Alkanolamine

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In organic chemistry, alkanolamines (amino alcohols) are organic compounds that contain both hydroxyl (−OH) and amino (−NH2, −NHR, and −NR2) functional groups on an alkane backbone. Most alkanolamines are colorless. [1]

Contents

1-Aminoalcohols

1-Aminoalcohols are better known as hemiaminals. Methanolamine is the simplest member.

2-Aminoalcohols

2-Aminoalcohols are an important class of organic compounds that are often generated by the reaction of amines with epoxides:

C2H4O + R−NH2 → RNHC2H4OH

Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases. [2]

Hydrogenation or hydride reduction of amino acids gives the corresponding 2-aminoalcohols. Examples include prolinol (from proline), valinol (from valine), tyrosinol (from tyrosine).

Key members: ethanolamine, dimethylethanolamine, N-methylethanolamine, Aminomethyl propanol. Two popular drugs, often called alkanolamine beta blockers, are members of this structural class: propranolol, pindolol. Isoetarine is yet another medicinally useful derivative of ethanolamine.[ citation needed ]

1,3-, 1,4-, and 1,5-amino alcohols

Natural products

Most proteins and peptides contain both alcohols and amino groups. Two amino acids are alkanolamines, formally speaking: serine and hydroxyproline.

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Transamination</span> Chemical reaction that transfers an amino group to a ketoacid

Transamination is a chemical reaction that transfers an amino group to a ketoacid to form new amino acids. This pathway is responsible for the deamination of most amino acids. This is one of the major degradation pathways which convert essential amino acids to non-essential amino acids.

<span class="mw-page-title-main">Ethanolamine</span> Chemical compound

Ethanolamine is a naturally occurring organic chemical compound with the formula HOCH
2
CH
2
NH
2
or C
2
H
7
NO
. The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.

<i>N</i>-Methylethanolamine Chemical compound

N-Methylethanolamine is an alkanolamine with the formula CH3NHCH2CH2OH. It is flammable, corrosive, colorless, viscous liquid. It is an intermediate in the biosynthesis of choline.

In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl functional group by formaldehyde and a primary or secondary amine or ammonia. The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich.

<span class="mw-page-title-main">Dimethylethanolamine</span> Chemical compound

Dimethylethanolamine is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care products for improving skin tone and also taken orally as a nootropic. It is prepared by the ethoxylation of dimethylamine.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Ethylenediamine</span> Chemical compound

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

<span class="mw-page-title-main">Propanolamines</span>

Propanolamines are a class of chemical compounds, many of which are pharmaceutical drugs. They are amino alcohols that are derivatives of 1-amino-2-propanol.

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

Amine alkylation (amino-dehalogenation) is a type of organic reaction between an alkyl halide and ammonia or an amine. The reaction is called nucleophilic aliphatic substitution, and the reaction product is a higher substituted amine. The method is widely used in the laboratory, but less so industrially, where alcohols are often preferred alkylating agents.

<span class="mw-page-title-main">Oxazoline</span> Chemical compound

Oxazoline is a five-membered heterocyclic organic compound with the formula C3H5NO. It is the parent of a family of compounds called oxazolines, which contain non-hydrogenic substituents on carbon and/or nitrogen. Oxazolines are the unsaturated analogues of oxazolidines, and they are isomeric with isoxazolines, where the N and O are directly bonded. Two isomers of oxazoline are known, depending on the location of the double bond.

<span class="mw-page-title-main">Imidic acid</span> Class of organic compounds

In chemistry, an imidic acid is any molecule that contains the -C(=NH)-OH functional group. It is the tautomer of an amide and the isomer of an oxime.

<span class="mw-page-title-main">Valinol</span> Chemical compound

Valinol is an organic compound named after, and commonly produced from, the amino acid valine. The compound is chiral and is produced almost exclusively as the S‑isomer, due to the abundant supply of S-valine. It is part of a broader class of amino alcohols.

<span class="mw-page-title-main">1-Aminoethanol</span> Chemical compound

1-Aminoethanol is an organic compound with the formula CH3CH(NH2)OH. It is classified as an alkanolamine. Specifically, it is a structural isomer of 2-aminoethanol (ethanolamine). These two compounds differ in the position of the amino group. Since the central carbon atom in 1-aminoethanol has four different substituents, the compound has two stereoisomers. Unlike 2-aminoethanol, which is of considerable importance in commerce, 1-aminoethanol is not encountered as a pure material and is mainly of theoretical interest.

In organic chemistry, propanolamine can describe any of the following parent compounds:

<span class="mw-page-title-main">3-Amino-1-propanol</span> Chemical compound

3-Amino-1-propanol is the organic compound with the formula HOCH2CH2CH2NH2. A colorless liquid, the compound is one of the simplest aminopropanols.

Alaninol is the organic compound with the formula CH3CH(NH2)CH2OH. A colorless solid, the compound is classified as an amino alcohol. It can be generated by converting the carboxylic group of alanine to an alcohol with a strong reducing agent such as lithium aluminium hydride. The compound is chiral, and as is normal for chiral compounds, the physical properties of the racemate differ somewhat from those of the enantiomers. It is a precursor to numerous chiral ligands used in asymmetric catalysis. The compound is an example of a 1,2-ethanolamine.

<span class="mw-page-title-main">Tyrosinol</span> Chemical compound

Tyrosinol is an organic compound with the formula HOC6H4CH2CH(NH2)CH2OH. A colorless or white solid, it is produced by the reduction of the amino acid tyrosine with borane dimethylsulfide. The compound, which is chiral, is an example of a 1,2-ethanolamine as well as a phenethylamine.

References

  1. Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN   978-0-471-72091-1
  2. Martin Ernst; Johann-Peter Melder; Franz Ingo Berger; Christian Koch (2022). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.pub2. ISBN   978-3527306732.