4-Bromo-1,1,1-trimethoxybutane

Base Information

• Chemical Name: 4-Bromo-1,1,1-trimethoxybutane
• CAS No.: 55444-67-2
• Molecular Formula: C7 H15 Br O3
• Molecular Weight: 227.098
• European Community (EC) Number: 627-581-9
• DSSTox Substance ID: DTXSID90409285
• Nikkaji Number: J1.728.041D
• Wikidata: Q82215048
• Mol file: 55444-67-2.mol

Synonyms:4-Bromo-1,1,1-trimethoxybutane;55444-67-2;Trimethyl 4-bromoorthobutyrate;SCHEMBL835470;1-bromo-4,4,4-trimethoxybutane;DTXSID90409285;QBLJMYITBNHQOT-UHFFFAOYSA-N;MFCD00075197;Trimethyl 4-bromoorthobutyrate, 95%;BS-23879;CS-0204809

Chemical Property of 4-Bromo-1,1,1-trimethoxybutane

Chemical Property:

• Vapor Pressure: 0.0271mmHg at 25°C
• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 70 °C0.7 mm Hg(lit.)
• Flash Point: 163 °F
• PSA: 27.69000
• Density: 1.309 g/mL at 25 °C(lit.)
• LogP: 1.75450
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 226.02046
• Heavy Atom Count: 11
• Complexity: 85.4

Purity/Quality:

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

Trimethyl 4-bromoorthobutyrate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(CCCBr)(OC)OC
• Uses: Trimethyl 4-bromoorthobutyrate is used in the synthesis of an intermediate of hydrophilic chemiluminescent acridinium esters containing N-sulfopropyl groups which are extremely useful labels in the clinical diagnostics industry especially in automated immunochemical analyzers such as Siemens Healthcare Diagnostics'' ADVIA Centaur systems.

Technology Process of 4-Bromo-1,1,1-trimethoxybutane

There total 2 articles about 4-Bromo-1,1,1-trimethoxybutane 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%

methanol (67-56-1) + methyl-4-bromo-1-butane imidate hydrochloride (21367-90-8) → trimethyl ortho-4-bromobutanoate (55444-67-2)

Guidance literature:

In hexane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96065-X

Reference yield:

→ trimethyl ortho-4-bromobutanoate (55444-67-2)

Guidance literature:

4-Br-butyronitril;

Reference yield: 89.0%

(3R*,4S*)-3-(but-3-enyl)-4-(tert-butyldimethylsilyloxy)-3-ethynyl-2-methylcyclohexene + trimethyl ortho-4-bromobutanoate (55444-67-2) → methyl 6-((1R*,6S*)-1-(but-3-enyl)-6-(tert-butyldimethylsilyloxy)-2-methylcyclohex-2-enyl)hex-5-ynoate

Guidance literature:

(3R*,4S*)-3-(but-3-enyl)-4-(tert-butyldimethylsilyloxy)-3-ethynyl-2-methylcyclohexene; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

trimethyl ortho-4-bromobutanoate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/ejoc.201100871

upstream raw materials:

methanol

methyl-4-bromo-1-butane imidate hydrochloride

Downstream raw materials:

3-(3-Carboxypropyl)-2-cyclohexenon-methylester

(R)-1-(4,4,4-Trimethoxy-butoxy)-3-trityloxy-propan-2-ol

trimethyl-4-(p-tolylsulfonyl)-orthobutanoate

dimethyl subarate