27489-62-9

Basic information

• Product Name: trans-4-Aminocyclohexanol
• Synonyms: Cyclohexanol, 4-amino-, trans-;(1α)-4β-Aminocyclohexanol;trans-4-Aminocyclohexanol,97%;trans-4-Aminocyclohexanol;(1r,4r)-4-aminocyclohexanol;(1s,4s)-4-Aminocyclohexanol;Trans-4-Amimocyclohexanol;trans-4-Aminocyclohexanol ,99%
• CAS NO: 27489-62-9
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17352
• EINECS: 248-492-8
• Product Categories: Ambroxol;Amines;blocks;BuildingBlocks;chiral
• Mol File: 27489-62-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 108-113°C
• Boiling Point: 127 °C / 14mmHg
• Flash Point: 75.4 °C
• Appearance: White to almost white/Crystals
• Density: 0.9837 (rough estimate)
• Refractive Index: 1.4713 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 15.12±0.40(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• CAS DataBase Reference: trans-4-Aminocyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-Aminocyclohexanol(27489-62-9)
• EPA Substance Registry System: trans-4-Aminocyclohexanol(27489-62-9)

Safety Data

• Hazard Codes: Xi,C,Xn
• Statements: 36/37/38-34-41-37/38-22
• Safety Statements: 26-37/39-45-36/37/39-39
• RIDADR: 3259
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 27489-62-9(Hazardous Substances Data)

Usage

Description

Trans-4-Aminocyclohexanol is also named as Cis-4-Aminocyclohexanol. It was a medical intermediate of ambroxol, which is used in the treatment of respiratory diseases associated with viscid or excessive mucus.1 It is used as a raw material in organic synthesis, such as in the synthesis of N-substituted 7-azabicyclo [2.2.1] hepatanes, which are good substrates for microbial oxidation of unactivated carbons by B.bassiana.2

Reference

Y. Jian, Improved Process of the Synthesis of Trans-4-aminocyclohexanol, Fine Chemicals, 2000, vol. 2 H. F. Olivo, M. S. Hemenway, M. H. Gezginci, Synthesis and Microbial Hydroxylation of Some Azabicycloalkanes, Tetrahedron Letters, 1998, vol. 39, pp. 1309-1312

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 27489-62-9 differently. You can refer to the following data:
1. trans-4-aminocyclohexanol be used as organic intermediates.
2. trans-4-Aminocyclohexanol is used as raw material in organic synthesis and is an important intermediate in the synthesis of drugs such as Ambroxol hydrochloride. It can react with butyric acid-(2-chloro-ethyl ester) to get butyric acid 4-amino-cyclohexyl ester. This reaction needs catalytic agent Aspergillus niger lipase and solvent 2-methyl-butan-2-ol.

InChI:InChI=1/C6H13NO/c7-5-1-3-6(8)4-2-5/h5-6,8H,1-4,7H2/t5-,6+

Upstream product

• 100-02-7 4-nitro-phenol 
• 123-30-8 4-amino-phenol 
• 71118-96-2 trans-4-Aethoxycarbonylamino-cyclohexanol 
• 1380214-98-1 trans-4-azidocyclohexan-1-ol 
• 248585-29-7 trans-4-(benzylidene-amino)-cyclohexanol 
• 27489-61-8 cis-(N-4-hydroxycyclohexyl)acetamide 
• 637-88-7 1,4-Cyclohexanedione 
• 27489-60-7 N-((trans)-4-hydroxycyclohexyl)acetamide 
• 123-31-9 hydroquinone 
• 103-90-2 4-acetaminophenol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 50910-54-8 trans-4-aminocyclohexanol hydrochloride 
• 17419-82-8 trans-4-Hydroxy-cyclohexanecarboxylic acid hydrazide 
• 3685-26-5 trans-4-hydroxycyclohexanecarboxylic acid 

Downstream Products

• 27489-61-8 cis-(N-4-hydroxycyclohexyl)acetamide 
• 27514-07-4 7-azabicyclo[2.2.1]heptane hydrochloride 
• 116350-36-8 7-Ethyl-7-azabicyclo<2.2.1>heptane hydrochloride 
• 128924-80-1 C₁₄H₂₀N₂O₄S 
• 162337-94-2 4-Isopropylamino-cyclohexanol 
• 99337-98-1 2-((1R,4R)-4-hydroxycyclohexyl) isoindoline-1,3-dione 
• 244008-54-6 N-(diphenylphosphinoyl)-trans-1,4-aminocyclohexanol 
• 267239-73-6 2-{[(E)-4-Hydroxy-cyclohexylimino]-methyl}-phenol 
• 248585-34-4 4-{[(E)-4-Hydroxy-cyclohexylimino]-methyl}-phenol 
• 248585-32-2 4-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-cyclohexanol 
• 170737-37-8 trans-5-(4-hydroksycyclohexyl)-1,3-dimethylhexahydro-2-oxo-1,3,5-triazine 

Relevant articles and documents

Method for recovering trans - P-aminocyclohexanol by low-concentration waste liquid

The invention relates to the technical field of medical chemical raw material recycling, and particularly discloses a method for recovering trans -amino cyclohexanol from low-concentration waste liquid. The method comprises the following steps: adjusting the waste liquor to alkalinity, adding benzaldehyde and stirring, filtering and drying to obtain trans -4 - (benzylidene - amino) - cyclohexanol. The trans -4 - (benzylidene - amino) - cyclohexanol was added to a sulfuric acid solution, and after stirring, the liquid was left standing to obtain trans - p-aminocyclohexanol sulfate aqueous solution. After stirring and decoloring, the alkali content of the filtrate is adjusted to - and after the reaction is stirred, the oil layer is left to stand, and extraction, concentration and purification of the extractant are added to the oil layer to obtain trans 10 - 25% -amino cyclohexanol. To the method, waste liquid discharged in industrial synthesis of ambroxol hydrochloride and alkali waste liquid generated by trans -amino cyclohexanol can be produced, and trans -amino cyclohexanol can be recycled.

A process for preparing trans to amino cyclohexanol

The invention discloses a process for preparing trans to amino cyclohexanol, the method takes the aminophenol as raw material, adding metal catalyst, in order to carbonate or sulfate as an additive, in the ketone solvent in the judgement of the hydrogenation reaction to obtain the amino cyclohexanol, then post-processed to obtain trans to amino cyclohexanol. The invention uses relatively inexpensive to amino phenol, to replace the more expensive acetaminophen, the production cost is reduced, and improves the economic benefit, and exploration by the experiment, it was found that the reaction of the preparation process is relatively gentle, the reaction temperature and the reaction pressure is greatly reduced, it is easy to operate, is suitable for industrial production. Reaction of the resulting product yield can reach 80 - 90%, a high proportion of trans to amino cyclohexanol, small pollution to the environment.

ISOTOPE ENHANCED AMBROXOL FOR LONG LASTING AUTOPHAGY INDUCTION

The present invention is directed to 13C and/or 2H isotope enhanced ambroxol ("isotope enhanced ambroxol") and its use in the treatment of autophagy infections, especially mycobacterial and other infections, disease states and/or conditions of the lung, such as tuberculosis, especially including drug resistant and multiple drag resistant tuberculosis. Pharmaceutical compositions comprising isotope enhanced amhroxol, alone or in combination with an additional bioactive agent, especially rifamycin antibiotics, including an additional autophagy modulator (an agent which is active to promote or inhibit autophagy), thus being useful against, an autophagy mediated disease state and/or condition), especially an antophagy mediated disease state and/or condition which occurs in the lungs, for example, a Mycobacterium infection. Chronic Obstructive Pulmonary Disease (COPD), asthma, pulmonary fibrosis, cystic fibrosis, Sjogren's disease and lung cancer (small cell and non-small cell lung cancer, among other disease states and/or conditions, especially of the lung. Methods of treating autophagy disease states and/or conditions, especially including autophagy disease states or conditions which occur principally in the lungs of a patient represent a further embodiment of the present invention. An additional embodiment includes methods of synthesizing compounds according to the present invention as otherwise disclosed herein.