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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
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form

powder

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

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

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.

Disclaimer

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Codes

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 (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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