15901-42-5

Basic information

• Product Name: 3,3,5-TRIMETHYLCYCLOHEXYLAMINE
• Synonyms: 3,3,5-TRIMETHYLCYCLOHEXYLAMINE 99+% GC;3,3,5-TRIMETHYLCYCLOHEXYLAMINE;3,3,5-TRIMETHYLCYCLOHEXANAMINE;3,3,5-trimethyl-cyclohexanamin;3,3,5-trimethylcyclohexylamine,mixtureofcisandtrans;3,5,5-Trimethylcyclohexylamine;3,3,5-Trimethylcyclohexylamine, mixture of cis and trans,99+%;Cyclohexanamine, 3,3,5-trimethyl-
• CAS NO: 15901-42-5
• Molecular Formula: C₉H₁₉N
• Molecular Weight: 141.25
• EINECS: 240-041-3
• Mol File: 15901-42-5.mol

Chemical Properties

• Melting Point: -79.9°C
• Boiling Point: 177 °C
• Flash Point: 60°C
• Appearance: /
• Density: 0,84 g/cm3
• Refractive Index: 1.4520-1.4560
• PKA: 10.69±0.70(Predicted)
• CAS DataBase Reference: 3,3,5-TRIMETHYLCYCLOHEXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,5-TRIMETHYLCYCLOHEXYLAMINE(15901-42-5)
• EPA Substance Registry System: 3,3,5-TRIMETHYLCYCLOHEXYLAMINE(15901-42-5)

Safety Data

• Statements: 10-34
• Safety Statements: 26-36/37/39
• RIDADR: 2734
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 15901-42-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

InChI:InChI=1/C9H19N/c1-7-4-8(10)6-9(2,3)5-7/h7-8H,4-6,10H2,1-3H3

Upstream product

• 77287-34-4 formamide 
• 873-94-9 dihydroisophorone 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 2157-58-6 3,5,5-trimethyl-cyclohex-2-enone oxime 
• 134734-56-8 (E)-O-acetyl 3,5,5-trimethyl-2-cyclohexene-1-one oxime 
• 37694-11-4 3,3,5-trimethylcyclohexanone oxime 
• 37690-43-0 trans-3.3.5-Trimethylcyclohexanol-tosylat 
• 7027-11-4 isophoronenitrile 
• 3968-96-5 (E)-3,5,5-trimethylcyclohex-2-en-1-one oxime 
• 540-69-2 ammonium formate 

Downstream Products

• 1803274-65-8 3-(2-{[4-(trifluoromethoxy)phenyl]amino}-1-[(1R,5R)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-5-yl)propanoic acid 
• 900165-47-1 N-dimethylaminomethylene-4-methoxy-3-[(3,3,5-trimethylcyclohexylamino)methyl]-benzenesulfonamide 
• 13909-10-9 C₁₂H₂₂ClN₃O₂ 
• 38008-56-9 (3,3,5-Trimethyl-cyclohexyl)-carbamic acid 3-methylsulfanylcarbonylamino-phenyl ester 
• 13908-16-2 1-(2-chloroethyl)-3-(3,3,5-trimethylcyclohexyl)-urea 
• 36101-74-3 (3,3,5-trimethyl-cyclohexyl)-(3,3,5-trimethyl-cyclohexyliden)-amine 

Relevant articles and documents

Production of Primary Amines by Reductive Amination of Biomass-Derived Aldehydes/Ketones

Transformation of biomass into valuable nitrogen-containing compounds is highly desired, yet limited success has been achieved. Here we report an efficient catalyst system, partially reduced Ru/ZrO2, which could catalyze the reductive amination of a variety of biomass-derived aldehydes/ketones in aqueous ammonia. With this approach, a spectrum of renewable primary amines was produced in good to excellent yields. Moreover, we have demonstrated a two-step approach for production of ethanolamine, a large-market nitrogen-containing chemical, from lignocellulose in an overall yield of 10 %. Extensive characterizations showed that Ru/ZrO2-containing multivalence Ru association species worked as a bifunctional catalyst, with RuO2 as acidic promoter to facilitate the activation of carbonyl groups and Ru as active sites for the subsequent imine hydrogenation.

METHOD FOR THE PRODUCTION OF ISOPHORONDIAMINE (IPDA, 3-AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXYLAMINE) HAVING A HIGH CIS/TRANS-ISOMER RATIO

The invention relates to a method for the production of 3 aminomethyl-3,5,5- trimethylcyclohexylamine (isophorondiamine, IPDA) which has a high cis/trans isomer ratio. IPDA having a cis/trans isomer ratio in the range of 63/37 - 66/34 can be obtained in a temperature-independent manner by reacting IPDA having any particular cis/trans isomer ratio with H2 and NH3 in the presence of a hydrogenating catalyst. IPDA having a cis/trans isomer ratio of at least 73/27, which is an important starting material for the synthesis of polyurethanes and polyamides, can be obtained by combining said isomerization method with distillation methods.

Tetracyclic benzimidazole derivatives and combinatorial libraries thereof

The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.

Activity of copper- and iron-containing catalysts in the reaction of isophorone with ammonia and hydrogen

An investigation has been made of the vapour-phase reaction of isophorone (3,5,5-trimethyl-2-cyclohexen-1-one) with ammonia and hydrogen at a temperature of 160-230°C on an oxide copper-zinc-aluminium catalyst SNM-1 and a reduced, promoted, sintered iron catalyst. The composition of the main reaction products has been established, and schemes of their formation are proposed.

SYNTHESIS AND REACTIONS OF α,β-UNSATURATED AMINES AND THEIR DERIVATIVES. PART VI. ACTION OF DIBORANE ON O-ACETYL 3,5,5-TRIMETHYL-2-CYCLOHEXENE-1-ONE OXIME

The reaction of diborane with O-acetyl 3,5,5-trimethyl-2-cyclohexene-1-one oxime (1) has been examined.The effect of the temperature, molar ratio of substrates and O-acetyl oxime configuration on the stoichiometry and direction of the reaction is described.

REDUCTION OF CONJUGATED CYCLOHEXENONE OXIMES WITH ALUMINIUM HYDRIDE

The reduction of representative conjugated cyclohexenone oximes with aluminium hydride in tetrahydrofuran yields 2-cyclohexenylamines and saturated aziridines - 7-azabicycloheptane derivatives, as the main reaction products.Small quantities of cyclohexylamines and perhydroazepines are also formed.Regioselectivity of the reduction depends on oxime configuration.Higher yields of 2-cyclohexenylamines are obtained from E than Z isomers.The reaction mechanism is proposed.

Fiber-reactive disazo brown dye having vinylsulfone-type reactive group

A compound, or a salt thereof, represented by the following formula, STR1 wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is STR2 in which R3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R1 and R3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO2 CH=CH2 or --SO2 CH2 CH2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.

Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl Carbon-Nitrogen ? Systems with Hydride Reagents

Reductions of 3- and 4-substituted cyclohexyl imines, iminium salts, and enamines (via iminium ions) with various hydride reagents reveal that while small reagents (NaBH4, NaBH3CN) favor axial approach as observed with the corresponding ketones, even moderately bulky reagents (i.e., acetoxyboranes) attack preferentially from the equatorial side.This is in direct contrast to the results observed for the same reagents with the corresponding ketones and is interpreted as implying that additional steric interactions induced by the nitrogen substituents encumber axial attack by substituted hydride reagents and force approach from the equatorial direction.The very bulky tri-sec-butylborohydride anion affords highly stereodiscriminating equatorial attack.Reductions of 2-alkylcyclohexyl and 2-alkylcyclopentyl imines and enamines also proceed with high stereoselectivity to give cis-2-alkyl cyclic amines with both hindered and unhindered reagents.This is interpreted to be the result of (1) augmented steric interactions between nitrogen substituents and equatorial 2-alkyl groups (1,3-allylic strain) which induces conformational changes to favor the axial 2-alkyl conformer and (2) hindrance toward equatorial approach by reagents induced by axial alkyl substituents.The result is that equatorial approach is favored with equatorial 2-alkyl conformers and preferential axial approach with axial 2-alkyl conformers, leading to stereoselective production of cis-2-alkylamines. trans-2-n-Propyl-4-tert-butylcyclohexanone is reduced by LiBH(sec-Bu)3 preferentially from the axial direction in contrast to the usual highly selective equatorial attack observed with other cyclohexanones.

Cyclohexylamines

This invention relates to the reductive amination of unsaturated cyclic ketones; to cyclic amines prepared thereby; and to uses thereof. For example, when isophorone is reductively aminated, trimethyl cyclohexylamines and cyclohexenamines are obtained. This invention also relates to uses thereof, for example, as fuel additives, particularly for stabilizing distillate fuels.