(2R,3R)-1,4-disulfanylbutane-2,3-diol

• ChemBase ID: 155127
• Molecular Formular: C4H10O2S2
• Molecular Mass: 154.251
• Monoisotopic Mass: 154.01222156
• SMILES: C([C@@H]([C@H](CS)O)O)S
• Canonical SMILES: SC[C@@H]([C@H](CS)O)O
• InChI: InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1
• InChIKey: VHJLVAABSRFDPM-IMJSIDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-1,4-disulfanylbutane-2,3-diol
• IUPAC Traditional name: L-dithiothreitol
• Synonyms: L-DTT; Cleland reagent chiral; L-(-)-Dithiothreitol; (-)-Cleland’s Reagent; (2R,3R)-1,4-Dimercapto-2,3-butanediol

Database IDs

• CAS Number: 16096-97-2
• EC Number: 240-263-0
• MDL Number: MFCD00064305
• Beilstein Number: 2036371
• PubChem SID: 24894326; 162249265
• PubChem CID: 439196

CALCULATED PROPERTIES

• Acid pKa: 9.6162195
• H Acceptors: 2
• H Donor: 4
• LogD (pH = 5.5): -0.27845594
• LogD (pH = 7.4): -0.28087094
• Log P: -0.2784251
• Molar Refractivity: 38.8438 cm^3
• Polarizability: 15.481865 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 110 °C; 230 °F

Safety Information

• RTECS: EK1612000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 21/22-36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C4H10O2S2

DETAILS

Sigma Aldrich - D9760

Application
Proposed as a stereoselective reducing agent for disulfide bridges in complex molecules.