NorrChemica™
(4-Boc-aminophenyl)boronic Acid
(4-Boc-aminophenyl)boronic Acid | CAS 380430-49-9 | ≥98.0%
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Technical Specifications
| CAS Number | 380430-49-9 |
| EC / EINECS Number | 670-415-5 |
| MDL Number | MFCD02093054 |
| SMILES | B(C1=CC=C(C=C1)NC(=O)OC(C)(C)C)(O)O |
| InChI | InChI=1S/C11H16BNO4/c1-11(2,3)17-10(14)13-9-6-4-8(5-7-9)12(15)16/h4-7,15-16H,1-3H3,(H,13,14) |
| InChIKey | UBVOLHQIEQVXGM-UHFFFAOYSA-N |
| PubChem CID | 3613184 |
| Molecular Formula | C₁₁H₁₆BNO₄ |
| Molecular Weight | 237.06 g/mol |
| Melting Point | 199-204 °C |
| Solubility | Slightly soluble in water; soluble in alcoholic solvents, acetonitrile, DMF, DMSO |
| Purity | ≥98%. May contain varying amounts of the corresponding boronic acid anhydrides. |
| Physical Form | White to light orange powder |
| HS Code | 2931.90 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store refrigerated (2–8 °C) in a tightly sealed container |
Product Description & Scientific Applications
(4-Boc-aminophenyl)boronic Acid is a Boc-protected aminophenylboronic acid for introducing a masked 4-aminophenyl unit into coupled aryl frameworks.
May contain small amounts of the cyclic anhydride 4-Boc-aminophenylboroxine. Under aqueous or basic coupling conditions the two forms re-equilibrate and the impact on yield is minor.
Applications and Reactions
Suzuki–Miyaura cross-coupling: couples with aryl, heteroaryl, or alkenyl electrophiles to give Boc-protected 4-aminobiaryl and related heteroaryl products.
Orthogonal protected-aniline handle: the boronic acid reacts at C–B while the Boc-protected amine is retained through many neutral or basic coupling conditions.
4-Aminobiaryl precursor: acid-mediated Boc removal after coupling reveals the corresponding aniline for downstream functionalisation.
Amide, sulfonamide, and urea diversification: the deprotected aniline provides a practical handle for late-stage derivatisation of coupled biaryl intermediates.
Rhodium-catalysed allylic substitution: documented as an arylboronic-acid partner in desymmetrisation of meso-cyclic allylic dicarbonates via SN2′-type C–C bond formation.
Protected boronate derivatives: precursor to pinacol, neopentyl glycol, and related boronate forms where improved handling or staged coupling is preferred.
Further Reading
For boronic acids, boronic esters, protodeboronation, boroxine content, and Suzuki–Miyaura reagent selection, see NorrChemica's Lab Journal guide: Choosing Your Boron Source for Suzuki–Miyaura Coupling.
Shipping Destinations
- EU & UK: Priority delivery, 2–5 business days.
- United States (DDP): 3–7 business days, duties and taxes prepaid.
- EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
- Worldwide: 7–14 business days, selected locations.
Safety Information
| GHS Pictograms |
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| Signal Word | Warning |
| Hazard Class | None — not subject to transport regulations |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
| H-Statements | H315 - H319 - H335 |
| P-Statements | P261 - P264 - P271 - P280 - P302+P352 - P304+P340 - P305+P351+P338 - P332+P313 - P337+P313 - P362+P364 - P501 |
Documentation
| Safety Data Sheet | Download PDF |
