(2R,3R)-2,3-dihydroxy-N,N'-bis(prop-2-en-1-yl)butanediamide

• ChemBase ID: 145486
• Molecular Formular: C10H16N2O4
• Molecular Mass: 228.24504
• Monoisotopic Mass: 228.111007
• SMILES: C=CCNC(=O)[C@@H]([C@H](C(=O)NCC=C)O)O
• Canonical SMILES: C=CCNC(=O)[C@@H]([C@H](C(=O)NCC=C)O)O
• InChI: InChI=1S/C10H16N2O4/c1-3-5-11-9(15)7(13)8(14)10(16)12-6-4-2/h3-4,7-8,13-14H,1-2,5-6H2,(H,11,15)(H,12,16)/t7-,8-/m1/s1
• InChIKey: ZRKLEAHGBNDKHM-HTQZYQBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxy-N,N'-bis(prop-2-en-1-yl)butanediamide
• IUPAC Traditional name: (2R,3R)-2,3-dihydroxy-N,N'-bis(prop-2-en-1-yl)butanediamide
• Synonyms: DATD; N,N′-Diallyl L-tartardiamide; N,N′-Diallyltartramide; (+)-N,N′-Diallyltartramide; N,N′-Diallyl L-tartardiamide; N,N'-Diallyl-L-tartardiamide; N,N′-二烯丙基 L-酒石酸二胺; N,N′-二烯丙基-L-酒石酰胺; (+)-N,N′-二烯丙基酒石酸二酰胺; 己二烯酒石酸二胺; N,N'-二烯丙基-L-酒石酰胺

Database IDs

• CAS Number: 58477-85-3
• EC Number: 261-277-3
• MDL Number: MFCD00008640
• Beilstein Number: 1712934
• PubChem SID: 24859607; 162239691; 24849641; 24859608
• PubChem CID: 94074

CALCULATED PROPERTIES

• Acid pKa: 11.680951
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.5328336
• LogD (pH = 7.4): -1.5328561
• Log P: -1.5328333
• Molar Refractivity: 57.9766 cm^3
• Polarizability: 22.403265 Å^3
• Polar Surface Area: 98.66 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 183-185 °C; 184-186°C; 186-188 °C(lit.)
• Optical Rotation: [α]20/D +108°, c = 2.4 in H2O; [α]20/D +118±2°, c = 3% in methanol; +118 (c=3 in methanol)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (N); ≥99%; ≥99.0% (TLC); 99%
• Grade: purum
• Linear Formula: [CH(OH)CONHCH2CH=CH2]2
• Empirical Formula (Hill Notation): C10H16N2O4

DETAILS

Sigma Aldrich - 156868

Packaging
25 g in poly bottle
Application
Cross-linking co-monomer for the polymerization of soluble polyacrylamide gels.1

Sigma Aldrich - 32664

Other Notes
Cross-linker for the preparation of transparent polyacrylamide gels for IEF1; Quantitative measurement of protein mass and radioactivity in DATD crosslinked polyacrylamide slab gels2