2-bromo-2-methylpropane

• ChemBase ID: 88899
• Molecular Formular: C4H9Br
• Molecular Mass: 137.01826
• Monoisotopic Mass: 135.98876229
• SMILES: BrC(C)(C)C
• Canonical SMILES: CC(Br)(C)C
• InChI: InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3
• InChIKey: RKSOPLXZQNSWAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-2-methylpropane
• IUPAC Traditional name: tert-butyl bromide
• Synonyms: 2-Bromo-2-methylpropane; tert-Butyl bromide; tert-Butyl bromide; 2-BROMO-2-METHYLPROPANE; 1-Bromo-1,1-dimethylethane; Bromotrimethylmethane; 1,1-Dimethylethyl bromide; Trimethylbromomethane; 2-methyl-2-bromopropane; tert-Butyl bromide; 2-Bromo-2-methylpropane; 叔丁基溴; 2-甲基-2-溴丙烷; 叔丁基溴; 2-溴-2-甲基丙烷

Database IDs

• CAS Number: 507-19-7
• EC Number: 208-065-9
• MDL Number: MFCD00000125
• Beilstein Number: 1730892
• Merck Index: 141555
• PubChem SID: 162075796; 24848212; 24851816
• PubChem CID: 10485
• CHEMBL: 347644
• Chemspider ID: 10053
• Wikipedia Title: Tert-Butyl_bromide

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.0754697
• LogD (pH = 7.4): 2.0754697
• Log P: 2.0754697
• Molar Refractivity: 28.1014 cm^3
• Polarizability: 10.851001 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Melting Point: -16.20°C (256.95K); -20 °C(lit.); -20°C; -20°C
• Boiling Point: 71-73 °C(lit.); 71-73°C; 73.25°C (346.4K); 74-76°C
• Flash Point: 16 °C; 18°C; 18°C(64°F); 60.8 °F
• Density: 1.189; 1.210; 1.22 g mL^-1 (at 20 °C); 1.22 g/mL at 20 °C(lit.)
• Refractive Index: 1.4279; 1.4280; n20/D 1.4279(lit.); n20/D 1.428
• Partition Coefficient: 2.574
• Henry Constant: 310 nmol Pa^-1 kg^-1
• Heat Capacity: 165.7 J K mol^-1
• Std enthalpy of formation: -133.4 kJ mol^-1

Safety Information

• Storage Warning: Highly Flammable/Light Sensitive
• RTECS: TX4150000
• European Hazard Symbols: Flammable (F)
• UN Number: 2342; UN2342
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11; R11
• Safety Statements: 16-33; 9-16-33-60; S16, S33
• TSCA Listed: 是
• GHS Pictograms: GHS flame; GHS02
• GHS Signal Word: DANGER; Danger
• LD50: 1.25 g kg^-1 (intraperitoneal, rat); 4.4 g kg^-1 (intraperitoneal, mouse)
• GHS Hazard statements: 225; H225
• GHS Precautionary statements: 210; P210; P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2342 3/PG 2

Product Information

• Purity: ≥97.0% (GC); 98%; 98+%, stab. with potassium carbonate
• Grade: purum
• Contains: 0.5% potassium carbonate as stabilizer
• Linear Formula: (CH3)3CBr

DETAILS

MP Biomedicals - 05206782

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 135615

Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - 19700

Caution
may discolor to brownish-yellow on storage

REFERENCES

• Reduces sulfoxides to sulfides via a bromosulfonium intermediate: Synthesis, 141 (1981):
  
• For use of tert-halides in the direct alkylation of malonic acid derivatives under Lewis acid conditions, see Malononitrile, A15046. Similarly, silyl enol ethers can be alkylated by tert-butyl halides in the presence of TiCl₄: Angew. Chem. Int. Ed., 17, 48 (1978).
• In the presence of K₂CO₃ and BTEAC in DMA, N-protected amino acids can be readily converted to their t-butyl esters: Tetrahedron Lett., 34, 7409 (1993).
• Similarly, with DMSO is equivalent to bromodimethylsulfonium bromide, and has been used to cleave ethylene thioacetals: Synthesis, 151 (1982), and as a highly selective brominating agent for alkenes and alkynes: Gazz. Chim. Ital., 115, 29 (1985), aldehydes and ketones: Tetrahedron, 40, 2035 (1984).