88390-32-3

Basic information

• Product Name: (R)-4-AMINO-2-METHYL-1-BUTANOL
• Synonyms: (R)-4-AMINO-2-METHYL-1-BUTANOL;(R)-4-AMINO-2-METHYLBUTANOL;(R)-2-Methyl-4-amino-1-butanol;(2R)-4-Amino-2-methyl-1-butanol;(R)-4-Amino-2-methyl-1-butanol
• CAS NO: 88390-32-3
• Molecular Formula: C₅H₁₃NO
• Molecular Weight: 103.16
• Product Categories: Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry
• Mol File: 88390-32-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 80 °C / 1.8mmHg
• Flash Point: 59.446°C
• Appearance: /
• Density: 0,94 g/cm3
• Vapor Pressure: 0.369mmHg at 25°C
• Refractive Index: 14.5 ° (C=neat)
• PKA: 14.96±0.10(Predicted)
• CAS DataBase Reference: (R)-4-AMINO-2-METHYL-1-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-AMINO-2-METHYL-1-BUTANOL(88390-32-3)
• EPA Substance Registry System: (R)-4-AMINO-2-METHYL-1-BUTANOL(88390-32-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39
• Hazardous Substances Data: 88390-32-3(Hazardous Substances Data)

Usage

Uses

(R)-4-Amino-2-methyl-1-butano is a useful research reagent for the improved synthesis of dihydrozeatin and it’s resolution.

InChI:InChI=1/C5H13NO/c1-5(4-7)2-3-6/h5,7H,2-4,6H2,1H3/t5-/m1/s1

Upstream product

• 63987-58-6 (R)-2-methyl-4-phthalimido-butyric acid 
• 63987-58-6 rac-2-methyl-4-phthalimidobutanoic acid 
• 78-92-2 iso-butanol 
• 13931-35-6 4-(Tetrahydro[2H]pyran-2-yloxy)-3-methyl-2-butenenitrile 
• 42453-21-4 4-Amino-2-methylbutyric acid 
• 201230-82-2 carbon monoxide 
• 109-75-1 but-3-enenitrile 
• 96192-37-9 (R)-2MeGABA 
• 73616-96-3 (S)-4-hydroxy-3-methyl-butyronitrile 

Downstream Products

• 1437-87-2 4-Amino-2-methyl-butylhydrogensulfat 
• 1028119-65-4 2-methyl-4-(2-nitrobenzylamino)butanol 
• 1392843-27-4 C₇H₁₃NO₃ 
• 1392843-04-7 C₁₅H₂₉NO₃ 
• 404849-99-6 C₉H₁₇NO₃ 
• 1392843-19-4 C₇H₁₃NO₃ 
• 1392842-92-0 C₁₅H₂₉NO₃ 
• 404849-98-5 C₉H₁₇NO₃ 

Relevant articles and documents

APOPTOSIS SIGNAL-REGULATING KINASE INHIBITORS AND USES THEREOF

Described herein are ASK1 inhibitors and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of blood disease, autoimmune disorders, pulmonary disorders, hypertension, inflammatory diseases, fibrotic diseases, diabetes, diabetic nephropathy, renal diseases, respiratory diseases, cardiovascular diseases, acute lung injuries, acute or chronic liver diseases, and neurodegenerative diseases.

Synthesis and application of a new bisphosphite ligand collection for asymmetric hydroformylation of allyl cyanide

A series of mono- and bidentate phosphites was prepared with (S)-5,5',6,6'-tetramethyl-3,3'-di-tertbutyl-1,1'-biphenyl-2,2'-dioxy [(S)-BIPHEN] as a chiral auxiliary and screened in the asymmetric hydroformylation of allyl cyanide. These hydroformylation results were compared with those of two existing chiral ligands, Chiraphite and BINAPHOS, whose utility in asymmetric hydroformylation has been previously demonstrated. Bisphosphite 11 with a 2,2'-biphenol bridge was found to be the best overall ligand for asymmetric hydroformylation of allyl cyanide with up to 80% ee and regioselectivities (branch-to-linear ratio, b/l) of 20 with turnover frequency of 625 [h-1] at 35 °C. BINAPHOS gave enantioselectivities up to 77% ee when the reaction was conducted in either acetone or neat but with poor regioselectivity (b/l 2.8) and activities 7 times lower than that of 11. The product of allyl cyanide hydroformylation using (R,R)-11 was subsequently transformed into (R)-2-methyl-4-aminobutanol, a useful chiral building block. Single-crystal X-ray structures of (S,S)-11 and its rhodium complex 19 were determined.

Process for the preparation of trans-3-formylbut-2-enenitrile

A process is provided for the preparation of trans-3-formylbut-2-enenitrile (V), a key intermediate in the synthetic pathway leading to trans-zeatin (I) and dihydrozeatin (II), both of which are naturally occurring cytokinins. The process involves a base catalyzed condensation of a dialkyl or cyclic acetal of pyruvaldehyde (III) with acetonitrile to yield the corresponding dialkyl or cyclic acetal of 3-formylbut-2-enenitrile (IV). The reaction proceeds regioselectively to form the favored trans-isomer in good yield. The α,β-unsaturated nitrile thus formed is hydrolyzed under acidic conditions to yield trans-3-formylbut-2-enenitrile (V), which can be easily distilled without contamination of the cis-isomer. The trans-3-formylbut-2-enenitrile can be selectively or exhaustively reduced to form either trans-3-hydroxymethylbut-2-enylamine (VI) or 3-hydroxymethylbutylamine (VII), which compounds can be condensed with 6-chloropurine (IX) by known methods to form trans-zeatin or dihydrozeatin respectively.