5-BROMO-2-METHYL-2-PENTENE

Base Information

• Chemical Name: 5-BROMO-2-METHYL-2-PENTENE
• CAS No.: 2270-59-9
• Molecular Formula: C6H11Br
• Molecular Weight: 163.057
• Hs Code.: 29033990
• Mol file: 2270-59-9.mol

Synonyms:5-Bromo-2-methyl-2-pentene;

Chemical Property of 5-BROMO-2-METHYL-2-PENTENE

Chemical Property:

• Appearance/Colour: Colorless Liquid
• Vapor Pressure: 4.44mmHg at 25°C
• Melting Point: -102.35°C (estimate)
• Refractive Index: n20/D 1.476(lit.)
• Boiling Point: 152.6 °C at 760 mmHg
• Flash Point: 22.8 °C
• PSA: 0.00000
• Density: 1.215 g/cm³
• LogP: 2.73760
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly miscible with water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Bromo-2-methyl-2-pentene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-Bromo-2-methyl-2-pentene acts as a synthetic reagent, which is useful in the formation of sesqueterpenoid. It is also employed in the preparation of geranlol-3-14C. Further, it is used in the preparation of penifulvin A, which is a sesquiterpenoid with a novel dioxa-fenestrane structure.

Technology Process of 5-BROMO-2-METHYL-2-PENTENE

There total 15 articles about 5-BROMO-2-METHYL-2-PENTENE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2-cyclopropyl-2-propanol (930-39-2) → 1-bromo-4-methylpent-3-ene (2270-59-9)

Guidance literature:

With magnesium bromide; In diethyl ether; for 3h; Heating;

DOI:10.1080/00397919408010239

Reference yield: 88.0%

Cyclopropyl methyl ketone (765-43-5) + methylmagnesium bromide (75-16-1) → 1-bromo-4-methylpent-3-ene (2270-59-9)

Guidance literature:

Cyclopropyl methyl ketone; methylmagnesium bromide; In tetrahydrofuran; for 1h; Reflux; Inert atmosphere;

With sulfuric acid; In tetrahydrofuran; water; at 10 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03810

Reference yield: 82.0%

4-methylpent-3-en-1-ol (763-89-3) → 1-bromo-4-methylpent-3-ene (2270-59-9)

Guidance literature:

With pyridine; phosphorus tribromide; In diethyl ether; for 8h; Ambient temperature;

upstream raw materials:

2,5-dibromo-2-methylpentane

4-methylpent-3-en-1-ol

2-cyclopropyl-2-propanol

Potassium benzoate

Downstream raw materials:

3,7-dimethylocta-1,6-dien-3-ol

4-methyl-1,3-pentadiene

5-methylhex-4-ene-1-ol

2-(1-Hydroxy-1,5-dimethyl-hex-4-enyl)-5-methyl-phenol

Refernces

• 1、 Hiranuma, Sayoko,Shibata, Misako,Hudlicky, Tomas. "Studies in Cephalotaxus Alkaloids. Stereospecific Total Synthesis of Homoharringtonine". . p. 5321 - 5326. Retrieved 1983.
• 2、 Langhanki, Jens,Rudolph, Kristina,Erkel, Gerhard,Opatz, Till. "Total synthesis and biological evaluation of the natural product (-)-cyclonerodiol, a new inhibitor of IL-4 signaling". . p. 9707 - 9715. Retrieved 2014.
• 3、 Peter et al.. "". . p. 1262,1270. Retrieved 1977.
• 4、 Schwartz, Brett D.,Tilly, David P.,Heim, Ralf,Wiedemann, Stefan,Williams, Craig M.,Bernhardt, Paul V.. "Towards the total synthesis of vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A". . p. 3181 - 3192. Retrieved 2006.
• 5、 Harmon, Nyema M.,Huang, Xueting,Hsiao, Chia-Hung Christine,Wiemer, Andrew J.,Wiemer, David F.. "Incorporation of a FRET pair within a phosphonate diester". . . Retrieved 2021/06/16.
• 6、 Wang, Rui,Chen, Yi,Shu, Mao,Zhao, Wenwen,Tao, Maoling,Du, Chao,Fu, Xiaoya,Li, Ao,Lin, Zhihua. "AuCl3-Catalyzed Ring-Closing Carbonyl–Olefin Metathesis". supporting information. p. 1941 - 1946. Retrieved 2020/02/11.