33129-84-9

Basic information

• Product Name: p-tert-butylphenyl chloroformate
• Synonyms: p-tert-butylphenyl chloroformate;4-t-Butyl Phenoxy Acetyl Chloride;Chloridocarbonic acid 4-tert-butylphenyl ester;4-(tert-Butyl)phenyl carbonochloridate
• CAS NO: 33129-84-9
• Molecular Formula: C₁₁H₁₃ClO₂
• Molecular Weight: 212.67272
• EINECS: 251-386-4
• Mol File: 33129-84-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 252.2°C at 760 mmHg
• Flash Point: 92.4°C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 0.0196mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: p-tert-butylphenyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: p-tert-butylphenyl chloroformate(33129-84-9)
• EPA Substance Registry System: p-tert-butylphenyl chloroformate(33129-84-9)

Safety Data

• Hazardous Substances Data: 33129-84-9(Hazardous Substances Data)

Usage

Description

p-tert-butylphenyl chloroformate is a chloroformate ester with the molecular formula C11H15ClO2. It is a colorless liquid that is soluble in organic solvents such as ethanol and ether. This versatile intermediate is commonly used in organic synthesis and has the ability to undergo various chemical reactions.

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 articles and documents

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.

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.

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.