124-68-5 Usage
Chemical Properties
white crystals or viscous liquid
Uses
Different sources of media describe the Uses of 124-68-5 differently. You can refer to the following data:
1. 2-Amino-2-methylpropanol is used for the preparation of buffer solutions, suitable for the determination of alkaline phosphatase.
2. 2-Amino-2-methyl-1-propanol is also used in ATR-FTIR spectroscopic investigation of the carbon monoxide absorption characteristics of a series of heterocyclic diamines.
3. 2-Amino-2-methyl-1-propanol has been used as an component in enzyme assay for screening the alkaline phosphatase activity in sarcoma osteogenic (SaOS-2) cells..
General Description
A clear light colored liquid. Insoluble in water and about the same density as water. Flash point 172°F. Used to make other chemicals.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2-Amino-2-methyl-1-propanol is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Hazard
Toxic by ingestion.
Health Hazard
Causes severe irritation. Inhalation may be fatal as a result of spasm, inflammation, and edema of laryns and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting.
Fire Hazard
Special Hazards of Combustion Products: Emits toxic fumes during fire conditions.
Biochem/physiol Actions
2-Amino-2-methyl-1-propanol is a substituted aliphatic alcohol and is used majorly as a pH balancer in cosmetic formulations. It has phototoxic effect as it can interact and penetrate above the sebum layer. However, it is not carcinogenic.
Safety Profile
On March 21, 2014, the Environmental Protection Agency (EPA) issued a direct final rule with a parallel proposal identifying 2-Amino-2-methyl-1-propanol (also known as AMP) as a chemical compound that it will no longer be regulated as a volatile organic compound (VOC) under the Clean Air Act. This will remove AMP from regulatory requirements related to controlling VOC emissions in order to meet the national ambient air quality standards (NAAQS) for ozone. EPA will add AMP to the list of negligibly reactive compounds in EPA’s regulatory definition of VOC.AMP is used for pigment dispersion in water-based coatings such as house paints. Excluding this compound from the regulatory definition of VOC, facilitates access to AMP for manufacturers of water-based coatings in order to meet VOCs limits without impairing the performance of their products or using other more toxic chemicals.
Synthesis
The synthesis of?2-Amino-2-methyl-1-propanol is as follows:
In a 1L three-neck flask with mechanical stirring, first add 200ml of water, add a few drops of dilute sulfuric acid to make it slightly acidic (pH=3.5-4), then heat to 40-50, and start adding 99.0 at the same time. 2,2-Dimethylaziridine and 400ml dilute sulfuric acid aqueous solution, keep the temperature and slightly acidic condition, drop 2,2-dimethylaziridine, then continue to react at this temperature 1h, then under reduced pressure distillation to remove 80% of the water, add 500ml ethanol to the obtained system, neutralize with 30% sodium hydroxide to pH=9.5-10, filter and remove the salt, the obtained filtrate is distilled out of ethanol under normal pressure , And then distilled under reduced pressure to obtain crude 2-amino-2-methyl-1-propanol. This crude product is then rectified to obtain 112.9g 2-amino-2-methyl-1-propanol refined product with a yield of about 91.0%, chromatographic purity is about 99.4%.
Purification Methods
Purify it by distilling and fractional freezing. The hydrochloride has m 204o-206o. [Beilstein 4 III 783, 4 IV 1740.]
Check Digit Verification of cas no
The CAS Registry Mumber 124-68-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 4 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 124-68:
(5*1)+(4*2)+(3*4)+(2*6)+(1*8)=45
45 % 10 = 5
So 124-68-5 is a valid CAS Registry Number.
124-68-5Relevant articles and documents
A simple total synthesis of naturally occurring hydroxy-amino acids by enzymatic kinetic resolution
Lu,Miet,Kunesch,Poisson
, p. 893 - 902 (1993)
Both optically pure enantiomers of GABOB and isoserine were obtained by enzymatic kinetic resolution of acetylated precursors in three or four steps. The key intermediates were cyanohydrins available from simple aldehydes. This procedure can be applied to other unusual hydroxy amino acids widely distributed in biologically important peptides.
Synthesis and characterization of lanthanide complexes prepared with 2-((E)-(1-hydroxy-2-methylpropan-2-ylimino)methyl)-6-methoxyphenol
Abrahams, Abubak'r,Madanhire, Tatenda,Hosten, Eric,Betz, Richard
, p. 1994 - 2014 (2017)
Rare-earth complexes of the general formula [Ln(H2L1)2(NO3)3] [Ln?=?Gd (1), Ho (2) or Nd (3)] were prepared from an o-vanillin derived Schiff base ligand, 2-((E)-(1-hydroxy-2-methylpropan-2-ylimino)methyl)-6-methoxyphenol (H2L1). The single-crystal X-ray diffraction studies and SHAPE analyses of the Gd(III) and Ho(III) complexes show that the complexes are ten-coordinate and exhibit distorted tetradecahedron geometries. The phenolate oxygen-bridged dinuclear complex, [Ce2(H2L1)(ovan)3(NO3)3] (4, ovan?=?monodeprotonated o-vanillin), was obtained from the reaction of Ce(NO3)3?6H2O with H2L1. X-ray analysis revealed that hydrolysis of H2L1 occurred to yield o-vanillin, which bridged two cerium atoms with the Ce?Ce distance equal to 3.8232(6) ?. The Ce(III) ions are both ten-coordinate, but have different coordination environments, showing tetradecahedron and staggered dodecahedron geometries, respectively. With proton migration occurring from the phenol group to the imine function, complexation of the lanthanides to the ligand gives the Schiff base a zwitterionic phenoxo-iminium form.
PROCESS FOR PREPARATION OF AMINO ALCOHOLS
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Paragraph 0050; 0051, (2020/01/31)
A process for the preparation of amino alcohols includes condensing a compound of Formula (II), a stereoisomer, a tautomer, or a salt thereof with a compound of Formula (IlIa) or Formula (Illb), a stereoisomer, a tautomer, or a salt thereof to form a condensation product; hydroxylating or acyloxylating the condensation product in the presence of an oxidant to obtain a hydroxylation or acyloxylation product; and subjecting the hydroxylation or acyloxylation product to one or more subsequent reactions comprising a hydrolysis reaction, alcohol deprotection, an amino lysis reaction, or a combination of two or more thereof to obtain an amino alcohol of Formula (I).
Palladium-Catalyzed Oxidation of β-C(sp3)-H Bonds of Primary Alkylamines through a Rare Four-Membered Palladacycle Intermediate
Bunescu, Ala,Ernst, Martin,Hartwig, John F.,Qiu, Yehao,Su, Bo,Zuend, Stephan J.
supporting information, p. 7912 - 7919 (2020/05/22)
Site-selective functionalizations of C-H bonds are often achieved with a directing group that leads to five- or six-membered metallacyclic intermediates. Analogous reactions that occur through four-membered metallacycles are rare. We report a challenging palladium-catalyzed oxidation of primary C-H bonds β to nitrogen in an imine of an aliphatic amine, a process that occurs through a four-membered palladacyclc intermediate. The success of the reaction relies on the identification, by H/D exchange, of a simple directing group (salicylaldehyde) capable of inducing the formation of this small ring. To gain insight into the steps of the catalytic cycle of this unusual oxidation reaction, a series of mechanistic experiments and density functional theory (DFT) calculations were conducted. The experimental studies showed that cleavage of the C-H bond is rate-limiting and formation of the strained four-membered palladacycle is thermodynamically uphill. DFT calculations corroborated these conclusions and suggested that the presence of an intramolecular hydrogen bond between the oxygen of the directing group and hydroxyl group of the ligating acetic acid is crucial for stabilization of the palladacyclic intermediate.
