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264431

Sigma-Aldrich

2,6-Difluorobenzyl bromide

97%

Synonym(s):

α-Bromo-2,6-difluorotoluene

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About This Item

Linear Formula:
F2C6H3CH2Br
CAS Number:
85118-00-9
Molecular Weight:
207.02
Beilstein:
2083943
EC Number:
285-652-6
MDL number:
MFCD00000329
UNSPSC Code:
12352100
PubChem Substance ID:
24856016
NACRES:
NA.22

Assay

97%

form

solid

mp

52-55 °C (lit.)

functional group

bromo

SMILES string

Fc1cccc(F)c1CBr

InChI

1S/C7H5BrF2/c8-4-5-6(9)2-1-3-7(5)10/h1-3H,4H2

InChI key

LSXJPJGBWSZHTM-UHFFFAOYSA-N

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Application

2,6-Difluorobenzyl bromide has been used:
  • as reagent in alkylation of the quinazoline-2-thioxo-4-one
  • in the synthesis of 1,3,5-triazine-2,4,6-triones
  • in the preparation of new classes of inhibitors of bovine viral diarrhea virus (as a surrogate virus for hepatitis C virus)

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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2,6-Difluorobenzylamine

Efficient solid-phase synthesis of quinazoline-2-thioxo-4-ones with SynPhase? lanterns.
Makino S, et al.
Tetrahedron Letters, 41(43), 8333-8337 (2000)
Zhiqiang Guo et al.
Bioorganic & medicinal chemistry letters, 15(3), 693-698 (2005-01-25)
A convenient one-pot synthetic route was developed for the preparation of asymmetric 1,3-dialkyl-1,3,5-triazine-2,4,6-triones from readily available alkyl- or aryl-isocyanates, primary amines and N-chlorocarbonyl isocyanate in excellent yields. Subsequent alkylation with N-protected amino alcohols afforded the desired 1,3,5-triazine-2,4,6-triones in good yields.
Gwang-Noh Ahn et al.
Lab on a chip, 19(20), 3535-3542 (2019-09-27)
Microreactors are emerging as an efficient, sustainable synthetic tool compared to conventional batch reactors. Here, we present a new numbering-up metal microreactor by integrating a flow distributor and a copper catalytic module for high productivity of a commercial synthetic drug.
Gerhard Puerstinger et al.
Bioorganic & medicinal chemistry letters, 16(20), 5345-5349 (2006-08-12)
A novel class of inhibitors of pestiviruses (5-substituted 2-phenyl-5H-imidazo[4,5-c]pyridines) is described. Modification of the substituent in position 5 resulted in analogues with high activity (EC(50)<100nM) and selectivity (SI>1000) against the pestivirus BVDV (bovine viral diarrhea virus).

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