Adipoyl chloride

Base Information

• Chemical Name: Adipoyl chloride
• CAS No.: 111-50-2
• Molecular Formula: C6H8Cl2O2
• Molecular Weight: 183.034
• Hs Code.: 29171900
• European Community (EC) Number: 203-876-4
• UNII: X7CW7C2XXR
• DSSTox Substance ID: DTXSID5059402
• Nikkaji Number: J5.111J
• Wikipedia: Adipoyl_chloride
• Wikidata: Q504119
• Mol file: 111-50-2.mol

Synonyms:adipoyl chloride

Chemical Property of Adipoyl chloride

Chemical Property:

• Appearance/Colour: colourless to dark brown liquid with a pungent odour
• Vapor Pressure: 0.00557mmHg at 25°C
• Melting Point: 262-264 °C
• Refractive Index: n20/D 1.471(lit.)
• Boiling Point: 273.9 °C at 760 mmHg
• Flash Point: 99.4 °C
• PSA: 34.14000
• Density: 1.265 g/cm³
• LogP: 2.07760
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Water Solubility.: reacts
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 181.9901349
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

98% ^*data from raw suppliers

Adipoyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-29-20/21/22-14
• Safety Statements: 26-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C(CCC(=O)Cl)CC(=O)Cl
• Uses: Adipoyl Chloride can be used in the synthesis of nylon. Also it is used in the synthesis of chiral polymer for membrane application. Adipoyl chloride is used in the production of nylon by reacting with hexamethylene diamine. It is also used in the preparation of biphenyl end-capped liquid crystals. Further, it is employed in the synthesis of chiral polymer for membrane applications.

Technology Process of Adipoyl chloride

There total 10 articles about Adipoyl chloride 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: 98.2%

Adipic acid (124-04-9) → Adipic acid dichloride (111-50-2)

Guidance literature:

With phosgene; N,N-dimethyl-formamide; In toluene; at 50 - 55 ℃;

Reference yield: 87.5%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + adipic acid monomethyl ester (627-91-8) → Adipic acid dichloride (111-50-2) + 1-methyl 6-succinimidyl adipate (118380-06-6)

Guidance literature:

With triethylamine; In thionyl chloride; dichloromethane;

Reference yield: 78.3%

Adipic acid (124-04-9) → adipic acid monomethyl ester (102939-46-8) + Adipic acid dichloride (111-50-2)

Guidance literature:

With phosgene; N,N-dimethyl-formamide; In toluene; at 50 - 55 ℃; Product distribution / selectivity;

upstream raw materials:

Adipic acid

Dichloromethyl methyl ether

bis(4-nitrophenyl)adipate

1,10-decanedioic acid

Downstream raw materials:

Adipinoyl-bis-ε-caprolactam

1,8-bis-(1,3,3-trimethyl-indolin-2-yliden)-octane-2,7-dione

N,N'-bis-biphenyl-2-yl-adipamide

1,6-bis(4-methoxyphenyl)hexa-1,6-dione

Refernces

• 1、 Mauri, Laura,Casellato, Riccardo,Ciampa, Maria G.,Uekusa, Yoshinori,Kato, Koichi,Kaida, Ken-Ichi,Motoyama, Mayumi,Kusunoki, Susumu,Sonnino, Sandro. "Anti-GM1/GD1a complex antibodies in GBS sera specifically recognize the hybrid dimer GM1-GD1a". . p. 352 - 360. Retrieved 2012.
• 2、 Fan, Yinqing,Zhu, Jun,Yan, Shifeng,Chen, Xuesi,Yin, Jingbo. "Nucleating effect and crystal morphology controlling based on binary phase behavior between organic nucleating agent and poly(l-lactic acid)". . p. 63 - 71. Retrieved 2015.
• 3、 Yang, Ke-Wu,Feng, Lei,Yang, Shao-Kang,Aitha, Mahesh,Lacuran, Alecander E.,Oelschlaeger, Peter,Crowder, Michael W.. "New β-phospholactam as a carbapenem transition state analog: Synthesis of a broad-spectrum inhibitor of metallo-β-lactamases". . p. 5855 - 5859. Retrieved 2013.
• 4、 Chooi, K. Phin,Galan, Sebastien R. G.,Raj, Ritu,McCullagh, James,Mohammed, Shabaz,Jones, Lyn H.,Davis, Benjamin G.. "Synthetic phosphorylation of p38α recapitulates protein kinase activity". . p. 1698 - 1701. Retrieved 2014.
• 5、 Zhang, Hong,Zeng, Huahui,Zhang, Huabei,Wu, Xiangxiang,Chao, Fangfang,Yu, Gang,Zhang, Liqing,Jiang, Han,Liu, Hongbiao,Hou, Haifeng,Zhan, Hongwei,Tian, Mei. "Preliminary studies of a novel cyclopentadienyl tricarbonyl technetium-99m fatty acid derivative for myocardical imaging". . p. 1 - 5. Retrieved 2013.
• 6、 Zeng, Huahui,Zhang, Huabei. "Synthesis and biological evaluation of fatty acids conjugates bearing cyclopentadienyl-donors incorporated [99mTc/Re(CO)3] + for myocardical imaging". . p. 10 - 17. Retrieved 2014.
• 7、 Ishmuratov, G. Yu.,Sayakhov, R. R.,Talipov, R. F.,Vydrina, V. A.,Yakovleva, M. P.,Zileeva, Z. R.. "Synthesis of α,ω-Diketodiesters from Betulin". . p. 706 - 711. Retrieved 2021/07/31.
• 8、 Leite, Irena,Andrianov, Victor,Zelencova-Gopejenko, Diana,Loza, Einars,Kazhoka-Lapsa, Iveta,Domracheva, Ilona,Stoyak, Marta,Chlopicki, Stefan,Kalvins, Ivars. "Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors". . p. 1086 - 1106. Retrieved 2022/01/12.