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CAS RN: 558-13-4 | Product Number: T0038

Carbon Tetrabromide


Purity: >99.0%(GC)
Synonyms:
  • Tetrabromomethane
Product Documents:
25G
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10   ≥100 
100G
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500G
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15   ≥100 

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Product Number T0038
Purity / Analysis Method >99.0%(GC)
Molecular Formula / Molecular Weight CBr__4 = 331.63 
Physical State (20 deg.C) Solid
Storage Temperature Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN 558-13-4
Reaxys Registry Number 1732799
PubChem Substance ID 87576058
SDBS (AIST Spectral DB) 3969
MDL Number

MFCD00000117

Specifications
Appearance White powder to crystal
Purity(GC) min. 99.0 %
Melting point 91.0 to 95.0 °C
Solubility in Methanol almost transparency
Properties (reference)
Melting Point 94 °C
Boiling Point 190 °C
Solubility in water Insoluble
Degree of solubility in water 0.24 g/l   30 °C
GHS
Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H302 : Harmful if swallowed.
H315 : Causes skin irritation.
H318 : Causes serious eye damage.
H371 : May cause damage to organs.
H370 : Causes damage to organs.
H372 : Causes damage to organs through prolonged or repeated exposure.
H373 : May cause damage to organs through prolonged or repeated exposure.
H336 : May cause drowsiness or dizziness.
Precautionary Statements P260 : Do not breathe dust.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P308 + P311 : IF exposed or concerned: Call a POISON CENTER/doctor.
P304 + P340 + P312 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
Related Laws:
EC Number 209-189-6
RTECS# FG4725000
Transport Information:
UN Number UN2516
Class 6.1
Packing Group III
HS Number 2903691990
Application
TCI Practical Example: Bromination of Alkyl Alcohols through Appel Reaction

Used Chemicals

Procedure

To a mixture of 2-phenylethyl alcohol (0.196 mL, 1.64 mmol) and carbon tetrabromide (0.652 g, 1.96 mmol) in CH2Cl2 (8.2 mL) was added a solution of PPh3 (0.644 g, 2.46 mmol) in CH2Cl2 (3.3 mL) at 0 ºC. The reaction mixture was stirred at room temperature for 1 h, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate = 7:3) to give (2-bromoethyl)benzene (0.290 g, 96% yield) as a colorless liquid.

Experimenter’s Comments

The reaction mixture was monitored by TLC (hexane:ethyl acetate = 4:1, Rf = 0.7).

Analytical Data

1H NMR (400 MHz, CDCl3); δ 7.36-7.20 (m, 5H), 3.78 (t, 2H, J = 11.2 Hz), 3.17 (t, 2H, J = 11.2 Hz).

13C NMR (101 MHz, CDCl3); δ 138.9, 128.6, 128.5, 126.9, 39.4, 32.9.

Lead Reference

  • Hexabromoacetone and ethyl tribromoacetate: a highly efficient reagent for bromination of alcohol

  • Application
    Bromination of Alcohols

    T0038

    References


    Application
    Corey-Fuchs Alkyne Synthesis

    Typical Procedure:
    Carbon tetrabromide (34.67 g, 104.5 mmol) and anhydrous CH2Cl2 (175 mL) are added to a 500 mL round bottom flask equipped with a magnetic stir bar and septum under N2 atmosphere. The reaction flask is cooled to 0 ℃ with an ice bath for 10 min. Triphenylphosphine (54.84 g, 209.1 mmol) is added in portions over 5 min, and the dark red solution is stirred at 0 ℃ for 30 min. 3,4-Dimethoxybenzaldehyde (17.37 g, 104.5 mmol) is added and the mixture is stirred at 0 ℃ for 1 h. A 1 : 1 mixture of H2O : brine is added and the layers are separated. The aqueous layer is extracted with a 1 : 1 mixture of hexanes : CH2Cl2, and the combined organic layers are dried, filtered, and concentrated under reduced pressure. The crude material is chromatographed on SiO2 (0-15% EtOAc/hexanes) to afford the dibromide 1 (29.37 g, Y. 88%) as a yellow oil.
    Then, 1 (4.41 g, 13.79 mmol, 1.0 equiv) and THF (45 mL) are added to a 250 mL round bottom flask equipped with a magnetic stir bar and septum, and the reaction flask is cooled to -78 ℃ under N2 atmosphere. 2.5M n-BuLi solution in hexane (11.6 mL) is added slowly via syringe and the reaction solution is stirred at -78 ℃ for 45 min and then at 0 ℃ for 45 min. The flask is recooled to -78 ℃, and freshly distilled methyl chloroformate (1.1 mL, 1.3 mmol, 1.0 equiv) is added slowly via syringe. The mixture is stirred at -78 ℃ for 10 min, then 0 ℃ for 1 h. Saturated aqueous NH4Cl solution is added, and the layers are separated. The aqueous layer is extracted with Et2O, and the combined organic layers are dried, filtered and concentrated under reduced pressure. The residue is chromatographed (SiO2, 2-20% EtOAc / hexanes) to afford the desired alkyne 2 (2.83 g, Y. 93%) as a white solid.

    References


    PubMed Literature


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