19916-65-5

Basic information

• Product Name: 2,2-dichlorobicyclo[2.2.1]heptane
• Synonyms: 2,2-dichlorobicyclo[2.2.1]heptane;Bicyclo[2.2.1]heptane, 2,2-dichloro- (9CI)
• CAS NO: 19916-65-5
• Molecular Formula: C₇H₁₀Cl₂
• Molecular Weight: 165.0603
• EINECS: 243-425-9
• Product Categories: CYCLOPENTANE
• Mol File: 19916-65-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 208.2°Cat760mmHg
• Flash Point: 81.8°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 0.312mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: 2,2-dichlorobicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dichlorobicyclo[2.2.1]heptane(19916-65-5)
• EPA Substance Registry System: 2,2-dichlorobicyclo[2.2.1]heptane(19916-65-5)

Safety Data

• Hazardous Substances Data: 19916-65-5(Hazardous Substances Data)

Usage

Structure

Bicyclic organic compound It is composed of two fused cyclopropane rings, which are three-carbon rings.

Physical state

Colorless liquid at room temperature It is a liquid and has no color when it is not heated or cooled.

Solubility

Insoluble in water 2,2-dichlorobicyclo[2.2.1]heptane does not dissolve well in water.

Uses

Synthetic intermediate It is primarily used as a synthetic intermediate in the production of drugs and other organic chemicals.

Applications

Research and development 2,2-dichlorobicyclo[2.2.1]heptane is used in research and development in organic chemistry.

Role

Building block in synthesis It serves as a building block in the synthesis of complex organic molecules.

Importance

Creation of pharmaceuticals and agrochemicals It plays a crucial role in the production of various pharmaceuticals and agrochemicals.

Additional applications

Material science 2,2-dichlorobicyclo[2.2.1]heptane is also used in the field of material science for the synthesis of polymers and other materials.

InChI:InChI=1/C7H10Cl2/c8-7(9)4-5-1-2-6(7)3-5/h5-6H,1-4H2

Upstream product

• 497-38-1 Norbornan-2-on 
• 497-36-9 (+/-)-endo-2-norborneol 
• 497-38-1 2-norbornanone 

Downstream Products

• 765-67-3 1-chlorobicyclo[2.2.1]heptane 
• 765-67-3 1-Norbornyl-chlorid 
• 87774-53-6 1,3-dichlorobicyclo<2.2.1>heptane 
• 17294-82-5 4-chlorobicyclo<2.2.1>heptan-2-one tosylhydrazone 
• 83053-77-4 p-bromobenzenesulphonamide bicyclo<4.1.0>hep-2-en-1-ylmethanamine 
• 83053-76-3 bicyclo<4.1.0>hep-2-en-1-ylmethanamine 
• 87785-63-5 1,2-dichlorobicyclo<2.2.1>heptane 

Relevant articles and documents

Single Electron Transfer in Nucleophilic Aliphatic Substitution. Evidence for Single Electron Transfer in the Reactions of 1-Halonorbornanes with Various Nucleophiles

A series of 1-halonorbornanes was used as a model system in reactions with several nucleophiles in order to determine the involvement of single electron transfer (SET) in nucleophilic aliphatic substitution in the absence of light.The 1-halonorbornanes were allowed to react with Me3Sn(1-), Ph2P(1-), AlH4(1-), N(iPr)2(1-), SPh(1-), and the 2-nitropropyl anion in the ether solvents at room temperature to 0 deg C.The results of product analyses, the use of radical and radical anion trapping reagents, the results of deuterium labeling studies, and the nucleofugality effect support a SET mechanism for the reactions involving 1-iodonorbornane.Convincing evidence that reduction of hindered alkyl iodides with LiAlH4 takes place by a SET pathway rather than by an impurity-initiated halogen atom radical chain process followed by an SN2 pathway, is presented.

Acid-catalyzed cleavage of 4-halonortricyclanes. Evidence that the 2-norbornyl cation is an unsymmetrical species

Nortricyclanes 4a, 4c, 4d, and 4e were prepared and ring opened in D2SO4/CD3COOD.We found that the ratios of endo/exo deuterium at C(6) were 1.09+/-0.02, 1.30+/-0.03, 1.40+/-0.04, and 1.45+/-0.05 for cleavage of 4a, 4c, 4d, and 4e, respectively.The amount of 6,2-hydride shift decreased from 14.3+/-1.0percent in the case of nortricyclane (4a) to 6.0+/-1.1percent, 6.4+/-0.5percent, and 8.1+/-0.7percent for 4c, 4d, and 4e, respectively.Although four distinct mechanisms involving either nonclassical or rapidly-equilibrating cations are possible, cleavage most probably occurs to generate 6,2-unsymmetrically-bridged norbornyl cations.