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D2388

Sigma-Aldrich

Dimethyl 3,3′-dithiopropionimidate dihydrochloride

powder

Synonym(s):

DTBP, Dimethyl 3,3′-dithio-bis(propionimidate) dihydrochloride, Wang/Richards’ reagent

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About This Item

Empirical Formula (Hill Notation):
C8H16N2O2S2 · 2HCl
CAS Number:
38285-78-8
Molecular Weight:
309.28
MDL number:
MFCD00043245
UNSPSC Code:
12352116
PubChem Substance ID:
57654084
NACRES:
NA.22

form

powder

Quality Level

100

reaction suitability

reagent type: cross-linking reagent

solubility

H2O: 50 mg/mL

storage temp.

2-8°C

SMILES string

Cl.Cl.COC(=N)CCSSCCC(=N)OC

InChI

1S/C8H16N2O2S2.2ClH/c1-11-7(9)3-5-13-14-6-4-8(10)12-2;;/h9-10H,3-6H2,1-2H3;2*1H

InChI key

CQBCVFHLZAVNPF-UHFFFAOYSA-N

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Application

Reactant for:
  • Synthesis of glutathione-sensitive cross-linked polyethylenimine gene vector
  • Preparation of cyclodextrin-containing polymers designed for gene delivery
  • Crosslinking of chick oviduct progesterone-receptor subunits

Caution

The reagant is readily hydrolyzed at neutral pH. Avoid use of reducing agents during coupling reactions.

Other Notes

Note that the amidine linkage preserves original primary amine positive charge. The disulfide linkage is cleavable by mild reduction. Incorporates an eight atom linker.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV1197
MKCQ6855
MKCK3158
MKCK3156
MKCG2165

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Carine F Djuika et al.
Scientific reports, 7(1), 4410-4410 (2017-07-02)
Artemisinins are the current mainstay of malaria chemotherapy. Their exact mode of action is an ongoing matter of debate, and several factors have recently been reported to affect an early stage of artemisinin resistance of the most important human malaria
Lalit Yadav et al.
Organic & biomolecular chemistry, 18(30), 5927-5936 (2020-07-22)
A Bu4NI-catalyzed, DTBP-promoted, regioselective C(sp2)-C(sp3) cross dehydrogenative coupling (CDC) protocol for the direct C-3 benzylation of 2H-indazoles is reported. The metal-free protocol is operationally simple and proceeds mechanistically via the generation of stable benzylic free-radicals followed by regioselective addition at
Choong Eun Jin et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 5(10), 1800614-1800614 (2018-10-26)
Cell-free nucleic acids (cfNAs) are emerging diagnostic biomarkers for monitoring the treatment and recurrence of cancers. In particular, the biological role and clinical usefulness of cfNAs obtained from the plasma of patients with various cancers are popular and still intensely
K K Sharma et al.
Experimental eye research, 61(4), 413-421 (1995-10-01)
Alpha crystallin can function as a molecular chaperone in suppressing the heat-induced aggregation of other crystallins and proteins. During cataractogenesis, alpha-crystallin becomes a water-insoluble, high-molecular-weight, cross-linked aggregate. To determine whether the chaperone activity of alpha crystallin is lost during this
Xiaoqiang Liu et al.
The Analyst, 136(24), 5204-5210 (2011-10-19)
An ultrasensitive electrochemical immmunosensor was demonstrated to be capable of detecting the hormone cortisol down to concentrations as low as 16 pg mL(-1). In addition, the immunosensor displayed a sensitivity of 1.6 μA pg(-1) mL(-1) and a linear range up
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