Methyl 2-octynoate supplier

Name
METHYL 2-OCTYNOATE
EINECS 203-836-6
CAS No. 111-12-6
Article Data17
CAS DataBase
Density 0.92 g/mL at 25 °C(lit.)
Solubility Almost insoluble in water
Melting Point
Formula C9H14 O2
Boiling Point 217-220 °C(lit.)
Molecular Weight 154.209
Flash Point 192 °F
Transport Information
Appearance colorless liquid
Safety Moderately toxic by ingestion and skin contact. A moderate skin and eye irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
Risk Codes 22-38
Molecular Structure
Hazard Symbols Xn
Synonyms Folione;Methyl 2-octynate; Methyl 2-octynoate; Methyl pentylacetylenecarboxylate; NSC72098; Vert de violette, artificial
PSA 26.30000
LogP 1.74310

Synthetic route

: 628-71-7
1-Heptyne

: 79-22-1
methyl chloroformate

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran 1.) -78 deg C, 30 min, 2.) -78 deg C to r.t., 15 min;	97%

: 186581-53-3, 908094-01-9
diazomethane

: 5663-96-7
oct-2-ynoic acid

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
In diethyl ether	95%
In diethyl ether	10.03 g

: 5663-96-7
oct-2-ynoic acid

: 74-88-4
methyl iodide

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 10 - 15℃; for 24h;	90%

: 67-56-1
methanol

: 628-71-7
1-Heptyne

: 201230-82-2
carbon monoxide

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
With sodium hydrogencarbonate; copper(ll) bromide; palladium(II) bromide at 20℃; under 760 Torr; for 2h;	83%
With oxygen; sodium acetate; triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 20℃; for 48h;	75%
With sodium acetate; copper dichloride; palladium dichloride under 760 Torr; for 2h; Ambient temperature;	74 % Chromat.

...Expand

: 93296-09-4
4-methoxyphenylzinc chloride

: 176246-52-9
methyl (E)-2,3-dibromo-2-octenoate

A: 111-12-6
methyl 2-octynoate

B: 2132-80-1
4,4'-Dimethoxybiphenyl

C: methyl (E)-2-bromo-3-(4-methoxyphenyl)-2-octenoate

D: (Z)-2,3-Bis-(4-methoxy-phenyl)-oct-2-enoic acid methyl ester

Conditions

Conditions	Yield
With palladium diacetate; triphenyl-arsane In tetrahydrofuran at 20℃; for 21.5h; Further byproducts given;	A n/a B n/a C 61% D n/a

...Expand

: 68113-72-4
1-octynylzinc chloride

: 176246-52-9
methyl (E)-2,3-dibromo-2-octenoate

A: 111-12-6
methyl 2-octynoate

B: methyl (E)-2-bromo-4-pentyl-2-undecen-4-ynoate

C: (Z)-2-Oct-1-ynyl-3-pentyl-undec-2-en-4-ynoic acid methyl ester

Conditions

Conditions	Yield
With palladium diacetate; triphenyl-arsane In tetrahydrofuran at 20℃; for 23h;	A n/a B 57% C n/a

...Expand

: 133472-27-2
4-fluorophenylzinc chloride

: 176246-52-9
methyl (E)-2,3-dibromo-2-octenoate

A: 111-12-6
methyl 2-octynoate

B: 398-23-2
4,4'-difluorobiphenyl

C: methyl (E)-2-bromo-3-(4-fluorophenyl)-2-octenoate

D: (Z)-2,3-Bis-(4-fluoro-phenyl)-oct-2-enoic acid methyl ester

Conditions

Conditions	Yield
With palladium diacetate; triphenyl-arsane In tetrahydrofuran at 20℃; for 24h;	A n/a B n/a C 56% D n/a

...Expand

: (2-methoxymethoxy)phenylzinc chloride

: 176246-52-9
methyl (E)-2,3-dibromo-2-octenoate

A: 111-12-6
methyl 2-octynoate

B: 121169-22-0
2,2'-bis(methoxymethoxy)-1,1'-biphenyl

C: methyl (E)-2-bromo-3-<(2-methoxymethoxy)phenyl>-2-octenoate

D: (Z)-2,3-Bis-(2-methoxymethoxy-phenyl)-oct-2-enoic acid methyl ester

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 71h;	A n/a B n/a C 43% D n/a

...Expand

: 67-56-1
methanol

: 35087-30-0
5-pentyl-2,4-dihydro-3H-pyrazol-3-one

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
With lead(IV) acetate for 0.25h;	38%

: 67-56-1
methanol

: 5663-96-7
oct-2-ynoic acid

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
With sulfuric acid
With hydrogenchloride	8.9 g

: 74198-05-3
sodioheptyne

: 79-22-1
methyl chloroformate

: 111-12-6
methyl 2-octynoate

: 63125-02-0
Methyl-2-hexanoyl-2-triphenylphosphoranylidenacetat

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
at 220 - 250℃;

: 67-56-1
methanol

: 1,1-dichloro-2-octynyl phenyl sulfide

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
With sodium carbonate at -20℃; for 0.5h; Hydrolysis;

: 67-56-1
methanol

octyn-(2)-oic acid (1)-chloride: octyn-(2)-oic acid (1)-chloride

: 111-12-6
methyl 2-octynoate

: 194856-56-9
Oct-2-ynylsulfanyl-benzene

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; sulfuryl chloride / CCl4 / 0.5 h / 0 °C 2: sodium carbonate / 0.5 h / -20 °C View Scheme

: 142-61-0
Hexanoyl chloride

: 111-12-6
methyl 2-octynoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene 2: 220 - 250 °C View Scheme

: 111-12-6
methyl 2-octynoate

: 2396-85-2
methyl oct-2-enoate

Conditions

Conditions	Yield
With formic acid; (1,2-dimethoxyethane)dichloronickel(II); zinc; bis(2-diphenylphosphinoethyl)phenylphosphine In 1,4-dioxane at 120℃; for 16h; Sealed tube;	100%

: 111-12-6
methyl 2-octynoate

: 176246-52-9
methyl (E)-2,3-dibromo-2-octenoate

Conditions

Conditions	Yield
With pyridinium hydrobromide perbromide In dichloromethane for 192h;	98%

: 111-12-6
methyl 2-octynoate

: 68854-59-1
2-cis octenoic acid methyl ester

Conditions

Conditions	Yield
With ammonium formate In N,N-dimethyl-formamide at 80℃; Green chemistry; diastereoselective reaction;	96%
Stage #1: methyl 2-octynoate With tris-(dibenzylideneacetone)dipalladium(0); 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 20℃; for 0.25h; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane at 80℃; for 3h; Inert atmosphere; optical yield given as %ee; stereoselective reaction;	90%
With formic acid; nickel dibromide; zinc In 1,4-dioxane at 120℃; for 16h; Sealed tube; stereoselective reaction;	82%
With hydrogen; Lindlar's catalyst
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; formic acid; tributylphosphine; triethylamine In tetrahydrofuran at 40℃; for 2h;	95 % Chromat.

: 500-99-2
3,5-dimethoxyphenol

: 111-12-6
methyl 2-octynoate

: 5,7-dimethoxy-4-n-pentylcoumarin

Conditions

Conditions	Yield
With palladium diacetate In trifluoroacetic acid at 20℃; for 77h;	96%

: 111-12-6
methyl 2-octynoate

: 98-80-6
phenylboronic acid

: 189890-29-7
(E)-methyl 3-phenyloct-2-enoate

Conditions

Conditions	Yield
With copper diacetate In methanol at 28℃; for 2.5h; Inert atmosphere; stereoselective reaction;	96%
With methanol; copper (I) acetate at 28℃; for 24h; Inert atmosphere; stereoselective reaction;	94%
With cobalt acetylacetonate; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere; stereoselective reaction;	93%

: 111-12-6
methyl 2-octynoate

: 5720-07-0
4-methoxyphenylboronic acid

: 176246-71-2
methyl (E)-3-(4-methoxyphenyl)-2-octenoate

Conditions

Conditions	Yield
With cobalt acetylacetonate; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere; stereoselective reaction;	96%

: 111-12-6
methyl 2-octynoate

: 723-51-3
N-benzylpyridine-4-sulfonamide

: methyl (Z)-3-(benzylamino)-2-(pyridin-4-yl)oct-2-enoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 16h; Sealed tube;	96%

: 3262-89-3
triphenylboroxine

: 111-12-6
methyl 2-octynoate

: 189890-29-7
(E)-methyl 3-phenyloct-2-enoate

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 10h; Inert atmosphere; stereoselective reaction;	94%

: 111-12-6
methyl 2-octynoate

: 17933-03-8
m-tolylboronic acid

: C16H22O2

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 10h; Inert atmosphere; stereoselective reaction;	94%

: 111-12-6
methyl 2-octynoate

: 5720-05-8
4-methylphenylboronic acid

: C16H22O2

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 4h; Inert atmosphere; stereoselective reaction;	94%

: 111-12-6
methyl 2-octynoate

: 1679-18-1
4-Chlorophenylboronic acid

: C15H19ClO2

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 4h; Inert atmosphere; stereoselective reaction;	94%

: 111-12-6
methyl 2-octynoate

: 5467-74-3
4-Bromophenylboronic acid

: 1126701-07-2
methyl (E)-3-(4-bromophenyl)-2-octenoate

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 24h; Inert atmosphere; stereoselective reaction;	94%
With cobalt acetylacetonate; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere; stereoselective reaction;	93%

: 111-12-6
methyl 2-octynoate

: 13331-27-6
m-nitrobenzene boronic acid

: 1126701-04-9
methyl (E)-3-(3-nitrophenyl)-2-octenoate

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 5h; Inert atmosphere; stereoselective reaction;	94%
With cobalt acetylacetonate; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere; stereoselective reaction;	67%

: 111-12-6
methyl 2-octynoate

: 87199-16-4
3-Formylphenylboronic acid

: 1126701-02-7
methyl (E)-3-(3-formylphenyl)-2-octenoate

Conditions

Conditions	Yield
With cobalt acetylacetonate; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere; stereoselective reaction;	94%

: 111-12-6
methyl 2-octynoate

: 7367-81-9
methyl (E)-oct-2-enoate

Conditions

Conditions	Yield
Stage #1: methyl 2-octynoate With tris-(dibenzylideneacetone)dipalladium(0); 1,4-di(diphenylphosphino)-butane In 1,4-dioxane; water at 20℃; for 0.25h; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane at 80℃; for 10h; Inert atmosphere; optical yield given as %ee; stereoselective reaction;	93%
Stage #1: methyl 2-octynoate With Triethoxysilane; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate In dichloromethane at 20℃; for 0.5h; Stage #2: With copper(l) iodide; tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 20h; Further stages.;	83%

: 573-57-9
1,4-dihydronaphthalene-1,4-epoxide

: 111-12-6
methyl 2-octynoate

: methyl (E)-3-[(1S,2R)-1-hydroxy-1,2-dihydro-2-naphthalenyl]-2-octenoate

Conditions

Conditions	Yield
Stage #1: 1,4-dihydronaphthalene-1,4-epoxide With zinc; dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) In acetonitrile at 20℃; Stage #2: methyl 2-octynoate With water In acetonitrile at 20℃; for 16h; Further stages.;	93%

: 111-12-6
methyl 2-octynoate

: 149104-90-5
4-acetylphenylboronic acid

: 1033424-61-1
C17H22O3

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 5h; Inert atmosphere; stereoselective reaction;	93%

: 292638-84-7
styrene

: 111-12-6
methyl 2-octynoate

: 1392484-85-3
(E)-3-(1-chlorohexylidene)-dihydro-5-phenylfuran-2(3H)-one

Conditions

Conditions	Yield
With copper(II) choride dihydrate; oxygen; palladium dichloride In acetonitrile; benzene at 100℃; under 760.051 Torr; for 12h;	93%

: 111-12-6
methyl 2-octynoate

: 72824-04-5
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 1379654-29-1
C12H20O2

Conditions

Conditions	Yield
With copper diacetate In methanol at -78 - 25℃; for 3h; Inert atmosphere; stereoselective reaction;	92%

: 111-12-6
methyl 2-octynoate

: 111-11-5
methyl octanate

Conditions

Conditions	Yield
Stage #1: methyl 2-octynoate With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 20℃; for 0.25h; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane at 80℃; Inert atmosphere; chemoselective reaction;	91%
With o-phenylenebis(diphenylphosphine); copper diacetate; poly(methylhydrosiloxane) In toluene; tert-butyl alcohol at 20℃; for 3h;	90%
With magnesium In methanol Ambient temperature; reacted until the Mg had dissolved;	76%

: 111-12-6
methyl 2-octynoate

: 16419-60-6
2-Methylphenylboronic acid

: C16H22O2

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 6h; Inert atmosphere; stereoselective reaction;	91%

: 111-12-6
methyl 2-octynoate

: 5122-99-6
4-iodophenylboronic acid

: C15H19IO2

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 3h; Inert atmosphere; stereoselective reaction;	91%
With methanol; copper (I) acetate at 28℃; for 3h; stereoselective reaction;	91%

: 111-12-6
methyl 2-octynoate

: 10365-98-7
3-methoxyphenylboronic acid

: 1126701-00-5
methyl (E)-3-(3-methoxyphenyl)-2-octenoate

Conditions

Conditions	Yield
With cobalt acetylacetonate; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere; stereoselective reaction;	91%

: 111-12-6
methyl 2-octynoate

: 3119-02-6
4-cyanobenzenesulfonamide

: methyl (Z)-3-amino-2-(4-cyanophenyl)oct-2-enoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Sealed tube;	91%

: 111-12-6
methyl 2-octynoate

: 32316-92-0
naphthalene-2-boronic acid

: C19H22O2

Conditions

Conditions	Yield
With copper (I) acetate In methanol at 28℃; for 24h; Inert atmosphere; stereoselective reaction;	90%

: 111-12-6
methyl 2-octynoate

: 20469-72-1
phenylboronic acid-d2

: 1033424-99-5
C15H19(2)HO2

Conditions

Conditions	Yield
With cobalt acetylacetonate; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere; stereoselective reaction;	90%

: 111-12-6
methyl 2-octynoate

: 107-18-6
allyl alcohol

: 1446623-66-0
(E)-methyl2-allyl-3-bromooct-2-enoate

Conditions

Conditions	Yield
With copper(ll) bromide; palladium dichloride In tetrahydrofuran at 25℃; for 12h; Solvent; Reagent/catalyst; regioselective reaction;	90%

Methyl 2-octynoate Chemical Properties

IUPAC: Methyl oct-2-ynoate
Methyl 2-octynoate (111-12-6) is also called for 2-Octynoic acid, methyl ester ; 4-02-00-01715 (Beilstein Handbook Reference) ; AI3-03938 ; BRN 1756887 ; EINECS 203-836-6 ; FEMA No. 2729 ; Folione ; Methyl 2-octinate ; Methyl 2-octynate ; Methyl hept-1-yne-1-carboxylate ; Methyl heptine carbonate ; Methyl pentylacetylenecarboxylate ; NSC 72098 ; Vert de violette, artificial and so on.
Molecular Formula: C₉H₁₄O₂
Molecular Weight: 154.21
EINECS: 203-836-6
LogP: ACD/LogP: 3.56
XLogP: 3.30
ALOGPS: 3.08
ACD/LogD (pH 5.5): 3.56
ACD/LogD (pH 7.4): 3.56
ACD/BCF (pH 5.5): 299.29
ACD/BCF (pH 7.4): 299.29
ACD/KOC (pH 5.5): 2060.62
ACD/KOC (pH 7.4): 2060.62
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 5
Heavy Atom Count: 11
Formal Charge: 0
Complexity: 171
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 0
Undefined Atom StereoCenter Count: 0
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 1
Index of Refraction: 1.443
Molar Refractivity: 43.52 cm³
Molar Volume: 163.8 cm³
Surface Tension: 33.1 dyne/cm
Density: 0.94 g/cm³
Flash Point: 88.9°C
Enthalpy of Vaporization: 45.49 kJ/mol
Boiling Point: 218.5°C at 760 mmHg
Vapour Pressure: 0.125 mmHg at 25°C
The molecular structure of Methyl 2-octynoate (111-12-6):

Methyl 2-octynoate Toxicity Data With Reference

1.	skn-rbt 500 mg/24H MOD	FCTXAV Food and Cosmetics Toxicology. 17 (1979),375.
2.	orl-rat LD50:1530 mg/kg	FCTXAV Food and Cosmetics Toxicology. 17 (1979),375.
3.	skn-rbt LD50:3300 mg/kg	FCTXAV Food and Cosmetics Toxicology. 17 (1979),375.

Methyl 2-octynoate Consensus Reports

Reported in EPA TSCA Inventory.

Methyl 2-octynoate Safety Profile

Moderately toxic by ingestion and skin contact. A moderate skin and eye irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Hazard Codes: Xn
Risk Statements: 22-38
R22: Harmful if swallowed
R38: Irritating to the skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
WGK Germany: 2
RTECS: RI2735000

Methyl 2-octynoate Specification

Treatment of Methyl 2-octynoate (111-12-6) in Wastewater,see as follows :
Total removal:8.15 percent
Total biodegradation:0.10 percent
Total sludge adsorption:3.20 percent
Total to air:4.85 percent
(using 10000 hr Bio P,A,S)

Product Name

METHYL 2-OCTYNOATE

Synthetic route

Methyl 2-octynoate Chemical Properties

Methyl 2-octynoate Toxicity Data With Reference

Methyl 2-octynoate Consensus Reports

Methyl 2-octynoate Safety Profile

Methyl 2-octynoate Specification

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