680190-96-9

Basic information

• Product Name: tert-Butyl 4-ethynylbenzylcarbamate
• Synonyms: tert-Butyl 4-ethynylbenzylcarbamate;tert-butyl N-[(4-ethynylphenyl)methyl]carbamate
• CAS NO: 680190-96-9
• Molecular Formula: C₁₄H₁₇NO₂
• Molecular Weight: 231.29028
• Mol File: 680190-96-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: tert-Butyl 4-ethynylbenzylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl 4-ethynylbenzylcarbamate(680190-96-9)
• EPA Substance Registry System: tert-Butyl 4-ethynylbenzylcarbamate(680190-96-9)

Safety Data

• Hazardous Substances Data: 680190-96-9(Hazardous Substances Data)

Usage

Description

Tert-Butyl 4-ethynylbenzylcarbamate is a chemical compound with the molecular formula C16H17NO2. It is an ethynylbenzylcarbamate derivative characterized by the presence of a tert-butyl group and an ethynyl group attached to the benzene ring, along with a carbamate functional group attached to the benzyl group. tert-Butyl 4-ethynylbenzylcarbamate is widely utilized in organic synthesis and medicinal chemistry due to its versatile chemical properties.

Uses

Used in Organic Synthesis:
Tert-Butyl 4-ethynylbenzylcarbamate is used as a building block for the synthesis of various biologically active compounds. Its unique structure allows it to be a key component in creating pharmaceutical drugs and agrochemicals, contributing to the development of new and effective treatments and products.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, tert-Butyl 4-ethynylbenzylcarbamate is employed as a precursor in the design and synthesis of potential therapeutic agents. Its functional groups enable it to be modified and incorporated into diverse molecular frameworks, enhancing the discovery of novel drugs with improved pharmacological properties.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
Tert-Butyl 4-ethynylbenzylcarbamate is used as a reagent in Suzuki-Miyaura cross-coupling reactions, a class of palladium-catalyzed reactions that facilitate the formation of carbon-carbon bonds. Its participation in these reactions allows for the efficient construction of complex organic molecules, which are valuable in the synthesis of pharmaceuticals and other specialty chemicals.
Used in Sonogashira Coupling Reactions:
Additionally, tert-Butyl 4-ethynylbenzylcarbamate is utilized in Sonogashira coupling reactions, which are palladium-catalyzed reactions that form carbon-carbon bonds between sp and sp carbons. This reagent plays a crucial role in the synthesis of conjugated molecules, such as those found in organic materials and pharmaceutical agents, further expanding its applications in chemical research and development.

Upstream product

• 680190-95-8 (4-trimethylsilylethyn-1-ylbenzyl)carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 39959-59-6 4-iodobenzyl amine 
• 189132-01-2 4-[(N-tert-butyloxycarbonylamino)methyl]iodobenzene 
• 16004-15-2 1-bromomethyl-4-iodobenzene 
• 680190-94-7 1-azidomethyl-4-iodo-benzene 
• 59528-27-7 p-iodobenzylamine hydrochloride 
• 68819-84-1 tert-butyl N-(4-bromobenzyl)carbamate 
• 26177-44-6 4-bromobenzylamine hydrochloride 

Downstream Products

• 803704-45-2 4,4'-butadiynedibenzylamine 
• 197844-23-8 (4-ethynylphenyl)methanamine 
• 1381949-73-0 ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate 
• 1482499-10-4 C₂₉H₂₆Fe₂N₂O₇S₂ 

Relevant articles and documents

The Delicate Balance of Preorganisation and Adaptability in Multiply Bonded Host–Guest Complexes

Rigidity and preorganisation are believed to be required for high affinity in multiply bonded supramolecular complexes as they help reduce the entropic penalty of the binding event. This comes at the price that such rigid complexes are sensitive to small geometric mismatches. In marked contrast, nature uses more flexible building blocks. Thus, one might consider putting the rigidity/high-affinity notion to the test. Multivalent crown/ammonium complexes are ideal for this purpose as the monovalent interaction is well understood. A series of divalent complexes with different spacer lengths and rigidities has thus been analysed to correlate chelate cooperativities and spacer properties. Too long spacers reduce chelate cooperativity compared to exactly matching ones. However, in contrast to expectation, flexible guests bind with chelate cooperativities clearly exceeding those of rigid structures. Flexible spacers adapt to small geometric host–guest mismatches. Spacer–spacer interactions help overcome the entropic penalty of conformational fixation during binding and a delicate balance of preorganisation and adaptability is at play in multivalent complexes.

Exceptional poly(acrylic acid)-based artificial [FeFe]-hydrogenases for photocatalytic H2 production in water

Light, polymer, action: A set of water-soluble poly(acrylic acid) catalysts PAA-g-Fe2S2 containing {Fe2S2}, an [FeFe]-hydrogenase active-site mimic, is synthesized. This system, combined with CdSe quantum dots a

Lacosamide isothiocyanate-based agents: Novel agents to target and identify lacosamide receptors

(R)-Lacosamide ((R)-2, (R)-N-benzyl 2-acetamido-3-methoxypropionamide) has recently gained regulatory approval for the treatment of partial-onset seizures in adults.Whole animal pharmacological studies have documented that (R)-2 function is unique. A robust strategy is advanced for the discovery of interacting proteins associated with function and toxicity of (R)-2 through the use of (R)-2 analogues, 3, which contain "affinity bait (AB)" and "chemical reporter (CR)" functional groups. In 3, covalent modification of the interacting proteins proceeds at the AB moiety, and detection or isolation of the selectively captured protein occurs through the bioorthogonal CR group upon reaction with an appropriate probe. We report the synthesis, pharmacological evaluation, and interrogation of the mouse soluble brain proteome using 3 where the AB group is an isothiocyanate moiety. One compound, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy) propionamide ((R)-9), exhibited excellent seizure protection in mice, and like (R)-2, anticonvulsant activity principally resided in the (R)-stereoisomer. Several proteins were preferentially labeled by (R)-9 compared with (S)-9, including collapsin response mediator protein 2. 2009 American Chemical Society.