27063-48-5

Basic information

• Product Name: 5-NORBORNENE-2-CARBONYL CHLORIDE
• Synonyms: BICYCLO[2.2.1]HEPT-5-ENE-2-CARBONYL CHLORIDE;5-NORBORNENE-2-CARBONYL CHLORIDE;TIMTEC-BB SBB010381;5-NORBORNENE-2-CARBONYL CHLORIDE 95%;Bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride (9CI);5-NORBORNENE-2-CARBONYL CHLORIDE, 96-98%;Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid chloride;Bicyclo[2.2.1]hepta-2-ene-5-carboxylic acid chloride
• CAS NO: 27063-48-5
• Molecular Formula: C₈H₉ClO
• Molecular Weight: 156.61
• EINECS: 248-200-9
• Product Categories: ACIDHALIDE;Norbornene Derivatives
• Mol File: 27063-48-5.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 201.1 °C at 760 mmHg
• Flash Point: 97.2 °C
• Appearance: /
• Density: 1.256 g/cm³
• Vapor Pressure: 0.314mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: 5-NORBORNENE-2-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NORBORNENE-2-CARBONYL CHLORIDE(27063-48-5)
• EPA Substance Registry System: 5-NORBORNENE-2-CARBONYL CHLORIDE(27063-48-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 27063-48-5(Hazardous Substances Data)

Usage

General Description

5-Norbornene-2-carbonyl chloride is a highly reactive chemical compound commonly used in organic chemistry for reactions including substitutions, additions, and eliminations, due to its functionality as a carboxylic acid chloride. This role as an acid chloride allows it to react with nucleophiles such as alcohol and amines, creating functional group conversions. Distilled in a high vacuum, it appears as a liquid that is very sensitive to moisture and should, therefore, be stored in sealed containers. Despite its usefulness, 5-Norbornene-2-carbonyl chloride poses health risks and is deemed harmful if swallowed or if in contact with the skin or eyes. It is also toxic to aquatic life and may cause long-term adverse effects in the aquatic environment.

InChI:InChI=1/C8H9ClO/c9-8(10)7-4-5-1-2-6(7)3-5/h1-2,5-7H,3-4H2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 814-68-6 acryloyl chloride 
• 120-74-1 5-carboxybicyclo<2.2.1>hept-2-ene 
• 934-30-5 5-norbornene-endo-2-carboxylic acid 
• 10138-32-6 bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid ethyl ester 
• 79-10-7 acrylic acid 
• 157874-64-1 bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-[2-(2-methoxyethoxy)ethoxy]ethyl ester 
• 862072-76-2 bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-[2-(2-{2-[2-(2-methoxyethoxy)ethoxy]acetoxy}ethoxy)ethoxy]ethyl ester 
• 934-30-5 exo-5-norbornene-2-carboxylic acid 

Downstream Products

• 117869-43-9 N-(endo-bicyclo<2.2.1>hept-5-en-2-carbonyl)-L-phenylalanine 
• 51757-85-8 bicyclo[2.2.1]hept-5-ene-2-carboxamide 
• 95-17-0 bicyclo[2.2.1]hept-5-ene-2-carboxamide 
• 18530-45-5 endo-5-Aminobicyclo[2.2.1]hept-2-ene 
• 1338723-24-2 C₂₂H₂₈N₂O₅ 
• 6056-35-5 endo/exo-bicyclo[2.2.1]hept-5-en-2-yl(phenyl)methanone 
• 939-23-1 p-phenylpyridine 
• 1352656-12-2 6-(N,N-dimethylamino)hexyl bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 69365-80-6 5-exo-Ureidoformyl-norbornen-(2) 
• 51757-84-7 (+/-)-2-methyl-norborn-5-ene-2endo-carboxylic acid amide 

Relevant articles and documents

Discotic liquid crystals of transition metal complexes 58: Novel phthalocyanine-based mesogenic monomers and polymers exhibiting spontaneous homeotropic alignment and helical tetragonal columnar structure

Two synthetizations of a novel series of phthalocyanine-based discotic liquid crystals substituted by a polymerizable group, acryloyl group or a norbornene group: 2-(12-acryloyloxydodecyloxy)-3-methoxy-9,10,16,17,23,24-hexakis (3,4-dialkoxyphenoxy)phthalocyaninato copper(II) [abbreviated as (n,12)PcCu(OCH3)(Acryloyl) (7: e (n = 10), f (n = 12), g (n = 14))] and 2-(12-norborn-2-ene carbonyloxydodecyloxy)-3-methoxy-9,10,16,17,23,24-hexakis(3,4-dialkoxyphenoxy)-phthalocyaninato copper(II): [abbreviated as (n, 12)PcCu(OCH3)(Norb) (9e, f, g)]. Their liquid crystalline properties and homeotropic alignment were investigated using a polarizing microscope, a differential scanning calorimetry (DSC), and a temperature-variable X-ray diffractometer. As a result, each of the derivatives gave a Coltet mesophase in the higher temperature region, displaying perfect homeotropic alignment between the two glass plates. In order to obtain the thin film while keeping their homeotropic alignment at room temperature, attempts to polymerize the monomers, 7 and 9, in the Coltet phase showed homeotropic alignment. The polymerization of the acryloyl-substituted monomers (7) was not successful in any of the methods, whereas the polymerization of norbornene-substituted monomers (9) was quite successful by ring-opening metathesis polymerization with a Grubbs catalyst to obtain the novel polymers, poly-(n, 12)PcCu(OCH3)(Norb) (10e, f, g). Each of the polymers (10) were found to show a perfect homeotropic alignment from room temperature to ca. 200°C of the decomposition temperature. Moreover, it was also revealed from temperature-variable small-angle X-ray diffraction studies that each of the polymers 10 showed a helical Coltet (helical tetragonal columnar) structure. The helical Coltet phase structure may be able for use in organic electroluminescent devices and solar cells in the future.

Synthesis of Bicyclic Isocyanates and Bioisosteric 1,3-Disubstituted Ureas as Soluble Epoxide Hydrolase Inhibitors

(1S)-1-Isocyanato-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one and 2-isocyanatobicyclo[2.2.1]-hept-5-ene were prepared by the Curtius rearragement reaction from the corresponding carboxylic acids. The synthesized isocyanates were used to synthesize, in high yields of 74–93%, bioisosteric 1,3-disubstituted ureas as potential human soluble epoxide hydrolase inhibitors.

Dye functionalized-ROMP based terpolymers for the use as a light up-converting material: Via triplet-triplet annihilation

In this paper we introduce and compare different terpolymers comprising covalently attached sensitizer and emitter chromophores for the use as a light up-converting material via triplet-triplet annihilation (TTA). Using the advantages of ring opening metathesis polymerisation it was possible to prepare five different polymer architectures in order to investigate the influence of polymer architecture and chromophore arrangement on the photon up-conversion behaviour. First, two new monomers containing the chromophores have been synthesized and characterized in regard to their photophysical characteristics suitable for triplet-triplet annihilation dye pair. For this purpose, a derivative of Pt(ii) meso-tetraphenyltetra(tert-butyl)benzoporphyrin as sensitizer and a perylenediester as emitter were attached to norbornene moieties via ester linkages. Polymerisations of these monomeric chromophores were performed in combination with dimethyl 5-norbornene-2,3-dicarboxylate as matrix monomer. Depending on the location of the dye molecules on the polymer chain, large differences in the TTA efficiency were observed. The best quantum yields have been achieved with a completely statistically distributed terpolymer showing an up-conversion quantum yield of up to 3% in solution.