37608-29-0

Basic information

• Product Name: 1,1-dichloro-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene
• Synonyms: 1H-Cyclopropa(l)phenanthrene, 1,1-dichloro-1a,9b-dihydro-
• CAS NO: 37608-29-0
• Molecular Formula: C₁₅H₁₀Cl₂
• Molecular Weight: 261.1459
• Mol File: 37608-29-0.mol

Chemical Properties

• Boiling Point: 399.8°C at 760 mmHg
• Flash Point: 200.3°C
• Density: 1.4g/cm³
• Vapor Pressure: 3.07E-06mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 1,1-dichloro-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-dichloro-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene(37608-29-0)
• EPA Substance Registry System: 1,1-dichloro-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene(37608-29-0)

Safety Data

• Hazardous Substances Data: 37608-29-0(Hazardous Substances Data)

Usage

Class

1,1'-dichloro-1a,9b-dihydro-1H-cyclopropa[l]phenanthrenes

Explanation

1,1-dichloro-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene belongs to a specific class of organic compounds, which are characterized by their unique chemical structure and properties.

Explanation

The compound is in a liquid state at room temperature and is colorless, meaning it does not have any visible color.

Explanation

The compound has a distinct smell, which is similar to that of chloroform, a well-known solvent.

Explanation

It is primarily used as a solvent in various chemical processes and is also utilized in the production of other chemicals.

Explanation

Due to its persistence and potential toxic effects on certain organisms, it is considered a potential environmental contaminant.

Explanation

The compound's structure contains a cyclopropane ring, which is a three-membered carbon ring, and multiple chlorine (chloro) substituents attached to the carbon atoms.

Explanation

Given its potential effects on human health and the environment, further research is necessary to understand its impact and develop appropriate regulations or mitigation strategies.

Physical state

Colorless liquid

Odor

Strong chloroform-like

Uses

Solvent and chemical production

Environmental concern

Potential contaminant

Chemical structure

Cyclopropane ring and multiple chloro substituents

Importance

Further study on human health and environment

Upstream product

• 67-66-3 chloroform 
• 85-01-8 phenanthrene 
• 56-23-5 tetrachloromethane 

Downstream Products

• 1605-72-7 dichlorocarbene 
• 85-01-8 phenanthrene 
• 4444-43-3 2,3;4,5-Dibenztropon 
• 53137-51-2 6,7-dihydro-5H-dibenzocyclohepten-5-one 
• 24471-57-6 9-bromomethylphenantrene 
• 883-20-5 9-methylphenanthrene 
• 126191-47-7 pyridinium dichloromethyl ylide 

Relevant articles and documents

Flow-vacuum pyrolysis of polycyclic compounds. 131. Pyrolysis of 5H-6,7-dihydrodibenzo[a,c]cycloheptene

Flow-vacuum pyrolysis of title hydrocarbon affords at temperatures above 900°C (1 mm Hg) mixtures of phenanthrene (main product) and 9-methylphenanthrene and fluorene (minor products). The suggested reaction mechanism includes two parallel routes, one generating phenanthrene and 9-methylphenanthrene via radical transformations and the other producing fluorene via a concerted [2 + 2 + 2] reaction.

Inversion Barriers of ortho,ortho'-Bridged Biphenyls

The syntheses and spectroscopic properties of the ortho,ortho'-bridged biphenyls 2-19 are described.In the case of 5, 15, and 16 the inversion barrier is determined from the temperature dependence of the NMR spectra (lineshape analysis), in the case of 12, 13, and 14 from the temperature of coalescence, and in the case of 2a, 3b, 7, 17, 18, and 19 from the rate of racemization of the optically active compounds.The experimental inversion barriers, including data from the literature, are compared with those calculated using the extended force field (MM2erw).Theconformational behavior of the title systems is significantly affected upon transformation into the corresponding dianion salts.The relevant energy terms are discussed.

Biological evaluation of novel cyclopropyl analogues of stilbene, stilbenediol, and phenanthrene for estrogenic and antiestrogenic activity

The triphenylethylene-type antiestrogens, such as tamoxifen, are known to be useful in the treatment of estrogen-dependent tumors. However, these compounds display mixed estrogen agonist/antagonist activity which may limit their therapeutic effectiveness. This problem of mixed activity led to the synthesis and identification of a cyclopropyl derivative of cis-stilbene which we have named Analog I. This compound (1,1-dichloro-cis-2,3-diphenylcyclopropane) displayed only antiestrogenic activity in the mouse. The present study was designed to evaluate cyclopropyl derivatives of Analog II for estrogenic and antiestrogenic activity in the rate using the standard 3-d uterotropic assay and the uterine cytoplasmic estrogen receptor assay. Five compounds (B-F) which are cyclopropyl derivatives of stilbene, stilbenediol, and phenanthrene were evaluated in this study. Three of the compounds (B-D) displayed neither estrogenic nor antiestrogenic activity in the rat. The relative estrogenic activities of E and F were 11.3 and 1.5%, respectively, of diethylstilbestrol in the uterotropic assay, and 39 and 6.2%, respectively, of estradiol in the estrogen receptor assay. Neither E nor F was found to display antiestrogenic activity in the rat. The results indicate that the relative estrogenic and receptor binding activities of E and F are similar to those previously observed in the mouse, while B-D appear to be inactive in both species.

Studies in the Cycloproparene Series: Halogenation and Dehydrohalogenation of Some 1a,9b-Dihydrocyclopropaphenanthrenes

Dehydrohalogenation of (1α,1aβ,9aβ)-1-chloro-1a,9b-dihydrocyclopropaphenanthrene (4b) yields products by way of the corresponding dibenzobicyclohepta-2,4,6-triene (5b) whilst under solvolytic conditions the 7-t-butoxydibenzocyclohepta-1,3,5-triene (11b) is formed by cyclopropyl-allyl ring expansion.When subjected to bromination the cyclopropaphenanthrenes (4a,c) yield halophenanthrenes (14a) and (15c) by cleavage of an external bond of the cyclopropane ring.

Generation of Bicycloheptatrienes

Derivatives of bicycloheptatriene have been generated in solution by the base-induced dehydrochlorination of gem-dichlorocyclopropanes.Reaction of 7,7-dichlorodibenzobicycloheptane with potassium tert-butoxide in tetrahydrofuran at 0 deg C gives mainly products derived from solvent incorporation by carbene insertion.Evidence that the carbene results from rearrangement of the bicycloheptatriene derives from the successful interception of the bicycloheptatriene with nucleophile (MeS-). endo-7-Chlorodibenzobicycloheptane failed to reactwith potassium tert-butoxide in tetrahydrofuran.Generation of benzobicycloheptatrienes was also accomplished via the base-induced dehydrochlorination of gem-dichlorocyclopropanes. 1-Methylbenzobicycloheptatriene gives products derived from multiple carbene-carbene rearrangements.In contrast, nonannelated methylbicycloheptatrienes generated by the dehydrochlorination route give only carbene-derived products resulting from the initially produced bicycloheptatriene.