16369-05-4

Basic information

• Product Name: DL-2-AMINO-3-METHYL-1-BUTANOL
• Synonyms: 2-AMINO-3-METHYL-1-BUTANOL;DL-VALINOL;DL-2-AMINO-3-METHYL-1-BUTANOL;rac-(R*)-2-Amino-3-methylbutane-1-ol;rac-(R*)-3-Methyl-2-amino-1-butanol;DL-2-Amino-3-methyl-1-butanol,95%;[1-(Hydroxymethyl)-2-methylpropyl]amine;N-(1-Hydroxy-3-methylbutan-2-yl)amine
• CAS NO: 16369-05-4
• Molecular Formula: C5H13NO
• Molecular Weight: 103.16
• EINECS: 240-425-0
• Mol File: 16369-05-4.mol

Chemical Properties

• Melting Point: 31-32℃
• Boiling Point: 75-77 °C8 mm Hg(lit.)
• Flash Point: 194 °F
• Appearance: Clear yellow/Liquid
• Density: 0.936 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.182mmHg at 25°C
• Refractive Index: n20/D 1.4543(lit.)
• Storage Temp.: Refrigerator (+4°C)
• PKA: 12.82±0.10(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: DL-2-AMINO-3-METHYL-1-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-AMINO-3-METHYL-1-BUTANOL(16369-05-4)
• EPA Substance Registry System: DL-2-AMINO-3-METHYL-1-BUTANOL(16369-05-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• RIDADR: 2735
• WGK Germany: 3
• Hazardous Substances Data: 16369-05-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
DL-2-AMINO-3-METHYL-1-BUTANOL is used as a chiral nucleophile for the total synthesis of benanomicin-pradimicin antibiotics, which are important due to their potent antimicrobial properties.
Used in Organic Synthesis:
DL-2-AMINO-3-METHYL-1-BUTANOL is used as a chiral building block in the synthesis of 1-allyl-2-pyrroleimines, which are valuable for their potential applications in various chemical and pharmaceutical processes.
Used in Supramolecular Chemistry:
DL-2-AMINO-3-METHYL-1-BUTANOL is used as a homochiral guest compound during the synthesis of crown ethers containing two chiral subunits, which are significant in supramolecular chemistry for their ability to form complexes with various cations and other molecular species.

InChI:InChI=1/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/p+1/t5-/m0/s1

Upstream product

• 13893-45-3 valine ethyl ester 
• 56430-36-5 (RS)-N-acetyl valine ethyl ester 
• 77392-54-2 nitroisoamyl alcohol 
• 4070-48-8 L-valine methyl ester 
• 516-06-3 D,L-valine 
• 13474-14-1 valinamide 
• 17016-83-0 4-isopropyloxazolidin-2-one 
• 77426-65-4 ethyl isopropylglyoxylate oxime 
• 16940-66-2 sodium tetrahydroborate 
• 72-18-4 L-valine 
• 13292-87-0 dimethyl sulfide borane 

Downstream Products

• 20826-30-6 2-(2,4-dinitro-anilino)-3-methyl-butan-1-ol 
• 17016-83-0 4-isopropyloxazolidin-2-one 
• 96835-57-3 C₂₄H₃₂N₂O₄S₂ 
• 4276-09-9 (R)-2-amino-3-methylbutanol 
• 78617-54-6 N-Methylvalinol 
• 127180-89-6 1-methoxy-3-methyl-2-butanamine 
• 127180-91-0 (+/-)-2--3-methyl-1-butanol 
• 87119-03-7 [3-amino-2,4-dihydroxyphenyl]phenylmethanone 
• 220772-37-2 solid N-(1-hydroxymethyl-2-methyl-propyl)-4-methyl-benzamide 

Relevant articles and documents

Copper(I) Phosphinooxazoline Complexes: Impact of the Ligand Substitution and Steric Demand on the Electrochemical and Photophysical Properties

A series of seven homoleptic CuI complexes based on hetero-bidentate P^N ligands was synthesized and comprehensively characterized. In order to study structure–property relationships, the type, size, number and configuration of substituents at the phosphinooxazoline (phox) ligands were systematically varied. To this end, a combination of X-ray diffraction, NMR spectroscopy, steady-state absorption and emission spectroscopy, time-resolved emission spectroscopy, quenching experiments and cyclic voltammetry was used to assess the photophysical and electrochemical properties. Furthermore, time-dependent density functional theory calculations were applied to also analyze the excited state structures and characteristics. Surprisingly, a strong dependency on the chirality of the respective P^N ligand was found, whereas the specific kind and size of the different substituents has only a minor impact on the properties in solution. Most importantly, all complexes except C3 are photostable in solution and show fully reversible redox processes. Sacrificial reductants were applied to demonstrate a successful electron transfer upon light irradiation. These properties render this class of photosensitizers as potential candidates for solar energy conversion issues.

CO2 Methanation via Amino Alcohol Relay Molecules Employing a Ruthenium Nanoparticle/Metal Organic Framework Catalyst

Methanation of carbon dioxide (CO2) is attractive within the context of a renewable energy refinery. Herein, we report an indirect methanation method that harnesses amino alcohols as relay molecules in combination with a catalyst comprising ruthenium nanoparticles (NPs) immobilized on a Lewis acidic and robust metal–organic framework (MOF). The Ru NPs are well dispersed on the surface of the MOF crystals and have a narrow size distribution. The catalyst efficiently transforms amino alcohols to oxazolidinones (upon reaction with CO2) and then to methane (upon reaction with hydrogen), simultaneously regenerating the amino alcohol relay molecule. This protocol provides a sustainable, indirect way for CO2 methanation as the process can be repeated multiple times.

PYRAZOLO[1,5-A]PYRIMIDINYL CARBOXAMIDE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted pyrazolo[1,5-a]pyrimidinyl carboxamide and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted pyrazolo[1,5-a]pyrimidinyl carboxamide compounds described herein include 2-heterocyclyl-4-alkyl-pyrazolo[1,5-a]pyrirnidine-3-carboxarnide compounds and variants thereof.

A catalyst-free, convenient construction of eight-membered [1,4]oxazocane-5,8-dione heterocycles from aminoethanols with divinyl succinate

A convenient protocol for the synthesis of [1,4]oxazocane-5,8-dione heterocycles by direct cyclization using 2-substituted aminoethanols and divinyl succinate without any catalysts and additives was established. This strategy is quite simple and effective to obtain eight-membered rings incorporating lactone and lactam functional groups. Georg Thieme Verlag Stuttgart.

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS

The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed

Large scale synthesis of optically pure aziridines

Disclosed is an efficient, inexpensive method for the preparation of chiral aziridines on a large scale.

Chiral ionic liquids

The invention relates to chiral ionic liquids of the general formula [A]n+[Y]n?, whereby n=1 or 2, the anion [Y]n? is the anion of an organic or inorganic proton acid and the cation [A]+ an optically active organic ammonium cation with up to 50 carbon atoms, at least one chirality center and at least one functional group that can produce a co-ordination by forming hydrogen bridges or by providing free electron pairs. At least one chirality center is provided with a distance of up to 5 atomic bonds from the functional group. The invention also relates to a method for producing said chiral ionic liquids and to the use thereof in methods for the asymmetric synthesis, the asymmetric catalysis and for separating racemates.

New, convenient methods of synthesis and resolution of 1,2-amino alcohols

Oximes of α-keto esters are reduced to obtain the corresponding amino alcohols using NaBH4 in combination with I2, CH 3COOH, TiCl4, ZrCl4, COCl2, H 2SO4, and TMS-Cl in 60-85% yields. The racemic phenylglycinol, phenylalaninol, and 2-aminobutanol are resolved using dibenzoyl-L-tartaric acid to obtain enantiomeric samples of >98% ee.

Metallocene compounds from amino alcohol-derived ligands

A method is provided for synthesizing metallocene compounds useful as polymerization catalysts and the like. The method involves (a) preparation of an amino alcohol-derived ligand by reacting a silane reactant with an amino alcohol in the presence of base, followed by (b) metallation of the ligand so provided. The metallocenes may be provided in chiral form when the amino alcohol contains an asymmetric center, and are thus useful in catalyzing stereospecific polymerization and other stereospecific bond formation reactions.

Convenient methods for the hydrolysis of oxazolidinones to vicinal aminoalcohols

We have developed two convenient methods for hydrolysis of 2-oxazolidinones to the corresponding vicinal aminoalcohols. N-Substituted oxazolidinones can be readily hydrolyzed using Dowex 1×8-100 resin. N-Unsubstituted oxazolidinones cannot be hydrolyzed using Dowex resins but are effectively hydrolyzed using polymer supported ethylenediamine.