of dimethyl-α-naphthylamine
Germuth, Frederick G., Journal of the American Chemical Society, 1929, 51, 1555-7

Production Method 11

Reaction Conditions
1.1 Reagents: Chloro(1-methylethyl)magnesium Catalysts: Nickel dichloride ,  1,1-Bis(diphenylphosphino)ferrocene Solvents: Tetrahydrofuran ;  rt; 24 h, rt
Reference
Solid-phase synthesis of unfunctionalized arenes via the traceless cleavage of sulfonate linkers
Kim, Chul-Bae; et al, Bulletin of the Korean Chemical Society, 2011, 32(10), 3655-3659

Production Method 12

Reaction Conditions
1.1 Reagents: Sodium tert-butoxide Catalysts: 1902911-46-9 Solvents: Tetrahydrofuran ;  16 h, 110 °C
Reference
Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design
Lavoie, Christopher M.; et al, Nature Communications, 2016, 7,

Production Method 13

Reaction Conditions
1.1 Reagents: Ammonium chloride
Reference
Substitution of hydroxy and alkoxy groups for amino groups in derivatives of the naphthalene and quinoline series
Terenin, V. I.; et al, Vestnik Moskovskogo Universiteta, 1990, 31(1), 68-72

Production Method 14

Reaction Conditions
1.1 Solvents: Diethyl ether ;  -30 °C → 0 °C
Reference
N,N-Dimethyl-O-(methylsulfonyl)-hydroxylamine
Boche, Gernot, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 15

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Dimethyl sulfoxide ;  50 °C
1.2 Reagents: Water
Reference
Copper(II)-catalyzed C-H (sp3) oxidation and C-N cleavage: synthesis of methylene-bridged compounds using TMEDA as a carbon source in water
Zhao, Dan; et al, RSC Advances, 2013, 3(26), 10272-10276

Production Method 16

Reaction Conditions
1.1 Reagents: 3,5-Bis(1,1-dimethylethyl) 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate Catalysts: Tris(2,2′-bipyridyl)dichlororuthenium(II) hexahydrate Solvents: Acetonitrile ;  10 min, rt
Reference
Highly Chemoselective Deoxygenation Of N-Heterocyclic N-Oxides Using Hantzsch Esters As Mild Reducing Agents
An, Ju Hyeon; et al, Journal of Organic Chemistry, 2021, 86(3), 2876-2894

Production Method 17

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Water Catalysts: Bis(1,5-cyclooctadiene)nickel ,  7H-Acenaphth[1,2-d]imidazolium, 7,9-bis[2,6-bis(1-methylethyl)phenyl]-, chloride… Solvents: Toluene ;  rt; 24 h, 35 °C
1.2 Reagents: Water
Reference
Nickel-Catalyzed Amination of Aryl Chlorides with Amides
Li, Jinpeng; et al, Organic Letters, 2021, 23(3), 687-691

Production Method 18

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Sodium borohydride Solvents: Tetrahydrofuran ,  Water
Reference
Reductive aminations of carbonyl compounds with borohydride and borane reducing agents
Baxter, Ellen W.; et al, Organic Reactions (Hoboken, 2002, 59,

Production Method 19

Reaction Conditions
1.1 < 0 °C
1.2 Reagents: Sodium carbonate Solvents: Water ;  0 °C; 2 h, rt
1.3 Reagents: Potassium hydroxide Solvents: Water ;  basified, rt
Reference
Highly Twisted N,N-Dialkylamines as a Design Strategy to Tune Simple Aromatic Hydrocarbons as Steric Environment-Sensitive Fluorophores
Sasaki, Shunsuke; et al, Journal of the American Chemical Society, 2016, 138(26), 8194-8206

Production Method 20

Reaction Conditions
1.1 Catalysts: Palladium (supported on KPCN) ,  Aluminum chloride ,  Carbon nitride (K-intercalated) Solvents: Acetonitrile ,  Water ;  6 - 48 h, rt
Reference
Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride
Xu, Yangsen ; et al, ChemSusChem, 2021, 14(2), 582-589

Production Method 21

Reaction Conditions
1.1 Reagents: Phenylsilane Catalysts: Dimanganese decacarbonyl ,  2-(Dicyclohexylphosphino)-9-(2-pyridinyl)-9H-carbazole Solvents: Acetonitrile ;  15 h, 1 bar, 100 °C
Reference
Mn-Catalyzed Selective Double and Mono-N-Formylation and N-Methylation of Amines by using CO2
Huang, Zijun; et al, ChemSusChem, 2019, 12(13), 3054-3059

Production Method 22

Reaction Conditions
1.1 Reagents: Trimethylamineborane Catalysts: 2-Amino-6-methylpyridine Solvents: 1,2-Dichloroethane ;  6 h, 1 atm, 100 °C; 100 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water
Reference
Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2
Zhang, Yanmeng; et al, Organic Letters, 2021, 23(21), 8282-8286

Production Method 23

Reaction Conditions
1.1 Solvents: Diethyl ether
Reference
Electrophilic amination of carbanions, enolates, and their surrogates
Ciganek, Engelbert, Organic Reactions (Hoboken, 2008, 72, 1-366

Production Method 24

Reaction Conditions
1.1 Reagents: Stannous chloride Solvents: Dimethyl sulfoxide ;  10 min, rt
1.2 Catalysts: Allyl chloride ;  6 h, rt
Reference
SnCl2 mediated efficient N,N-dialkylation of azides to tertiary-amine via potential stannaimine intermediate
Roy, Ujjal Kanti; et al, Journal of Organometallic Chemistry, 2006, 691(8), 1525-1530

Production Method 25

Reaction Conditions
1.1 Reagents: Phenylsilane Solvents: Dimethylformamide ;  24 h, 1 atm, 90 °C; 90 °C → rt
1.2 Reagents: Water ;  rt
Reference
Catalyst-free N-methylation of amines using CO2
Niu, Huiying; et al, Chemical Communications (Cambridge, 2017, 53(6), 1148-1151

Production Method 26

Reaction Conditions
1.1 Reagents: Phenylsilane Catalysts: Platinum Solvents: Toluene ;  rt → 80 °C; 15 h, 80 °C; 80 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Ethyl acetate ,  Water ;  rt
Reference
Methylation of aromatic amines and imines using formic acid over a heterogeneous Pt/C catalyst
Zhu, Lei; et al, Catalysis Science & Technology, 2016, 6(16), 6172-6176

Production Method 27

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Acetonitrile ;  16 h, reflux
1.2 Reagents: Sodium chloride Solvents: Water
Reference
Visible-Light-Induced C(sp2)-C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions
Zhang, Hong-Yu ; et al, Journal of Organic Chemistry, 2021, 86(17), 11723-11735

Production Method 28

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  4 h, 90 °C
Reference
Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols
Zhang, Hua; et al, RSC Advances, 2020, 10(29), 16942-16948

Production Method 29

Reaction Conditions
1.1 Reagents: Ammonium chloride Catalysts: Methylamine
2.1 Reagents: Ammonium chloride
Reference
Substitution of hydroxy and alkoxy groups for amino groups in derivatives of the naphthalene and quinoline series
Terenin, V. I.; et al, Vestnik Moskovskogo Universiteta, 1990, 31(1), 68-72

N,N-Dimethyl-1-naphthylamine Raw materials

N,N-Dimethyl-1-naphthylamine Preparation Products

N,N-Dimethyl-1-naphthylamine Related Literature

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