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Merck
CN

D2388

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
NACRES:
NA.22
PubChem Substance ID:
57654084
UNSPSC Code:
12352116
MDL number:
MFCD00043245
Form:
powder

Key Documents

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Product Name

Dimethyl 3,3′-dithiopropionimidate dihydrochloride, powder

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

SMILES string

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

InChI key

CQBCVFHLZAVNPF-UHFFFAOYSA-N

form

powder

reaction suitability

reagent type: cross-linking reagent

solubility

H2O: 50 mg/mL

storage temp.

2-8°C

Quality Level

100

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Application

A homobifunctional, cleavable cross-linking reagent. Typically, reacted with primary amines in the pH range 7.0-10.0 to form amidine bonds.
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

Disclaimer

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

signalword

Warning

hcodes

H315

Hazard Classifications

Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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
John G Lock et al.
Nature cell biology, 20(11), 1290-1302 (2018-10-27)
Adhesion to the extracellular matrix persists during mitosis in most cell types. However, while classical adhesion complexes, such as focal adhesions, do and must disassemble to enable mitotic rounding, the mechanisms of residual mitotic cell-extracellular matrix adhesion remain undefined. Here
V L Chashchin et al.
Biochimica et biophysica acta, 828(3), 313-324 (1985-04-29)
A cleavable cross-linking reagent, dimethyl-3,3'-dithiobispropionimidate, was used to study the molecular organization of adrenocortical cytochrome P-450scc. Extensive cross-linking was found to occur, resulting in the formation of heterologous oligomers up to octamer. The covalently cross-linked complex of adrenocortical cytochrome P-450scc
Zhifei Chen et al.
Polymers, 12(1) (2020-01-17)
A random copolymer of isobutylene (IB) and 4-vinylbenzenecyclobutylene (4-VBCB) was synthesized by cationic polymerization at -80 °C using 2-chloro-2,4,4-trimethylpentane (TMPCl) as initiator. The laws of copolymerization were investigated by changing the feed quantities of 4-VBCB. The molecular weight of the
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