1238196-66-1 | 4-Chloro-2-hydroxyphenylboronic acid

Packsize	Purity	Availability	Price	Discounted Price
250mg	98%	in stock	$20.00	$14.00
1g	98%	in stock	$25.00	$18.00
2500mg	98%	in stock	$62.00	$44.00
5g	98%	in stock	$75.00	$53.00
10g	98%	in stock	$143.00	$101.00
25g	98%	in stock	$353.00	$248.00
100g	98%	in stock	$1,314.00	$920.00

Description

• Catalog Number: AA27166
• Chemical Name: 4-Chloro-2-hydroxyphenylboronic acid
• CAS Number: 1238196-66-1
• Molecular Formula: C6H6BClO3
• Molecular Weight: 172.37404
• MDL Number: MFCD18383546
• SMILES: Clc1ccc(c(c1)O)B(O)O

Computed Properties

• Complexity: 133
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 1

Upstream Synthesis Route

The upstream synthetic route of 4-Chloro-2-hydroxyphenylboronic acid can proceed as follows:

1. **Synthesis of 4-Chlorophenol:**
- Chlorobenzene can be hydroxylated using NaOH under elevated temperatures and pressure in the presence of a catalyst such as copper to obtain 4-chlorophenol.

2. **Protection of the Hydroxyl Group:**
- The hydroxyl group of 4-chlorophenol can be protected by converting it to its tert-butyldimethylsilyl (TBDMS) ether using tert-butyldimethylsilyl chloride and imidazole in the presence of an organic solvent like dichloromethane (DCM).

3. **Boronate Ester Formation:**
- The protected 4-chlorophenol can be treated with a boronic ester-forming reagent, such as triisopropyl borate, in the presence of a catalytic amount of palladium on carbon (Pd/C) under an inert atmosphere to yield the 4-chlorophenylboronic ester.

4. **Deprotection:**
- The TBDMS group can be removed using acids like hydrochloric acid or tetrabutylammonium fluoride (TBAF), regenerating the free hydroxyl group.

5. **Purification:**
- The resulting mixture can be purified by column chromatography or crystallization, yielding pure 4-Chloro-2-hydroxyphenylboronic acid.

Throughout this process, stoichiometry, temperature, solvents, and reaction times are optimized based on specific reactant behavior. Safety protocols for handling chlorinated compounds and boronic acids must be adhered to at all times to ensure a safe and efficient synthesis pathway.