1576-69-8

Basic information

• Product Name: 2,7-Dimethylphenanthrene
• Synonyms: 2,7-Dimethylphenanthrene;NSC 407670
• CAS NO: 1576-69-8
• Molecular Formula: C₁₆H₁₄
• Molecular Weight: 206.2824
• Mol File: 1576-69-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 369.6°Cat760mmHg
• Flash Point: 168.4°C
• Appearance: /
• Density: 1.084g/cm³
• Vapor Pressure: 2.49E-05mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 2,7-Dimethylphenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dimethylphenanthrene(1576-69-8)
• EPA Substance Registry System: 2,7-Dimethylphenanthrene(1576-69-8)

Safety Data

• Hazardous Substances Data: 1576-69-8(Hazardous Substances Data)

Usage

Chemical Class

Polycyclic aromatic hydrocarbon (PAH)

Structure

Three fused benzene rings

Physical State

Colorless solid at room temperature

Solubility

Insoluble in water, soluble in organic solvents

Uses

Research and development of organic electronic materials (e.g. organic light-emitting diodes and organic photovoltaics), building block for synthesis of new molecules in pharmaceutical and chemical industries

Safety Precautions

Combustible, may cause skin and eye irritation upon contact

InChI:InChI=1/C16H14/c1-11-3-7-15-13(9-11)5-6-14-10-12(2)4-8-16(14)15/h3-10H,1-2H3

Upstream product

• 2941-83-5 2,7-dimethyl-9,10-dihydrophenanthrene 
• 71871-10-8 2.2'-Bis(chlormethyl)-4.4'-dimethylbiphenyl 
• 698376-80-6 2,7-dimethyl-9-phenanthrol 
• 776-35-2 9,10-dihydrophenanthrene 
• 43012-24-4 2,7-bis(bromomethyl)-9,10-dihydrophenanthrene 
• 19399-61-2 2,7-Bis-chlormethyl-9,10-dihydro-phenanthren 

Downstream Products

• 199807-75-5 2,7-Bis-[(Z)-2-(4-bromo-phenyl)-vinyl]-phenanthrene 

Relevant articles and documents

Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho and remote metalation - Suzuki-Miyaura cross coupling strategy

Using a combined directed ortho metalation (DoM) - Suzuki-Miyaura cross coupling - directed remote metalation (DreM) approach, the alkylphenanthrenes (APs) 1-methyl- (5a), 1,7-dimethyl- (5b), 2,7-dimethyl- (Sc), 7-ethyl-1-methyl- (15), and 7-tert-butyl-1-methylphenanthrenes (27) have been synthesized in four to seven steps and 21%-36% overall yields. In contrast to classical protocols, this method, which may be scaled to gram quantities, provides single isomers of APs in high purity of value as analytical standards for environmental studies. Aminocarbonylation of triflates to N,N-diethylbenzamides (9 → 10) and anionic Fries rearrangement (23 → 24) provide other potential links to DoM chemistry.

Electron transfer in bis-porphyrin donor-acceptor compounds with polyphenylene spacers shows a weak distance dependence

A series of phenylene-bridged bis-porphyrin adducts have been synthesized, containing one, two, or three phenyl bridges. Complete synthetic details are provided. For studies of photochemical electron transfer, mixed metals wre incorporated, with zinc in one porphyrin macrocycle and FeIII (bis-imidazole) in the other macrocycle. When photoexcited, an electron is transferred from Zn to FeIII. The rate of this process drops only slowly with distance: kα exp(βr), with β = 0.4 A?-1. This dependence can be predicted by a simple theory which assumes that the drop does not reflect increased distance, but rather reflects the break in conjugation which occurs at each phenyl juncture due to the biphenyl twist angle of ca. 50°. Inefficient overlap in this angle results in a rate drop of ca. 6-fold per phenyl ring, in good agreement with the observed results.