5-(Bromomethyl)-2-fluorobenzonitrile

Base Information

• Chemical Name: 5-(Bromomethyl)-2-fluorobenzonitrile
• CAS No.: 180302-35-6
• Molecular Formula: C8H5BrFN
• Molecular Weight: 214.037
• Hs Code.: 2926909090
• European Community (EC) Number: 820-920-3
• DSSTox Substance ID: DTXSID50378781
• Nikkaji Number: J1.276.335B
• Wikidata: Q82168344
• Mol file: 180302-35-6.mol

Synonyms:5-(bromomethyl)-2-fluorobenzonitrile;180302-35-6;3-cyano-4-fluorobenzyl bromide;Benzonitrile, 5-(bromomethyl)-2-fluoro-;5-bromomethyl-2-fluorobenzonitrile;MFCD03094341;SCHEMBL51855;DTXSID50378781;GUUKPGIJZYZERR-UHFFFAOYSA-N;5-bromomethyl-2-fluoro-benzonitrile;AKOS009159497;AB13324;CS-W003004;AS-11491;SY023128;3-cyano-4-fluorobenzyl bromide, AldrichCPR;FT-0753393;EN300-106813;F8889-3870

Chemical Property of 5-(Bromomethyl)-2-fluorobenzonitrile

Chemical Property:

• Boiling Point: 272.7±25.0 °C(Predicted)
• PSA: 23.79000
• Density: 1.59±0.1 g/cm3(Predicted)
• LogP: 2.59228
• Sensitive.: Lachrymatory
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 212.95894
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

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

5-Bromomethyl-2-fluorobenzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CBr)C#N)F
• Uses: 3-CYANO-4-FLUOROBENZYL BROMIDE is used in the synthetic preparations of thrombin inhibitors.

Technology Process of 5-(Bromomethyl)-2-fluorobenzonitrile

There total 8 articles about 5-(Bromomethyl)-2-fluorobenzonitrile 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: 91.0%

2-fluoro-5-(hydroxymethyl)benzonitrile (227609-85-0) → 5-bromomethyl-2-fluorobenzonitrile (180302-35-6)

Guidance literature:

With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1080/00304940009356752

Reference yield: 84.0%

2-fluoro-5-methylbenzonitrile (64113-84-4) → 5-bromomethyl-2-fluorobenzonitrile (180302-35-6)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 20 - 80 ℃; for 20.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b00968

Reference yield:

2,2i-azobisisobutyronitrile + 2-fluoro-5-methylbenzonitrile (64113-84-4) → 5-bromomethyl-2-fluorobenzonitrile (180302-35-6)

Guidance literature:

With N-Bromosuccinimide; In benzene;

upstream raw materials:

2-fluoro-5-methylbenzonitrile

2-fluoro-5-(hydroxymethyl)benzonitrile

3-bromo-4-fluorobenzaldehyde

2-fluoro-5-formylbenzonitrile

Downstream raw materials:

C₃₈H₃₄F₂N₄O₃

2-fluoro-5-formylbenzonitrile

5-[3-(2-Butynyl)-4-oxo-2-(piperazin-1-yl)-3,4-dihydroimidazo[4,5-d]pyridazin-5-ylmethyl]-2-fluorobenzonitrile trifluoroacetate

5-chloro-1-(3-cyano-4-fluorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide

Refernces

• 1、 Cain, Gary A.. "An improved synthesis of 3-cyano-4-fluorobenzyl bromide". . p. 88 - 91. Retrieved 2000.
• 2、 Quattropani, Anna,Sauer, Wolfgang H. B.,Crosignani, Stefano,Dorbais, Jerome,Gerber, Patrick,Gonzalez, Jerome,Marin, Delphine,Muzerelle, Mathilde,Beltran, Fanny,Nichols, Anthony,Georgi, Katrin,Schneider, Manfred,Vitte, Pierre-Alain,Eligert, Valerie,Novo-Perez, Laurence,Hantson, Jennifer,Nock, Sebastien,Carboni, Susanna,De Souza, Adriano Luis Soares,Arrighi, Jean-Fran?ois,Boschert, Ursula,Bombrun, Agnes. "Pharmacophore-based design of novel oxadiazoles as selective sphingosine-1-phosphate (S1P) receptor agonists with in vivo efficacy". . p. 688 - 714. Retrieved 2015/04/14.