146000-39-7

Basic information

• Product Name: BOC-N,2-DIMETHYLALANINE
• Synonyms: N-TERT-BUTOXYCARBONYL-2-DIMETHYLALANINE;N-BOC-ALPHA-(METHYLAMINO)ISOBUTYRIC ACID;N-BOC-N,2-DIMETHYLALANINE;BOC-N-METHYL-AIB;BOC-N,2-DIMETHYLALANINE;N-BOC-N,2-Dimethylalanine, 98+%;boc-n-me-aib-oh;n-boc-α-(methylamino)isobutyric acid
• CAS NO: 146000-39-7
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• Mol File: 146000-39-7.mol

Chemical Properties

• Melting Point: 154-158 °C
• Boiling Point: 306.4°Cat760mmHg
• Flash Point: 139.1°C
• Appearance: White/Crystalline Powder
• Density: g/cm³
• Vapor Pressure: 0.000176mmHg at 25°C
• Storage Temp.: Refrigerator (+4°C)
• PKA: 4.18±0.10(Predicted)
• BRN: 7371082
• CAS DataBase Reference: BOC-N,2-DIMETHYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-N,2-DIMETHYLALANINE(146000-39-7)
• EPA Substance Registry System: BOC-N,2-DIMETHYLALANINE(146000-39-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 146000-39-7(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C10H19NO4/c1-9(2,3)15-8(14)11(6)10(4,5)7(12)13/h1-6H3,(H,12,13)/p-1

Upstream product

• 84758-55-4 N-(tert-butoxycarbonyl)-α-methylalanine methyl ester 
• 30992-29-1 Boc-Aib-OH 
• 74-88-4 methyl iodide 
• 2566-34-9 2-(methylamino)isobutyric acid 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1223405-15-9 Me-Aib-OH*HCl 
• 1229649-47-1 tert-butyl 1-(4-((4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)methyl)pyridin-2-ylamino)-2-methyl-1-oxopropan-2-yl(methyl)carbamate 
• 1590396-89-6 2-[(4-fluorobenzenesulfonyl)-methylamino]-2-methyl-N-(4'-trifluoromethylbiphenyl-3-ylmethyl)propionamide 
• 1229649-20-0 N-(4-((4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)methyl)pyridin-2-yl)-2-methyl-2-(methylamino)propanamide 
• 1240516-70-4 N₁-[(3-{[3-{[(5-Chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]-N₂,2-dimethylalaninamide formate 
• 1162342-61-1 tert-butyl 1-(4-methoxyphenethylamino)-2-methyl-1-oxopropan-2-yl(methyl)carbamate 
• 1071481-83-8 C₃₄H₄₆Cl₂N₄O₅ 
• 286011-63-0 N,N(diMe)-Aib-OBzl 

Relevant articles and documents

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

New active series of growth hormone secretagogues

New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.

An efficient and high yield method for the N-tert-butoxycarbonyl protection of sterically hindered amino acids

An important method for the N-tert-butoxycarbonyl protection of the amino functionality of α-alkylated prolines and other sterically hindered α,α-disubstituted amino acids has been developed in which the lipophilic base tetramethylammonium hydroxide is used to solubilize the otherwise insoluble zwitterionic amino acid in acetonitrile, thereby obviating the need for an aqueous medium.