1-Bromo-4-(Dimethylamino)Naphthalene

Base Information

• Chemical Name: 1-Bromo-4-(Dimethylamino)Naphthalene
• CAS No.: 59557-93-6
• Molecular Formula: C12H12BrN
• Molecular Weight: 250.138
• Hs Code.: 2921450090
• DSSTox Substance ID: DTXSID50399133
• Nikkaji Number: J1.982.172B
• Wikidata: Q82201510
• Mol file: 59557-93-6.mol

Synonyms:59557-93-6;1-Bromo-4-(Dimethylamino)Naphthalene;4-bromo-N,N-dimethylnaphthalen-1-amine;SCHEMBL2949640;DTXSID50399133;MFCD02093945;AKOS023540956;N,N-Dimethyl-4-bromonaphthalene-1-amine;AS-63855;CS-0319744;FT-0607492

Chemical Property of 1-Bromo-4-(Dimethylamino)Naphthalene

Chemical Property:

• Vapor Pressure: 0.000158mmHg at 25°C
• Refractive Index: 1.6361
• Boiling Point: 137-139°C 2mm
• PKA: 4.41±0.40(Predicted)
• Flash Point: 137-139°C/2mm
• PSA: 3.24000
• Density: 1,4305 g/cm3
• LogP: 3.66830
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 249.01531
• Heavy Atom Count: 14
• Complexity: 193

Purity/Quality:

98%Min ^*data from raw suppliers

1-BROMO-4-(DIMETHYLAMINO)NAPHTHALENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Hazard Codes: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Statements: 20/21/22
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C2=CC=CC=C21)Br

Technology Process of 1-Bromo-4-(Dimethylamino)Naphthalene

There total 5 articles about 1-Bromo-4-(Dimethylamino)Naphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-Bromo-1-naphthylamine (2298-07-9) + methyl iodide (74-88-4) → 4-bromo-1-(N,N-dimethylamino)naphthalene (59557-93-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; 1.) 65 deg C, 25 h, 2.) 120 Deg C, 3 h; 16 h;

DOI:10.1021/jo00118a023

Reference yield: 97.0%

N,N-dimethyl-1-naphthalenamine (86-56-6,112790-02-0,651316-60-8) → 4-bromo-1-(N,N-dimethylamino)naphthalene (59557-93-6)

Guidance literature:

With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; In dichloromethane; at -10 - 20 ℃;

Reference yield: 56.0%

1-(N,N-dimethylamino)naphthalene-N-oxide (830-70-6) → 4-bromo-1-(N,N-dimethylamino)naphthalene (59557-93-6)

Guidance literature:

1-(N,N-dimethylamino)naphthalene-N-oxide; With sulfurous dibromide; In tetrahydrofuran; at -78 ℃; for 4h; Inert atmosphere;

With triethylamine; In tetrahydrofuran; at -78 - 23 ℃; for 0.75h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.8b01590

upstream raw materials:

N,N-dimethyl-1-naphthalenamine

4-Bromo-1-naphthylamine

dimethyl sulfate

methyl iodide

Downstream raw materials:

4-dimethylamino-1-naphthaldehyde

C₅₇H₆₄N₉O₆P

C₄₈H₄₇N₇O₅

1-[3,5-bis(tert-butyldimethylsilyloxymethyl)phenyl]-4-(dimethylamino)naphthalene

Refernces

• 1、 -. "Method for preparing bromo reagent by oxidative bromination reaction and method for further preparing bromine-containing compound". Paragraph 0034-0035. . Retrieved 2020/03/17.
• 2、 Shi, Renyi,Lu, Lijun,Xie, Hangyu,Yan, Jingwen,Xu, Ting,Zhang, Hua,Qi, Xiaotian,Lan, Yu,Lei, Aiwen. "C8-H bond activation vs. C2-H bond activation: From naphthyl amines to lactams". supporting information. p. 13307 - 13310. Retrieved 2016/11/17.