2099-72-1

Usage

Molecular structure

Bicyclic compound with a nitrogen-containing ring

Functional groups

Amine (NH) and hydrochloride (HCl)

Physical state

Solid

Appearance

Colorless to white crystalline solid

Solubility

Soluble in water and polar organic solvents

Melting point

247-249°C

Boiling point

Decomposes before boiling

Density

1.1 g/cm3

Use as a catalyst

Organic synthesis, specifically in Michael additions, aldol condensations, and epoxide ring openings

Industrial applications

Production of polyurethane foams, epoxy resins, and other polymer materials

Biochemical and pharmaceutical applications

pH buffer

Reactivity

Facilitates various chemical reactions due to its unique catalytic properties

Safety

Handle with care, as it is an irritant and corrosive substance

Storage

Store in a cool, dry place, away from heat and moisture

Regulatory status

Listed as a chemical of commerce and subject to various regulations depending on the region

Environmental impact

Potentially harmful to aquatic life and should be disposed of properly

Synonyms

1,4-Diazabicyclo[2.2.2]octane, monohydrochloride, 1,4-Diazabicyclo[2.2.2]octane hydrochloride

Chemical classification

Heterocyclic compound, amine, and hydrochloride salt

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 13389-70-3 bis(4-methylphenyl)methyl chloride 
• 7525-23-7 4,4'-dimethoxydiphenylmethyl chloride 
• 6731-11-9 4-methoxybenzhydryl chloride 
• 7525-21-5 4-methoxy-4'-methylbenzhydryl chloride 
• 147000-89-3 N-tert-butyloxycarbonylsulfamoyl chloride 

Relevant academic research and scientific papers

N-(tert -butoxycarbonyl)- N -[(triethylenediammonium)sulfonyl]azanide: A convenient sulfamoylation reagent for alcohols

A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl] azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary ? tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.

Suppression of common-ion return by amines: A method to measure rates of fast SN1 reactions

(Chemical Equation Presented) Rate constants for solvolyses of benzhydryl chlorides, which take place on the 10 ms to minute time scale, have been determined in aqueous acetone and acetonitrile by conductometry, using conventional conductometers as well as stopped-flow techniques. Secondary and tertiary amines were used to suppress ion recombination (common-ion return) thus giving access to the ionization rate constants k1. The observed common-ion rate depressions can be rationalized by the correlation equation for electrophile-nucleophile combinations, log k(20 °C) = s(E + N), where electrophiles (here: carbocations) are characterized by the parameter Eand nucleophiles (here: chloride anions and solvents) are characterized by N and s. 2009 American Chemical Society.