913835-51-5 | Ethyl 3-boronocinnamate

Packsize	Purity	Availability	Price	Discounted Price
250mg	98%	in stock	$50.00	$35.00
1g	98%	in stock	$106.00	$75.00
5g	98%	in stock	$387.00	$271.00
10g	98%	in stock	$682.00	$478.00
25g	98%	in stock	$1,319.00	$923.00

Description

• Catalog Number: AD10287
• Chemical Name: Ethyl 3-boronocinnamate
• CAS Number: 913835-51-5
• Molecular Formula: C11H13BO4
• Molecular Weight: 220.0295
• MDL Number: MFCD08689480
• SMILES: CCOC(=O)/C=C/c1cccc(c1)B(O)O

Computed Properties

• Complexity: 252
• Covalently-Bonded Unit Count: 1
• Defined Bond Stereocenter Count: 1
• Heavy Atom Count: 16
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 5

Upstream Synthesis Route

The upstream synthesis route of Ethyl 3-boronocinnamate typically involves the following steps:

1. **Preparation of Ethyl Cinnamate:**
Starting from cinnamic acid, esterification is performed using ethanol in the presence of a strong acid catalyst like sulfuric acid to produce ethyl cinnamate.

2. **Formation of the Boronic Ester:**
The next key step involves the conversion of ethyl cinnamate into its boronate counterpart. This is performed via a hydroboration reaction, where ethyl cinnamate undergoes an addition reaction with a boron-containing reagent such as triisopropyl borate (i-Bu_3B) or bis(pinacolato)diboron [(Bpin)_2] in the presence of a suitable catalyst, commonly a palladium catalyst like Pd(dppf)Cl_2, and a base like potassium acetate.

3. **Purification:**
After the formation of the boronic ester, purification is necessary to remove any side-products or unreacted starting materials. This is typically carried out through chromatography or recrystallization.

4. **Verification:**
The final product, Ethyl 3-boronocinnamate, is then characterized and verified using techniques such as NMR, IR, and MS to ensure the structure and purity meet the required specifications.

Each of these steps must be optimized in terms of reaction conditions – including temperature, reaction time, and stoichiometry of reagents – to maximize yield and purity of the final product.