tert-Butyl (3-amino-2,6-difluorophenyl)carbamate: FAQs
tert-Butyl (3-amino-2,6-difluorophenyl)carbamate: FAQs
tert-Butyl (3-amino-2,6-difluorophenyl)carbamate is a Boc-protected aromatic diamine building block bearing two ortho-fluorine substituents, widely used as a versatile intermediate in medicinal chemistry and drug discovery synthesis.
- Chemical Name
- tert-Butyl (3-amino-2,6-difluorophenyl)carbamate
- SKU / Catalog Number
- T734784
- Functional Groups
- Boc-protected secondary amine and free primary amine on a difluorinated aromatic ring
- Key Application
- Intermediate for synthesis of fluorinated pharmaceuticals and agrochemicals
- Protecting Group
- tert-Butoxycarbonyl (Boc), removable under mild acidic conditions
- Fluorine Substitution Pattern
- 2,6-difluoro (ortho, ortho) on the aniline ring
What Is tert-Butyl (3-amino-2,6-difluorophenyl)carbamate?
tert-Butyl (3-amino-2,6-difluorophenyl)carbamate (Aladdin SKU: T734784) is an aromatic compound featuring a 1,3-diamine motif on a benzene ring that also carries fluorine atoms at the 2- and 6-positions (ortho to the Boc-protected nitrogen). One amino group is protected as the tert-butoxycarbonyl (Boc) carbamate, leaving the other amino group free for selective synthetic transformations.
The combination of a free primary amine, a Boc-masked amine, and two electron-withdrawing fluorine substituents in defined positions makes this molecule a highly differentiated bifunctional building block. It is particularly valuable in medicinal chemistry workflows where chemoselective reactions and controlled orthogonal deprotection strategies are required.
What Are the Key Chemical Properties and Handling Requirements?
The molecule contains two distinct nitrogen functionalities: a free aryl amine (–NH2) at the 3-position and a Boc carbamate at the 1-position of the difluorophenyl ring. The flanking fluorine atoms at positions 2 and 6 exert strong inductive electron-withdrawing effects, reducing the nucleophilicity of the adjacent Boc-nitrogen and influencing the reactivity of the free amine.
As with most Boc-protected amines, the carbamate is stable under basic and neutral conditions but is cleaved under mild acid conditions (e.g., trifluoroacetic acid in dichloromethane, or dilute HCl in dioxane), regenerating the free diamine. The free primary amine is reactive toward acylation, sulfonylation, reductive amination, and palladium-catalysed cross-coupling reactions.
Standard laboratory precautions for handling aromatic amine compounds apply: avoid inhalation of dust, use appropriate personal protective equipment (gloves, lab coat, eye protection), and conduct operations in a well-ventilated area or fume hood. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for full hazard information before use.
What Are the Typical Synthetic Applications?
tert-Butyl (3-amino-2,6-difluorophenyl)carbamate serves as a versatile intermediate in the construction of complex fluorinated molecules. Representative applications include:
- Pharmaceutical synthesis: The difluorophenyl motif is a recurring structural element in approved drugs and clinical candidates. Fluorine substitution modulates lipophilicity, metabolic stability, and membrane permeability of drug molecules.
- Orthogonal protection strategies: The Boc group allows chemists to selectively engage the free amine first, then unmask the second amine at a later stage for further elaboration without cross-reactivity.
- Heterocycle formation: The 1,3-diamine pattern (once both groups are deprotected or selectively activated) can be exploited in cyclisation reactions to access fluorinated benzimidazoles, quinoxalines, and related scaffolds.
- Agrochemical intermediates: Fluorinated aniline derivatives are widely used in the synthesis of herbicides, fungicides, and insecticides.
Researchers are advised to validate reaction conditions with small-scale trials before scale-up, particularly when deprotecting the Boc group in the presence of the ortho-fluorines, which may alter the rate of acid-mediated cleavage relative to unsubstituted analogues.
Storage, Stability, and Shipping
As a general guideline for Boc-protected aromatic amine building blocks of this type, the compound should be stored in a cool, dry, and well-ventilated location away from heat, moisture, and incompatible materials such as strong acids and strong oxidising agents. Refrigerated storage (2–8 °C) in a tightly sealed container under inert atmosphere (nitrogen or argon) is recommended to maximise shelf life and prevent degradation of the amine functionality.
Please refer to the Aladdin Scientific product page for T734784 and the accompanying SDS for the confirmed storage temperature, shelf life, and any specific stability data. For international shipments, customs regulations regarding aromatic amine compounds may apply; Aladdin Scientific's logistics team can advise on documentation requirements.
How to Order T734784 from Aladdin Scientific
tert-Butyl (3-amino-2,6-difluorophenyl)carbamate is available from Aladdin Scientific under catalog number T734784. To place an order:
- Search for T734784 or the full IUPAC name on the Aladdin Scientific website.
- Select the required pack size and quantity, then add to cart.
- Proceed through the checkout process. Purchase orders from institutions can typically be accommodated; contact the sales team for invoicing arrangements.
- For bulk quantities, custom packaging, or technical enquiries, contact Aladdin Scientific customer support directly.
Aladdin Scientific offers multiple payment options and can arrange domestic and international shipping. Reward points, coupons, and promotional pricing may be available — check your account dashboard or contact your regional sales representative for current offers.
Frequently asked questions
What is the difference between the two amine groups in this compound, and how do I selectively react each one?
The compound contains a free primary aryl amine at the 3-position and a Boc-protected amine at the 1-position. The free amine can be selectively acylated, alkylated, or coupled under standard conditions without disturbing the Boc group. Once transformations on the free amine are complete, the Boc group can be removed using mild acidic conditions (e.g., TFA/DCM or HCl in dioxane) to reveal the second amine for further synthetic steps.
How do the ortho-fluorine substituents affect the reactivity of the compound?
The two fluorine atoms at the 2- and 6-positions exert strong electron-withdrawing inductive effects on the ring, which reduces the nucleophilicity of both nitrogen atoms compared with non-fluorinated analogues. This effect also influences the rate of Boc deprotection under acidic conditions and may require optimisation of reaction conditions relative to standard Boc-protected anilines. The fluorines can also participate in nucleophilic aromatic substitution under appropriate conditions, which should be taken into account when planning synthetic routes.
What solvents are suitable for dissolving T734784?
As a general guide for aromatic Boc-amine building blocks of this class, common polar aprotic solvents such as DMSO, DMF, and acetonitrile, as well as chlorinated solvents such as dichloromethane, are expected to provide good solubility. Solubility in aqueous systems is generally low for lipophilic fluorinated aryl amines. Researchers should verify solubility experimentally for their specific application, and consult the product SDS for any additional guidance.
Is T734784 available for bulk or custom orders?
Yes. Aladdin Scientific can accommodate bulk quantity requests and custom packaging for T734784. Contact the Aladdin Scientific sales or customer service team with your specific quantity requirements, timeline, and any purity or analytical documentation needs. Quotations for bulk orders are available upon request.
What safety precautions should I follow when handling this compound?
Standard precautions for handling aromatic amine compounds apply: wear appropriate PPE including chemical-resistant gloves, a laboratory coat, and safety eyewear. Avoid inhaling dust or vapours and work in a well-ventilated area or fume hood. In case of skin or eye contact, rinse immediately with plenty of water and seek medical advice. Always consult the full Safety Data Sheet (SDS) for T734784 provided by Aladdin Scientific before handling the compound.
References
- Aladdin Scientific product page for tert-Butyl (3-amino-2,6-difluorophenyl)carbamate, SKU T734784.
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience: Hoboken, NJ, 2007. (General reference for Boc protection/deprotection chemistry.)
- Hagmann, W. K. The Many Roles for Fluorine in Medicinal Chemistry. J. Med. Chem. 2008, 51, 4359–4369. doi:10.1021/jm800219f
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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