1776-53-0

Basic information

• Product Name: 4-AMINOCYCLOHEXANECARBOXYLIC ACID
• Synonyms: CYCLOHEXANECARBOXYLIC ACID, 4-AMINO-;4-AMINOHEXAHYDROBENZOIC ACID;4-AMINOCYCLOHEXANECARBOXYLIC ACID;4-Aminocyclohexanecarboxylic acidcis/trans mixture;AMINOCYCLOHEXANECARBOXYLIC ACID;AKOS BB-9763;4-Aminocyclohexylcarboxylic Acid;P-AMINOCYCLOHEXYLCARBOXYLIC ACID
• CAS NO: 1776-53-0
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• EINECS: 1592732-453-0
• Product Categories: 4-Substituted Cyclohexanecarboxylic Acids;Bifunctional Compounds (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials
• Mol File: 1776-53-0.mol

Chemical Properties

• Melting Point: 299-301 ºC
• Boiling Point: 280°C at 760 mmHg
• Flash Point: 123.1°C
• Appearance: /
• Density: 1.133g/cm³
• Vapor Pressure: 0.00103mmHg at 25°C
• Refractive Index: 1.503
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.46±0.10(Predicted)
• Water Solubility: almost transparency
• CAS DataBase Reference: 4-AMINOCYCLOHEXANECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOCYCLOHEXANECARBOXYLIC ACID(1776-53-0)
• EPA Substance Registry System: 4-AMINOCYCLOHEXANECARBOXYLIC ACID(1776-53-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-36-39
• Hazardous Substances Data: 1776-53-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Aminocyclohexanecarboxylic acid is used as a building block for the synthesis of various drugs and pharmaceutical compounds. Its cyclic structure and amino group provide a foundation for the development of new medicinal products with potential therapeutic applications.
Used in Drug Synthesis:
As an intermediate in the production of diverse pharmaceuticals, 4-aminocyclohexanecarboxylic acid is utilized for its ability to be incorporated into the molecular structures of various drugs, enhancing their efficacy and pharmacological properties.
Used in Research and Development:
4-Aminocyclohexanecarboxylic acid is also used in research settings to explore its potential biological and pharmacological activities, with the aim of discovering new therapeutic agents and expanding the understanding of its role in medicine.

InChI:InChI=1/C7H13NO2/c8-6-3-1-5(2-4-6)7(9)10/h5-6H,1-4,8H2,(H,9,10)

Upstream product

• 7732-18-5 water 
• 150-13-0 4-amino-benzoic acid 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 6297-22-9 4-carbomethoxycyclohexanone 
• 38446-95-6 4-oxocyclohexanecarboxylic acid tert-butyl ester 
• 57555-71-2 4-hydroxyimino-cyclohexanecarboxylic acid 
• 90942-89-5 ethyl 4-(hydroxyimino)cyclohexane-1-carboxylate 
• 71-41-0 pentan-1-ol 

Downstream Products

• 105562-49-0 4-Isocyanatocyclohexancarbonylchlorid 
• 130309-46-5 trans-4-(tert-butoxycarbonylamino)cyclohexane carboxylic acid 
• 181308-53-2 {4-[(E)-Benzylimino-methyl]-cyclohexyl}-carbamic acid tert-butyl ester 
• 220851-34-3 cis/trans-4-benzyloxycarbonylamino-cyclohexanecarboxylic acid 
• 1350550-50-3 tert-butyl 4-(bromomethyl)cyclohexylcarbamate 
• 342578-12-5 C₁₁H₂₁NO₄S 

Relevant articles and documents

NMR AND RAMAN SPECTROSCOPIC STUDY OF COMPLEX FORMATION BETWEEN 2-METHYL-2-AZABICYCLO--OCTA-3-ONE AND TiCl4

From analysis of 1H and 13C NMR and Raman specroscopic data, in CDCl3 and 1,1,2,2-tetrachloroethane-d2 solution, the lactam 2-methyl-2-azabicyclo--octa-3-one (L) was found to form complexes with TiCl4 (M) of overall composition M2/

An improved preparation of 2-azabicyclo[2.2.2]octane

An improved preparative four-step synthesis to isoquinuclidine tosylate salt 4 has been demonstrated in 70% overall yield from p-aminobenzoic acid (PABA) 1. Hydrogenation of PABA 1 affords 4-aminocyclohexane carboxylic acid 2 as an 80 : 20 mixture of cis- and trans-isomers. Heating the mixture at 250°C effected epimerization and cyclization to provide the bicyclic lactam 3. Subsequent Red-A1 reduction and treatment with tosic acid furnished the desired bicyclic amine, tosylate salt 4.

Preparation method of trans 4 - (tert-butyloxycarbonylamino) cyclohexanecarboxylic acid and intermediate thereof

The invention provides a preparation method of trans 4 - (tert-butyloxycarbonylamino) cyclohexanecarboxylic acid and an intermediate thereof. The preparation method is characterized by comprising the following steps of 4 - oxocyclohexane carboxylic ester and chiral ligand reagent tert-butyl sulfinamide as a raw material, reducing amination to obtain trans -4 -tert-butyl sulfinyl sulfenamide cyclohexane carboxylic acid ester by virtue of chiral ligand reagent tert-butyl sulfinamide and 4 - 95% -oxocyclohexane carboxylic ester, and is stable in basic conditions and easy to leave under an acidic condition. Reaction conditions are mild, operation is simple and convenient, yield is high, and industrial production is easy.

PROCESS FOR THE PREPARATION OF TRANS-4-AMINO-1-CYCLOHEXANECARBOXILIC ACID AND ITS DERIVATIVES

The present invention relates to a one-pot process for the preparation of trans-4-amino-l-cyclohexanecarboxylic acid derivatives where the trans ratio is more than 75% by reaction of a 4-aminobenzoic acid derivative using an appropriate catayst and an appropriate solvent or solvent mixture under basic conditions. The process uses low hydrogen pressure and is therefore suitable for industrial application.

Upgrading of aromatic compounds in bio-oil over ultrathin graphene encapsulated Ru nanoparticles

Fast pyrolysis of biomass for bio-oil production is a direct route to renewable liquid fuels, but raw bio-oil must be upgraded in order to remove easily polymerized compounds (such as phenols and furfurals). Herein, a synthesis strategy for graphene encapsulated Ru nanoparticles (NPs) on carbon sheets (denoted as Ru@G-CS) and their excellent performance for the upgrading of raw bio-oil were reported. Ru@G-CS composites were prepared via the direct pyrolysis of mixed glucose, melamine and RuCl3 at varied temperatures (500-800 °C). Characterization indicated that very fine Ru NPs (2.5 ± 1.0 nm) that were encapsulated within 1-2 layered N-doped graphene were fabricated on N-doped carbon sheets (CS) in Ru@G-CS-700 (pyrolysis at 700 °C). And the Ru@G-CS-700 composite was highly active and stable for hydrogenation of unstable components in bio-oil (31 samples including phenols, furfurals and aromatics) even in aqueous media under mild conditions. This work provides a new protocol to the utilization of biomass, especially for the upgrading of bio-oil.

NOVEL MULTIMERIC MOLECULES, A PROCESS FOR PREPARING THE SAME AND THE USE THEREOF FOR MANUFACTURING MEDICINAL DRUGS

The invention relates to a compound of the formula (I): in which k and j are independently 0 or 1, Y is a macrocycle in which the cycle includes 9 to 36 carbon atoms and is functionalised by three amino functions and by a chain for attaching the spacer arm Z via an X bond, Rc is a binding pattern with a receptor of the TNF superfamily, X is a chemical function for binding the Y group to the space arm, and Z is a bi-, tri- or tetra-functional spacer arm.

NOVEL MULTIMERIC CD40 LIGANDS, METHOD FOR PREPARING SAME AND USE THEREOF FOR PREPARING DRUGS

The invention concerns a compound of formula (I), wherein Y represents a macrocycle whereof the cycle comprises 9 to 36 atoms, and is functionalized by three amine or COOH functions; Rc represents a group of formula H—Xa—Xb—Xc—Xd—Xe—(Xf)i—, wherein i represents 0 or 1, Xn is in particular selected among lysine, arginine, ornithine residues, Xb is in particular selected among glycine, asparagine, L-proline or D-proline residues, Xc et Xd are in particular selected among tyrosine, phenylalanine or 3-nitrotyrosine residues, Xe et Xf are in particular selected among the following amino acid residues: NH2—(CH2)n—COOH, n ranging from 1 to 10 or NH2—(CH2—CH2—O)m—CH2CH2COOH, m ranging from 3 to 6, provided that one at least of the amino acid residues Xa, Xb, Xc and Xd is different from the corresponding amino acid in the sequence of the natural CD40 143Lys-Gly-Tyr-Tyr146 fragment

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H 2 pressures (10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellet yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.

Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(α-methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the α-methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg-1, TD50 = 36.4 mg kg-1, PI = 6.3). Replacement of the piperidine ring of 1 by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man.

Opioid deltorphin C analogues containing cis- or trans-2- or 3- or 4- aminocyclohexanecarboxylic acid residues

The solid phase synthesis, based on the Fmoc chemical protocol, was used to prepare ten deltorphin C (Del-C; H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2) analogues containing cis- and trans- 2 or 3- or 4- aminocyclohexanecarboxylic acid (ACCA) residues at position 2, ACCA-peptides showed high resistance to degradation by plasma or brain enzymes, negligible affinity for the κ- binding site and modest δ- and/or μ-receptor affinities. Both [cis-3- ACCA2]Del-C analogues and one trans isomer are the only deltorphin analogues of this series exhibiting an appreciable δ-affinity and selectivity. These data suggest that the presence of a conformationally constrained ACCA residue in position 2 of the 'message' sequence of deltorphin C is slightly tolerated.