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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

Quality Level

200

Assay

97%

form

solid

mp

52-55 °C (lit.)

functional group

bromo
fluoro

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

264431-BULK:
264431-25G:
264431-VAR:
264431-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG2722
BCBV8508
BCBR7827V
BCBR5971V
BCBK7625V

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Sigma-Aldrich

112186

4-Bromobenzyl bromide

Benzyl bromide reagent grade, 98%

Sigma-Aldrich

B17905

Benzyl bromide

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.
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).
Efficient solid-phase synthesis of quinazoline-2-thioxo-4-ones with SynPhase? lanterns.
Makino S, et al.
Tetrahedron Letters, 41(43), 8333-8337 (2000)
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.

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