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74-95-3 - Dibromomethane, 99%, stab. with 50ppm BHT - Methylene bromide - A10456 - Alfa Aesar

A10456 Dibromomethane, 99%, stab. with 50ppm BHT

CAS Number
74-95-3
Synonyms
Methylene bromide

Size Price ($) Quantity Availability
100g 14.83
500g 25.75
2500g 94.76
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Dibromomethane, 99%, stab. with 50ppm BHT

MDL
MFCD00000168
EINECS
200-824-2

Chemical Properties

Formula
CH2Br2
Formula Weight
173.85
Melting point
-53°
Boiling Point
96-98°
Density
2.495
Refractive Index
1.5410
Solubility
Miscible with water, chloroform, acetone, ether and alcohol.

Applications

Dibromomethane is used as solvent in organic synthesis. It acts as an intermediate in the manufacture of specialty chemicals, agrochemicals and pharmaceuticals. It is useful as extractant and utilized for the determination of 5-nitroimidazoles (5-NDZ) in environmental waters. It is involved in the convertion of catechols to their methylenedioxy derivatives.

Notes

Store in cool place. Incompatible with strong oxidizing agents, aluminum and magnesium.

Literature References

For in situ formation of dibromomethyllithium by reaction with lithiated 2,2,6,6-Tetramethyl­piperidine, A18712, and use in a one-pot ester homologation sequence, safer and more convenient than the classical Arndt-Eistert (diazomethane) method, see: Org. Synth. Coll., 9, 426 (1998):

Reaction with NaHMDS generates monobromocarbene, which reacts with alkenes to give bromocyclopropanes: Synthesis, 201 (1972). It can also be generated by reaction with diethylzinc in the presence of O2: J. Chem. Soc., Chem. Commun., 364 (1975).

The Simmons-Smith reaction (see Diiodomethane, A15457) may be extended to the use of dibromomethane in the cyclopropanation of simple electron-deficient alkenes, using a reducing agent prepared from NiBr2, NaI and Zn: Bull. Chem. Soc. Jpn., 56, 1025 (1983); or with CuCl/Zn: J. Org. Chem., 55, 2491 (1990).

With TiCl4/Zn, methylenation of ketones occurs, as a useful mild alternative to the Wittig reaction: Tetrahedron Lett., 23, 4293 (1982); Org. Synth. Coll., 8, 386 (1993). For a variant using Zn, CuCl and catalytic TiCl4, see: J. Org. Chem., 54, 2388 (1989).

With alcohols, formaldehyde acetals can be formed under phase-transfer conditions: Bull. Chem. Soc. Jpn., 66, 2149 (1993). Diols give methylenedioxy derivatives, which are components of many biologically-important molecules. For use of KF in DMF as base in the methylenation of catechols, see: Tetrahedron Lett., 3361 (1976). KOH in DMSO has been recommended for the methylenation of base-stable carbohydrate diols: Synthesis, 421 (1982). For the methylenation of ribonucleosides under phase-transfer conditions, see: Synthesis, 715 (1981).

Chorazewski, M.; Troncoso, J.; Jacquemin, J. Thermodynamic Properties of Dichloromethane, Bromochloromethane, and Dibromomethane under Elevated Pressure: Experimental Results and SAFT-VR Mie Predictions. Ind. Eng. Chem. Res. 2015, 54 (2), 720-730.

Stoeckel, D.; Wallacher, D.; Zickler, G. A.; Thommes, M.; Smarsly, B. M. Elucidating the Sorption Mechanism of Dibromomethane in Disordered Mesoporous Silica Adsorbents. Langmuir 2015, 31 (23), 6332-6342.

GHS Hazard and Precautionary Statements

Hazard Statements: H332-H412

Harmful if inhaled. Harmful to aquatic life with long lasting effects.

Precautionary Statements: P261-P273-P271-P304+P340-P312-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Use only outdoors or in a well-ventilated area. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician if you feel unwell. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6061
Beilstein
969143
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2903.39
TSCA
Yes
RTECS
PA7350000

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