105906-07-8

Basic information

• Product Name: 4-TERT-BUTYLCYCLOHEXYL ACETIC ACID
• Synonyms: 4-TERT-BUTYLCYCLOHEXYL ACETIC ACID;SALOR-INT L128406-1EA;Butylcyclohexyl acetic acid;2-[4-(tert-Butyl)cyclohexyl]ethanoic acid, 1-(tert-Butyl)-4-(carboxymethyl)cyclohexane
• CAS NO: 105906-07-8
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• Mol File: 105906-07-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 81-83 °C
• Boiling Point: 300.1°Cat760mmHg
• Flash Point: 140.7°C
• Appearance: /
• Density: 0.967g/cm³
• Vapor Pressure: 0.00027mmHg at 25°C
• Refractive Index: 1.466
• PKA: 4.72±0.10(Predicted)
• CAS DataBase Reference: 4-TERT-BUTYLCYCLOHEXYL ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTYLCYCLOHEXYL ACETIC ACID(105906-07-8)
• EPA Substance Registry System: 4-TERT-BUTYLCYCLOHEXYL ACETIC ACID(105906-07-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 105906-07-8(Hazardous Substances Data)

Usage

General Description

4-TERT-BUTYLCYCLOHEXYL ACETIC ACID, often abbreviated as TBCHA, is a synthetic organic compound used in the fragrance industry. Characterized by its strong, woody, amber-like smell, it's a dominant ingredient in various perfumes and scented products. As an acetic acid, it's a weak acid and ultimately presents as a white crystal solid at room temperature. Though generally regarded as safe, direct contact may cause skin irritation or discomfort, therefore necessary protective measures should be taken while handling. It is relatively stable under standard conditions but may be sensitive to light, heat, and moisture. Detailed studies on the long-term effects of TBCHA on human health or the environment are limited.

InChI:InChI=1/C12H22O2/c1-12(2,3)10-6-4-9(5-7-10)8-11(13)14/h9-10H,4-8H2,1-3H3,(H,13,14)

Synthetic route

4-tert-butylcyclohexylacetic acid ethyl ester → 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8)

Conditions	Yield
With water; sodium hydroxide at 85℃; for 6h;	85%

(4-tert-Butylcyclohexyl)acetic acid methyl ester (191613-96-4) → 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8)

Conditions	Yield
With potassium hydroxide In ethanol; water for 3h; Heating; Yield given;
With sodium hydroxide In methanol

(4-tert-Butyl-cyclohexyl)-cyano-acetic acid ethyl ester (114145-17-4) → 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8)

Conditions	Yield
With potassium hydroxide In ethylene glycol

ethyl (4-t-butylcyclohexylidene)cyanoacetate (22700-58-9) → 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / ethanol / 1 h / 0 °C 2: KOH / ethane-1,2-diol View Scheme

ethyl (4-tert-butylcyclohexylidene)acetate (129518-99-6, 129519-00-2, 13733-50-1) → 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / palladium dichloride, activated carbon / methanol; aq. HCl 2: potassium hydroxide / ethanol; H2O / 3 h / Heating View Scheme

4-tercbutyl-cyclohexanone (98-53-3) → 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / dimethylformamide / 1) 20 deg C, 1 h, 2) 90 deg C to 100 deg C, 8 h 2: hydrogen / palladium dichloride, activated carbon / methanol; aq. HCl 3: potassium hydroxide / ethanol; H2O / 3 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C 1.2: 2 h / 20 °C 2.1: hydrogen / methanol / 9 h / 55 °C / 7500.75 Torr 3.1: sodium hydroxide; water / 6 h / 85 °C View Scheme

trans-4-tert-Butylcyclohexanecarbonitrile (15619-18-8) → 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8)

Conditions	Yield
With potassium hydroxide In ethanol; water

diazomethane (186581-53-3, 908094-01-9) + 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → (4-tert-Butylcyclohexyl)acetic acid methyl ester (191613-96-4)

Conditions	Yield
	94%

diazomethane (186581-53-3, 908094-01-9) + 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → methyl trans-(4-t-butylcyclohexyl)acetate (28125-17-9) + methyl cis-(4-t-butylcyclohexyl)acetate (28125-15-7)

Conditions	Yield
Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2-chloro-1,4-naphthoquinone (1010-60-2) + 1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → 2-(4-tert-Butyl-cyclohexylmethyl)-3-chloro-[1,4]naphthoquinone (344563-43-5)

Conditions	Yield
With ammonium persulfate; silver nitrate method of Jacobsen and Torssell;

1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) → (R)-4-Benzyl-3-[2-(4-tert-butyl-cyclohexyl)-acetyl]-oxazolidin-2-one

Conditions	Yield
With n-butyllithium; pivaloyl chloride; triethylamine In tetrahydrofuran at -78 - 20℃;

1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → (R)-2-(4-tert-Butyl-cyclohexyl)-succinic acid 1-benzyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: pivaloyl chloride, Et3N, n-BuLi / tetrahydrofuran / -78 - 20 °C 2: NaHMDS / tetrahydrofuran / -78 - 20 °C 3: nBuLi / tetrahydrofuran / -5 °C 4: TFA / CH2Cl2 / 4 °C View Scheme

1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → (R)-2-(4-tert-Butyl-cyclohexyl)-succinic acid 1-benzyl ester 4-(2-methyl-allyl) ester

Conditions	Yield
Multi-step reaction with 5 steps 1: pivaloyl chloride, Et3N, n-BuLi / tetrahydrofuran / -78 - 20 °C 2: NaHMDS / tetrahydrofuran / -78 - 20 °C 3: nBuLi / tetrahydrofuran / -5 °C 4: TFA / CH2Cl2 / 4 °C 5: EDC, DMAP / CH2Cl2 / Ambient temperature View Scheme

1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → (R)-2-(4-tert-Butyl-cyclohexyl)-succinic acid 1-benzyl ester 4-tert-butyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: pivaloyl chloride, Et3N, n-BuLi / tetrahydrofuran / -78 - 20 °C 2: NaHMDS / tetrahydrofuran / -78 - 20 °C 3: nBuLi / tetrahydrofuran / -5 °C View Scheme

1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → (R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-tert-butyl-cyclohexyl)-4-oxo-butyric acid tert-butyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: pivaloyl chloride, Et3N, n-BuLi / tetrahydrofuran / -78 - 20 °C 2: NaHMDS / tetrahydrofuran / -78 - 20 °C View Scheme

1-trans-(4-t-butylcyclohexyl)-acetic acid (105906-07-8) → 2-(trans-4-tert-butylcyclohexyl)methyl-3-hydroxynaphtho-1,4-quinone (86790-15-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: silver nitrate, ammonium persulphate / method of Jacobsen and Torssell 2: hydrolysis View Scheme

Upstream product

• 15619-18-8 trans-4-tert-Butylcyclohexanecarbonitrile 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 129518-99-6 ethyl (4-tert-butylcyclohexylidene)acetate 
• 22700-58-9 ethyl (4-t-butylcyclohexylidene)cyanoacetate 
• 114145-17-4 (4-tert-Butyl-cyclohexyl)-cyano-acetic acid ethyl ester 
• 191613-96-4 (4-tert-Butylcyclohexyl)acetic acid methyl ester 

Downstream Products

• 28125-17-9 methyl trans-(4-t-butylcyclohexyl)acetate 
• 28125-15-7 methyl cis-(4-t-butylcyclohexyl)acetate 
• 191613-96-4 (4-tert-Butylcyclohexyl)acetic acid methyl ester 
• 86790-15-0 3-hydroxy-2-(trans-4-tert-butylcyclohexyl)methylnaphtho-1,4-quinone 

Relevant articles and documents

Synthetic method for 4-tertiary butyl cyclohexaneacetic acid

The invention provides a synthetic method for 4-tertiary butyl cyclohexaneacetic acid. The synthetic method comprises the steps of: firstly adding sodium hydride into dried tetrahydrofuran; stirring the mixture and reducing the temperature to 0 DEG C; adding triethyl phosphonoacetate and stirring the mixture; adding a tetrahydrofuran solution of 4-tertiary butyl cyclohexanone, and raising the temperature to room temperature and stirring the mixture; then adding obtained 4-tertiary butyl ethyl cyclohexylideneacetate into methanol; then adding raney nickel to react in a hydrogen atmosphere; and finally mixing the 4-tertiary butyl ethyl cyclohexylacetate with an aqueous solution of sodium hydroxide, and heating and stirring the mixture to obtain the 4-tertiary butyl cyclohexaneacetic acid. The method provides the effective method for producing the 4-tertiary butyl cyclohexaneacetic acid. The method is few in step, high in yield, simple in post-treatment such as purification and easy for industrial production and operation.

Cycloalkylamides and their therapeutic applications

The present invention relates to the use of compounds of formula (I) for the treatment of a variety of disorders including, but not limited to, epilepsy, bipolar disorder, psychiatric disorders, migraine, pain, neuroprotection, and movement disorders.

SYNTHESIS OF CYCLOHEXYLALIPHATIC ACIDS AND THEIR PHARMACOLOGICAL PROPERTIES

A series of substituted cyclohexylacetic acids I has been obtained by hydrogenation of the unsaturated analogues II and III.Esters of these analogues were prepared by the Horner-Wittig reaction of the corresponding cyclohexanones IV and/or 2-cyclohexenones V with triethyl phosphonoacetate.These esters were obtained in two isomeric forms (Z and E), differing in the double bond in the exo-position.The derivatives with a substituent in the 2-position exhibited a partial shift of the double bond to the cyclohexane ring; this shift was especially marked in the 2-phenyl derivative.With the acids I-III, activation of fibrinolysis was assessed by the hanging clot method; the anti-inflammatory effect was assessed by inhibition of two experimental model inflammations.The regression equation relating fibrinolytic capacity to lipophilicity was a quadratic one, the logarithm of optimum lipophilicity being log Popt = 5.55.A qualitative assessment of the anti-inflammatory effect in relation to lipophilicity suggests that log Popt is probably higher than with arylaliphatic acids.These acids seem to have an active site different from that of the acids I-III.