59557-93-6

Basic information

• Product Name: 1-BROMO-4-(DIMETHYLAMINO)NAPHTHALENE
• Synonyms: 1-BROMO-4-(DIMETHYLAMINO)NAPHTHALENE;4-Bromo-N,N-dimethyl-1-naphthylamine;1-NaphthalenaMine, 4-broMo-N,N-diMethyl-;4-Bromo-N,N-dimethylnaphthalen-1-amine
• CAS NO: 59557-93-6
• Molecular Formula: C₁₂H₁₂BrN
• Molecular Weight: 250.13
• EINECS: -0
• Mol File: 59557-93-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 137-139°C 2mm
• Flash Point: 137-139°C/2mm
• Appearance: /
• Density: 1,4305 g/cm3
• Vapor Pressure: 0.000158mmHg at 25°C
• Refractive Index: 1.6361
• PKA: 4.41±0.40(Predicted)
• BRN: 3254839
• CAS DataBase Reference: 1-BROMO-4-(DIMETHYLAMINO)NAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-4-(DIMETHYLAMINO)NAPHTHALENE(59557-93-6)
• EPA Substance Registry System: 1-BROMO-4-(DIMETHYLAMINO)NAPHTHALENE(59557-93-6)

Safety Data

• Statements: 20/21/22
• Safety Statements: 26-36/37
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 59557-93-6(Hazardous Substances Data)

Usage

General Description

1-Bromo-4-(dimethylamino)naphthalene, also commonly known as Proton Sponge or CAS number 20734-58-1, is an organic chemical compound primarily used in various fields of research and in the synthesis of other chemical compounds. The 'proton sponge' nickname comes from its strong basicity and ability to absorb protons, due to the presence of two dimethylamino groups. This particular compound stands out because of its unusual resistance to forming salts and its pronounced steric expansion. It is a white to off-white crystalline powder at room temperature and insoluble in water. Despite its utility in several scientific applications, it should be carefully handled due to its potential harmful effects to skin, eyes, and respiratory system.

InChI:InChI=1/C12H12BrN/c1-14(2)12-8-7-11(13)9-5-3-4-6-10(9)12/h3-8H,1-2H3

Upstream product

• 86-56-6 N,N-dimethyl-1-naphthalenamine 
• 2298-07-9 4-Bromo-1-naphthylamine 
• 74-88-4 methyl iodide 
• 512-56-1 trimethyl phosphite 
• 830-70-6 1-(N,N-dimethylamino)naphthalene-N-oxide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1971-81-9 4-dimethylamino-1-naphthaldehyde 
• 353457-09-7 N,N-dimethyl-2-chlorodifluoroacetyl-4-bromo-1-naphthylamine 
• 1419165-36-8 C₅₇H₆₄N₉O₆P 
• 1419165-30-2 C₄₈H₄₇N₇O₅ 
• 1261237-70-0 1-[3,5-bis(tert-butyldimethylsilyloxymethyl)phenyl]-4-(dimethylamino)naphthalene 
• 83300-27-0 <4-(dimethylamino)-1-naphthyl>diphenylphosphine 
• 1026167-95-2 {4-[Bis-(4-pyrrolidin-1-yl-phenyl)-methyl]-naphthalen-1-yl}-dimethyl-amine 
• 944741-30-4 {4-[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-phenylethynyl]naphthalen-1-yl}dimethylamine 

Relevant articles and documents

Syntheses of Rigid and Semirigid Molecules for Investigations of Photoinduced Electron Transfer Reactions

Investigations of electron transfer reactions in donor-spacer-acceptor (DSA) molecules posessing small numbers of reactive conformations have significantly increased understanding of factors that control transfer rate constants.The synthese of polynorbornane-based DSA molecules 12, 16, 20, 26, 30, and 34 and heptacyclotetradecane-based DSA molecules 40, 47, 51, and 60 are described.These molecules have been used to explore the effects of electronic symmetry, solvent electronic structure, and temperature on photoinduced electron transfer reactions.

Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides

The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N-O bond via treatment with thionyl bromide or thionyl chloride at low temperature.

A novel tunable aromatic bromination method using alkyl bromides and sodium hydride in DMSO

Aromatic bromination on various aromatic systems with different substitutions was performed in the presence of alkyl bromide and sodium hydride in DMSO. Mono-bromination on a wide range of substrates was achieved by selecting proper alkyl bromides and controlling its amount. Further bromination could happen with more active alkyl bromides and additional amount of bromides and sodium hydride. The yields ranged from moderate to excellent. In addition, reaction mechanism was postulated to explain our observations.