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C11081

Sigma-Aldrich

Tetrabromomethane

ReagentPlus®, 99%

Synonym(s):

Carbon tetrabromide

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About This Item

Empirical Formula (Hill Notation):
CBr4
CAS Number:
558-13-4
Molecular Weight:
331.63
Beilstein:
1732799
EC Number:
209-189-6
MDL number:
MFCD00000117
UNSPSC Code:
12352101
PubChem Substance ID:
24892347
NACRES:
NA.22
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vapor pressure

40 mmHg ( 96 °C)

Quality Level

200

product line

ReagentPlus®

Assay

99%

form

crystals

bp

190 °C (lit.)

mp

88-90 °C (lit.)

SMILES string

BrC(Br)(Br)Br

InChI

1S/CBr4/c2-1(3,4)5

InChI key

HJUGFYREWKUQJT-UHFFFAOYSA-N

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General description

Tetrabromomethane can serve as a mediator, catalyst, and reagent in the synthesis of valuable chemicals.[1]

Application

Tetrabromomethane may be used in the following applications:
  • As a transfer agent for the copolymerization of methylmethacrylate and p-divinylbenzene to form soluble crosslinked polymers.[2]
  • As a catalyst for the aerobic photooxidative synthesis of aromatic esters from benzyl alcohols under metal-free conditions.[3]
  • Bromination of adamantane and its derivatives in the presence of iron compounds as catalyst.[4]

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5138
MKCW9780
MKCT6705
MKCV0051
MKCS3732

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Recent advances in the application of tetrabromomethane in organic synthesis
Kumar S, et al.
Inorganic chemistry frontiers, 8(15), 4288-4314 (2021)
Preparation of soluble microgel by the copolymerization of methylmethacrylate with p?divinylbenzene in the presence of tetrabromomethane.
Chen H
Journal of Polymer Science Part A: Polymer Chemistry, 22(9), 2123-2130 (1984)
Bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds.
Khusnutdinov RI
Russ. J. Org. Chem., 51(2), 184-187 (2015)
Aerobic oxidative esterification of benzyl alcohols with catalytic tetrabromomethane under visible light irradiation.
Nobuta T
Tetrahedron Letters, 53(39), 5306-5308 (2012)
Yuko Shingu et al.
Organic & biomolecular chemistry, 1(14), 2518-2521 (2003-09-06)
The reaction of a 2-O-benzyl-1-hydroxy sugar with CBr4 and Ph3P generates a glycosyl bromide in situ, which is coupled with an acceptor alcohol in the presence of N,N-tetramethylurea to afford an alpha-glycosyl product virtually quantitatively. In a proposed pathway, the
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Questions

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  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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