L-2,4-diaminobutyric acid

Base Information

• Chemical Name: L-2,4-diaminobutyric acid
• CAS No.: 1758-80-1
• Molecular Formula: C4H11BrN2O2
• Molecular Weight: 118.136
• Hs Code.: 2922499990
• UNII: 61HPH2F0W7
• Nikkaji Number: J80.310C
• Wikidata: Q27094699
• Metabolomics Workbench ID: 38851
• ChEMBL ID: CHEMBL321357
• Mol file: 1758-80-1.mol

Synonyms:2,4-diaminobutyric acid;2,4-diaminobutyric acid dihydrochloride, (+-)-isomer;2,4-diaminobutyric acid dihydrochloride, (S)-isomer;2,4-diaminobutyric acid monohydrochloride, (+-)-isomer;2,4-diaminobutyric acid monohydrochloride, (S)-isomer;2,4-diaminobutyric acid, (+)-isomer;2,4-diaminobutyric acid, (+-)-isomer;2,4-diaminobutyric acid, (R)-isomer;2,4-diaminobutyric acid, (S)-isomer;L-2,4-diaminobutyric acid

Chemical Property of L-2,4-diaminobutyric acid

Chemical Property:

• Vapor Pressure: 6.36E-05mmHg at 25°C
• Melting Point: 216-218 °C
• Refractive Index: 1.513
• Boiling Point: 320.986 °C at 760 mmHg
• PKA: 2.00±0.10(Predicted)
• Flash Point: 147.927 °C
• PSA: 89.34000
• Density: 1.219 g/cm³
• LogP: 1.10580
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -4.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 118.074227566
• Heavy Atom Count: 8
• Complexity: 84.1

Purity/Quality:

99% ^*data from raw suppliers

L-DABHBR 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: other linear non-peptide (BMAA)
• Canonical SMILES: C(CN)C(C(=O)O)N
• Isomeric SMILES: C(CN)[C@@H](C(=O)O)N

Technology Process of L-2,4-diaminobutyric acid

There total 47 articles about L-2,4-diaminobutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

<2,6-bis(1,1-dimethylethyl)-4-methoxyphenyl>-2,4-bis(acetamido)butanoat (113719-16-7) → 2,4-diaminobutanoic acid (305-62-4,1758-80-1,2577-63-1,26908-94-1,60484-56-2)

Guidance literature:

With formic acid; dihydrogen peroxide; for 0.0833333h; Ambient temperature; then 30 min. 60 deg.C;

DOI:10.1002/hlca.19870700607

Reference yield:

polymyxin B6 → L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-2,4-diaminobutyrate (1758-80-1) + (R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 24h;

DOI:10.1016/j.peptides.2011.08.004

Reference yield:

benzoylglycyl-Nγ-(pivaloyloxy)glutamine N-methylamide (85701-37-7) → 2,4-diaminobutanoic acid (305-62-4,1758-80-1,2577-63-1,26908-94-1,60484-56-2) + L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + glycine (56-40-6,18875-39-3,25718-94-9) + methylamine (74-89-5)

Guidance literature:

With Lossen degradation; Product distribution;

DOI:10.1021/jo00160a015

upstream raw materials:

propane-1,1,3-tricarboxylic acid

3-amino-pyrrolidin-2-one

Pht-D/L-Dab(Pht)-OH

3-thioxo-tetrahydro-pyrrolo[1,2-c]imidazole-1,5-dione

Downstream raw materials:

(2S)-2-{[(benzyloxy)carbonyl]amino}-4-(dimethylamino)butanoic acid

(2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid

γ-DNP-L-2,4-DAB

(2S)-4-(benzyloxycarbonyl)amino-2-(tert-butoxycarbonyl)aminobutyric acid

Refernces

• 1、 Talbot et al.. "-". . p. 593,594. Retrieved 1958.
• 2、 Rothchild,Fields. "-". . p. 1080. Retrieved 1951.
• 3、 STANSLY,BROWNLEE. "Nomenclature of polymyxin antibiotics.". . p. 611 - 611. Retrieved 1949.
• 4、 Galan, M. Carmen,Ghirardello, Mattia,Ledru, Helene,Sau, Abhijit. "Chemo-selective Rh-catalysed hydrogenation of azides into amines". supporting information. . Retrieved 2020/02/18.
• 5、 -. "Preparation method of L-2,4-diaminobutyrate hydrochloride". Paragraph 0020-0023. . Retrieved 2019/10/22.