Cyclopentanecarbonitrile,1-hydroxy- supplier

Name
1-Hydroxycyclopentane carbonitrile
EINECS
CAS No. 5117-85-1
Article Data29
CAS DataBase
Density 1.1 g/cm³
Solubility
Melting Point
Formula C₆H₉NO
Boiling Point 246.4 °C at 760 mmHg
Molecular Weight 111.144
Flash Point 102.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-Hydroxycyclopentanecarbonitrile;Cyclopentanone, cyanohydrin;
PSA 44.02000
LogP 0.81508

Synthetic route

: 75-86-5
2-hydroxy-2-methylpropanenitrile

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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

: 96-41-3
Cyclopentanol

: 540-72-7
sodium thiocyanide

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

Conditions	Yield
With sodium metabisulfite	95%

: 151-50-8
potassium cyanide

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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

: 151-50-8
potassium cyanide

: 6950-56-7
Sodium; 1-hydroxy-cyclopentanesulfonate

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

Conditions	Yield
In water for 1h;	77%

: 19686-40-9
1-hydroxycyclopentane-1-sulfonic acid

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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

: 123-91-1
1,4-dioxane

: 74-90-8
hydrogen cyanide

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

Conditions	Yield
at 25℃; Equilibrium constant;

...Expand

: 64-17-5
ethanol

: 74-90-8
hydrogen cyanide

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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

...Expand

: 74-90-8
hydrogen cyanide

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

Conditions	Yield
With potassium hydroxide
With potassium hydroxide In methanol

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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

: 143-33-9
sodium cyanide

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

Conditions	Yield
With sulfuric acid

: 120-92-3
cyclopentanone

diluted alcoholic KOH: diluted alcoholic KOH

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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

: 773837-37-9
sodium cyanide

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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;

: 7677-24-9
trimethylsilyl cyanide

: 120-92-3
cyclopentanone

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

Conditions

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;

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 66461-70-9
α-hydroxycyclopentanecarboxamide

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 811-93-8
1,1-dimethylethylenediamine

: 1429171-90-3
8,8-dimethyl-6,9-diazaspiro[4.5]decan-10-one

Conditions

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

: 64-17-5
ethanol

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 41248-23-1
hydroxycyclopentanecarboxylic acid ethyl ester

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 16841-19-3
1-hydroxy-cyclopentanecarboxylic acid

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 103-80-0
phenylacetyl chloride

: phenyl-1-cyanocyclopentyl ester

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: N-(1-cyanocyclopentyl)formamide

Conditions

Conditions	Yield
With acetic acid Inert atmosphere;	77%

: 674-82-8
4-methyleneoxetan-2-one

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 139003-84-2
1-cyano-cyclopentyl acetoacetate

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 76066-27-8
1-(aminomethyl)cyclopentanol hydrochloride

Conditions

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%

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 49830-37-7
1-amino-1-cyanocyclopentane

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 105-53-3
diethyl malonate

: 139003-79-5
ethyl 4-amino-2-oxo-1-oxaspiro<4.4>-3-nonene-3-carboxylate

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

A: 5264-33-5
5-cyanopentanoic acid

B cycloalkynone: cycloalkynone

Conditions

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

: 54-85-3
isoniazid

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 1373018-77-9
1-(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)cyclopentanol

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 105-45-3
acetoacetic acid methyl ester

: 139003-75-1
3-acetyl-4-amino-1-oxaspiro<4.4>-3-nonen-2-one

Conditions

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

: 19172-47-5
Lawessons reagent

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 2-(p-methoxyphenyl)-2,4-dithia-1,3,2-thiazaphospholidine-5,1'-spirocyclopentane

Conditions

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

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 5264-33-5
5-cyanopentanoic acid

Conditions

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;

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 5351-23-5
4-hydroxybenzoic acid hydrazide

: 1373018-75-7
4-(5-(1-hydroxycyclopentyl)-4H-1,2,4-triazol-3-yl)phenol

Conditions

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

: 110-87-2
3,4-dihydro-2H-pyran

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 37802-93-0
1-tetrahydropyran-2-yloxy-cyclopentanecarbonitrile

Conditions

Conditions	Yield
With hydrogenchloride; diethyl ether

: 917-64-6
methyl magnesium iodide

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 1462-03-9
1-methylcyclopentanol

Conditions

Conditions	Yield
With diethyl ether

: 64-17-5
ethanol

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

A: 74-90-8
hydrogen cyanide

B: 120-92-3
cyclopentanone

Conditions

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

...Expand

: 926-65-8
vinyl isopropyl ether

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 19300-92-6
1-hydroxy-1-benzoylcyclopentane

Conditions

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

: 95-80-7
4-methylbenzene-1,3-diamine

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 854731-62-7
1-(3-amino-4-methyl-anilino)-cyclopentanecarbonitrile

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 18852-51-2
sodium cyanoacetic acid ethyl ester

: 99497-12-8
ethyl-α-<1-(cyano)-1-cyclopentyl>-α-cyanopropionate

Conditions

Conditions	Yield
With ethanol anschliessendes Behandeln mit Methyljodid;

: 5117-85-1
1-hydroxycyclopentanecarbonitrile

: 18852-51-2
sodium cyanoacetic acid ethyl ester

: 2-cyano-2-(1-cyano-cyclopentyl)-3-phenyl-propionic acid ethyl ester

Conditions

Conditions	Yield
With ethanol anschliessend Erwaermen mit Benzylchlorid;

Cyclopentanecarbonitrile,1-hydroxy- Specification

The Cyclopentanecarbonitrile,1-hydroxy-, with the CAS registry number 5117-85-1, is also known as 1-Hydroxycyclopentanecarbonitrile and Cyclopentanone, cyanohydrin. It belongs to the product categories of Cycloalkanes; Miscellaneous. This chemical's molecular formula is C₆H₉NO and molecular weight is 111.1418. What's more, its IUPAC name is 1-Hydroxycyclopentane-1-carbonitrile.

Physical properties about Cyclopentanecarbonitrile,1-hydroxy- are: (1) ACD/LogP: -0.27; (2) # of Rule of 5 Violations: 0; (3) #H bond acceptors: 2; (4) #H bond donors: 1; (5) #Freely Rotating Bonds: 1; (6) Polar Surface Area: 33.02 Å²; (7) Index of Refraction: 1.491; (8) Molar Refractivity: 29.26 cm³; (9) Molar Volume: 100.8 cm³; (10) Polarizability: 11.6×10^-24 cm³; (11)Surface Tension: 46.4 dyne/cm; (12) Density: 1.1 g/cm³; (13) Flash Point: 102.8 °C; (14) Enthalpy of Vaporization: 56.19 kJ/mol; (15) Boiling Point: 246.4 °C at 760 mmHg; (16) Vapour Pressure: 0.00447 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: N#CC1(O)CCCC1
(2) InChI: InChI=1/C6H9NO/c7-5-6(8)3-1-2-4-6/h8H,1-4H2
(3) InChIKey: JZHFFOQSXKDOSX-UHFFFAOYAN

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	18 mg/kg (18 mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04176,

Product Name

1-Hydroxycyclopentane carbonitrile

Synthetic route

Cyclopentanecarbonitrile,1-hydroxy- Specification

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