3-Bromopropionitrile

Base Information

• Chemical Name: 3-Bromopropionitrile
• CAS No.: 2417-90-5
• Molecular Formula: C3H4 Br N
• Molecular Weight: 133.975
• Hs Code.: 29269090
• European Community (EC) Number: 219-332-4
• NSC Number: 8021
• UNII: 6EP8MS6M7U
• DSSTox Substance ID: DTXSID0062397
• Nikkaji Number: J51.098J
• Wikidata: Q72511574
• Mol file: 2417-90-5.mol

Synonyms:3-Bromopropionitrile;3-Bromopropanenitrile;2417-90-5;Propanenitrile, 3-bromo-;3-Bromopropiononitrile;2-Bromoethyl cyanide;beta-Bromopropionitrile;1-Bromo-2-cyanoethane;2-Cyanoethyl bromide;PROPIONITRILE, 3-BROMO-;USAF DO-51;beta-Bromopriopionitrile;C3H4BrN;Propionitrile, beta-bromo-;NSC 8021;3-Bromo-propionitrile;.beta.-Bromopropionitrile;EINECS 219-332-4;BRN 1738565;6EP8MS6M7U;AI3-17851;NSC-8021;MFCD00001951;4-02-00-00766 (Beilstein Handbook Reference);NSC8021;3-bromopropanitrile;3-Bromopropionitril;3-bromopropanonitrile;3-bromoproprionitrile;3-bromo propionitrile;3-bromanylpropanenitrile;3-Bromopropanenitrile #;.beta.-Bromopriopionitrile;UNII-6EP8MS6M7U;WLN: NC2E;3-Bromopropionitrile, 97%;3-Bromopropionitrile, 99%;C3-H4-Br-N;Propionitrile, .beta.-bromo-;SCHEMBL117800;DTXSID0062397;BBL011566;STL146738;AKOS005206871;CS-W001262;BP-21229;MS-20753;LS-124908;B1762;FT-0615244;EN300-56972;A817130;J-802110;W-107342;F2190-0288

Chemical Property of 3-Bromopropionitrile

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.317mmHg at 25°C
• Refractive Index: n20/D 1.481(lit.)
• Boiling Point: 200.9°Cat760mmHg
• Flash Point: 97.2°C
• PSA: 23.79000
• Density: 1.583g/cm³
• LogP: 1.29498
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in ethanol, ether.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 132.95271
• Heavy Atom Count: 5
• Complexity: 51.2

Purity/Quality:

99% ^*data from raw suppliers

3-Bromopropionitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(CBr)C#N
• Uses: 3-Bromopropionitrile was used as the initiator in the atom transfer radical polymerization of acrylonitrile. It was used in coupling reactions of a number of aromatic and heteroaromatic phenols with alkyl, acyl or benzoyl halides in acetonitrile with cesium fluoride-Celite.

Technology Process of 3-Bromopropionitrile

There total 5 articles about 3-Bromopropionitrile 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: 70.9%

acrylonitrile (107-13-1,25014-41-9) → bromopropionitrile (2417-90-5)

Guidance literature:

With trimethylsilyl bromide; In water; acetonitrile; at 20 - 40 ℃; Temperature; Solvent; Inert atmosphere; Large scale;

Reference yield:

3-Hydroxypropionitrile (109-78-4) → bromopropionitrile (2417-90-5)

Guidance literature:

With phosphorus tribromide;

DOI:10.1039/P29770001914

Reference yield:

→ bromopropionitrile (2417-90-5)

Guidance literature:

With phosphorus tribromide;

upstream raw materials:

acrylonitrile

3-Hydroxypropionitrile

N-Bromosuccinimide

2-cyano-ethyl

Downstream raw materials:

2,2-diphenyl-pentanedinitrile

(2-cyano-ethyl)-phenyl-phosphinic acid butyl ester

ethyl 2-cyanoethyl(phenyl)-phosphinate

3-Bromopropionic acid

Refernces

Facile syntheses of 4-(2-cyanoethylthio)-1,3-dithiole-2-thione and new electron donors with two TTF units and compounds with bis(1,3-dithiole-2-thione) groups

10.1055/s-2002-34837

The research presents a facile and efficient approach to synthesize 4-(2-cyanoethylthio)-1,3-dithiole-2-thione (1), a key compound for the preparation of tetrathiafulvalene (TTF) derivatives, from TBA2[Zn(dmit)2]. The study explores the synthetic conditions for preparing compound 1 and uses it to synthesize new electron donors with two TTF units. The chemicals used in the process include TBA2[Zn(dmit)2], 3-bromopropionitrile, pyridine hydrochloride, Hg(OAc)2, and various electrophilic reagents such as 1,2-dibromoethane and 1,3-dibromopropane. The research concludes that compound 1 can be synthesized with high efficiency using four equivalents of an organic ammonium salt, yielding new electron donors with two TTF units, which are significant for the study of organic conductors and molecular spin-ladder systems.