33129-84-9

Usage

Uses

Used in Pharmaceutical Production:
p-tert-butylphenyl chloroformate is used as a versatile intermediate for the synthesis of pharmaceuticals. Its ability to undergo various chemical reactions makes it a valuable component in the production of a wide range of medications.
Used in Pesticide Production:
In the agricultural industry, p-tert-butylphenyl chloroformate is used as a key intermediate in the synthesis of pesticides. Its reactivity and solubility in organic solvents contribute to the development of effective pest control agents.
Used in Organic Synthesis:
p-tert-butylphenyl chloroformate is utilized as a reagent in organic synthesis across various chemical industries. Its capacity to participate in numerous chemical reactions allows for the creation of a broad spectrum of organic compounds.
Used as a Protecting Group in Peptide Synthesis:
In the field of peptide synthesis, p-tert-butylphenyl chloroformate serves as a protecting group for amines. This function is crucial for the selective protection of functional groups during the synthesis process, ensuring the successful formation of desired peptide sequences.
Used as a Precursor for Carbamates and Ureas Synthesis:
p-tert-butylphenyl chloroformate is employed as a precursor in the synthesis of carbamates and ureas in organic chemistry. Its role in the formation of these compounds is essential for the development of various chemical products and materials.
However, it is important to note that p-tert-butylphenyl chloroformate is a hazardous chemical with potential health and safety risks. Therefore, it should be handled and stored with care to minimize any risks associated with its use.

InChI:InChI=1/C11H13ClO2/c1-11(2,3)8-4-6-9(7-5-8)14-10(12)13/h4-7H,1-3H3

Upstream product

• 75-44-5 phosgene 
• 98-54-4 para-tert-butylphenol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 1002100-91-5 C₂₁H₂₄N₂O₃ 
• 1083072-41-6 C₄₂H₅₁N₃O₁₂ 
• 1202247-61-7 C₂₀H₂₄ClN₃O₂ 
• 1202247-74-2 C₂₁H₂₄F₃N₃O₂ 
• 1378950-04-9 C₂₁H₂₇NO₂ 
• 1417519-98-2 C₂₂H₂₄N₂O₃ 

Relevant academic research and scientific papers

Asymmetric o-to-c aryloxycarbonyl migration of indolyl carbonates using single-handed dynamic helical polyquinoxalines bearing 4-aminopyridyl groups as chiral nucleophilic catalysts

Use of single-handed dynamic helical macromolecules as nucleophilic catalysts in asymmetric Steglich-type O-to-C aryloxycarbonyl rearrangement of 3-substituted indol-2-yl aryl carbonates is demonstrated. Among several single-handed poly-(quinoxaline-2,3-diyl) copolymers (PQXap) bearing achiral 4-aminopyridin-3-yl groups at the 5-position of the quinoxaline rings, PQXmdpp and PQXapy, containing N-methylpyrrolidine-fused pyridin-3-yl and 4-(1-azetidinyl)pyridin-3-yl groups, respectively, showed higher enantioselectivity and catalytic activity than PQXdmap, bearing 4-dimethylamino-pyridine-3-yl groups. Substrates bearing p-(trifluoromethyl)phenyloxycarbonyl groups on both the nitrogen and oxygen atoms showed high reactivity, giving oxindoles with a quaternary stereogenic carbon center at their 3-positions in up to 97:3 enantiomeric ratio in THF. The macromolecular catalysts underwent inversion of their helix sense by solvent effect, allowing the same catalyst to give the opposite enantiomer in a mixture of methyl t-butyl ether and 1,1,2-trichloroethane (3:1). The macromolecular catalysts could be easily recovered by adding acetonitrile to the reaction mixture and were reused four times without reduction in enantioselectivity.

Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions

Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.

Visible-Light-Induced Intramolecular C(sp2)-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

Catalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates have been achieved under visible-light irradiation, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic aziridines. Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate. The chemoselectivity of the reaction, with alkyl olefin aziridination ? electron deficient olefin aziridination ≈ C(sp2)-H amination ? C(sp3)-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.

Evaluation of the analgesic effect of 4-anilidopiperidine scaffold containing ureas and carbamates

Fentanyl is a powerful opiate analgesic typically used for the treatment of severe and chronic pain, but its prescription is strongly limited by the well-documented side-effects. Different approaches have been applied to develop strong analgesic drugs with reduced pharmacologic side-effects. One of the most promising is the design of multitarget drugs. In this paper we report the synthesis, characterization and biological evaluation of twelve new 4-anilidopiperidine (fentanyl analogues). In vivo hot-Plate test, shows a moderate antinociceptive activity for compounds OMDM585 and OMDM586, despite the weak binding affinity on both μ and δ-opioid receptors. A strong inverse agonist activity in the GTP-binding assay was revealed suggesting the involvement of alternative systems in the brain. Fatty acid amide hydrolase inhibition was evaluated, together with binding assays of cannabinoid receptors. We can conclude that compounds OMDM585 and 586 are capable to elicit antinociception due to their multitarget activity on different systems involved in pain modulation.

Effect of acyclic monoterpene alcohols and their derivatives on TRP channels

A series of thirty-six geraniol, nerol, citronellol, geranylamine, and nerylamine derivatives was synthesized and tested on TRPA1, TRPM8, and TRPV1 channels. Most of them acted as strong modulators of TRPA1 channels with EC50 and/or IC50 values 1 μM. None was able to significantly activate TRPM8 channels, while thirteen of them behaved as 'true' TRPM8 antagonists. Little or no effect was generally observed on TRPV1 channels. Some of the compounds examined, that is, compounds 1d,g,n, 2c,d,h,i,o, 3b,e exhibited an appreciable selectivity for TRPA1 subtype.

Tetrahydro-β-carboline derivatives targeting fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channels

A series of twenty-five derivatives of tetrahydro-β-carbolines 1-3 was synthesized and assayed on FAAH and TRPV1 and TRPA1 channels. Four carbamates, that is, 5a,c,e, and 9b inhibited FAAH with significant potency and interacted also effectively with TRPV1 and TRPA1 nociceptive receptors, while ureas 7b,d,f, and 8a,b were endowed with specific submicromolar TRPV1 modulating activities.

β-type glycosidic bond formation by palladium-catalyzed decarboxylative allylation

The efficient and stereoselective construction of glycosidic linkages is of great significance in carbohydrate chemistry due to the ubiquitous existence of numerous biologically active natural products and saccharides. Although great efforts have been devoted to stereoselective glycosylations in the past few decades, constructing glycosidic bonds with high efficiency and selectivity remains a challenge and continues to be an important area in carbohydrate research. Phenols are widely used as nucleophiles in palladium-catalyzed allylation. In contrast, the possibility of using aliphatic alcohols as nucleophiles is not as thoroughly explored. The modified reaction conditions were then applied to other substrates. Originating from easily prepared carbonates, various glycosides, such as phenolic Oglycosides, thiophenolic S-glycoside, aliphatic O-glycosides, and even disaccharides, were synthesized in good yields by means of a palladium-catalyzed decarboxylative allylation.

Modulation of thermo-transient receptor potential (thermo-TRP) channels by thymol-based compounds

A series of thirty-three thymol, p-cymene-3-carboxylic acid, and 3-amino-p-cymene derivatives was synthesized and tested on TRPA1, TRPM8, and TRPV3 channels. Most of them acted as strong modulators of TRPA1, TRPM8, and TRPV3 channels with EC50 and/or IC50 values distinctly lower than those of thymol and related monoterpenoids. Some of the compounds examined, that is, 3c, 4e, f, 6b, and 8b exhibited an appreciable subtype-selectivity.

Synthesis and biological evaluation of piperazinyl carbamates and ureas as fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channel dual ligands

The evaluation of a series of piperazinyl carbamates and ureas, designed on the basis of previously reported TRPV1 antagonists and FAAH inhibitors, led to the identification of some 'dual-action' compounds targeting both FAAH and TRPV1 or TRPA1 receptors.

Carbamate triserine lactone receptors for anion recognition

We have taken advantage of the ability of the cyclic triester of l-serine to organize ligand units appended to the three α-amine functionalities, as in enterobactin, a siderophore produced by enteric bacteria that binds ferric ion exceptionally well (Kf = 1049). As an extension of the preorganization concept, this work describes the preparation and characterization of carbamate triserine lactone receptors 1-6 and their ability to act as molecular receptors for anions. These receptors bind halides (F- ? Cl- > Br- > I-) with binding constants K in the range 21-7350 L mol-1.