95-12-5

Basic information

• Product Name: 5-Norbornene-2-methanol
• Synonyms: TIMTEC-BB SBB008580;2-(Hydroxymethyl)bicyclo(2.2.1)hept-5-ene;2-Hydroxymethyl-1-bicyclo[2.2.1]-5-ene;5-Hydroxymethyl-2-norbornene;5-Hydroxymethylbicyclo(2.2.1)hept-2-ene;Bicyclo[2.2.1]hept-5-en-2-ylmethanol;Cyclol;5-NORBORNENE-2-METHANOL, 98%, MIXTURE OF ENDO AND EXO
• CAS NO: 95-12-5
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18
• EINECS: 202-392-0
• Product Categories: Alkenes;Cyclic;Organic Building Blocks;Norbornene Derivatives
• Mol File: 95-12-5.mol

Chemical Properties

• Boiling Point: 97 °C20 mm Hg(lit.)
• Flash Point: 188 °F
• Appearance: /
• Density: 1.027 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.158mmHg at 25°C
• Refractive Index: n20/D 1.500(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.92±0.10(Predicted)
• CAS DataBase Reference: 5-Norbornene-2-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Norbornene-2-methanol(95-12-5)
• EPA Substance Registry System: 5-Norbornene-2-methanol(95-12-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37/39-45
• WGK Germany: 3
• Hazardous Substances Data: 95-12-5(Hazardous Substances Data)

Usage

Uses

Used in Polymer Industry:
5-Norbornene-2-methanol is used as a monomer for the modification of condensation and addition polymers for coatings. Its ability to react with other monomers and polymers allows for the creation of new materials with improved properties, such as enhanced durability and resistance to environmental factors.
Used in Chemical Synthesis:
5-Norbornene-2-methanol has been used in the preparation of complex organic compounds, such as 4-(norborn-2-ene-5-ylmethyleneoxy)-2,2′:6′,2′′-terpyridine and 5-[(3,5-di-t-butyl-4-hydroxy-benzoyl)oxy]methyl-2-norbornene (BHBN). These compounds have potential applications in various fields, including pharmaceuticals, materials science, and catalysis, due to their unique structures and properties.

InChI:InChI=1/C8H12O/c9-5-8-4-6-1-2-7(8)3-6/h1-2,6-9H,3-5H2/t6-,7+,8-/m1/s1

Upstream product

• 120-74-1 (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 120-74-1 endo-norbornenecarboxylic acid 
• 89156-14-9 Acrylic acid (1S,2R,4R)-1-benzenesulfonylmethyl-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 542-92-7 cyclopenta-1,3-diene 
• 96304-11-9 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(naphthalene-1-sulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 96304-12-0 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(naphthalene-2-sulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 96304-14-2 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(2,4,6-trimethyl-benzenesulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 96304-13-1 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(phenanthrene-9-sulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 85718-79-2 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,3R,4S)-3-(2,2-dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 159759-20-3 C₂₈H₃₆O₈ 
• 211758-35-9 bicyclo[2.2.1]hept-5-ene-2-methyl benzoate 
• 138752-03-1 (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate 
• 4835-96-5 (-)-menthyl acrylate 

Downstream Products

• 211758-35-9 bicyclo[2.2.1]hept-5-ene-2-methyl benzoate 
• 135560-60-0 ((1R,2R,4R,5S,6S)-6-Bromo-5-phenylselanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 135560-59-7 ((1S,2S,4S,5S,6S)-5-Bromo-6-phenylselanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 42070-73-5 Toluene-4-sulfonic acid (1S,2R,4S)-1-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 135560-61-1 ((1R,2R,4R,5S,6S)-6-Chloro-5-phenylsulfanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 135583-61-8 ((1S,2S,4S,5S,6S)-5-Chloro-6-phenylsulfanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 135560-47-3 (+/-)-exo-bicyclo[2.2.1]hept-5-en-2-ylmethyl benzoate 
• 149654-56-8 methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate 
• 149654-55-7 methyl (1R,2S,4S)-4-hydroxy-2-<(trityloxy)methyl>cyclopentaneacetate 
• 149654-60-4 5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine 
• 149654-61-5 N²-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O⁶-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine 
• 149551-00-8 (1R,4R,5S)-5-(<(tert-butyl)diphenylsilyloxy>methyl)bicyclo<2.2.1>heptan-2-one 
• 149551-02-0 (1R,4R,6R)-6-(<(tert-butyl)diphenylsilyloxy>methyl)bicyclo<2.2.1>heptan-2-one 
• 149551-01-9 (1R,4R,5S)-5-<(trityloxy)methyl>bicyclo<2.2.1>heptan-2-one 

Relevant articles and documents

Mannich Bases from Bicyclo[2.2.1]hept-5-en-2-ylmethanol, Secondary Amines and Formaldehyde

New Mannich bases were synthesized by reacting bicyclo[2.2.1]hept-5-en-2-ylmethanol with secondary amines and formaldehyde. Physicochemical characteristics, composition and structure of the synthesized compounds were determined by elemental analysis, IR,

Thermodynamics of Counterion Release Is Critical for Anion Exchange Membrane Conductivity

As the field of anion exchange membranes (AEMs) employs an increasing variety of cations, a critical understanding of cation properties must be obtained, especially as they relate to membrane ion conductivity. Here, to elucidate such properties, metal cation-based AEMs, featuring bis(norbornene) nickel, ruthenium, or cobalt complexes, were synthesized and characterized. In addition, isothermal titration calorimetry (ITC) was used to probe counterion exchange thermodynamics in order to understand previously reported differences in conductivity. The ion conductivity data reported here further demonstrated that nickel-complex cations had higher conductivity as compared to their ruthenium and cobalt counterparts. Surprisingly, bulk hydration number, ion concentration, ion exchange capacity, and activation energy were not sufficient to explain differences in conductivity, so the thermodynamics of metal cation-counterion association were explored using ITC. Specifically, for the nickel cation as compared to the other two metal-based cations, a larger thermodynamic driving force for chloride counterion release was observed, shown through a smaller ΔHtot for counterion exchange, which indicated weaker cation-counterion association. The use of ITC to study cation-counterion association was further exemplified by characterizing more traditional AEM cations, such as quaternary ammoniums and an imidazolium cation, which demonstrated small variances in their enthalpic response, but an overall ΔHtot similar to that of the nickel-based cation. The cation hydration, rather than its hydration shell or the bulk hydration of the membrane, likely played the key role in determining the strength of the initial cation-counterion pair. This report identifies for the first time how ITC can be used to experimentally determine thermodynamic quantities that are key parameters for understanding and predicting conductivity in AEMs.

Method for preparing single-configuration C-2-position-monosubstituted norbornene derivative

The invention discloses a method for preparing a single-configuration C-2-position-monosubstituted norbornene derivative. The method comprises the following steps of: firstly, preparing exo-isomer enriched exo-isomer mixed 5-norbornene-2-carboxylic ester by taking commercial exo-isomer/endoisomer mixed 5-norbornene-2-carboxylic acid and large-steric-hindrance monohydric alcohol as raw materials; separating 5-norbornene-2-carboxylate with a single configuration through common column chromatography separation or fractionation; and finally, preparing the C-2-position-monosubstituted norbornene derivative with the single configuration from the separated 5-norbornene-2-carboxylate with the single configuration. The raw materials used in the invention are easy to obtain, the preparation process is simple, and the C-2-position-monosubstituted norbornene derivative with high purity (greater than 98%) and single configuration can be obtained.

Fragment-Based Discovery of Pyrazolopyridones as JAK1 Inhibitors with Excellent Subtype Selectivity

Herein, we report the discovery of a series of JAK1-selective kinase inhibitors with high potency and excellent JAK family subtype selectivity. A fragment screening hit 1 with a pyrazolopyridone core and a JAK1 bias was selected as the starting point for our fragment-based lead generation efforts. A two-stage strategy was chosen with the dual aims of improving potency and JAK1 selectivity: Optimization of the lipophilic ribose pocket-targeting substituent was followed by the introduction of a variety of P-loop-targeting functional groups. Combining the best moieties from both stages of the optimization afforded compound 40, which showed excellent potency and selectivity. Metabolism studies in vitro and in vivo together with an in vitro safety evaluation suggest that 40 may be a viable lead compound for the development of highly subtype-selective JAK1 inhibitors.

Selective hydrogenation of unsaturated carbonyls by Ni-Fe-based alloy catalysts

Ni-Fe alloy catalysts prepared by a simple hydrothermal method and subsequent H2 treatment exhibited the greatest activity and selectivity for the hydrogenation of biomass-derived furfural to furfuryl alcohol among the examined second metals, such as Al, Ga, In, Co, and Ti. This work reveals that the alloying of Ni and Fe is a key factor in achieving highly selective hydrogenation of the CO moiety in unsaturated carbonyl substrates. We found that decreasing the temperature of H2 treatment (i.e. decreasing the crystallite size), e.g. Ni-Fe(2)HT-573 K (TOF = 952 h-1), increased the activity compared to that over Ni-Fe(2)HT-673 (TOF = 375 h-1) for furfural hydrogenation. This result suggests that a low-coordinated Ni-Fe alloy was imperative for the catalytic cycle. Moreover, the effect of the metal/support interface was critical; despite the high catalytic performance of Ni-Fe/TiO2, Ni-Fe/Al2O3, and Ni-Fe/CeO2, Ni-Fe supported on SiO2, taeniolite, and hydrotalcite catalysts were ineffective. Vibrational studies using FT-IR measurement confirmed that furfural was physically adsorbed on the surface of the Ni-Fe alloy catalyst via an η1(O) configuration. The synthetic scope of the Ni-Fe catalytic system was very broad; various types of unsaturated carbonyls, such as unsaturated aromatics, unconjugated aliphatics, and a large substituent, were selectively converted into the corresponding unsaturated alcohols.

Approach Matters: The Kinetics of Interfacial Inverse-Electron Demand Diels–Alder Reactions

Rapid and quantitative click functionalization of surfaces remains an interesting challenge in surface chemistry. In this regard, inverse electron demand Diels–Alder (IEDDA) reactions represent a promising metal-free candidate. Herein, we reveal quantitative surface functionalization within 15 min. Furthermore, we report the comprehensive effects of substrate stereochemistry, surrounding microenvironment and substrate order on the reaction kinetics as obtained by surface-bound mass spectrometry (DART-HRMS).

Photoreactive polymer and its preparation method

Provided are a photoreactive polymer that includes a multi-cyclicmulticyclic compound at as its main chain and a method of preparing the same. The photoreactive polymer exhibits excellent thermal stability since it includes a multi-cyclicmulticyclic compound having a high glass transition temperature at as its main chain. In addition, the photoreactive polymer has a relatively large vacancy so that a photoreactive group can move relatively freely in the main chain therein. As a result, a slow photoreaction rate, which is a disadvantage of a conventional polymer material used to form an alignment layer for a liquid crystal display device, can be overcome.

Exploring the Potential of Norbornene-Modified Mannosamine Derivatives for Metabolic Glycoengineering

Metabolic glycoengineering (MGE) allows the introduction of unnaturally modified carbohydrates into cellular glycans and their visualization through bioorthogonal ligation. Alkenes, for example, have been used as reporters that can react through inverse-electron-demand Diels–Alder cycloaddition with tetrazines. Earlier, norbornenes were shown to be suitable dienophiles; however, they had not previously been applied for MGE. We synthesized two norbornene-modified mannosamine derivatives that differ in the stereochemistry at the norbornene (exo/endo linkage). Kinetic investigations revealed that the exo derivative reacts more than twice as rapidly as the endo derivative. Through derivatization with 1,2-diamino-4,5-methylenedioxybenzene (DMB) we confirmed that both derivatives are accepted by cells and incorporated after conversion to a sialic acid. In further MGE experiments the incorporated sugars were ligated to a fluorophore and visualized through confocal fluorescence microscopy and flow cytometry.

Structure-Based Design of β5c Selective Inhibitors of Human Constitutive Proteasomes

This work reports the development of highly potent and selective inhibitors of the β5c catalytic activity of human constitutive proteasomes. The work describes the design principles, large hydrophobic P3 residue and small hydrophobic P1 residue, that led to the synthesis of a panel of peptide epoxyketones; their evaluation and the selection of the most promising compounds for further analyses. Structure-activity relationships detail how in a logical order the β1c/i, β2c/i, and β5i activities became resistant to inhibition as compounds were diversified stepwise. The most effective compounds were obtained as a mixture of cis- and trans-biscyclohexyl isomers, and enantioselective synthesis resolved this issue. Studies on yeast proteasome structures complexed with some of the compounds provide a rationale for the potency and specificity. Substitution of the N-terminus in the most potent compound for a more soluble equivalent led to a cell-permeable molecule that selectively and efficiently blocks β5c in cells expressing both constitutive proteasomes and immunoproteasomes.

High Tg sulfonated insertion polynorbornene ionomers prepared by catalytic insertion polymerization

A simple method to synthesize high Tg sulfonated ionomers based on catalytic insertion polynorbornene is reported. Copolymers of norbornene and 5-methyl alcohol norbornene (endo:exo = 82:18) or 5-methyl bromide norbornene (endo:exo = 86:14) as well as terpolymers of norbornene, 5-methyl alcohol norbornene and 5-hexyl norbornene are prepared using a cationic Pd catalyst. These copolymers are then thioacetylated. Using hydrogen peroxide as oxidant, a sulfonated polynorbornene is obtained. Ionomers containing as much as 30 mol% SO3H and with Tgs above 200 °C are obtained in a four-step procedure of overall 40-75% yield.