• Name

  Cyclopropyl carbinol

• EINECS 219-735-5
• CAS No. 2516-33-8
• Article Data64
• CAS DataBase
• Density 1.004 g/cm³
• Solubility miscible with water
• Melting Point -60 °C
• Formula C₄H₈O
• Boiling Point 124.3 °C at 760 mmHg
• Molecular Weight 72.1069
• Flash Point 35 °C
• Transport Information UN 1987 3/PG 3
• Appearance Clear colorless liquid
• Safety 16-26-36-45-36/37/39
• Risk Codes 10-22-36-34
• Molecular Structure
• Hazard Symbols Xn, Xi, C, F
• Synonyms Cyclopropylcarbinyl alcohol;Cyclopropanemethyl alcohol;Cyclopropanemethanol;Cyclopropylmethyl alcohol;Cyclopropylmethanol;1-Cyclopropylmethanol;Cyclopropyl Methanol;
• PSA 20.23000
• LogP 0.38870

Synthetic route

1759-53-1

cyclopropanecarboxylic acid

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In tert-butyl methyl ether at 0 - 50℃; for 24h;	95%
With lithium aluminium tetrahydride	83%
With lithium aluminium tetrahydride	67%

(2-methoxy-ethoxymethoxymethyl)-cyclopropane

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With cerium(III) chloride In acetonitrile for 1h; Heating;	95%

6228-73-5

Cyclopropancarbamid

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;	91%

1344115-77-0

2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation;	90%

2868-37-3

methyl cyclopropylcarboxylate

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With sodium In methanol at 45 - 65℃; for 2h; Inert atmosphere; Large scale;	88%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h;	85%
Stage #1: methyl cyclopropylcarboxylate With methanol; aluminum (III) chloride; sodium tetrahydroborate at 2℃; Stage #2: With ammonium chloride In water Temperature; Reagent/catalyst;	74.3%

(cyclopropylmethyl)trifluoroboron potassium hydride

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation;	85%

5500-21-0

cyclopropropanecarbonitrile

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water; toluene at 90℃;	77%

186581-53-3, 908094-01-9

diazomethane

107-18-6

allyl alcohol

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
bis(benzonitrile)palladium(II) dichloride In dichloromethane at 0 - 10℃; catalytic cyclopropanation of other unsaturated compounds;	72%
bis(benzonitrile)palladium(II) dichloride In diethyl ether; dichloromethane at 0 - 10℃; for 0.5h;	72%
bis(benzonitrile)palladium(II) dichloride In dichloromethane at 0 - 10℃;	72%
palladium(II) acetylacetonate In diethyl ether at -10℃;	45%
With bis(benzonitrile)palladium(II) dichloride In dichloromethane at 0 - 10℃; Yield given;

75-11-6

diiodomethane

107-18-6

allyl alcohol

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With 1,2-dimethoxyethane; zinc In diethyl ether Heating;	67%
With lanthanum; iodine In tetrahydrofuran for 5h;	67%

70458-21-8

cyclobutanecarbonyl m-chlorobenzoyl peroxide

A

627-27-0

homoalylic alcohol

B

2516-33-8

Cyclopropylmethanol

C

70458-29-6

3-butenyl m-chlorobenzoate

D

70458-27-4

cyclobutyl m-chlorobenzoate

E

70458-28-5

cyclopropylmethyl m-chlorobenzoate

F

2919-23-5

cyclobutanol

Conditions

Conditions	Yield
With acetic acid; potassium iodide In tetrachloromethane at 26℃; Rate constant; on silica;	A 4.3% B 9.6% C 19.5% D 11.8% E 45.5% F 6.5%
With acetic acid; potassium iodide In neat (no solvent) at 26℃; Rate constant; on silica;
With acetic acid; potassium iodide In chloroform at 55℃; Rate constant;
With acetic acid; potassium iodide In tetrachloromethane at 55℃; Rate constant;

...Expand

70458-21-8

cyclobutanecarbonyl m-chlorobenzoyl peroxide

A

2516-33-8

Cyclopropylmethanol

B

70458-29-6

3-butenyl m-chlorobenzoate

C

70458-27-4

cyclobutyl m-chlorobenzoate

D

70458-28-5

cyclopropylmethyl m-chlorobenzoate

Conditions

Conditions	Yield
With acetic acid; potassium iodide In tetrachloromethane at 26℃; Further byproducts given;	A 9.6% B 19.5% C 11.8% D 45.5%

...Expand

Ti(OCH2CH(CH2)2)4

A

627-27-0

homoalylic alcohol

B

2516-33-8

Cyclopropylmethanol

C

22597-56-4

Di-(1-butenyl)ether (trans/trans)

D

74976-40-2

bis(cyclopropylmethyl) ether

E

74976-38-8

allylcarbinyl cyclopropylcarbinyl ether

Conditions

Conditions	Yield
In gas byproducts: CH2CH(CH2)2, CH2(CH)2CH2; decomposition at a pressure of 0.01 mm Hg at 550°C; further compounds: (CH2)2CHCHO (trace), TiO2, H2 (<0.5%), C (4%); NMR; GC; mass spectra;	A 37% B 23% C 12% D 10% E 18%

...Expand

13287-42-8

(2-bromoethyl)oxirane

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With copper; triphenylphosphine In tetrahydrofuran	89 % Chromat.
With copper(l) iodide; lithium dihydronaphthylide radical; triphenylphosphine In tetrahydrofuran 1) -45 deg C, 5 min, -23 deg C, 3 h, r.t.; Yields of byproduct given;	89 % Chromat.

13287-42-8

(2-bromoethyl)oxirane

A

2516-33-8

Cyclopropylmethanol

B

2919-23-5

cyclobutanol

Conditions

Conditions	Yield
With copper; triphenylphosphine In toluene Product distribution; other reagent and solvent;

594-11-6

methylcyclopropane

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With phosphate buffer; air; 1,4-dihydronicotinamide adenine dinucleotide at 45℃; methane mono-oxygenase from Methylococcus capsulatus (Bath);

1015-45-8

cyclopropylmethyl tosylate

A

2516-33-8

Cyclopropylmethanol

B

104-15-4

toluene-4-sulfonic acid

Conditions

Conditions	Yield
With sodium acetate In formic acid; acetic acid at 25℃; Rate constant;
With sodium methylate In ethanol; water at 25℃; Rate constant;

70561-86-3

cyclopropylcarbinyl pentamethylbenzenesulfonate

A

2516-33-8

Cyclopropylmethanol

B

99861-57-1

1,2,3,4,5-pentamethylbenzene-6-sulfonic acid

Conditions

Conditions	Yield
With sodium methylate In ethanol; water at 25℃; Rate constant;
With sodium acetate In formic acid; acetic acid at 25℃; Rate constant;

99700-70-6

2-(2-Iodo-ethyl)-oxirane

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With tert.-butyl lithium 1.) Et2O, pentane, -78 deg C, 5 min; 2.) warming; Yield given. Multistep reaction;
With tert.-butyl lithium In diethyl ether; pentane at -78℃; Product distribution; Effect of various additives or warming.;

4023-34-1

cyclopropanecarboxylic acid chloride

2516-33-8

Cyclopropylmethanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride

76387-45-6

1,3-bis(cyclopropylcarbinyl)-3-methyltriazene

A

627-27-0

homoalylic alcohol

B

2516-33-8

Cyclopropylmethanol

C

2919-23-5

cyclobutanol

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 22℃; Product distribution; Mechanism;

...Expand

7732-18-5

water

5911-08-0

chloro(cyclopropyl)methane

lithium carbonate

lithium carbonate

A

927-73-1

3-butenyl chloride

B

2516-33-8

Cyclopropylmethanol

C

1120-57-6

chlorocyclobutane

D

2919-23-5

cyclobutanol

...Expand

CYCLOPROPYL CARBINOL Chemical Properties

CYCLOPROPYL CARBINOL Uses

CYCLOPROPYL CARBINOL Safety Profile

Safety Information of CYCLOPROPYL CARBINOL(2516-33-8):
Hazard Codes:Xn,Xi  ,C  ,F
Risk Statements:10-22-36-34
10:Flammable 
22:Harmful if swallowed 
36:Irritating to the eyes 
34:Causes burns 
Safety Statements:16-26-36-45-36/37/39
16:Keep away from sources of ignition - No smoking 
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:Wear suitable protective clothing 
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
36/37/39:Wear suitable protective clothing, gloves and eye/face protection  
RIDADR:UN 1987 3/PG 3
WGK Germany:1
RTECS:GZ2212250
Hazard Note:Irritant
HazardClass:3
PackingGroup:III

CYCLOPROPYL CARBINOL Specification