6892-68-8

Basic information

• Product Name: Dithioerythritol
• Synonyms: (S,R)-DITHIOERYTHRITOL;(r*,s*)-1,4-dimercapto-2,3-butanediol;1,4-dimercapto-,(r*,s*)-3-butanediol;1,4-dimercapto-,(theta,s)-3-butanediol;1,4-dithio-erythrito;3-Butanediol,1,4-dimercapto-,(R*,S*)-2;DTE;DITHIOERYTHREITOL
• CAS NO: 6892-68-8
• Molecular Formula: C₄H₁₀O₂S₂
• Molecular Weight: 154.25
• EINECS: 229-998-8
• Product Categories: Pharmaceutical Intermediates;Antioxidant;Biochemistry;Erythrose;O-Substituted Sugars;Sugar Alcohols;Sugars;proteinmod
• Mol File: 6892-68-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 82-84 °C(lit.)
• Boiling Point: 247.65°C (rough estimate)
• Flash Point: 174.215 °C
• Appearance: White to pale yellow or beige/Powder
• Density: 1.156 (estimate)
• Vapor Pressure: 8.68E-07mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 10 mg/mL, clear, colorless
• PKA: pK1:9.5 (25°C)
• Water Solubility: Soluble
• Sensitive: Air Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1719756
• CAS DataBase Reference: Dithioerythritol(CAS DataBase Reference)
• NIST Chemistry Reference: Dithioerythritol(6892-68-8)
• EPA Substance Registry System: Dithioerythritol(6892-68-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• RIDADR: UN 3335
• WGK Germany: 3
• RTECS: KF2410000
• F: 3-10-13-23
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 6892-68-8(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

Different sources of media describe the Uses of 6892-68-8 differently. You can refer to the following data:
1. Reagent for the reduction of disulfide group. Prevents oxidation of sulfhydryl-containing proteins during SDS-polyacrylamide gel electrophoresis. Cleavage of disulfide bonds in proteins
2. 1,4-Dithioerythritol is a Michael reaction acceptor; inducers of enzymes that protect against carcinogenesis: reactivity with sulfhydryl groups.
3. Reagent for maintaining ?SH groups in the reduced state; quantitatively reduces disulfides.

Definition

ChEBI: The meso-diastereomer of 1,4-dimercaptobutane-2,3-diol; a sulfur-containing sugar derived from the monosaccharide erythrose; and an epimer of dithiothreitol.

Purification Methods

Crystallise DTE from ether/hexane and store it in the dark at 0o. [Beilstein 1 III 2360.]

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

Synthetic route

2,3-diacetylthiomethyl ethylene oxide → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With sodium hydroxide In water at 50℃; for 5h; Reagent/catalyst;	83%

C4H10O8S2 → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 18h;	79%

cis-4,5-dihydroxy-1,2-dithiane (40227-25-6) → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With tris-(2-carboxyethyl)-phosphine hydrochloride; potassium carbonate In methanol; chloroform; water at 20℃; for 6h;	70%

Dithiothreitoltetraacetat (1194723-61-9) → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With hydrogenchloride In methanol at 25℃; for 5h; Inert atmosphere;	70%

tetraacetyl derivative of erythro-1.4-dimercapto-butanediol-(2.3) → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With hydrogenchloride

epoxybutene (930-22-3) + 1,2:3,4-Diepoxybutane (564-00-1, 1464-53-5, 30031-64-2, 30419-67-1, 34897-03-5, 298-18-0) → 1,4-dithio-erythritol (6892-68-8) + 1,4-dithio-D,L-threitol (27565-41-9)

Conditions	Yield
With sodium hydroxide; water In methanol; water at 20 - 35℃; under 4500.45 Torr; for 14h;

1,4-dithio-erythritol (6892-68-8) → cis-4,5-dihydroxy-1,2-dithiane (40227-25-6)

Conditions	Yield
With 2-(4-nitrophenyl)-1,2-benzoisoselenazole-3(2H)-one; dihydrogen peroxide In d(4)-methanol for 2h; Reagent/catalyst;	100%
In dimethyl sulfoxide at 110℃; for 3h;	92%
With potassium hydroxide; oxygen In methanol at 20℃; for 60h;	65%
With oxygen; potassium hydroxide In methanol; water for 48h;

1,4-dithio-erythritol (6892-68-8) + bicyclopropylidene (27567-82-4) → (2R,3S)-1,4-Bis-(bicyclopropyl-1-ylsulfanyl)-butane-2,3-diol

Conditions	Yield
In benzene-d6 at 75℃; for 2h; in dark;	99%

1,4-dithio-erythritol (6892-68-8) + 4-tert-butyl-2,6-bis[(2,2'',6,6''-tetramethyl-m-terphenyl-2'-yl)methyl]benzenesulfenic acid (186256-53-1) → (2R,3S)-1-[4-tert-Butyl-2,6-bis-(2,6,2'',6''-tetramethyl-[1,1';3',1'']terphenyl-2'-ylmethyl)-phenyldisulfanyl]-4-mercapto-butane-2,3-diol

Conditions	Yield
In dichloromethane Ambient temperature;	81%

1-bromoglycerol + ((2-p-methoxybenzyloxycarbonyl)ethyl)disulfide (167767-80-8) + 1,4-dithio-erythritol (6892-68-8) → 6,7-dihydroxy-4-thiaheptanoic acid p-methoxybenzyl ester (167767-81-9)

Conditions	Yield
With sodium bicarbonate; triethylamine; citric acid In N-methyl-acetamide; chloroform; nitrogen; water	67%

1,4-dithio-erythritol (6892-68-8) → cis-4,5-dihydroxy-1,2-dithiane (40227-25-6) + (1R,2S,7R,8S)-1,2,7,8-tetrahydroxy-4,5,10,11-tetrathiacyclododecane

Conditions	Yield
With AcOH-NaOH buffer; potassium hexacyanoferrate(III) for 24h; pH = 4.0;	A 60% B 15%

1,4-dithio-erythritol (6892-68-8) + 2-<<(2-hydroxyethyl)sulfonyl>methyl>-m-nitro-2(Z)-pentadienophenone (115321-58-9) → ((E)-(3S,4R)-3,4-Dihydroxy-1,6-dithia-cycloundec-9-en-8-yl)-(3-nitro-phenyl)-methanone (115321-74-9, 115403-95-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; hydroquinone In methanol at -40℃;

1,4-dithio-erythritol (6892-68-8) → C4H9O2S2 (59177-12-7, 66460-22-8, 66460-23-9)

Conditions	Yield
In water pH 3.75 (phosphate buffer), pulse radiolysis, N2O;

1,4-dithio-erythritol (6892-68-8) → C4H8O2S2(1-) (14193-38-5, 16096-98-3, 37031-12-2, 40227-25-6, 74185-01-6, 86023-22-5, 89825-28-5)

Conditions	Yield
In water pH 6.9 (phosphate buffer), pulse radiolysis, N2O;

1,4-dithio-erythritol (6892-68-8) → Octahydrodithieno<3,4-b:3',4'-e>-1,4-dithiin (81197-94-6)

Conditions	Yield
With hydrogenchloride at 75℃; Yield given;

1,4-dithio-erythritol (6892-68-8) + 3-methyl-7,8-dimethyl-10-(1'-D-ribityl)isoalloxazine (28721-76-8) → 4,5-dihydroxy-1,2-dithiane (74185-01-6) + C18H23N4O6(1-)

Conditions	Yield
With potassium chloride; acetic acid at 25℃; Rate constant; other acids;

1,4-dithio-erythritol (6892-68-8) → C4H9NO3S2

Conditions	Yield
With sodium nitrite Ambient temperature; pH 1-2;

1,4-dithio-erythritol (6892-68-8) → C4H8N2O4S2

Conditions	Yield
With sodium nitrite Ambient temperature; pH 1-2;

1,4-dithio-erythritol (6892-68-8) + C4H9NO3S2 → (2S,3R)-1-((2R,3S)-2,3-Dihydroxy-4-mercapto-butyldisulfanyl)-4-mercapto-butane-2,3-diol

Conditions	Yield
In water at 25℃; Rate constant;

1,4-dithio-erythritol (6892-68-8) + C56H58OSe (380305-91-9) → C60H66O2S2Se

Conditions	Yield
In chloroform-d1 at 20℃;	100 % Spectr.

1-bromo-butane (109-65-9) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → (1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide

Conditions	Yield
Multistep reaction;

1-bromo-butane (109-65-9) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-(tBu)Asp-OH (71989-14-5) → (S)-3-{[(1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid

Conditions	Yield
Multistep reaction;

1-bromo-butane (109-65-9) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-Glu(OtBu)-OH (71989-18-9) → (S)-4-{[(1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-4-carbamoyl-butyric acid

Conditions	Yield
Multistep reaction;

o-fluorobenzyl bromide (446-48-0) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → (1R,2S,3S,4S,5R)-2-[4-(2-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide

Conditions	Yield
Multistep reaction;

o-fluorobenzyl bromide (446-48-0) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-(tBu)Asp-OH (71989-14-5) → (S)-3-({(1R,2S,3S,4S,5R)-2-[4-(2-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid

Conditions	Yield
Multistep reaction;

o-fluorobenzyl bromide (446-48-0) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-Glu(OtBu)-OH (71989-18-9) → (S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[4-(2-fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + 1-bromo-octane (111-83-1) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → (1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + 1-bromo-octane (111-83-1) + shikimic acid (138-59-0) + Fmoc-(tBu)Asp-OH (71989-14-5) → (S)-3-{[(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + 1-bromo-octane (111-83-1) + shikimic acid (138-59-0) + Fmoc-Glu(OtBu)-OH (71989-18-9) → (S)-4-Carbamoyl-4-{[(1R,2S,3S,4S,5R)-2-(2,3-dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-butyric acid

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + bromoacetic acid tert-butyl ester (5292-43-3) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → {4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-acetic acid tert-butyl ester

Conditions	Yield
Multistep reaction;

Upstream product

• 40227-25-6 cis-4,5-dihydroxy-1,2-dithiane 
• 930-22-3 epoxybutene 
• 564-00-1 1,2:3,4-Diepoxybutane 
• 16096-98-3 trans-1,2-dithiane-4,5-diol 
• 1194723-61-9 Dithiothreitoltetraacetat 

Downstream Products

• 74185-01-6 4,5-dihydroxy-1,2-dithiane 
• 106991-84-8 2-(2-oxo-1,2-diphenyl-ethylsulfanyl)-1,2-diphenyl-ethanone 
• 70-18-8 glutathion 
• 109759-02-6 1-(2-Chloro-phenyl)-1-(2,3-dihydroxy-4-mercapto-butylsulfanyl)-nonan-3-one 
• 109770-04-9 1,4-Bis<1-(2-Chlorophenyl)-3-oxo-nonylthio>-2,3-dihydroxybutane 
• 68-11-1 mercaptoacetic acid 
• 5964-41-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine 

Relevant articles and documents

Preparation method of 1, 4-dithiothreitol

The invention discloses a preparation method of 1, 4-dithiothreitol, and the method comprises the following steps of: carrying out oxidation reaction on 1, 4-disulfonic acid-2-butene serving as an initial raw material and an oxidant to obtain a first intermediate; hydrolyzing the first intermediate obtained in the S1 in alkali liquor to obtain a second intermediate; and carrying out reduction reaction on the second intermediate obtained in the S2 and a reducing agent to prepare the 1, 4-dithiothreitol. According to the method, 1, 4-disulfonic acid-2-butene is used as the initial raw material,the dithiothreitol is synthesized through the three steps of oxidation, hydrolysis and reduction, the preparation method is simple in process and high in yield, the yield is 77% or above, and the application performance of the obtained product is consistent with that of a conventional product.

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.

Micellar systems

A complex is described that is deliverable to a cell comprising inserting a nucleic acid or other cargo into a reverse micelle. The reverse micelle has the property to compact the nucleic acid for easier delivery.