35718-08-2

Basic information

• Product Name: PROPARGYL CHLOROFORMATE
• Synonyms: PROPARGYL CHLOROFORMATE;PROPARGYL CHLOROFORM;Prop-2-ynyl carbonochloridate;Propargyloxycarbonyl chloride;2-Propynyl chloroformate;Carbonochloridic acid,2-propyn-1-yl ester
• CAS NO: 35718-08-2
• Molecular Formula: C₄H₃ClO₂
• Molecular Weight: 118.52
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 35718-08-2.mol

Chemical Properties

• Boiling Point: 118-122 °C(lit.)
• Flash Point: 30 °C
• Appearance: /
• Density: 1.215 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.65 psi ( 20 °C)
• Refractive Index: n20/D 1.435(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• BRN: 1745399
• CAS DataBase Reference: PROPARGYL CHLOROFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPARGYL CHLOROFORMATE(35718-08-2)
• EPA Substance Registry System: PROPARGYL CHLOROFORMATE(35718-08-2)

Safety Data

• Hazard Codes: T
• Statements: 10-22-23/24-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3390 6.1/PG 1
• WGK Germany: 3
• F: 19
• Hazardous Substances Data: 35718-08-2(Hazardous Substances Data)

Usage

Uses

Propargyl chloroformate can be utilized as a linker for various screening applications.

InChI:InChI=1/C4H3ClO2/c1-2-3-7-4(5)6/h1H,3H2

Upstream product

• 75-44-5 phosgene 
• 107-19-7 propargyl alcohol 
• 109-89-7 diethylamine 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 439912-45-5 ((prop-2-yn-1-yloxy)carbonyl)-L-phenylalanine 
• 444574-98-5 Poc-Phg-OH 
• 439912-32-0 propargyl pentafluorophenyl carbonate 
• 396684-09-6 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(5-fluoro-2-oxo-4-prop-2-ynyloxycarbonylamino-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 123477-57-6 pyrrolidine-1-carboxylic acid prop-2-ynyl ester 
• 768387-56-0 di(prop-2-ynyl) piperazine-1,4-dicarboxylate 
• 114406-39-2 prop-2-yn-1-yl morpholine-4-carboxylate 
• 146135-07-1 prop-1-yn-3-yl N-n-dodecylcarbamate 
• 828927-33-9 prop-2-yn-1-yl prop-2-yn-1-ylcarbamate 
• 828927-34-0 ((S)-1-Prop-2-ynylcarbamoyl-ethyl)-carbamic acid prop-2-ynyl ester 
• 828927-35-1 [(S)-1-((S)-1-Prop-2-ynylcarbamoyl-ethylcarbamoyl)-ethyl]-carbamic acid prop-2-ynyl ester 
• 845253-39-6 carbonic acid prop-2-ynyl ester 2-(4-prop-2-ynyloxycarbonylamino-phenyl)-ethyl ester 
• 904704-08-1 3-[3-(2-methoxycarbonyl-2-prop-2-ynyloxycarbonylamino-ethyl)-phenyl]-2-prop-2-ynyloxycarbonylaminopropionic acid methyl ester 

Relevant articles and documents

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Benzimidazolinone-Free Peptide o-Aminoanilides for Chemical Protein Synthesis

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Synthesis of Supramolecular Iridium Catalysts and Their Use in Enantioselective Visible-Light-Induced Reactions

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A Turn-On Fluorescent Probe for Highly Selective and Sensitive Detection of Palladium

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Thiol-yne radical reaction mediated site-specific protein labeling via genetic incorporation of an alkynyl-l-lysine analogue

Three alkyne-containing pyrrolysine derivatives were synthesized and genetically encoded into proteins by a mutant PylRS-tRNA pair with high efficiencies. With these alkyne handles, site-specific dual labeling of proteins can be achieved via a bioorthogonal thiol-yne ligation reaction.

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Sirtuins are NAD+ dependent deacetylases that modulate various essential cellular functions. Development of peptide based inhibitors of Sir2s would prove useful both as pharmaceutical agents and as effectors by which downstream cellular alterations can be monitored. Click chemistry that utilizes Huisgen's 1,3-dipolar cycloaddition permits attachment of novel modifications onto the side chain of lysine. Herein, we report the synthesis of peptide analogues prepared using click reactions on Nε-propargyloxycarbonyl protected lysine residues and their characterization as inhibitors of Plasmodium falciparum Sir2 activity. The peptide based inhibitors exhibited parabolic competitive inhibition with respect to acetylated-peptide substrate and parabolic non-competitive inhibition with NAD+ supporting the formation of EI2 and E·NAD+·I2 complexes. Cross-competition inhibition analysis with the non-competitive inhibitor nicotinamide (NAM) ruled out the possibility of the NAM-binding site being the second inhibitor binding site, suggesting the presence of a unique alternate pocket accommodating the inhibitor. One of these compounds was also found to be a potent inhibitor of the intraerythrocytic growth of P. falciparum with 50% inhibitory concentration in the micromolar range.

Base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates to 4-alkylidene-2-oxazolidinones

The base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates is studied in detail. The effect of various bases and solvents on the efficacy of this cyclization reaction is analyzed and a new base-solvent system (LiOH in DMF) for effective cyclization of these carbamates is reported. A number of differentially substituted O-propargyl carbamates were cyclized to the corresponding 2-oxazolidinones under these conditions. The reaction conditions reported here are mild and no side reactions were observed in any of the substrates studied. A propargyl carbonate group was unaffected during the course of the cyclization of the O-propargyl carbamate group. The propargyl carbamates were prepared from the corresponding alkyl or aryl amines and the corresponding propargyl chloroformate, resulting in oxazolidinones diversely substituted at the nitrogen atom. N-Aryl-O-propargyl carbamates cyclized readily to the corresponding oxazolidinones with LiOH in DMF, whereas N-alkyl-O-propargyl carbamates reacted slowly under the same conditions. O-Propargyl carbamates substituted at the 1-position tend to cyclize faster whereas those substituted at 3-position cyclize considerably slower than the unsubstituted carbamates.

Simultaneous protection and activation of amino acids using propargyl pentafluorophenyl carbonate

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Method for the preparation of aliphatic chloroformates

A method for preparing an aliphatic chloroformate comprising, introducing a mixture of at least one aliphatic hydroxyl compound, phosgene, at least one solvent, and optionally at least one organic base into a flow reactor to obtain a unidirectional flowing reaction mixture. The at least one aliphatic hydroxyl compound comprises at least one aliphatic hydroxyl group. The unidirectional flowing reaction mixture is maintained at a temperature between about 0° C. and about 60° C. to produce a single product stream comprising an aliphatic chloroformate.

Highly selective deblocking of propargyl carbonates in the presence of propargyl carbamates with tetrathiomolybdate

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