15177-68-1

Basic information

• Product Name: Cyclohexanecarboxylic acid, 4-cyano-, trans-
• Synonyms: trans-4-cyanocyclohexane-1-ylcarboxylic acid;trans-4-Cyan-cyclohexancarbonsaeure;Cyclohexanecarboxylic acid,4-cyano-,trans;trans-4-Cyan-cyclohexan-1-carbonsaeure;trans-4-cyanocyclohexanecarboxylic acid
• CAS NO: 15177-68-1
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.181
• Mol File: 15177-68-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboxylic acid, 4-cyano-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 4-cyano-, trans-(15177-68-1)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 4-cyano-, trans-(15177-68-1)

Safety Data

• Hazardous Substances Data: 15177-68-1(Hazardous Substances Data)

Usage

General Description

Cyclohexanecarboxylic acid, 4-cyano-, trans- is a chemical compound with the molecular formula C8H11NO2. It is a trans isomer of 4-cyano cyclohexanecarboxylic acid, which means that the cyano group is located on the opposite side of the carboxylic acid group in the cyclohexane ring. Cyclohexanecarboxylic acid, 4-cyano-, trans- has potential applications in pharmaceuticals and organic synthesis as a building block for various molecules due to its unique structure and properties. It is commonly used as a starting material in the synthesis of pharmaceuticals and agrochemical products.

Synthetic route

trans-1,4-cyclohexanedicarbonitrile (6550-85-2) → trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1)

Conditions	Yield
With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; Acremonium sp. D9K; Thiamine hydrochloride; magnesium sulfate; glycerol; sodium chloride; biotin In water at 30℃; Product distribution; at different pHs, effect of various carbon and nitrogen sources;
With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; Acremonium sp. D9K; Thiamine hydrochloride; magnesium sulfate; glycerol; sodium chloride; biotin In water at 30℃;

concentrated ammonia water + trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → trans-4-aminomethyl-cyclohexyl-carboxylic acid (1197-18-8)

Conditions	Yield
aluminum nickel In methanol; water; acetone	92%

methanol (67-56-1) + trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → methyl trans-4-cyanocyclohexane-1-carboxylate (19145-95-0)

Conditions	Yield
With sulfuryl dichloride for 2h; Heating;

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) + 1-chloroethyl trans-4-cyanocyclohexanecarboxylate (87589-40-0) → 1,1-ethylidene bis(trans-4-cyanocyclohexanecarboxylate) (87589-42-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate 2.) trichloroethylene, reflux, 8 h; Yield given. Multistep reaction;
With tetra(n-butyl)ammonium hydrogen sulfate In sodium hydroxide; Trichloroethylene

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) + 4-Cyano-cyclohexanecarboxylic acid 1-chloro-propyl ester → 1,1-propandiol bis-(trans-4-cyanocyclohexanecarboxylate) (87611-40-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate 2.) trichloroethylene, reflux, 8 h; Multistep reaction;

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → 4-Cyano-cyclohexanecarbonyl chloride (63136-90-3)

Conditions	Yield
With thionyl chloride for 0.5h; Heating;

3-(4-hydroxyphenyl)propionic acid benzyl ester (31770-76-0) + trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → 4-Cyano-cyclohexanecarboxylic acid 4-(2-benzyloxycarbonyl-ethyl)-phenyl ester (122224-25-3)

Conditions	Yield
(i) SOCl2, (ii) /BRN= 2217949/, Et3N; Multistep reaction;

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → 1-chloroethyl trans-4-cyanocyclohexanecarboxylate (87589-40-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfurous oxychloride / 0.5 h / Heating 2: ZnCl2 / 1.5 h / 90 °C View Scheme

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → 4-Cyano-cyclohexanecarboxylic acid 1-chloro-propyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfurous oxychloride / 0.5 h / Heating 2: ZnCl2 / 1.5 h / 90 °C View Scheme

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → (1-pivaloyloxy)ethyl trans-4-cyanocyclohexanecarboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfurous oxychloride / 0.5 h / Heating 2: ZnCl2 / 1.5 h / 90 °C 3: 1.) tetrabutylammonium hydrogen sulfate (QHSO4), 2 M aq. NaOH / 2.) trichloroethylene, reflux, 8 h View Scheme

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → 1-(pivaloyloxy)ethyl trans-4-aminomethylcyclohexanecarboxylate hydrochloride (100165-51-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfurous oxychloride / 0.5 h / Heating 2: ZnCl2 / 1.5 h / 90 °C 3: 1.) tetrabutylammonium hydrogen sulfate (QHSO4), 2 M aq. NaOH / 2.) trichloroethylene, reflux, 8 h 4: H2, CHCl3 / PtO2 / ethanol / 15 h / 22 °C / 25502 Torr View Scheme

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) → cetraxate (34675-84-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) SOCl2, (ii) /BRN= 2217949/, Et3N 2: H2, aq. NH3 / Raney-Ni View Scheme

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) + 1-[(6-chloronaphthalen-2-yl]sulfonyl]piperazine (203521-17-9) → 1-(6-chloronaphthalene-2-sulfonyl)-4-(trans-4-cyanocyclohexane-1-ylcarbonyl)piperazine

Conditions	Yield
	468 mg

trans-4-cyanocyclohexane-1-ylcarboxylic acid (15177-68-1) + paracetaldehyde (123-63-7) → 1-chloroethyl trans-4-cyanocyclohexanecarboxylate (87589-40-0)

Conditions	Yield
With thionyl chloride; Zinc chloride

Upstream product

• 6550-85-2 trans-1,4-cyclohexanedicarbonitrile 

Downstream Products

• 19145-95-0 methyl trans-4-cyanocyclohexane-1-carboxylate 
• 87589-42-2 1,1-ethylidene bis(trans-4-cyanocyclohexanecarboxylate) 
• 87611-40-3 1,1-propandiol bis-(trans-4-cyanocyclohexanecarboxylate) 
• 63136-90-3 4-Cyano-cyclohexanecarbonyl chloride 
• 122224-25-3 4-Cyano-cyclohexanecarboxylic acid 4-(2-benzyloxycarbonyl-ethyl)-phenyl ester 
• 87589-40-0 1-chloroethyl trans-4-cyanocyclohexanecarboxylate 
• 100165-51-3 1-(pivaloyloxy)ethyl trans-4-aminomethylcyclohexanecarboxylate hydrochloride 
• 1197-18-8 trans-4-aminomethyl-cyclohexyl-carboxylic acid