5117-85-1

Basic information

• Product Name: 1-Hydroxycyclopentane carbonitrile
• Synonyms: 1-Hydroxycyclopentane-1-carbonitrile;Alpha-hydroxycyclopentanecarbonitrile
• CAS NO: 5117-85-1
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.1418
• Product Categories: Cycloalkanes;Miscellaneous
• Mol File: 5117-85-1.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 246.4 °C at 760 mmHg
• Flash Point: 102.8 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0.00447mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: 1-Hydroxycyclopentane carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxycyclopentane carbonitrile(5117-85-1)
• EPA Substance Registry System: 1-Hydroxycyclopentane carbonitrile(5117-85-1)

Safety Data

• Hazardous Substances Data: 5117-85-1(Hazardous Substances Data)

Usage

General Description

1-Hydroxycyclopentane carbonitrile is a chemical compound with the molecular formula C6H9NO. It belongs to the family of nitriles and is composed of a cyclopentane ring structure, a hydroxyl group and a nitrile group. Its molecular weight is approximately 111.14 g/mol. In terms of its physical properties, little specific information is present in the literature. As a nitrile, it is expected to have similar chemical properties to related nitrile compounds, such as being polar and having a high dipole moment. It is likely to be used for various synthetic chemical applications, including as a building block in the manufacture of larger, more complex chemical entities.

InChI:InChI=1/C6H9NO/c7-5-6(8)3-1-2-4-6/h8H,1-4H2

Synthetic route

2-hydroxy-2-methylpropanenitrile (75-86-5) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With Hevea brasiliensis (S)-hydroxynitrile lyase pH=4.5; aq. buffer; Enzymatic reaction;	95%

Cyclopentanol (96-41-3) + sodium thiocyanide (540-72-7) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With sodium metabisulfite	95%

potassium cyanide (151-50-8) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With acetic acid In diethyl ether; water	93%
With water; acetic anhydride
With sodium hydrogensulfite 1.) water, RT, 30 min, 2.) RT, 2 h; Multistep reaction;
With sulfuric acid at 20℃;
With potassium hydrogensulfate In water for 16.25h;

potassium cyanide + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With sodium hypochlorite; sulfuric acid; iron(II) sulfate In water for 0.833333h; Cooling with ice;	87%
With sodium metabisulfite In water
With sodium dithionate In water at 25℃; for 6.75h;	3.6 g

potassium cyanide (151-50-8) + Sodium; 1-hydroxy-cyclopentanesulfonate (6950-56-7) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
In water for 1h;	77%

1-hydroxycyclopentane-1-sulfonic acid (19686-40-9) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With potassium cyanide In water for 1h; Ambient temperature;	75%

1,4-dioxane (123-91-1) + hydrogen cyanide (74-90-8) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
at 25℃; Equilibrium constant;

ethanol (64-17-5) + hydrogen cyanide (74-90-8) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
at 22℃;
at 25℃; Equilibrium constant;

hydrogen cyanide (74-90-8) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With potassium hydroxide
With potassium hydroxide In methanol

cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With diethyl ether; sodium hydrogensulfite Behandeln des Reaktionsprodukts mit wss. Kaliumcyanid-Loesung;

sodium cyanide (143-33-9) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With sulfuric acid

cyclopentanone (120-92-3) + diluted alcoholic KOH → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / sodium metabisulfite 2: 75 percent / potassium cyanide / H2O / 1 h / Ambient temperature View Scheme

sodium cyanide (773837-37-9) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With 2Na(2+)*O3S2(2-) In water
Stage #1: cyclopentanone With sodium hydrogensulfite In water at 40 - 50℃; for 0.75h; Stage #2: sodium cyanide In water at 30℃; for 1h;

trimethylsilyl cyanide (7677-24-9) + cyclopentanone (120-92-3) → 1-hydroxycyclopentanecarbonitrile (5117-85-1)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃;
With zinc dibromide at 20℃; for 12h;
With zinc(II) iodide In dichloromethane at 0 - 25℃; for 18h;

1-hydroxycyclopentanecarbonitrile (5117-85-1) → α-hydroxycyclopentanecarboxamide (66461-70-9)

Conditions	Yield
With silver trifluoromethanesulfonate; C33H33ClO7P3Pt(1+)*CF3O3S(1-) In tetrahydrofuran; water at 23℃; Catalytic behavior;	91%
With sulfuric acid for 24h; Ambient temperature;

1-hydroxycyclopentanecarbonitrile (5117-85-1) + 1,1-dimethylethylenediamine (811-93-8) → 8,8-dimethyl-6,9-diazaspiro[4.5]decan-10-one (1429171-90-3)

Conditions	Yield
In water for 48h; Reflux;	90%

ethanol (64-17-5) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → hydroxycyclopentanecarboxylic acid ethyl ester (41248-23-1)

Conditions	Yield
With hydrogenchloride In water at -10 - 25℃; for 14h;	90%

1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-hydroxy-cyclopentanecarboxylic acid (16841-19-3)

Conditions	Yield
With hydrogenchloride; acetic acid for 10h;	80%
With hydrogenchloride for 2.5h; Heating;	49%
With hydrogenchloride

1-hydroxycyclopentanecarbonitrile (5117-85-1) + phenylacetyl chloride (103-80-0) → phenyl-1-cyanocyclopentyl ester

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	78%

1-hydroxycyclopentanecarbonitrile (5117-85-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → N-(1-cyanocyclopentyl)formamide

Conditions	Yield
With acetic acid Inert atmosphere;	77%

4-methyleneoxetan-2-one (674-82-8) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-cyano-cyclopentyl acetoacetate (139003-84-2)

Conditions	Yield
With dmap for 24h; Ambient temperature;	73%

1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-(aminomethyl)cyclopentanol hydrochloride (76066-27-8)

Conditions	Yield
Stage #1: 1-hydroxycyclopentanecarbonitrile With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Reflux; Stage #2: With hydrogenchloride In 1,4-dioxane; tert-butyl methyl ether at 20℃; for 0.5h;	68%

1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-amino-1-cyanocyclopentane (49830-37-7)

Conditions	Yield
With titanium(IV) isopropylate; ammonia; benzoic acid In methanol; tert-butyl methyl ether for 18h; Heating;	63%

1-hydroxycyclopentanecarbonitrile (5117-85-1) + diethyl malonate (105-53-3) → ethyl 4-amino-2-oxo-1-oxaspiro<4.4>-3-nonene-3-carboxylate (139003-79-5)

Conditions	Yield
With tin(IV) chloride In ethyl acetate for 48h; Ambient temperature;	62%

1-hydroxycyclopentanecarbonitrile (5117-85-1) → 5-cyanopentanoic acid (5264-33-5) + cycloalkynone

Conditions	Yield
With sodium persulfate; cerium(III) sulfate In water at 80℃; for 3h; Product distribution; Mechanism; various cyanhydrins under different reaction conditions;	A 60% B n/a

isoniazid (54-85-3) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)cyclopentanol (1373018-77-9)

Conditions	Yield
With potassium carbonate In butan-1-ol at 115℃; Microwave irradiation;	57.91%

1-hydroxycyclopentanecarbonitrile (5117-85-1) + acetoacetic acid methyl ester (105-45-3) → 3-acetyl-4-amino-1-oxaspiro<4.4>-3-nonen-2-one (139003-75-1)

Conditions	Yield
With tin(IV) chloride In toluene for 3h; Heating;	55%

Lawessons reagent (19172-47-5) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → 2-(p-methoxyphenyl)-2,4-dithia-1,3,2-thiazaphospholidine-5,1'-spirocyclopentane

Conditions	Yield
In toluene for 5h; Heating;	55%

1-hydroxycyclopentanecarbonitrile (5117-85-1) → 5-cyanopentanoic acid (5264-33-5)

Conditions	Yield
With sodium persulfate; cerium(III) sulfate In water at 80℃; for 2h;	50%
With sodium persulfate In water at 60℃; for 4h; Mechanism;

1-hydroxycyclopentanecarbonitrile (5117-85-1) + 4-hydroxybenzoic acid hydrazide (5351-23-5) → 4-(5-(1-hydroxycyclopentyl)-4H-1,2,4-triazol-3-yl)phenol (1373018-75-7)

Conditions	Yield
With potassium carbonate In butan-1-ol at 115℃; Microwave irradiation;	44.88%

3,4-dihydro-2H-pyran (110-87-2) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-tetrahydropyran-2-yloxy-cyclopentanecarbonitrile (37802-93-0)

Conditions	Yield
With hydrogenchloride; diethyl ether

methyl magnesium iodide (917-64-6) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-methylcyclopentanol (1462-03-9)

Conditions	Yield
With diethyl ether

ethanol (64-17-5) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → hydrogen cyanide (74-90-8) + cyclopentanone (120-92-3)

Conditions	Yield
at 25℃; Equilibrium constant;
Equilibrium constant;

vinyl isopropyl ether (926-65-8) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-hydroxy-1-benzoylcyclopentane (19300-92-6)

Conditions	Yield
nachfolgende Umsetzung mit Phenylmagnesiumbromid und mit konz.wss.HCl;

4-methylbenzene-1,3-diamine (95-80-7) + 1-hydroxycyclopentanecarbonitrile (5117-85-1) → 1-(3-amino-4-methyl-anilino)-cyclopentanecarbonitrile (854731-62-7)

1-hydroxycyclopentanecarbonitrile (5117-85-1) + sodium cyanoacetic acid ethyl ester (18852-51-2) → ethyl-α-<1-(cyano)-1-cyclopentyl>-α-cyanopropionate (99497-12-8)

Conditions	Yield
With ethanol anschliessendes Behandeln mit Methyljodid;

1-hydroxycyclopentanecarbonitrile (5117-85-1) + sodium cyanoacetic acid ethyl ester (18852-51-2) → 2-cyano-2-(1-cyano-cyclopentyl)-3-phenyl-propionic acid ethyl ester

Conditions	Yield
With ethanol anschliessend Erwaermen mit Benzylchlorid;

Upstream product

• 64-17-5 ethanol 
• 74-90-8 hydrogen cyanide 
• 120-92-3 cyclopentanone 
• 151-50-8 potassium cyanide 
• 19686-40-9 1-hydroxycyclopentane-1-sulfonic acid 
• 143-33-9 sodium cyanide 
• 96-41-3 Cyclopentanol 
• 540-72-7 sodium thiocyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 773837-37-9 sodium cyanide 
• 6950-56-7 Sodium; 1-hydroxy-cyclopentanesulfonate 
• 123-91-1 1,4-dioxane 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 37802-93-0 1-tetrahydropyran-2-yloxy-cyclopentanecarbonitrile 
• 1462-03-9 1-methylcyclopentanol 
• 74-90-8 hydrogen cyanide 
• 120-92-3 cyclopentanone 
• 16841-19-3 1-hydroxy-cyclopentanecarboxylic acid 
• 45511-81-7 1-(aminomethyl)-1-hydroxycyclopentane 
• 100314-97-4 cyclohexyl-(1-hydroxy-cyclopentyl)-ketone 
• 10319-65-0 <1-Cyan-cyclopentyl>-N-<3-chlor-phenyl>-carbamat 
• 10319-66-1 3-(3-chloro-phenyl)-4-imino-1-oxa-3-aza-spiro[4.4]nonan-2-one 
• 10319-48-9 (3-chloro-phenyl)-[3-(3-chloro-phenyl)-2-oxo-1-oxa-3-aza-spiro[4.4]non-4-ylidene]-urea 
• 79662-82-1 4-Imino-1,3-diazaspiro<4.4>nonan-2-on 
• 130643-07-1 6-oxa-9-aza-spiro[4.5]decane 
• 49830-37-7 1-amino-1-cyanocyclopentane 
• 41248-23-1 hydroxycyclopentanecarboxylic acid ethyl ester 

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