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

Downstream Products

• 27489-61-8 cis-(N-4-hydroxycyclohexyl)acetamide 
• 83200-09-3 dembrexine 
• 248585-29-7 trans-4-(benzylidene-amino)-cyclohexanol 
• 248585-30-0 4-{[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-amino}-cyclohexanol 
• 248585-34-4 4-{[(E)-4-Hydroxy-cyclohexylimino]-methyl}-phenol 
• 248585-32-2 4-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-cyclohexanol 
• 380828-77-3 trans-4-(4-chlorophenoxy)cyclohexanamine 
• 910127-48-9 benzo[b]thiophene-2-carboxylic acid 4-oxocyclohexyl amide 
• 610786-08-8 C₂₀H₂₃ClN₆O 

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.

The Rhodium Catalysed Direct Conversion of Phenols to Primary Cyclohexylamines

Cyclohexylamines are important intermediates in chemical industry, which are currently produced from petrochemical sources. Phenols, however, are an attractive sustainable feedstock. We here demonstrate the transformation of phenols with ammonia to primary cyclohexylamines. In contrast to previously reported chemistry which used palladium catalysts, we here show that rhodium is an excellent catalyst for the formation of primary cyclohexylamines. Different parameters were studied and it was shown that the reaction is applicable to a scope of phenolic compounds providing high selectivity.