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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

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.

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.
  • As a catalyst for the aerobic photooxidative synthesis of aromatic esters from benzyl alcohols under metal-free conditions.
  • Bromination of adamantane and its derivatives in the presence of iron compounds as catalyst.

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

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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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)
Recent advances in the application of tetrabromomethane in organic synthesis
Kumar S, et al.
Inorganic chemistry frontiers, 8(15), 4288-4314 (2021)
Aerobic oxidative esterification of benzyl alcohols with catalytic tetrabromomethane under visible light irradiation.
Nobuta T
Tetrahedron Letters, 53(39), 5306-5308 (2012)
Bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds.
Khusnutdinov RI
Russ. J. Org. Chem., 51(2), 184-187 (2015)
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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