600733-91-3

Basic information

• Product Name: (R)-3-Amino-2-methyl-butan-2-ol
• Synonyms: (R)-3-Amino-2-methyl-butan-2-ol
• CAS NO: 600733-91-3
• Molecular Formula: C₅H₁₃NO
• Molecular Weight: 103.16282
• Mol File: 600733-91-3.mol

Chemical Properties

• Boiling Point: 178.2±13.0 °C(Predicted)
• Appearance: /
• Density: 0.915±0.06 g/cm3(Predicted)
• PKA: 13.01±0.50(Predicted)
• CAS DataBase Reference: (R)-3-Amino-2-methyl-butan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Amino-2-methyl-butan-2-ol(600733-91-3)
• EPA Substance Registry System: (R)-3-Amino-2-methyl-butan-2-ol(600733-91-3)

Safety Data

• Hazardous Substances Data: 600733-91-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Amino-2-methyl-butan-2-ol is used as a chiral auxiliary in asymmetric synthesis for the production of enantiomerically pure pharmaceuticals. Its ability to induce chirality in the synthesis process is crucial for creating drugs with desired biological activities and minimizing side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-3-Amino-2-methyl-butan-2-ol serves as a building block for the synthesis of enantioselective agrochemicals, ensuring the development of effective and environmentally friendly products.
Used in Asymmetric Catalysis:
(R)-3-Amino-2-methyl-butan-2-ol is utilized as a chiral ligand in asymmetric catalysis, enhancing the selectivity and efficiency of catalytic reactions, leading to the production of enantiomerically pure compounds.
Used in Medicinal Chemistry:
(R)-3-Amino-2-methyl-butan-2-ol has potential applications in medicinal chemistry, particularly in the development of new drugs and biologically active compounds. Its unique stereochemistry allows for the design and synthesis of molecules with specific therapeutic targets and improved pharmacological properties.
Used in Resolving Racemic Mixtures:
(R)-3-Amino-2-methyl-butan-2-ol also functions as a resolving agent for racemic mixtures, enabling the separation of enantiomers and facilitating the production of pure enantiomerically enriched compounds for various applications.

Upstream product

• 75-16-1 methylmagnesium bromide 
• 14316-06-4 D-alanine methyl ester hydrochloride 
• 186466-64-8 ((R)-2-hydroxy-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester 
• 6291-17-4 3-amino-2-methylbutan-2-ol 

Downstream Products

• 598-74-3 (2R)-3-methyl-2-butylamine 
• 1610360-94-5 (R)-N-(3-hydroxy-3-methylbutan-2-yl)-2-nitrobenzenesulfonamide 
• 1610360-88-7 (R)-2,2,3-trimethyl-1-((2-nitrophenyl)sulfonyl)aziridine 
• 1610361-04-0 (R)-N-(3-methyl-3-phenoxybutan-2-yl)-2-nitrobenzenesulfonamide 
• 1607434-42-3 C₁₈H₂₃N₃OSi 
• 1223498-31-4 (RS)-S-cyclopropyl-S-(4-{[4-{[(R)-2-hydroxy-1,2-dimethylpropyl]amino}-5-(trifluoromethyl)-pyrimidin-2-yl]amino}phenyl)sulfoximide 
• 1223498-87-0 C₁₇H₂₂F₃N₅O₂S 
• 1223498-86-9 C₁₇H₂₂F₃N₅O₂S 
• 1223498-83-6 C₁₈H₂₄F₃N₅O₂S 
• 1223498-82-5 C₁₈H₂₄F₃N₅O₂S 
• 1223498-76-7 C₁₉H₂₄F₃N₅O₂S 
• 1223498-74-5 C₁₉H₂₄F₃N₅O₂S 
• 1365801-85-9 (R)-3-[2-(4-Methanesulphonylphenylamino) 5-trifluoro-methylpyrimidin-4-ylamino]-2-methylbutan-2-ol 

Relevant articles and documents

Benzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate

Carboxamide pyrazinyloxy benzoxaboroles were investigated with the goal to identify a molecule with satisfactory antimalarial activity, physicochemical properties, pharmacokinetic profile, in vivo efficacy, and safety profile. This optimization effort discovered 46, which met our target candidate profile. Compound 46 had excellent activity against cultured Plasmodium falciparum, and in vivo against P. falciparum and P. berghei in infected mice. It exhibited good PK properties in mice, rats, and dogs. It was highly active against the other 11 P. falciparum strains, which are mostly resistant to chloroquine and pyrimethamine. The rapid parasite in vitro reduction and in vivo parasite clearance profile of 46 were similar to those of artemisinin and chloroquine, two rapid-acting antimalarials. It was nongenotoxic in an Ames assay, an in vitro micronucleus assay, and an in vivo rat micronucleus assay when dosed orally up to 2000 mg/kg. The combined properties of this novel benzoxaborole support its progression to preclinical development.

Possible reason for the unusual regioselectivity in nucleophilic ring opening of trisubstituted aziridines under mildly basic conditions

2,2,3-Trisubstituted aziridines are known to undergo ring opening at the more substituted carbon under mildly basic conditions. However, the reason for the formation of the more sterically encumbered product has never been examined. Several trisubstituted aziridines, with different substitution patterns at the C-2 and C-3 carbons, were synthesized to change the electronics of the aziridine ring system. These changes had no effect on the regioselectivity of the ring-opening reaction. Using the B3LYP/6-31G* DFT basis set it was determined that the transition state for opening at the more substituted carbon proceeds at a lower energy than the transition state at the less substituted carbon.