38289-27-9

Basic information

• Product Name: trans-4-Propylcyclohexanecarboxylic acid
• Synonyms: propylcyclohexanecarboxylicacid;Trans-4-PropylcyclohexaneCarboxylicAcid,3HaC10H18O2;trans-4-(Prop-1-yl)cyclohexanecarboxylic acid;POLYCHLORONAPHTHALENE(N=3-5);3HA;4α-Propylcyclohexane-1β-carboxylic acid;Polychloronaphthalene(Cl=3-5);Polychloronapthalene
• CAS NO: 38289-27-9
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 1308068-626-2
• Product Categories: blocks;Carboxes;Biphenyl & Diphenyl ether;4-Alkylcyclohexanecarboxylic Acids (Building Blocks for Liquid Crystals);4-Substituted Cyclohexanecarboxylic Acids;Building Blocks for Liquid Crystals;Functional Materials
• Mol File: 38289-27-9.mol

Chemical Properties

• Melting Point: 93°C
• Boiling Point: 270.3 °C at 760 mmHg
• Flash Point: 129.5 °C
• Appearance: white to light yellow crystal powder
• Density: 0.985 g/cm³
• Vapor Pressure: 0.00195mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 4.92±0.10(Predicted)
• CAS DataBase Reference: trans-4-Propylcyclohexanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-Propylcyclohexanecarboxylic acid(38289-27-9)
• EPA Substance Registry System: trans-4-Propylcyclohexanecarboxylic acid(38289-27-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39-60-37
• Hazardous Substances Data: 38289-27-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Intermediates of Liquid Crystals

InChI:InChI=1/C10H18O2/c1-2-3-8-4-6-9(7-5-8)10(11)12/h8-9H,2-7H2,1H3,(H,11,12)/t8-,9-

Synthetic route

4-n-propylbenzoic acid (2438-05-3) → trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9)

Conditions	Yield
Stage #1: 4-n-propylbenzoic acid With sodium hydroxide; hydrogen In water at 140 - 150℃; under 22502.3 - 30003 Torr; for 1h; Stage #2: With sodium hydroxide In water at 260 - 280℃; under 22502.3 - 30003 Torr; for 2h; Further stages.;	85%
With hydrogen Multistep reaction;
With potassium hydroxide; thiourea; aluminum nickel In methanol; sodium hydroxide; water; hydrogen

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → trans-4-propyl-1-(hydroxymethyl)cyclohexane (71458-06-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;	100%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
With lithium aluminium tetrahydride; thionyl chloride 2.) ether; Multistep reaction;
Multi-step reaction with 2 steps 1: 100 percent / SOCl2 2: 91 percent / LiAlH4 / diethyl ether View Scheme

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → trans-4-propylcyclohexanecarbonyl chloride (67589-88-2)

Conditions	Yield
With thionyl chloride	100%
With thionyl chloride
With thionyl chloride In toluene for 3h; Heating;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-(2-(4-(3,4-difluoro-1H-pyrrol-1-yl)phenyl)ethynyl)phenol (1437796-91-2) → 4-(2-(4-(3,4-difluoro-1H-pyrrol-1-yl)phenyl)ethynyl)phenyl trans-4-propylcyclohexanecarboxylate (1437796-86-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 90℃; for 12h;	91.84%

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-(1H-3,4-difluoropyrrole-1-yl)phenol → trans-4-n-propylcyclohexanecarboxylic acid 4'-(3,4-difluoropyrrole-1-yl) phenyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 80℃; for 12h; Sealed tube;	86%

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-(3,3,4,4-tetrafluoropyrrolidin-1-yl)phenol → trans-4-n-propylcyclohexanecarboxylic acid 4'-(3,3,4,4-tetrafluoropyrrolidin-1-yl) phenyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 80℃; for 12h; Sealed tube;	85%

tetrakis(Nγ-trichloroethoxycarbonyl)polymyxin B (2-10) hydrochloride (1013028-77-7) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → trans-4-propylcyclohexanecarbonyl-tetrakis(Nγ-trichloroethoxycarbonyl)polymyxin B (2-10) (1013029-02-1)

Conditions	Yield
With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; pH=7.8;	84.54%

tetrakis(Nγ-trichloroethoxycarbonyl)colistin (2-10) hydrochloride (1013028-78-8) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → trans-4-propylcyclohexanecarbonyl-tetrakis(Nγ-trichloroethoxycarbonyl)colistin (2-10) (1013029-10-1)

Conditions	Yield
With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; pH=7.8;	81%

5-amino-1-naphthol (83-55-6) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → C20H25NO2

Conditions	Yield
Stage #1: trans-4-propyl-cyclohexanecarboxylic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: 5-amino-1-naphthol With dmap In dichloromethane at 20℃; for 12h;	81%

4-(1-pyrrolidinyl)phenol + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → trans-4-n-propylcyclohexanecarboxylic acid 4'-(pyrrolidin-1-yl) phenyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 80℃; for 12h; Sealed tube;	79%

4-ethynylphenol (2200-91-1) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → Trans-4-propylcyclohexanecarboxylic acid p-ethynylphenyl ester (402955-93-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	75%

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-(hex-5-yn-1-yloxy)phenol (402955-92-4) → 4-propyl-cyclohexanecarboxylic acid 4-hex-5-ynyloxy-phenyl ester (402955-98-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	73%

(1S,3R,4R,5R,6R,7R,8R,9S)-(9-hydroxymethylhexaspiro[2.0.0.0.0.0.2.1.1.1.1.1]pentadec-1-yl)methanol (837430-97-4) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → (1S,3R,4R,5R,6R,7R,8R,9S)-{9-[(4-trans-n-propylcyclohexanecarbonyl)oxymethyl]hexaspiro[2.0.0.0.0.0.2.1.1.1.1.1]pentadec-1-yl}methyl (4-trans-n-propyl)cyclohexanecarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	70%

4-[3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]phenyl 4-hexyl-benzoate (1342883-62-8) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → 4-{3-[4-(trans-4-n-propylcyclohexylcarbonyloxy)phenyl]-1,2,4-oxadiazol-5-yl}phenyl 4-hexylbenzoate (1342883-73-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;	70%

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + ethyl γ-aminobutyrate hydrochloride (6937-16-2) → ethyl 4-{[(trans-4-propylcyclohexyl)carbonyl]amino}butanoate (861819-95-6)

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	69%

(1S,3R,4R,5R,6R,7S)-(7-hydroxymethyltetraspiro[2.0.0.0.2.1.1.1]undec-1-yl)methanol (911032-01-4) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → (1S,3R,4R,5R,6R,7S)-{7-[(4-trans-n-propylcyclohexanecarbonyl)oxymethyl]tetraspiro[2.0.0.0.2.1.1.1]undec-1-yl}methyl (4-trans-n-propyl)cyclohexanecarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	69%

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-(4-pentynyloxy)phenol (155450-82-1) → 4-propyl-cyclohexanecarboxylic acid 4-pent-4-ynyloxy-phenyl ester (402955-95-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	65%

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 2-[(E)-carbazol-9-yliminomethyl]benzene-1,4-diol → [2-[(E)-carbazol-9-yliminomethyl]-4-hydroxyphenyl] trans-4-propylcyclohexanecarboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 23h;	60%

(1S,3R,4S,5S,6S,7S,8R,9S)-(9-hydroxymethylhexaspiro[2.0.0.0.0.0.2.1.1.1.1.1]pentadec-1-yl)methanol (911032-28-5) + trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → (1S,3R,4S,5S,6S,7S,8R,9S)-{9-[(4-trans-n-propylcyclohexanecarbonyl)oxymethyl]hexaspiro[2.0.0.0.0.0.2.1.1.1.1.1]pentadec-1-yl}methyl (4-trans-n-propyl)cyclohexanecarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	34%

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + D-phenylalanine methyl ester (21685-51-8) → N-<(trans-4-n-Propylcyclohexyl)carbonyl>-D-phenylalanine methyl ester

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide 1) CHCl3, 3 h, 2) CHCl3, 25 deg C, 1 d; Multistep reaction;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-Hydroxy-4'-pentoxy-2,2',3,3',5,5',6,6'-octafluorobiphenyl (127981-72-0) → 4-Propyl-cyclohexanecarboxylic acid 2,3,5,6,2',3',5',6'-octafluoro-4'-pentyloxy-biphenyl-4-yl ester

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; Yield given;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 2,3,5,6,2',3',5',6'-Octafluoro-4'-hexyloxy-biphenyl-4-ol → 4-Propyl-cyclohexanecarboxylic acid 2,3,5,6,2',3',5',6'-octafluoro-4'-hexyloxy-biphenyl-4-yl ester

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; Yield given;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 2,3,5,6,2',3',5',6'-Octafluoro-4'-heptyloxy-biphenyl-4-ol → 4-Propyl-cyclohexanecarboxylic acid 2,3,5,6,2',3',5',6'-octafluoro-4'-heptyloxy-biphenyl-4-yl ester

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; Yield given;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-Octyloxy-4'-hydroxy-2,2',3,3',5,5',6,6'-octafluorobiphenyl → 4-Propyl-cyclohexanecarboxylic acid 2,3,5,6,2',3',5',6'-octafluoro-4'-octyloxy-biphenyl-4-yl ester

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; Yield given;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-Nonyloxy-4'-hydroxy-2,2',3,3',5,5',6,6'-octafluorobiphenyl → 4-Propyl-cyclohexanecarboxylic acid 2,3,5,6,2',3',5',6'-octafluoro-4'-nonyloxy-biphenyl-4-yl ester

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; Yield given;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) + 4-Decyloxy-4'-hydroxy-2,2',3,3',5,5',6,6'-octafluorobiphenyl → 4-Propyl-cyclohexanecarboxylic acid 4'-decyloxy-2,3,5,6,2',3',5',6'-octafluoro-biphenyl-4-yl ester

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; Yield given;

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → 4-{[(trans-4-propylcyclohexyl)carbonyl]amino}butanoic acid (223465-95-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / 1-hydroxybenzotriazole monohydrate; triethylamine; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 20 °C 2: 100 percent / NaOH / methanol; H2O / 20 °C View Scheme

trans-4-propyl-cyclohexanecarboxylic acid (38289-27-9) → trans-N-(4-hydroxyamino-4-oxobutyl)-4-propylcyclohexanecarboxamide

Conditions	Yield
Multi-step reaction with 4 steps 1: 69 percent / 1-hydroxybenzotriazole monohydrate; triethylamine; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 20 °C 2: 100 percent / NaOH / methanol; H2O / 20 °C 3: 1-hydroxybenzotriazole monohydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 20 °C 4: HCl / methanol; H2O / 20 °C / pH 3 View Scheme

Upstream product

• 2438-05-3 4-n-propylbenzoic acid 

Downstream Products

• 71458-06-5 trans-4-propyl-1-(hydroxymethyl)cyclohexane 
• 67589-88-2 trans-4-propylcyclohexanecarbonyl chloride 
• 402955-93-5 Trans-4-propylcyclohexanecarboxylic acid p-ethynylphenyl ester 
• 1013029-10-1 trans-4-propylcyclohexanecarbonyl-tetrakis(N^γ-trichloroethoxycarbonyl)colistin (2-10) 
• 1013029-02-1 trans-4-propylcyclohexanecarbonyl-tetrakis(N^γ-trichloroethoxycarbonyl)polymyxin B (2-10) 
• 80361-78-0 trans-4-propylcyclohexyl carbaldehyde 
• 71458-18-9 trans-4-propylcyclohexylacetic acid 
• 82885-06-1 4-trans-propylcyclohexylacetonitrile 
• 95149-47-6 trans-4-propyl-1-(cyanomethyl)cyclohexane 
• 73899-61-3 trans-4-propylcyclohexyl acetyl chloride 
• 71458-12-3 trans-4-n-propyl-1-bromomethylcyclohexane 

Relevant articles and documents

Improved synthesis of trans-4-alkylcyclohexane carboxylic acids

Several stereomerically pure amino acid derivatives containing the N-terminal trans-4-alkylcyclohexanoyl fragment were obtained. Hydrogenation of 4-alkylbenzoic acids in the presence of a special Ru-Ni/C catalytic system and isomerization of the resulting mixture of trans- and cis-isomers of 4-alkylcyclohexanecarboxylic acids were used as the key steps. The stereomeric configuration of all compounds was confirmed by 1H NMR spectroscopy. The compounds obtained possess a broad biological activity potential and are useful intermediates in the synthesis of stereomerically pure modified peptides.

Epimerization of 2- or 4- substituted cyclohexanecarboxylic acids

The present invention relates to a new method for obtaining a purity of about 93% to 100% of the trans form of 2- or 4-substituted cyclohexanecarboxylic acid or reactive derivatives thereof from the cis form or a mixture of the cis and trans forms by a single step, particularly, to a method for obtaining a purity of substantially 100% of the trans form of 4-substituted cyclohexanecarboxylic acid.

Synthesis and Liquid Crystalline Phases of Pyridazine Derivatives II

Four more pyridazine compounds were synthesized.The compounds have a general structure R-X-Y-Z-R'; where Y is 3,6 disubstituted pyridazine ring, X and Z are either trans cyclohexyl or phenyl rings, R and R' are n-alkyl groups.The structure assignments were confirmed by carbon 13 NMR.Their liquid crystalline properties were evaluated.When both X and Z are cyclohexyl rings, the compounds have a single smectic b phase.However, if a phenyl ring is introduced into the system, the morphology becomes complicated.Keywords: synthesis, pyridazine, smectic, classification

Liquid crystal compounds

A liquid crystal compound having the formula: STR1 where X is --CH2.CH2 -- or CH2 O Y is STR2 and R is a straight or branched (possibly chiral) alkyl group having up to 15 carbon atoms.