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B17905

Sigma-Aldrich

Benzyl bromide

Benzyl bromide
1 of 1 reviewers received a sample product or took part in a promotion

reagent grade, 98%

Synonym(s):

α-Bromotoluene

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$73.30
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$199.00
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25 G
$15.70
100 G
$73.30
500 G
$199.00
2.5 KG
$212.00

About This Item

Linear Formula:
C6H5CH2Br
CAS Number:
100-39-0
Molecular Weight:
171.03
Beilstein/REAXYS Number:
385801
EC Number:
202-847-3
MDL number:
MFCD00000172
UNSPSC Code:
12352100
PubChem Substance ID:
24891612
NACRES:
NA.22
form:
liquid
assay:
98%

$15.70

In StockDetails

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grade

reagent grade

Quality Level

200

vapor density

5.8 (vs air)

assay

98%

form

liquid

impurities

≤0.5% p-bromotoluene

refractive index

n20/D 1.575 (lit.)

bp

198-199 °C (lit.)

mp

−3-−1 °C (lit.)

density

1.438 g/mL at 25 °C (lit.)

SMILES string

BrCc1ccccc1

InChI

1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

InChI key

AGEZXYOZHKGVCM-UHFFFAOYSA-N

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General description

Benzyl bromide is an aromatic halide that is mainly used as a protecting agent for protecting hydroxy group of alcohols via O-benzylation reaction.[1]

Application

Benzyl bromide has been used as an initiator in the synthesis of poly(styrene-b-methylmethacrylate) copolymers by atom transfer radical polymerization.[2] It can undergo Menschutkin reaction with 1, 2-dimethylimidazole to form 3-benzyl-1, 2-dimethylimidazolium bromide.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 2

flash_point_f

186.8 °F - closed cup

flash_point_c

86 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3258
STBL1556
STBK8004
MKCR2511
STBK1692

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Vanderlisa Rita Meleti et al.
Acta tropica, 202, 105248-105248 (2019-11-05)
This paper reports the synthesis of (±)-licarin A 1, a dihydrobenzofuran neolignan, resultant of an oxidative coupling reaction of isoeugenol and horseradish peroxidase (HRP) enzyme. Following, three semi-synthetic derivatives from this compound were obtained: benzylated (±)-licarin A 2, methylated (±)-licarin
Wing-Yiu Yu et al.
Organic letters, 11(2), 469-472 (2008-12-23)
A Pd-catalyzed cross-coupling reaction of benzyl bromides with alpha-aryldiazoesters is described, and E-alpha,beta-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).
Ke Gao et al.
The Journal of organic chemistry, 72(22), 8611-8613 (2007-10-09)
A multicomponent one-pot reaction of 2-alkynylbenzaldehydes, amines, zinc, and allylic bromide or benzyl bromide using the combination of Mg(ClO4)2/Cu(OTf)2 as catalyst in THF/DCE (1:20) is described, which provides an efficient and practical route for the synthesis of functionalized 1,2-dihydroisoquinolines.
Giuseppe Belletti et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(4), 839-844 (2019-10-31)
Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization
Rate constants for reaction of 1, 2-dimethylimidazole with benzyl bromide in ionic liquids and organic solvents.
Skrzypczak A and Neta P.
International Journal of Chemical Kinetics, 36(4), 253-258 (2004)
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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Reviews

1 of 1 reviewers received a sample product or took part in a promotion

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  1. Leiden, the Netherlands
    • Reviews 2
    • Votes 16
    2 out of 5 stars.

    Product needs purification before use

    Product came in fuming and with a very low pH, indicating that there was still HBr present. Had to purify the product over column before I could use it.

    Helpful?

    1. Response from MilliporeSigma:

      Thank you for taking the time to leave a review! We are sorry to hear that your experience did meet expectations. We would like to learn more about your experience to see if there is anything we can do to help correct the issue. When you have a moment, please contact us by visiting https://www.sigmaaldrich.com/support/customer-support and submit a Product Technical Inquiry. We look forward to hearing from you soon!

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