66228-31-7

Basic information

• Product Name: (R)-3,3-DIMETHYL-2-AMINOBUTANE
• Synonyms: (R)-(-)-3,3-DIMETHYL-2-BUTYLAMINE;(R)-3,3-DIMETHYL-2-BUTYLAMINE;(R)-(+)-3,3-DIMETHYL 2-AMINOBUTANE;(R)-3,3-DIMETHYL-2-AMINOBUTANE;(R)-(−)-3,3-Dimethyl-2-butylamine;(R)-(-)-3,3-DIMETHYL-2-BUTYLAMINE: CHIPROS 99% EE 99%;(R)-(-)-3,3-Dimethyl-2-butylamine, ChiPros, 99+%, ee 99+%;(R)-3,3-diMethylbutan-2-aMine
• CAS NO: 66228-31-7
• Molecular Formula: C₆H₁₅N
• Molecular Weight: 101.19
• EINECS: -0
• Mol File: 66228-31-7.mol

Chemical Properties

• Melting Point: -4°C
• Boiling Point: 103°C
• Flash Point: 2°C
• Appearance: /
• Density: 0.762 g/mL at 25 °C
• Vapor Pressure: 38.4mmHg at 25°C
• Refractive Index: 1.4127
• Storage Temp.: 2-8°C
• PKA: 10.86±0.13(Predicted)
• Sensitive: Air Sensitive
• BRN: 5237592
• CAS DataBase Reference: (R)-3,3-DIMETHYL-2-AMINOBUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3,3-DIMETHYL-2-AMINOBUTANE(66228-31-7)
• EPA Substance Registry System: (R)-3,3-DIMETHYL-2-AMINOBUTANE(66228-31-7)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34-22-52/53
• Safety Statements: 16-26-36/37/39-45-61
• RIDADR: 2734
• WGK Germany: 2
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 66228-31-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3,3-DIMETHYL-2-AMINOBUTANE is used as a key intermediate in the synthesis of substituted pyrrolecarboxamides. These pyrrolecarboxamides serve as hepatitis B capsid assembly modulators, which are crucial in the development of treatments for hepatitis B virus infections.
In the preparation of these modulators, (R)-3,3-DIMETHYL-2-AMINOBUTANE contributes to the formation of the desired molecular structure, enabling the development of effective therapeutic agents against hepatitis B. Its unique chiral properties and reactivity make it an essential component in the synthesis process, highlighting its importance in the pharmaceutical industry.

InChI:InChI=1/C6H15N/c1-5(7)6(2,3)4/h5H,7H2,1-4H3/t5-/m1/s1

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 464-07-3 3,3-dimethyl-2-butanol 
• 2550-26-7 4-Phenyl-2-butanone 
• 618-36-0 rac-methylbenzylamine 
• 183507-83-7 (R)-N-(2,2-dimethylpropylidene)-1-(1-napthyl)ethylamine 
• 630-19-3 pivalaldehyde 
• 183316-96-3 (2R,1'R)-[1'-(1-naphthyl)ethyl]-3,3-dimethyl-2-butylamine 
• 141393-92-2 (R)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine 
• 141294-37-3 (R,R)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine 
• 3850-30-4 2,2-dimethyl-1-methylpropylamine 
• 17640-21-0 isopropyl methoxyacetate 
• 112245-08-6 methyl (R)-2-amino-3,3-dimethylbutanoate 
• 62965-34-8 Trimethylpyruvic acid oxime 
• 141393-93-3 (S)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine 

Downstream Products

• 863605-26-9 (5-chloro-2-nitrophenyl)-(1-(R)-methyl-2,2-dimethylpropyl)amine 
• 220641-11-2 (R)-4-[[(Cyanoimino)[(1,2,2-trimethylpropyl)amino]-methyl] amino]benzonitrile 
• 948094-08-4 N,N-(R)-bis(diphenylphosphanyl)-3,3-dimethyl-2-butylamine 
• 1101-41-3 Tetraphenyldiphosphin 
• 1342310-14-8 C₂₅H₂₈NP 
• 1374687-56-5 N-(R)-3,3-dimethyl-2-butyl-O-benzoyl hydroxylamine hydrochloride 
• 1415548-29-6 C₂₄H₂₈N₆O₅ 
• 1415548-25-2 C₂₁H₂₅N₅O₂ 

Relevant articles and documents

Separate Sets of Mutations Enhance Activity and Substrate Scope of Amine Dehydrogenase

Mutations were introduced into the leucine amine dehydrogenase (L-AmDH) derived from G. stearothermophilus leucine dehydrogenase (LeuDH) with the goals of increased activity and expanded substrate acceptance. A triple variant (L-AmDH-TV) including D32A, F101S, and C290V showed an average of 2.5-fold higher activity toward aliphatic ketones and an 8.0 °C increase in melting temperature. L-AmDH-TV did not show significant changes in relative activity for different substrates. In contrast, L39A, L39G, A112G, and T133G in varied combinations added to L-AmDH-TV changed the shape of the substrate binding pocket. L-AmDH-TV was not active on ketones larger than 2-hexanone. L39A and L39G enabled activity for straight-chain ketones as large as 2-decanone and in combination with A112G enabled activity toward longer branched ketones including 5-methyl-2-octanone.

An Ammonium-Formate-Driven Trienzymatic Cascade for ω-Transaminase-Catalyzed (R)-Selective Amination

(R)-Amination mediated by (R)-specific ω-transaminases generally requires costly d-alanine in excess to obtain the desired chiral amines in high yield. Herein, a one-pot, trienzymatic cascade comprising an (R)-specific ω-transaminase, an amine dehydrogenase, and a formate dehydrogenase was developed for the economical and eco-friendly synthesis of (R)-chiral amines. Using inexpensive ammonium formate as the sole sacrificial agent, the established cascade system enabled efficient ω-transaminase-mediated (R)-amination of various ketones, with high conversions and excellent ee (>99%); water and CO2 were the only waste products.

(R)- SELECTIVE AMINATION

The present invention relates to a method for the enzymatic synthesis of enantiomerically enriched (R)-amines of general formula [1][c] from the corresponding ketones of the general formula [1][a] by using novel transaminases. These novel transaminases are selected from two different groups: either from a group of some 20 proteins with sequences as specified herein, or from a group of proteins having transaminase activity and isolated from a microorganism selected from the group of organisms consisting of Rahnella aquatilis, Ochrobactrum anthropi, Ochrobactrum tritici, Sinorhizobium morelense, Curtobacterium pusiffium, Paecilomyces lilacinus, Microbacterium ginsengisoli, Microbacterium trichothecenolyticum, Pseudomonas citronellolis, Yersinia kristensenii, Achromobacter spanius, Achromobacter insolitus, Mycobacterium fortuitum, Mycobacterium frederiksbergense, Mycobacterium sacrum, Mycobacterium fluoranthenivorans, Burkhoideria sp., Burkhoideria tropica, Cosmospora episphaeria, and Fusarium oxysporum.

Asymmetric Amination of Secondary Alcohols by using a Redox-Neutral Two-Enzyme Cascade

Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self-sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by employing an alcohol dehydrogenase and a newly developed amine dehydrogenase. The compatibility and the identical cofactor dependence of the two enzymes led to an ingenious in situ cofactor recycling system in the one-pot synthesis. The artificial redox-neutral cascade process allowed the transformation of racemic secondary alcohols into enantiopure amines with considerable conversions (up to 94 %) and >99 % enantiomeric excess at the expense of only ammonia; this method thus represents a concise and efficient route for the asymmetric synthesis of chiral amines. If you know what amine: A redox-neutral two-enzyme cascade encompassing an alcohol dehydrogenase (ADH) and an amine dehydrogenase (AmDH) is constructed for the synthesis of chiral amines from the corresponding racemic alcohols in one pot to afford considerable conversions (up to 94 %) and high enantiomeric excess values (>99 %) at the expense of only ammonia.

Optically active amines by enzyme-catalyzed kinetic resolution

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Method of inhibiting or treating chemotherapy-induced hair loss

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Influence of bulky substituents on histamine H3 receptor agonist/antagonist properties

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The (R)-enantiomer of 4-[[(cyanoimino)[(1,2,2-trimethylpropyl)amino]methyl]amino]benzonitrile as well as the corresponding (S)-enantiomer are useful for promoting hair growth such as in male pattern baldness.

Asymmetric addition of alkyllithium to chiral imines: α-Naphthylethyl group as a chiral auxiliary

The diastereoselective nucleophilic addition of alkyllithium to N- alkylidene-α-naphthylethylamine was carried out. In the presence of Lewis acids or Lewis bases, organolithiums reacted smoothly with imines to give the corresponding amines in high stereoselectivity (up to 100% de). Furthermore, the resulting optically active amines were found to be useful for asymmetric reactions as chiral ligands.