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
• Article Data: 4

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

• 402955-93-5 Trans-4-propylcyclohexanecarboxylic acid p-ethynylphenyl ester 
• 402955-95-7 4-propyl-cyclohexanecarboxylic acid 4-pent-4-ynyloxy-phenyl ester 
• 402955-98-0 4-propyl-cyclohexanecarboxylic acid 4-hex-5-ynyloxy-phenyl ester 
• 376642-44-3 trans-4-n-propylcyclohexylmethanol 
• 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) 
• 1640131-96-9 C₃₇H₄₂N₂O₅ 
• 86849-44-7 4-(2-trans-4-propylcyclohexyl-ethyl)-benzonitrile 
• 87002-34-4 1-Phenyl-2-(4-propyl-cyclohexyl)-ethanone 
• 89013-05-8 4-[2-(4-Propyl-cyclohexyl)-ethyl]-benzamide 
• 89013-09-2 4-[2-(4-Propyl-cyclohexyl)-ethyl]-benzoyl chloride 

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.

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