2-cyanoacetyl Chloride

Base Information

• Chemical Name: 2-cyanoacetyl Chloride
• CAS No.: 16130-58-8
• Molecular Formula: C3H2 Cl N O
• Molecular Weight: 103.508
• European Community (EC) Number: 817-902-2
• Nikkaji Number: J1.441.527K
• Mol file: 16130-58-8.mol

Synonyms:2-cyanoacetyl Chloride;16130-58-8;cyanoacetyl chloride;Acetyl chloride, cyano-;Cyanacetylchlorid;cyanoacetylchloride;2-cyanoacetylChloride;chloroformylacetonitrile;2-cyano-acetyl chloride;cyanoacetic acid chloride;SCHEMBL1002595;GEQZTCMVWVDEDF-UHFFFAOYSA-N;AKOS016015970;BS-12676;EN300-105706;J-509203

Chemical Property of 2-cyanoacetyl Chloride

Chemical Property:

• Refractive Index: 1.4510 (estimate)
• Boiling Point: 73-75 °C
• PKA: 0.26±0.10(Predicted)
• PSA: 40.86000
• Density: 1.2170 (rough estimate)
• LogP: 0.66548
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 102.9824914
• Heavy Atom Count: 6
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

CyanoacetylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 3
• Hazard Codes: 3:
• Safety Statements: A poison. A storage hazard. It may explode at room temperature. Upon decomposition it emits toxic fumes of Cl:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C#N)C(=O)Cl
• Uses: Cyanoacetyl Chloride is useful in the preparation of butadiene derivatives containing benzo[b]furo[3,2-d][1,3]oxazine which possessed anti-osteoclastic bone resorption activity, antagonistic avctivity for the cysLT1 receptor and growth inhibitory activity for MIA PaCa-2 and MCF-7.

Technology Process of 2-cyanoacetyl Chloride

There total 4 articles about 2-cyanoacetyl 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: 100.0%

cyanoacetic acid (372-09-8) → cyanoacetic acid chloride (16130-58-8)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 0.5h; Solvent; Temperature; Inert atmosphere;

Reference yield:

cyanoacetic acid (372-09-8) + p-toluenesulfonyl chloride (98-59-9) → cyanoacetic acid chloride (16130-58-8)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;

Reference yield:

oxalyl dichloride (79-37-8) + cyanoacetic acid (372-09-8) → cyanoacetic acid chloride (16130-58-8)

Guidance literature:

In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

cyanoacetic acid

oxalyl dichloride

p-toluenesulfonyl chloride

Downstream raw materials:

1,3-dimethylbarbituric acid

6-Amino-1,3-dimethylbarbituric acid

1-(2-cyanoacetyl)-1,3-dimethyl-urea

2-(4-methylnaphthalene-1-carbonyl)acetonitrile

Refernces

• 1、 Tchabanenko, Kirill,Simpkins, Nigel S.,Male, Louise. "A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy". . p. 4747 - 4750. Retrieved 2008.
• 2、 Kroeger, Mario,Folli, Cristina,Walter, Olaf,Doering, Manfred. "Alternating copolymerization of cyclohexene oxide and CO2 catalyzed by zinc complexes with new 3-amino-2-cyanoimidoacrylate ligands". . p. 1325 - 1328. Retrieved 2005.
• 3、 Guseva, T. I.,Senchenya, N. G.,Gol'ding, I. P.,Mager, K. A.,Gololobov, Yu. G... "Synthesis of functionally substituted cyanoacetates". . p. 478 - 480. Retrieved 1993.
• 4、 Humble, Robert W.,Middleton, Danielle F.,Banoub, Joseph,Ewing, David F.,Boa, Andrew N.,MacKenzie, Grahame. "A synthesis of bredinin (Mizoribine) from an acyclic precursor". . p. 6223 - 6227. Retrieved 2011.
• 5、 -. "KRAS MUTANT PROTEIN INHIBITOR". Page/Page column 51-52; 55-56. . Retrieved 2021/05/15.
• 6、 -. "SUBSTITUTED BICYCLIC COMPOUNDS USEFUL AS T CELL ACTIVATORS". Paragraph 0475; 0476. . Retrieved 2021/06/26.