13248-54-9

Basic information

• Product Name: Cyclohexyl chloroformate
• Synonyms: Cyclohexyl carbonochloridate;carbonochloridicacid,cyclohexylester;CYCLOHEXYL CHLOROFORMATE;chloroformic acid cyclohexyl ester;cyclohcxyl chlrorformate
• CAS NO: 13248-54-9
• Molecular Formula: C₇H₁₁ClO₂
• Molecular Weight: 162.61404
• EINECS: 236-230-5
• Product Categories: Pharmaceutical Intermediates;CHLOROFORMATES;API Intermediate
• Mol File: 13248-54-9.mol

Chemical Properties

• Boiling Point: 87.5℃
• Flash Point: 76.355 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0.387mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Cyclohexyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexyl chloroformate(13248-54-9)
• EPA Substance Registry System: Cyclohexyl chloroformate(13248-54-9)

Safety Data

• Statements: 23/24/25-34
• Safety Statements: 26-36/37/39
• RIDADR: 3277
• Hazardous Substances Data: 13248-54-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexyl chloroformate is used as a protecting group for amines and indoles in peptide synthesis. This application is essential for the development of various pharmaceuticals, as it helps in the synthesis of complex peptide structures without unwanted side reactions or degradation of the peptide backbone.
Used in Chemical Synthesis:
In the field of chemical synthesis, Cyclohexyl chloroformate is utilized as a protecting group for amines and indoles. This allows chemists to carry out reactions on other functional groups present in the molecule without affecting the amine or indole groups. This selective protection is vital for the synthesis of complex organic molecules and the development of new materials with specific properties.
Used in Research and Development:
Cyclohexyl chloroformate is also employed in research and development, particularly in the field of biochemistry and molecular biology. It serves as a valuable tool for the synthesis and modification of peptides and other biomolecules, enabling scientists to study their structure, function, and interactions with other molecules in detail.

InChI:InChI=1/C7H11ClO2/c8-7(9)10-6-4-2-1-3-5-6/h6H,1-5H2

Upstream product

• 75-44-5 phosgene 
• 108-93-0 cyclohexanol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 4078-59-5 N-cyclohexyloxycarbonyl-glycine 
• 3309-46-4 N-cyclohexyloxycarbonyl-alanine 
• 3309-53-3 N-cyclohexyloxycarbonyl-methionine 
• 542-18-7 cyclohexyl chloride 
• 101730-28-3 carbonic acid-(5-acetyl-[8]quinolyl ester)-cyclohexyl ester 
• 1124-54-5 carbamic acid cyclohexyl ester 
• 1561-49-5 dicyclohexyl peroxydicarbonate 
• 351-79-1 fluorocarbonic acid cyclohexyl ester 
• 3514-03-2 Cyclohexyloxycarbonyl-DL-valin 
• 6421-11-0 Cyclohexyl-o-tolyl-carbonat 
• 91766-85-7 1-chloro-2-cyclohexylbenzene 
• 829-32-3 1-chloro-4-cyclohexylbenzene 
• 27163-66-2 3-cyclohexyl-chlorobenzene 
• 3309-47-5 Cyclohexyloxycarbonyl-DL-leucin 

Relevant articles and documents

Configurational Statistics of Poly(cyclohexene carbonate)

Conformational characteristics of poly(cyclohexene carbonate) (PCHC) have been investigated via molecular orbital (MO) calculations and NMR experiments on model compounds. The MO energies established through comparison with the NMR experiments were applied to the rotational isomeric state scheme with Bernoulli and Markov stochastic processes to yield configurational properties such as unperturbed characteristic ratio, its temperature coefficient, configurational entropy, tacticity entropy, and coherence number of PCHC chains including various stereosequences. trans-PCHC composed of (R,R)- and/or (S,S)-repeating units prefers a tg+t conformation in the O-CH-CH-O bond sequence of the (R,R)-unit, and its unperturbed characteristic ratio depends considerably on stereoregularity: isotactic, 29, and syndiotactic, 0.83 (in chloroform at 25 °C). cis-PCHC comprising (R,S)- and/or (S,R)-units exclusively adopts either g-g+g+ or g-g-g+ conformation in the O-CH-CH-O bond sequence of the (R,S)-unit partly owing to intramolecular hydrogen bonds, and the dependence of the characteristic ratio of cis-PCHC on stereoregularity would be completely opposite to that of trans-PCHC: isotactic, 0.59, and syndiotactic, 25. In terms of the abovementioned characteristic parameters, properties of PCHCs synthesized so far with stereospecific catalysts are discussed.

Discovery of (3-Benzyl-5-hydroxyphenyl)carbamates as new antitubercular agents with potent in vitro and in vivo efficacy

A series of 3-amino-5-benzylphenol derivatives were designed and synthesized. Among them, (3-benzyl-5-hydroxyphenyl)carbamates were found to exert good inhibitory activity against M. tuberculosis H37Ra, H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.625-6.25 μg/mL). The privileged compounds 3i and 3l showed moderate cytotoxicity against cell line A549. Compound 3l also exhibited potent in vivo inhibitory activity on a mouse infection model via the oral administration. The results demonstrated 3-hydroxyphenylcarbamates as a class of new antitubercular agents with good potential.

Levorotatory meptazinol prodrug as well as preparation method and purpose thereof

The invention provides a levorotatory meptazinol prodrug as well as a preparation method and a purpose thereof, wherein the levorotatory meptazinol prodrug is a compound as shown in a formula I or a stereoisomer, a geometrical isomer, a tautomer, oxynitride, a hydrate, a solvate, a metabolite or a pharmaceutically acceptable salt of the compound as shown in the formula I. The compound is low in hepatic first pass effect and high in bioavailability; a medicine which uses the compound as an active component can be used for treating a neurodegenerative disease or various kinds of acute and chronic pain, such as a wound, postoperative, obstetrical and cancer pain, hemicrania, neuropathic pain and the like.

Preparation method of alicyclic and aromatic-aliphatic chloroformate

The invention belongs to the technical field of fine chemistry, and in particular relates to a preparation method of alicyclic and aromatic-aliphatic chloroformate. The preparation method is characterized in that alicyclic alcohol chloroformate or aromatic-aliphatic alcohol chloroformate is obtained by taking alicyclic alcohol or aromatic-aliphatic alcohol and bis(trichlormethyl)carbonate as raw materials, taking organic base as a catalyst and reacting in an organic solvent under certain reaction temperature and certain reaction time, wherein molar ratio among the alicyclic alcohol or the aromatic-aliphatic alcohol, the bis(trichlormethyl)carbonate and the organic base is 1 to (0.4 to 1) to (1.2 to 3); experiment time and experiment temperature are different in two stages, in the first stage, the reaction temperature is -10 to 0 DEG C, and the reaction time is 2 to 5 hours; in the second stage, the reaction temperature is 0 to 25 DEG C, and the reaction time is 7 to 13 hours; a mass ratio between the organic solvent and the alicyclic alcohol or the aromatic-aliphatic alcohol is (10 to 25) to 1; residue in a reaction system is effectively treated, and reaction waste is also recycled and utilized. The preparation method disclosed by the invention has the characteristics of stable reaction, high reaction yield and product purity, environment protection of a reaction process, low production cost, less emission of three wastes, simpleness in preparation technology and easiness in industrialization.

DEVICE AND PROCESS FOR CONTINUOUS PHOSGENATION

A continuous process for generation of phosgene from CO and Cl2 and consumption of the phosgene thus generated in a liquid-phase reaction so as to form organic products P. The process is implemented in two successive reactors R1 and R2, the first reactor R1 being a reactor for catalytic synthesis of phosgene from CO and Cl2 gas, and the second reactor R2 being a piston reactor, the second reactor R2 being equipped with a mechanical axial agitation device.

Perylen-3-ylmethyl: Fluorescent photoremovable protecting group (FPRPG) for carboxylic acids and alcohols

Perylen-3-ylmethyl demonstrated as a new fluorescent photoremovable protecting group (FPRPG) for carboxylic acids and alcohols. Carboxylic acids including amino acids were protected as their corresponding esters by coupling with FPRPG, perylen-3-ylmethyl. Photophysical studies of caged esters showed that they all exhibited strong fluorescence properties and their fluorescence quantum yields were in the range of 0.85-0.95. Irradiation of the caged esters using visible light (≥410 nm) in aqueous acetonitrile released the corresponding carboxylic acids in high chemical (94-97%) and quantum (0.072-0.093) yields. The results obtained from the photolysis of the caged ester in different solvents indicated that solvent has influence on the rate of photorelease. Further, we also explored the ability of FPRPG, perylen-3-ylmethyl for the protection of alcohols and phenols.

NOVEL VINBLASTINE DERIVATIVES, THEIR PREPARATION, USE AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAID DERIVATIVES

The invention provides vinblastine derivatives represented by the following formula 1 or their physiologically acceptable salts, their preparation, use and pharmaceutical compositions comprising the said derivatives. The said vinblastine derivatives show inhibiting activities against tumor cell lines and can be used as medicaments for treating malignant tumors.

Design, synthesis, structure-selectivity relationship, and effect on human cancer cells of a novel series of histone deacetylase 6-selective inhibitors

To uncover novel histone deacetylase 6 (HDAC6)-selective inhibitors and to elucidate the structural requirements for their inhibitory activity, we designed and prepared a series of thiolate analogues based on the structure of an HDAC6-selective substrate and evaluated their properties by Western blotting and enzyme assays. Several thiolate analogues were found to be potent and selective HDAC6 inhibitors. Study of the structure-selectivity relationship revealed that the presence of a bulky alkyl group and tert-butylcarbamate group in these compounds is important for HDAC6-selective inhibition. Compounds 16b and 20b, the most selective and active compounds in this series, exerted a synergistic inhibition of cancer cell growth in combination with paclitaxel. They also blocked the growth of estrogen receptor α-positive breast cancer MCF-7 cells that had been treated with estrogen. These findings suggested that HDAC6-selective inhibitors have potential as anticancer agents.

Method of treating cancer using FPT inhibitors and antineoplastic agents

Disclosed is a method of treating cancer in a patient in need of such treatment comprising administering a therapeutically effective amount of an FPT inhibitor and therapeutically effective amounts of one or more antineoplastic agents. Methods of treating non small cell lung cancer, squamous cell cancer of the head and neck, CML, AML, non-Hodgkin's lymphoma and multiple myeloma are disclosed.

Preparation of chloroformates using bis(trichloromethyl)carbonate

The synthesis of eight chloroformates using bis(trichloromethyl) carbonate(BTC) is reported. It has been found that the yields by this BTC method are improved over the earlier phosgene method, and sodium hydroxide is better than pyridine as catalyst for the preparation of phenyl chloroformate.