84695-29-4

Basic information

• Product Name: (E)-3-BroMo-2-Methyl-2-propen-1-ol
• Synonyms: (E)-3-BroMo-2-Methyl-2-propen-1-ol;(2E)-3-BroMo-2-Methyl-2-propen-1-ol;3-BroMo-2-Methyl-2-propen-1-ol
• CAS NO: 84695-29-4
• Molecular Formula: C₄H₇BrO
• Molecular Weight: 151
• Product Categories: Aliphatics
• Mol File: 84695-29-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 170.0±15.0 °C(Predicted)
• Appearance: /
• Density: 1.530±0.06 g/cm3(Predicted)
• PKA: 13.85±0.10(Predicted)
• CAS DataBase Reference: (E)-3-BroMo-2-Methyl-2-propen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-BroMo-2-Methyl-2-propen-1-ol(84695-29-4)
• EPA Substance Registry System: (E)-3-BroMo-2-Methyl-2-propen-1-ol(84695-29-4)

Safety Data

• Hazardous Substances Data: 84695-29-4(Hazardous Substances Data)

Usage

Description

(E)-3-Bromo-2-methyl-2-propen-1-ol is an organic compound with the chemical formula C4H7BrO. It is a chiral molecule with a double bond and a bromine atom, which gives it unique chemical properties and reactivity. (E)-3-BroMo-2-Methyl-2-propen-1-ol is known for its role in the synthesis of various biologically active compounds and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
(E)-3-Bromo-2-methyl-2-propen-1-ol is used as a key intermediate in the stereoselective and enantioselective preparation of omuralide, 7-epi-omuralide, and lactacystin. These compounds have significant biological activities and potential applications in the development of new drugs for the treatment of various diseases.
In the synthesis of omuralide, (E)-3-Bromo-2-methyl-2-propen-1-ol serves as a starting material, which undergoes a series of chemical reactions to form the final product. Omuralide is a potent immunosuppressive agent that has been used in the treatment of autoimmune diseases and transplantation.
7-epi-Omuralide, a derivative of omuralide, is also synthesized using (E)-3-Bromo-2-methyl-2-propen-1-ol as a key intermediate. It exhibits similar biological activities as omuralide and has potential applications in the pharmaceutical industry.
Lactacystin, another compound synthesized using (E)-3-Bromo-2-methyl-2-propen-1-ol, is a potent and selective inhibitor of the 20S proteasome. It has been extensively studied for its potential use in the treatment of cancer and neurodegenerative diseases.

Upstream product

• 75-24-1 trimethylaluminum 
• 107-19-7 propargyl alcohol 
• 40053-01-8 methyl 3-bromo-2-methyl-2-propenoate 
• 40053-01-8 methyl (E)-3-bromo-2-methyl-2-propenoate 
• 35911-17-2 1,3-dibromo-2-methylpropene 
• 24557-13-9 (E)-3-bromomethacrylic acid 

Downstream Products

• 1015841-29-8 [(E)-3-bromo-2-methylprop-2-en-(E)-ylidene]-((2R,4S,5R)-4-isopropyl-2-phenyl-[1,3]-dioxan-5-yl)amine 
• 221290-59-1 (E)-4-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-2-methyl-but-2-en-1-ol 

Relevant articles and documents

Single-electron/pericyclic cascade for the synthesis of dienes

The highly efficient and diastereoselective synthesis of E dienes has been accomplished through radical cyclization of bromoallyl hydrazones. This methodology has been further extended to generate these products through a one-pot condensation/radical cyclization/cycloreversion cascade from simple aldehyde starting materials in high yields (>75 %) and high diastereoselectivities (>95:5). Mechanistic investigations suggest that the cascade reaction proceeds through a cyclic diazene intermediate prior to the cycloreversion.

Synthesis of the Conjugated Tetraene Acid Side Chain of Mycolactone e by Suzuki-Miyaura Cross-Coupling Reaction of Alkenyl Boronates

The conjugated tetraene acid side chain of mycolactone E has been synthesized by the cross-coupling reaction of a trisubstituted triene bromide with a trisubstituted alkenyl boronate catalyzed by Pd(OAc)2-Aphos-Y under mildly basic conditions [K3PO4·3H2O, H2O, tetrahydrofuran (THF), 35 C, 18 h]. The conjugated tetraene product was obtained in 85 % yield without geometrical isomer(s) under the catalytic conditions. These results demonstrated that the coupling of alkenyl halides with alkenyl boronates catalyzed by Pd(OAc)2-Aphos-Y in combination with CuI-catalyzed regio- and stereoselective alkyne borylation offers an efficient synthetic tool for accessing conjugated polyene molecules.

Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment

(Chemical Equation Presented) A synthesis of the C(1)-C(11) fragment of apoptolidin A has been accomplished by a convergent route involving the stereoselective glycosidation of 9 and the Suzuki cross-coupling reaction of bromodienoate 7 and the vinylboran