methyl 3-[(3-imino-3-methoxypropyl)disulfanyl]propanecarboximidate dihydrochloride

• ChemBase ID: 130645
• Molecular Formular: C8H18Cl2N2O2S2
• Molecular Mass: 309.27672
• Monoisotopic Mass: 308.01867519
• SMILES: COC(=N)CCSSCCC(=N)OC.Cl.Cl
• Canonical SMILES: COC(=N)CCSSCCC(=N)OC.Cl.Cl
• InChI: 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
• InChIKey: CQBCVFHLZAVNPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-[(3-imino-3-methoxypropyl)disulfanyl]propanecarboximidate dihydrochloride
• IUPAC Traditional name: methyl 3-[(3-imino-3-methoxypropyl)disulfanyl]propanecarboximidate dihydrochloride
• Synonyms: DTBP; Dimethyl 3,3′-dithiopropionimidate dihydrochloride; Dimethyl 3,3′-dithio-bis(propionimidate) dihydrochloride; Wang/Richards’ reagent; 3,3′-二硫代丙亚氨酸二甲酯 二盐酸盐; Wang/Richards 试剂; 3,3′-二硫代双丙亚氨酸二甲酯 二盐酸盐

Database IDs

• CAS Number: 38285-78-8
• MDL Number: MFCD00043245
• PubChem SID: 162224923; 24893682; 24867398
• PubChem CID: 9815123

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.96882594
• LogD (pH = 7.4): 0.9021529
• Log P: 0.97957706
• Molar Refractivity: 83.6796 cm^3
• Polarizability: 24.49243 Å^3
• Polar Surface Area: 66.16 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 38
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (AT)
• Grade: purum
• Empirical Formula (Hill Notation): C8H16N2O2S2 · 2HCl

DETAILS

Sigma Aldrich - D2388

Caution
该试剂在中性 pH 下易水解。在偶联反应时应避免使用还原剂。
Other Notes
注意：脒键具有初始伯胺的正电荷。可由轻度还原反应裂解二硫键。含有一个八原子连接基。
包装
100 mg in poly bottle
Application
Reactant for:
• Synthesis of glutathione-sensitive cross-linked polyethylenimine gene vector1
• Preparation of cyclodextrin-containing polymers designed for gene delivery2
• Crosslinking of chick oviduct progesterone-receptor subunits3

Sigma Aldrich - 43780

Analysis Note
product decomposes at 111-115°C, residual melts at 160-164°C
Caution
The reagant is readily hydrolyzed at neutral pH. Avoid use of reducing agents during coupling reactions.
Other Notes
Cleavable bifunctional reagent used for cross-linking of membrane proteins and hemoglobin4; For the preparation of an activated solid support5; Cross-linking of a cytochrome oxidase complex6
Note that the amidine linkage preserves original primary amine positive charge. The disulfide linkage is cleavable by mild reduction. Incorporates an eight atom linker.
Application
Reactant for:
• Synthesis of glutathione-sensitive cross-linked polyethylenimine gene vector1
• Preparation of cyclodextrin-containing polymers designed for gene delivery2
• Crosslinking of chick oviduct progesterone-receptor subunits3