16096-97-2

Basic information

• Product Name: L-DITHIOTHREITOL
• Synonyms: OPTICALLY ACTIVE CLELAND'S REAGENT;(R,R)-(-)-1,4-DITHIO-L-THREITOL;1,4-dimercapto-,(r-(r*,r*))-3-butanediol;4-dimercapto-3-butanediol-threo-1;(2R,3R)-THREO-1,4-DIMERCAPTO-2,3-BUTANEDIOL;(2R,3R)-(-)-2,3-DIHYDROXY-1,4-BUTANEDITHIOL;(2R,3R)-(-)-1,4-DIMERCAPTO-2,3-BUTANEDIOL;(-)-1,4-DITHIO-L-THREITOL
• CAS NO: 16096-97-2
• Molecular Formula: C₄H₁₀O₂S₂
• Molecular Weight: 154.25
• EINECS: 240-263-0
• Product Categories: Biochemistry;Chiral Building Blocks;O-Substituted Sugars;Simple Alcohols (Chiral);Sugar Alcohols;Sugars;Synthetic Organic Chemistry
• Mol File: 16096-97-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 51 °C
• Boiling Point: 247.65°C (rough estimate)
• Flash Point: 110 °C
• Appearance: /solid
• Density: 1.156 (estimate)
• Vapor Pressure: 8.68E-07mmHg at 25°C
• Refractive Index: 26 ° (C=2.5, MeOH)
• Storage Temp.: −20°C
• Solubility: H2O: soluble50mg/mL, clear to hazy, colorless
• PKA: 9.28±0.10(Predicted)
• BRN: 2036371
• CAS DataBase Reference: L-DITHIOTHREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: L-DITHIOTHREITOL(16096-97-2)
• EPA Substance Registry System: L-DITHIOTHREITOL(16096-97-2)

Safety Data

• Hazard Codes: Xn
• Statements: 21/22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: UN 3335
• WGK Germany: 3
• RTECS: EK1612000
• F: 10-13-23
• Hazardous Substances Data: 16096-97-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

L-DTT [(2R,3R)-1,4-dimercapto-2,3-butanediol; L-dithiothreitol], a chiral bidentate dithiol with two stereogenic centers, may be used in chiroptical response research. L-DDT is proposed as a stereoselective reducing agent for disulfide bridges in complex molecules.

InChI:InChI=1/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1

Upstream product

• 16096-98-3 trans-1,2-dithiane-4,5-diol 
• 40227-25-6 cis-4,5-dihydroxy-1,2-dithiane 
• 16096-98-3 trans-1,2-dithiane-4,5-diol 

Downstream Products

• 27550-66-9 4-hydroxy-1,2-dithiolane 
• 70-18-8 glutathion 
• 14193-38-5 C₄H₈O₂S₂^(1-) 
• 135598-55-9 (2-{(2S,3S)-2,3-Dihydroxy-4-[2-(4-methoxy-benzyloxycarbonylamino)-ethyldisulfanyl]-butyldisulfanyl}-ethyl)-carbamic acid 4-methoxy-benzyl ester 
• 74185-01-6 4,5-dihydroxy-1,2-dithiane 
• 108-98-5 thiophenol 
• 116504-33-7 <2>(2,6)Naphthalino<2>paracyclophan-1,11-dien 
• 882-33-7 diphenyldisulfane 
• 109770-04-9 1,4-Bis<1-(2-Chlorophenyl)-3-oxo-nonylthio>-2,3-dihydroxybutane 
• 109759-02-6 1-(2-Chloro-phenyl)-1-(2,3-dihydroxy-4-mercapto-butylsulfanyl)-nonan-3-one 
• 106991-84-8 2-(2-oxo-1,2-diphenyl-ethylsulfanyl)-1,2-diphenyl-ethanone 
• 107-96-0 3-mercaptopropionic acid 
• 60-24-2 2-hydroxyethanethiol 
• 37031-12-2 (4S,5S)-1,2-dithiane-4,5-diol 

Relevant articles and documents

Charge Accumulation and Multi-Electron Photoredox Chemistry with a Sensitizer–Catalyst–Sensitizer Triad

Photoinduced electron transfer in donor–sensitizer–acceptor compounds usually leads to simple electron–hole pairs, and photoredox catalysis typically relies on single-electron transfer (SET) events. This work reports on a molecular triad able to accumulate two electrons on a central dibenzo[1,2]dithiin moiety flanked by two peripheral RuII photosensitizers. Under continuous illumination, the doubly reduced form of the dibenzo[1,2]dithiin undergoes thiolate–disulfide exchange with an aliphatic disulfide substrate, thereby acting as a two-electron catalyst after two initial SET events with triethylamine at the RuII sensitizers. The use of a relatively simple triad for coupling two separate SET processes to a subsequent two-electron reduction is an important conceptual advance from photoinduced SET and light-driven charge accumulation towards multi-electron photoredox catalysis. This is relevant for artificial photosynthesis and light-driven multi-electron chemistry in general.

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Phosphine-assisted rearrangement of 4,5-dihydroxy-1,2-dithianes to 4-hydroxy-3-mercaptotetrahydrothiophenes

Treatment of 4,5-dihydroxy-1,2-dithianes with trialkylphosphines and triphenylphosphine under neutral and moderately basic conditions led to the efficient and stereospecific production of 4-hydroxy-3-mercaptotetrahydrothiophenes. The reaction is projected

Interleukin-2/viral antigen protein chimers

Disclosed are (1) a fused protein obtained by combining an antigen used for vaccine and a lymphokine by the application of gene engineering, (2) a recombinant DNA containing a nucleotide sequence coding for the above fused protein, (3) a transformant bearing the above recombinant DNA, (4) a method for producing the fused protein which comprises cultivating the above transformant, producing and accumulating the above fused protein in a culture, and collecting the fused protein, and (5) a hybrid protein obtained by chemically combining an antigen used for vaccine with a lymphokine. The resulting fused and hybrid proteins have strong immunogenicity.