D2388

Dimethyl 3,3′-dithiopropionimidate dihydrochloride

powder

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

Properties

• 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

Description

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

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.

Safety Information

• Pictograms: 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