Iodoacetonitrile

Base Information

• Chemical Name: Iodoacetonitrile
• CAS No.: 624-75-9
• Molecular Formula: C2H2IN
• Molecular Weight: 166.949
• Hs Code.: 29269090
• European Community (EC) Number: 210-860-0
• NSC Number: 81208
• UNII: EXK5ZB5CF6
• DSSTox Substance ID: DTXSID8073215
• Nikkaji Number: J96.178G
• Wikidata: Q72483284
• Mol file: 624-75-9.mol

Synonyms:Iodoacetonitrile;2-iodoacetonitrile;624-75-9;Acetonitrile, iodo-;EXK5ZB5CF6;C2H2IN;EINECS 210-860-0;NSC-81208;Cyanoiodomethane;iodo-acetonitrile;cyanomethyl iodide;2-iodo acetonitrile;2-iodoaceto-nitrile;MFCD00001886;2-iodanylethanenitrile;Iodoacetonitrile, 98%;UNII-EXK5ZB5CF6;SCHEMBL48597;DTXSID8073215;C2-H2-I-N;NSC81208;CCG-40420;NSC 81208;AKOS000280495;CS-W016050;FS-4598;Iodoacetonitrile, purum, >=96.0% (GC);FT-0627258;I0419;EN300-207724;A833796;A928520

Chemical Property of Iodoacetonitrile

Chemical Property:

• Appearance/Colour: clear red to brown liquid
• Vapor Pressure: 0.71mmHg at 25°C
• Refractive Index: n20/D 1.574(lit.)
• Boiling Point: 185.1 °C at 760 mmHg
• Flash Point: 86.1 °C
• PSA: 23.79000
• Density: 2.307g/cm³
• LogP: 0.94498
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Water Solubility.: Soluble in benzene, alcohol, acetone, ether. Slightly soluble in water. Insoluble in hexane.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 166.92320
• Heavy Atom Count: 4
• Complexity: 41.2

Purity/Quality:

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

Iodoacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C; T
• Hazard Codes: C,T
• Statements: 22-34-36/37/38-23/24/25
• Safety Statements: 26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(C#N)I
• Uses: Iodoacetonitrile is used for alkylation of nucleophiles. It undergoes Reformatsky and Wittig-type reactions with aldehydes.

Technology Process of Iodoacetonitrile

There total 17 articles about Iodoacetonitrile 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%

cyanomethyl bromide (590-17-0) → iodoacetonitrile (624-75-9)

Guidance literature:

With sodium iodide; In acetone;

Reference yield:

N-ethyl-N-cyanomethyl-N-methyl-anilinium; iodide → iodoacetonitrile (624-75-9) + N-methyl-N-ethylaniline (613-97-8)

Guidance literature:

beim Schmelzen;

Reference yield:

2,4-difluoro-1-iodobenzene (2265-93-2) + acetonitrile (75-05-8,26809-02-9) → iodoacetonitrile (624-75-9) + 1,3-Difluorobenzene (372-18-9)

Guidance literature:

for 24h; Product distribution; Irradiation;

DOI:10.1246/bcsj.70.1875

upstream raw materials:

chloroacetonitrile

(N-methylanilino)acetonitrile

methyl iodide

2-(o-tolylamino)acetonitrile

Downstream raw materials:

tri-N-methyl-m-toluidinium; bromide

trimethyl(3-methylphenyl)ammonium iodide

(p-iodophenyl)-trimethylammonium iodide

iodobenzene

Refernces

• 1、 Wang, Hongxiang,Shao, Ying,Zheng, Hao,Wang, Hanghang,Cheng, Jiang,Wan, Xiaobing. "Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids". . p. 18333 - 18337. Retrieved 2015/12/24.
• 2、 Song, Yong-Qi,Yuzuri, Tomoaki,Suezawa, Hiroko,Sakakibara, Kazuhisa,Hirota, Minoru,Nakada, Masahiro. "The Photolyses of 2,6- and 2,4-Difluorohalobenzenes". . p. 1875 - 1878. Retrieved 2007/10/03.