N,N'-BIS(ACRYLOYL)CYSTAMINE

Base Information

• Chemical Name: N,N'-BIS(ACRYLOYL)CYSTAMINE
• CAS No.: 60984-57-8
• Molecular Formula: C₁₀H₁₆N₂O₂S₂
• Molecular Weight: 260.381
• Hs Code.: 2930909899
• European Community (EC) Number: 262-546-8
• NSC Number: 328582
• DSSTox Substance ID: DTXSID80209832
• Nikkaji Number: J208.083D
• Wikidata: Q83084302
• Mol file: 60984-57-8.mol

Synonyms:Bisacrylylcystamine;N,N'-Bis(acryloyl)cystamine; N,N'-Bisacrylylcystamine;N,N'-Cystaminebisacrylamide; NSC 328582

Chemical Property of N,N'-BIS(ACRYLOYL)CYSTAMINE

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 121-125 °C
• Boiling Point: 538oC at 760 mmHg
• PKA: 13.98±0.46(Predicted)
• Flash Point: 279.2oC
• PSA: 108.80000
• Density: 1.164g/cm3
• LogP: 1.75400
• Storage Temp.: 2-8°C
• Solubility.: acetic acid: 50 mg/mL
• Water Solubility.: Soluble in acetic acid. Slightly soluble in water.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 260.06532010
• Heavy Atom Count: 16
• Complexity: 231

Purity/Quality:

98%,99%, ^*data from raw suppliers

N,N''-Bis(acryloyl)cystamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C=CC(=O)NCCSSCCNC(=O)C=C
• Uses: suzuki reaction N,N'-Bis(acryloyl)cystamine is used as a reversible cross-linker for polyacrylamide gels. It is also used for DNA purification. Further, it finds application in Suzuki reaction and fabrication of hydrogel modified plasmonic crystal.

Technology Process of N,N'-BIS(ACRYLOYL)CYSTAMINE

There total 4 articles about N,N'-BIS(ACRYLOYL)CYSTAMINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

cystamine dihydrochioride (56-17-7) + acryloyl chloride (814-68-6,25189-84-8) → N,N’-cystamine-bis-acrylamide (60984-57-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 40 ℃; for 24h; Inert atmosphere;

DOI:10.1002/jccs.201300684

Reference yield: 75.0%

2,2'-dithio-bis[ethylamine] (51-85-4) + acryloyl chloride (814-68-6,25189-84-8) → N,N’-cystamine-bis-acrylamide (60984-57-8)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 6h;

DOI:10.1016/j.colsurfb.2018.06.029

Reference yield: 56.0%

2-mercaptoethylamine hydrochloride (156-57-0) + acryloyl chloride (814-68-6,25189-84-8) → N,N’-cystamine-bis-acrylamide (60984-57-8)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 0 - 20 ℃; for 2.66667h;

DOI:10.1246/cl.150064

upstream raw materials:

cystamine dihydrochioride

acryloyl chloride

2-mercaptoethylamine hydrochloride

cystamine hydrochloride

Refernces

• 1、 Lin, Yan-Su,Huang, Yi-Long,Lee, Wen-Fu,Lin, Chao-Hsiung. "Property and application of BACy-based functional hydrogels". . p. 945 - 952. Retrieved 2014.
• 2、 Dai, Yutong,Li, Qingman,Zhang, Shurong,Shi, Shan,Li, Yang,Zhao, Xudong,Zhou, Liping,Wang, Xin,Zhu, Yijian,Li, Wei. "Smart GSH/pH dual-bioresponsive degradable nanosponges based on β-CD-appended hyper-cross-linked polymer for triggered intracellular anticancer drug delivery". . . Retrieved 2021.
• 3、 Yang, Wen,Pan, Cai-Yuan,Luo, Ming-Deng,Zhang, Hong-Bin. "Fluorescent mannose-functionalized hyperbranched poly(amido amine)s: Synthesis and interaction with E. coli". . p. 1840 - 1846. Retrieved 2010.
• 4、 Catanzaro, Giuseppina,Curcio, Manuela,Cirillo, Giuseppe,Spizzirri, Umile Gianfranco,Besharat, Zein Mersini,Abballe, Luana,Vacca, Alessandra,Iemma, Francesca,Picci, Nevio,Ferretti, Elisabetta. "Albumin nanoparticles for glutathione-responsive release of cisplatin: New opportunities for medulloblastoma". . p. 168 - 174. Retrieved 2017.
• 5、 Li, Aihua,Ma, Hongjing,Feng, Shengyu,Liu, Jingquan. "A copolymer capsule with a magnetic core for hydrophilic or hydrophobic drug delivery via thermo-responsive stimuli or carrier biodegradation". . p. 33138 - 33147. Retrieved 2016.
• 6、 Qu, Jing,Wang, Qiu-yue,Chen, Kang-long,Luo, Jian-bin,Zhou, Qing-han,Lin, Juan. "Reduction/temperature/pH multi-stimuli responsive core cross-linked polypeptide hybrid micelles for triggered and intracellular drug release". . p. 373 - 381. Retrieved 2018.
• 7、 Won, Young-Wook,Ankon, Marc,Engbersen, Johan F. J.,Feijen, Jan,Kim, Sung Wan. "Poly(Amido Amine)s Containing Agmatine and Butanol Side Chains as Efficient Gene Carriers". . p. 619 - 626. Retrieved 2016.
• 8、 -. "Carbon dot modified hollow copolymer nanoparticle and preparation method and application thereof, and drug delivery system and application thereof". Paragraph 0104; 0107-0109. . Retrieved 2020/09/12.