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Name Erucylamide
EINECS204-009-2
CAS No. 112-84-5
Density0.874 g/cm³
PSA43.09000
LogP7.76990
Solubilitypractically insoluble in water
Melting Point79-81 °C(lit.)
FormulaC₂₂H₄₃NO
Boiling Point474.2 °C at 760 mmHg
Molecular Weight337.59
Flash Point240.6 °C
Transport InformationN/A
Appearancesolid
Safety26-36-37/39
Risk Codes36/37/38
Molecular Structure
Hazard SymbolsXi
SynonymsXi
Article Data2

Erucylamide Synthetic route

: 112-86-7
cis-13-docosenoic acid

: 112-84-5
Unislip 1753

Conditions

Conditions	Yield
With ammonia; zircornium(IV) n-propoxide at 165℃; for 6h; Reagent/catalyst;	98.8%
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / Inert atmosphere 2: ammonium hydroxide View Scheme

: 59044-32-5, 7459-29-2
erucic acid chloride

: 112-84-5
Unislip 1753

Conditions

Conditions	Yield
With ammonium hydroxide

: 112-84-5
Unislip 1753

: 26398-95-8
cis-docos-13-enylamine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 12h; Reflux;	100%

: 112-84-5
Unislip 1753

: 629-98-1
erucyl alcohol

Conditions

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 18h; Inert atmosphere; chemoselective reaction;	94%

: 27126-76-7
[hydroxy(tosyloxy)iodo]benzene

: 112-84-5
Unislip 1753

: 116749-38-3
cis-12-heneicosenylammonium tosylate

Conditions

Conditions	Yield
In acetonitrile at 65 - 70℃; for 0.0333333h;	63%

: 112-84-5
Unislip 1753

: (3R)-N-{(3R,6R,9R,12S,15R,18S,19R)-6-(3-amino-3-oxopropyl)-15-[(2S)-butan-2-yl]-12-(4-hydroxybenzyl)-9-[(1R)-1-hydroxyethyl]-3,19-dimethyl-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentaazacyclononadecan-18-yl}-15-carbamimidamido-3-hydroxypentadecanamide

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere 6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / -78 - 20 °C / Inert atmosphere 7.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; tert-butyl alcohol / 2 h / 20 °C 8.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h 8.2: 70 h / 20 °C 9.1: trifluoroacetic acid / dichloromethane; water / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux
2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C
3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 - 10 °C / Inert atmosphere
4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C
4.2: 16 h / -78 - 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C
5.2: 12 h / 20 °C
5.3: 120 h / Inert atmosphere
6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / -78 - 20 °C / Inert atmosphere
7.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; tert-butyl alcohol / 2 h / 20 °C
8.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h
8.2: 70 h / 20 °C
9.1: trifluoroacetic acid / dichloromethane; water / 1 h / 20 °C
View Scheme

: 112-84-5
Unislip 1753

: 9H-fluoren-9-ylmethyl (13Z)-docos-13-en-1-yl-carbamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C View Scheme

: 112-84-5
Unislip 1753

: 9H-fluoren-9-yl-methyl (13-hydroxyhexadec-15-en-1-yl)carbamate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux
2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C
3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 - 10 °C / Inert atmosphere
4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C
4.2: 16 h / -78 - 20 °C
View Scheme

: 112-84-5
Unislip 1753

: di-tert-butyl [(E)-{[13-(methoxymethoxy)hexadec-15-en-1-yl]amino}methylylidene]biscarbamate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere View Scheme

Yield

Multi-step reaction with 5 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux
2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C
3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 - 10 °C / Inert atmosphere
4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C
4.2: 16 h / -78 - 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C
5.2: 12 h / 20 °C
5.3: 120 h / Inert atmosphere
View Scheme

: 112-84-5
Unislip 1753

: di-tert-butyl [(E)-{[13-(methoxymethoxy)-15-oxopentadecyl]amino}methylylidene]biscarbamate

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere 6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / -78 - 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux
2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C
3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 - 10 °C / Inert atmosphere
4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C
4.2: 16 h / -78 - 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C
5.2: 12 h / 20 °C
5.3: 120 h / Inert atmosphere
6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / -78 - 20 °C / Inert atmosphere
View Scheme

Erucylamide Chemical Properties

Molecule structure of Erucamide (CAS NO.112-84-5):

IUPAC Name: (Z)-Docos-13-enamide
Molecular Weight: 337.58292 g/mol
Molecular Formula: C₂₂H₄₃NO
Density: 0.874 g/cm³
Melting Point: 79-81 °C(lit.)
Boiling Point: 474.2 °C at 760 mmHg
Flash Point: 240.6 °C
Index of Refraction: 1.469
Molar Refractivity: 107.59 cm³
Molar Volume: 386 cm³
Polarizability: 42.65×10^-24 cm³
Surface Tension: 33.4 dyne/cm
Enthalpy of Vaporization: 73.75 kJ/mol
Vapour Pressure: 3.69E-09 mmHg at 25 °C
Water Solubility: 0.200 mg/L
Storage Temp.: 0-6 °C
XLogP3-AA: 8.8
H-Bond Donor: 1
H-Bond Acceptor: 1
Rotatable Bond Count: 19
Tautomer Count: 2
Exact Mass: 337.334465
MonoIsotopic Mass: 337.334465
Topological Polar Surface Area: 43.1
Heavy Atom Count: 24
Complexity: 286
Canonical SMILES: CCCCCCCCC=CCCCCCCCCCCCC(=O)N
Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCCCCC(=O)N
InChI: InChI=1S/C22H43NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H2,23,24)/b10-9-
InChIKey: UAUDZVJPLUQNMU-KTKRTIGZSA-N
EINECS: 204-009-2
Product Categories: Amides;Chiral Compounds

Erucylamide Uses

Erucamide (CAS NO.112-84-5) is used for the synthesis of photosensitive materials.

Erucylamide Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
Hazardous Substances Data: 112-84-5(Hazardous Substances Data)

Erucylamide Specification

Erucamide (CAS NO.112-84-5) is also named as 13-Docosenamide ; 13-Docosenamide, (Z)- ; Erucic acid amide ; HSDB 5577 ; UNII-0V89VY25BN ; (Z)-Docos-13-enamide ; 13-Docosenamide, (13Z)- . Erucamide (CAS NO.112-84-5) is white flaky crystal. It is soluble in ethanol, ether and other organic solvents. It is stable and incompatible with strong oxidizing agents.

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