Bromoacetonitrile

Base Information

• Chemical Name: Bromoacetonitrile
• CAS No.: 590-17-0
• Molecular Formula: C2H2BrN
• Molecular Weight: 119.949
• Hs Code.: 29269090
• European Community (EC) Number: 209-672-1
• UN Number: 3276
• UNII: 07K08J16VK
• DSSTox Substance ID: DTXSID2021496
• Nikkaji Number: J446D
• Wikidata: Q27236310
• ChEMBL ID: CHEMBL2139477
• Mol file: 590-17-0.mol

Synonyms:2-Bromoacetonitrile;Bromomethyl cyanide;Cyanomethyl bromide;

Chemical Property of Bromoacetonitrile

Chemical Property:

• Appearance/Colour: clear colourless to yellowish liquid
• Vapor Pressure: 3.18mmHg at 25°C
• Melting Point: -36oC
• Refractive Index: 1.468
• Boiling Point: 154.5 °C at 760 mmHg
• Flash Point: 24.3 °C
• PSA: 23.79000
• Density: 1.761 g/cm³
• LogP: 0.90488
• Storage Temp.: 0-6°C
• Solubility.: 50-100g/l
• Water Solubility.: Insoluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 118.93706
• Heavy Atom Count: 4
• Complexity: 41.2
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2-Bromoacetonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(C#N)Br
• Uses: Bromoacetonitrile was used in the synthesis of 1-cyanomethyl-1,1-dimethylhydrazinium bromide. It is used as an alkalyting agent for the nitrogen phosphorus detector.

Technology Process of Bromoacetonitrile

There total 21 articles about Bromoacetonitrile 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: 78.0%

1-benzoyl-3-bromo-2-phenylpropene-1,3-dicarbonitrile + cyanoacetic acid amide (107-91-5) → 6-amino-5-benzoyl-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile (932021-64-2) + cyanomethyl bromide (590-17-0)

Guidance literature:

With potassium carbonate; In ethanol; water; for 3h; Heating;

DOI:10.1002/jhet.5570440110

Reference yield: 55.0%

4-methoxybenzoic acid (100-09-4) + acetonitrile (75-05-8,26809-02-9) → cyanomethyl 4-methoxybenzoate + cyanomethyl bromide (590-17-0)

Guidance literature:

With di-tert-butyl peroxide; C₁₁H₂₃N₂⁽¹⁺⁾*Br₄Fe^(1-); at 110 ℃; for 12h; Mechanism;

DOI:10.1016/j.tetlet.2019.150969

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + diethyl ether (60-29-7,927820-24-4) + bromocyane (506-68-3) → 4-bromo-1-methyl-1H-1,2,3-triazole (13273-53-5) + 4-bromo-2-methyl-2H-1,2,3-triazole (16681-67-7) + 5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6) + cyanomethyl bromide (590-17-0)

Guidance literature:

upstream raw materials:

diazomethane

diethyl ether

bromocyane

N,N-diisobutyl-glycine nitrile

Downstream raw materials:

2-(1-hydroxycyclohexyl)acetonitrile

3-hydroxy-3-phenylpropanenitrile

(E)-p-methoxycinnamonitrile

(2E)-3-(3,4-dimethoxyphenyl)prop-2-enenitrile

Refernces

A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters

10.1002/ejoc.201501084

The study investigates the use of a sterically congested α-cyanoamine as an effective cyanating reagent for the cyanation of acetals and orthoesters. The key chemicals used in the study include α-cyanoamines, which were prepared from secondary amines and α-bromoacetonitrile, and trichlorosilyl triflate (SiCl3OTf), which acts as a catalyst. These chemicals serve the purpose of facilitating the cyanation reaction, leading to the production of cyanated adducts in high yields. The α-cyanoamines were found to be influenced by steric effects, with more hindered amines improving the product yield, suggesting that they prevent the formation of unfavorable complexes with the catalyst and retain their cyanating functionality. The study also detected oxocarbenium cations as intermediates through NMR spectroscopy, providing insights into the reaction mechanism.