1883-09-6

Basic information

• Product Name: L-2,4-Diaminobutyric acid dihydrochloride
• Synonyms: (S)-(+)-2,4-DIAMINOBUTYRIC ACID DIHYDROCHLORIDE;(S)-(+)-2,4-DIAMINOBUTYRIC ACID HYDROCHLORIDE;(S)-(+)-2,4-DIAMINO-N-BUTYRIC ACID DIHYDROCHLORIDE;ALPHA,GAMMA-DIAMINOBUTYRIC ACID HYDROCHLORIDE SALT;L-ALPHA, GAMMA-DIAMINOBUTYRIC ACID DIHYDROCHLORIDE;L-2,4-DIAMINOBUTYRIC ACID HYDROCHLORIDE;L-2,4-DIAMINOBUTYRIC ACID MONOHYDROCHLORIDE;L-2,4-DIAMINOBUTYRIC ACID DIHYDROCHLORIDE
• CAS NO: 1883-09-6
• Molecular Formula: C₄H₁₂N₂O₂*2Cl
• Molecular Weight: 191.06
• EINECS: 217-542-0
• Product Categories: Amino Acids 13C, 2H, 15N;Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Amino Acids & Derivatives;Chiral Reagents;Inhibitors;A - HPeptide Synthesis;Amino Acids;DAB (2,4-Diaminobutyric Acid);Modified Amino Acids;Unnatural Amino Acid Derivatives;Peptide Synthesis
• Mol File: 1883-09-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 197-200 °C (dec.)
• Boiling Point: 321 °C at 760 mmHg
• Flash Point: 147.9 °C
• Appearance: white crystalline solid
• Vapor Pressure: 6.36E-05mmHg at 25°C
• Refractive Index: 14.5 ° (C=3.6, H2O)
• Storage Temp.: −20°C
• Solubility: water: soluble0.5g/10 mL
• Water Solubility: very faint turbidity
• BRN: 5763078
• CAS DataBase Reference: L-2,4-Diaminobutyric acid dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-2,4-Diaminobutyric acid dihydrochloride(1883-09-6)
• EPA Substance Registry System: L-2,4-Diaminobutyric acid dihydrochloride(1883-09-6)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36/39-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 1883-09-6(Hazardous Substances Data)

Usage

Description

L-2,4-Diaminobutyric acid dihydrochloride is an unnatural amino acid derivative, characterized as a white crystalline solid. It possesses unique properties that make it a versatile compound with various applications in different industries.

Uses

Used in Pharmaceutical Industry:
L-2,4-Diaminobutyric acid dihydrochloride is used as a pharmacological tool for its potential as a chiral building block in the development of new drugs. It also serves as an internal standard for amino acid analysis, which is crucial for the accurate determination of amino acid concentrations in biological samples.
Used in Neurochemistry Research:
L-2,4-Diaminobutyric acid dihydrochloride is used as a reagent for the differentiation of β-N-methylamino-L-alanine from other diamino acids using high-performance liquid chromatography with fluorescence detection (HPLC-FD), ultra-high-performance liquid chromatography with ultraviolet detection (UHPLC-UV), UHPLC-MS, and triple quadrupole tandem mass spectrometry (UHPLC-MS/MS). This differentiation is essential for the accurate identification and quantification of neurotoxins, such as β-N-methylamino-L-alanine (BMAA), in seafood.
Used in Anticancer Applications:
L-2,4-Diaminobutyric acid dihydrochloride exhibits antitumor activity in vitro and in vivo against mouse fibrosarcoma cells. It also inhibits GABA transaminase, leading to an elevation of GABA levels, which may have potential therapeutic implications in cancer treatment.
Used in Analytical Chemistry:
L-2,4-Diaminobutyric acid dihydrochloride is used as an internal standard for amino acid analysis, ensuring the accuracy and reliability of quantitative measurements in various research and diagnostic applications.

InChI:InChI:1S/C4H10N2O2.2ClH/c5-2-1-3(6)4(7)8;;/h3H,1-2,5-6H2,(H,7,8);2*1H

Upstream product

• 116864-55-2 (S)-3-(N-Tritylamino)-2-pyrrolidon 
• 103668-08-2 (R)-2,4-Diamino-butyric acid ethyl ester; hydrochloride 
• 34404-27-8 N^α,N^γ-bis(t-butoxycarbonyl)-L-α,γ-butyric acid 
• 127531-09-3 (S)-3-Cyano-2-[(1R,2R,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-propionic acid ethyl ester 

Downstream Products

• 1217645-10-7 (R)-2,4-bis((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid 
• 4128-00-1 (3S)-3-aminopyrrolidin-2-one 
• 25139-87-1 ⁽⁵⁾-(+)(D)-N,N'-Ditosyl-2,4-diamino-butanol 
• 126581-98-4 DPAB-L-DBA (trans) 
• 117106-22-6 (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminobutanoic acid 
• 97347-23-4 N^α,N^γ-diBoc-L-2,4-diaminobutyric acid p-nitrobenzyl ester 
• 55478-23-4 (S)-2,4-bis(((benzyloxy)carbonyl)amino)butanoic acid 

Relevant articles and documents

Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates

Enantiopure 1-phenylethylazetidine-2-carboxylates and 2-acylazetidines were prepared and reacted with chloroformates to yield α-chloro-γ-amino butyric acid esters and ketones from ring opening reaction of azetidinium ion intermediate in a completely regio- and stereoselective manner.

Application of N-Tritylmethionine in the Preparation of Heterocycles of Biological and Synthetic Interest

Treatment of the methylsulfonium salts of the corresponding N-tritylmethionine derivatives with sodium hydride or potassium tert-butoxide provides the heterocycles N-trityl-L-homoserine lactone (3), (S)- and (R)-3-(N-tritylamino)tetrahydrofuran (7a, 7b), (S)-1-hydroxy-3-(N-tritylamino)-2-pyrrolidinone (14), (S)-4-(N-tritylamino)-1,2-oxazinan-3-one (15), (S)-3-(N-tritylamino)-2-pyrrolidone (23), (S)-1-tert-butyloxycarbonylamino-3-(N-tritylamino)-2-pyrrolidone (27), and (S)-2-methyl-4-(N-tritylamino)-1,2-oxazinan-3-one (18).Methylation of 14 and 15 yields (S)-1-methoxy-3-(N-tritylamino)-2-pyrrolidone (17) and 18, respectively.The stereochemistry of compounds 3, 7a, and 17 has been determined by X-ray crystal structure analysis.