1-bromo-3-methylbut-2-ene

• ChemBase ID: 89100
• Molecular Formular: C5H9Br
• Molecular Mass: 149.02896
• Monoisotopic Mass: 147.98876229
• SMILES: BrCC=C(C)C
• Canonical SMILES: BrCC=C(C)C
• InChI: InChI=1S/C5H9Br/c1-5(2)3-4-6/h3H,4H2,1-2H3
• InChIKey: LOYZVRIHVZEDMW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-bromo-3-methylbut-2-ene
• IUPAC Traditional name: 1-bromo-3-methylbut-2-ene
• Synonyms: 1-Bromo-3-methyl-2-butene; 3,3-Dimethylallyl bromide; 3-Methylbut-2-en-1-yl bromide; 3,3-Dimethylallyl bromide; Prenyl bromide; 1-Bromo-3-methylbut-2-ene 93%; 1-Bromo-3-methyl-2-butene; 1-溴-3-甲基-2-丁烯; 溴代异戊烯; 3,3-二甲基烯丙基溴; 1-溴-3-甲基-2-丁烯

Database IDs

• CAS Number: 870-63-3
• EC Number: 212-799-5
• MDL Number: MFCD00000242
• Beilstein Number: 1420778
• PubChem SID: 24855022; 24864270; 24856581; 162075985
• PubChem CID: 70092

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.3827562
• LogD (pH = 7.4): 2.3827562
• Log P: 2.3827562
• Molar Refractivity: 33.414 cm^3
• Polarizability: 12.3956375 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 135°C; 82-83 °C/150 mmHg(lit.); 82-83°C/150mm
• Flash Point: 104 °F; 31 °C; 32°C(90°F); 40 °C; 40°C; 87.8 °F
• Density: 1.281; 1.29; 1.29 g/mL at 20 °C(lit.)
• Refractive Index: 1.4895; n20/D 1.489; n20/D 1.489(lit.)

Safety Information

• Storage Warning: Corrosive/Flammable/Lachrymatory/Light Sensitive/Keep Cold; Light Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2920; UN2920
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 10-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314; H314-H318-H226
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ~90%; ≥90% (GC); 90+%, stab. with silver; 95%
• Grade: technical; technical grade
• Contains: silver wool as stabilizer
• Linear Formula: (CH3)2C=CHCH2Br

DETAILS

Sigma Aldrich - 274372

Packaging
1, 10 g in glass bottle
Application
A useful source of the 3,3-dimethylallyl or prenyl group for the synthesis of natural products1 and in the synthesis of base-modified pyrimidine nucleosides.2

Sigma Aldrich - 249904

Packaging
5, 25 g in glass bottle

REFERENCES

• 3,3-Dimethylallyl (prenyl) building block group, useful in terpene synthesis. For use as an alkylating agent, see, e.g.: Org. Synth. Coll., 8, 381 (1993).
• In the presence of the hindered base lithium 2,2,6,6-tetramethylpiperidide (LTMP) forms a carbenoid species which reacts with alkenes to provide vinylcyclopropenes: Synlett, 647 (1991):