6-Bromoacetyl-2-dimethylaminonaphthalene

Base Information

• Chemical Name: 6-Bromoacetyl-2-dimethylaminonaphthalene
• CAS No.: 210832-86-3
• Molecular Formula: C14H14 Br N O
• Molecular Weight: 292.175
• DSSTox Substance ID: DTXSID30376326
• Nikkaji Number: J985.117H
• Wikidata: Q82165251
• Mol file: 210832-86-3.mol

Synonyms:6-bromoacetyl-2-dimethylaminonaphthalene;BADAN;BD-naphth

Chemical Property of 6-Bromoacetyl-2-dimethylaminonaphthalene

Chemical Property:

• Vapor Pressure: 4.13E-07mmHg at 25°C
• Melting Point: 117-120°C
• Refractive Index: 1.66
• Boiling Point: 415.4°Cat760mmHg
• Flash Point: 205°C
• PSA: 20.31000
• Density: 1.416g/cm³
• LogP: 3.48340
• Storage Temp.: -20?C Freezer
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 291.02588
• Heavy Atom Count: 17
• Complexity: 279

Purity/Quality:

98%Min ^*data from raw suppliers

6-Bromoacetyl-2-dimethylaminonaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC2=C(C=C1)C=C(C=C2)C(=O)CBr
• Uses: A highly flourescent compound

Technology Process of 6-Bromoacetyl-2-dimethylaminonaphthalene

There total 3 articles about 6-Bromoacetyl-2-dimethylaminonaphthalene 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: 92.0%

6,6'-dibromoacetyl-2-(dimethylamino)naphthalene (210832-83-0) → 6-bromoacetyl-2-dimethylaminonaphthalene (210832-86-3)

Guidance literature:

With Diethyl phosphonate; triethylamine; In tetrahydrofuran; 0 deg C; RT, 6 h;

DOI:10.1016/S0040-4039(98)00975-7

Reference yield:

1-(6-(dimethylamino)naphthalen-2-yl)ethan-1-one (68520-00-3) → 6-bromoacetyl-2-dimethylaminonaphthalene (210832-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. sulfuric acid; bromine / tetrahydrofuran / 4 h / 20 °C

2: 110 mg / diethyl phosphite; DIPEA / tetrahydrofuran / 20 °C

With Diethyl phosphonate; sulfuric acid; bromine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1039/b205224e

Reference yield:

6-methoxy-2-acetylnaphthalene (3900-45-6) → 6-bromoacetyl-2-dimethylaminonaphthalene (210832-86-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / hexane / 16 h / 20 °C

2: conc. sulfuric acid; bromine / tetrahydrofuran / 4 h / 20 °C

3: 110 mg / diethyl phosphite; DIPEA / tetrahydrofuran / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Diethyl phosphonate; sulfuric acid; bromine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane;

DOI:10.1039/b205224e

upstream raw materials:

6,6'-dibromoacetyl-2-(dimethylamino)naphthalene

6-methoxy-2-acetylnaphthalene

1-(6-(dimethylamino)naphthalen-2-yl)ethan-1-one

Downstream raw materials:

2-(α-(3,4-diaminophenoxy)acetyl)-6-(dimethylamino)naphthalene

C₂₀H₁₉N₃O₄