Conditions | Yield |
---|---|
With air; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h; | 100% |
With hydrogenchloride; calcium hypochlorite In tetrachloromethane; tert-butyl alcohol for 7h; | 58% |
11-cyanoundecanoic acid methyl ester
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water for 2.5h; Reflux; | 100% |
2-nitrocyclododecanone
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In methanol for 10h; Ambient temperature; | 92% |
With Oxone; sodium hydroxide; disodium hydrogenphosphate; water 1.) MeOH, 70 deg C, 4 h, 2.) MeOH, r.t., 4 h; Yield given. Multistep reaction; |
A
12-hydroxydodecanoic acid
B
1,12-dodecandiol
C
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h; | A 85% B 8% C 6% |
With sodium tetrahydroborate In tetrahydrofuran at 23℃; for 120h; | A 82% B 12% C n/a |
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 9h; Product distribution; influence of temperature, reaction time; | A 77% B 11% C 9% |
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h; | A 66% B 6% C 11% |
Conditions | Yield |
---|---|
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 24h; | 85% |
With tetrafluoroboric acid; iodomesitylene; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water; acetonitrile at 50℃; for 10h; Inert atmosphere; | 77 %Spectr. |
With potassium peroxymonosulfate; iodobenzene In water; acetonitrile at 60℃; for 8h; | 82 %Spectr. |
(1S,2S)-Cyclododecane-1,2-diol
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With potassium carbonate; stearic acid at 50℃; for 22.5h; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A; | 84% |
dec-1-en-3-ol
carbon monoxide
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction; | 83% |
Conditions | Yield |
---|---|
With oxygen; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h; | A 80% B 10% |
1,12-dimethoxydodecane
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With lithium nitrate In water; acetonitrile at 25℃; anodic oxidation; | 78% |
cyclododecanone
A
oxacyclotridecan-2-one
B
12-hydroxydodecanoic acid
C
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With maleic anhydride; dihydrogen peroxide In dichloromethane; acetic anhydride for 15h; Heating; | A 77% B n/a C n/a |
cis-1,2-cyclododecanediol
A
12-oxododecanoic acid
B
1,12-dodecanedioic acid
C
dodecanedial
D
cyclododecane-1,2-dione
Conditions | Yield |
---|---|
With Oxone; sodium ortho-iodobenzenesulfonate In acetonitrile at 70℃; for 1h; | A n/a B n/a C n/a D 72% |
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid at 70℃; under 760.051 Torr; for 14h; | 68% |
Conditions | Yield |
---|---|
Stage #1: cyclohexanone With dihydrogen peroxide In water at 25 - 30℃; for 0.25h; UV-irradiation; Stage #2: In water at 50℃; for 6h; Temperature; UV-irradiation; | 67.1% |
Multi-step reaction with 2 steps 1: H2O2; water 2: iron (II)-sulfate; aqueous sulfuric acid View Scheme | |
Multi-step reaction with 2 steps 1: H2O2; diethyl ether 2: iron (II)-sulfate heptahydrate; methanol View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride; calcium hypochlorite In tetrachloromethane; tert-butyl alcohol for 7h; | 65% |
With oleate hydratase from S. maltophilia In aq. buffer at 35℃; for 2h; pH=8; Enzymatic reaction; | 46% |
With chromium(VI) oxide; acetic acid |
Conditions | Yield |
---|---|
With jones reagent; osmium(VIII) oxide In water; acetone for 20h; Ambient temperature; | 65% |
C48H88O16
A
ethene
B
1,12-dodecanedioic acid
C
12-oxo-tetradecanoic acid
Conditions | Yield |
---|---|
In n-heptane at 100℃; Product distribution; var. solvent, var. temp.; | A n/a B 60% C 12% D n/a |
Conditions | Yield |
---|---|
With dihydrogen peroxide In methanol; water for 2h; Ambient temperature; | 47% |
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With potassium hydroxide for 48h; | 47% |
Conditions | Yield |
---|---|
Pseudomonas K24 | 7% |
2-Acetoxycyclododecanone
A
1,12-dodecanedioic acid
B
2-hydroxycyclododecanone
Conditions | Yield |
---|---|
With potassium hydroxide In methanol | A 4.9 g B 3.1% |
With potassium hydroxide In methanol Heating; | A 4.9 g B 3.1 g |
Conditions | Yield |
---|---|
With diethyl ether; magnesium bei der Einw. von Kohlendioxid auf das Reaktionsprodukt; |
Conditions | Yield |
---|---|
With sulfuric acid; iron(II) sulfate | |
With methanol; iron(II) sulfate |
1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide
A
Adipic acid
B
1,12-dodecanedioic acid
C
cyclohexanone
D
hexanoic acid
Conditions | Yield |
---|---|
at 110 - 160℃; |
dodec-6c-enedioic acid
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With 1,4-dioxane; platinum Hydrogenation; |
Conditions | Yield |
---|---|
With nitric acid | |
With ammonium vanadate bei Siedetemperatur; | |
With nitric acid |
Conditions | Yield |
---|---|
With nitric acid | |
With ammonium vanadate; nitric acid | |
With nitric acid |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium hydroxide; paraffin oil at 320℃; |
Conditions | Yield |
---|---|
With ethanol Erwaermen des Reaktionsgemisches mit wss.Natronlauge und Erhitzen des nach dem Ansaeuern erhaltenen Reaktionsprodukts auf 180grad; |
Conditions | Yield |
---|---|
With sodium ethanolate |
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide for 2h; Reflux; | 100% |
With thionyl chloride Heating; | 95% |
With thionyl chloride |
Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With sulfuric acid for 24h; Reflux; Inert atmosphere; | 100% |
With sulfuric acid Heating; | 99% |
1,12-dodecanedioic acid
1,1'-carbonyldiimidazole
1,12-Di-imidazol-1-yl-dodecane-1,12-dione
Conditions | Yield |
---|---|
In neat (no solvent) for 2h; | 100% |
In N,N-dimethyl acetamide at 40℃; | |
In tetrahydrofuran for 24h; Ambient temperature; | |
In tetrahydrofuran |
di(succinimido) carbonate
1,12-dodecanedioic acid
dodecanedioic acid bis(2,5-dioxopyrrolidin-1-yl) ester
Conditions | Yield |
---|---|
With pyridine In acetonitrile at 20℃; for 7h; | 100% |
With pyridine In acetonitrile at 20℃; for 7h; Inert atmosphere; | 100% |
With pyridine In acetonitrile at 20℃; for 3h; | 90% |
Conditions | Yield |
---|---|
With sulfuric acid; mercury(II) diacetate at 20 - 50℃; for 4h; | 100% |
With sulfuric acid; mercury(II) diacetate |
1,12-dodecanedioic acid
dodecanedial
Conditions | Yield |
---|---|
With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 1h; Ambient temperature; | 99% |
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 24h; | 75% |
With thexylchloroborane*methyl sulfide In dichloromethane for 0.25h; Ambient temperature; |
Conditions | Yield |
---|---|
With 1-hexadecyl-3-sulfo-1H-imidazol-3-ium chloride In neat (no solvent) at 110℃; for 16h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
for 2h; Reflux; Acidic conditions; | 98% |
With sulfuric acid for 2h; Reflux; | 98% |
With hydrogenchloride decane-dicarboxylic acid-(1.10)-di--ester; |
1-hydroxy-pyrrolidine-2,5-dione
1,12-dodecanedioic acid
dodecanedioic acid bis(2,5-dioxopyrrolidin-1-yl) ester
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; | 98% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dimethyl sulfoxide at 20℃; |
Conditions | Yield |
---|---|
In methanol at 21℃; for 48h; | 98% |
Conditions | Yield |
---|---|
With triphenylphosphine at 90℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With tricarbonyl(η(4)-cycloocta-1,5-diene)iron; phenylsilane In tetrahydrofuran at 20℃; for 24h; UV-irradiation; Inert atmosphere; chemoselective reaction; | 97% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; | 91% |
Multi-step reaction with 2 steps 1: sulfuric acid / Heating 2: LiAlH4 / diethyl ether / 0 °C View Scheme | |
Stage #1: 1,12-dodecanedioic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 2℃; for 0.25h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 2℃; |
1,12-dodecanedioic acid
isobutene
1,10-decanedicarboxylic acid mono-tert-butyl ester
Conditions | Yield |
---|---|
With graphene-ferric oxide composite nanomaterial In dichloromethane for 4h; Solvent; Reagent/catalyst; Cooling with ice; | 95.3% |
With graphene/ferric oxide composite nanomaterial In dichloromethane; di-isopropyl ether for 4h; Solvent; Cooling with ice; |
Conditions | Yield |
---|---|
With 3,5-bis-trifluromethylphenylboronic acid In 1,3,5-trimethyl-benzene for 24h; Heating; | 95% |
Conditions | Yield |
---|---|
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In 1,4-dioxane at 220℃; under 7500.75 Torr; for 42h; Solvent; Autoclave; Inert atmosphere; | 95% |
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
Stage #1: 1,12-dodecanedioic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: 11-amino-N-(strychnin-2-yl)undecanoic acid amide In dichloromethane at 20℃; for 14h; Inert atmosphere; Cooling with ice; | 93% |
tri-n-butylbenzylammonium hydroxide
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
at 20℃; for 12h; | 90.55% |
Conditions | Yield |
---|---|
With zinc(II) chloride at 230℃; for 20h; Condensation; | A 90% B 3% |
With zinc(II) chloride at 230℃; for 40h; Condensation; | A 12% B 61% |
2-methylglutaronitrile
1,12-dodecanedioic acid
A
3-methyl-piperidine-2,6-dione
B
1,12-dodecanedinitrile
Conditions | Yield |
---|---|
With aluminum (III) chloride at 200℃; for 5h; | A 88% B 81% |
Conditions | Yield |
---|---|
With 1-hexadecyl-3-sulfo-1H-imidazol-3-ium chloride In neat (no solvent) at 110℃; for 16h; Green chemistry; | 88% |
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran; chloroform; N,N-dimethyl-formamide 1.) 0 deg C, 4 h, 2. ) room temp., 2 days; | 87% |
4-[4’’-fluoro-3’’-(piperazine-1’’’-carbonyl)benzyl]-2H-phthalazin-1-one
1,12-dodecanedioic acid
Conditions | Yield |
---|---|
Stage #1: 1,12-dodecanedioic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 4-[4’’-fluoro-3’’-(piperazine-1’’’-carbonyl)benzyl]-2H-phthalazin-1-one In N,N-dimethyl-formamide at 20℃; for 16h; | 87% |
1,12-dodecanedioic acid
3β-hydroxy-14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide
hydrogen 14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide-3β-yl 1,10-decanedicarboxylate
Conditions | Yield |
---|---|
With pyridine; p-toluenesulfonyl chloride for 4h; Ambient temperature; | 86% |
1,12-dodecanedioic acid
diperoxydodecanedioic acid
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide at 15 - 20℃; for 5h; | 85% |
With dihydrogen peroxide In sulfuric acid at 20℃; for 4h; | 49% |
With sulfuric acid; dihydrogen peroxide |
IUPAC Name: Dodecanedioic acid
Synonyms of Dodecanedioic acid (CAS NO.693-23-2): 1,10-Decanedicarboxylic acid ; 1,10-Dicarboxydecane ; 1,12-Dodecanedioic acid ; Decamethylenedicarboxylic acid ; EINECS 211-746-3 ; HSDB 5745 ; NSC 400242
CAS NO: 693-23-2
Molecular Formula of Dodecanedioic acid (CAS NO.693-23-2): C12H22O4
Molecular Weight: 230.3007
Molecular Structure:
Product Categories: Industrial/Fine Chemicals ; alpha,omega-Alkanedicarboxylic Acids ; alpha,omega-Bifunctional Alkanes ; Monofunctional & alpha,omega-Bifunctional Alkanes
Melting Point: 127-129 °C
Polar Surface Area: 52.6 Å2
Index of Refraction: 1.474
Molar Refractivity: 60.77 cm3
Molar Volume: 215.8 cm3
Surface Tension: 43.1 dyne/cm
Density of Dodecanedioic acid (CAS NO.693-23-2): 1.066 g/cm3
Flash Point: 216.6 °C
Enthalpy of Vaporization: 70.68 kJ/mol
Boiling Point: 394 °C at 760 mmHg
Vapour Pressure: 2.63E-07 mmHg at 25°C
Dodecanedioic acid (CAS NO.693-23-2) is mainly used in antiseptics, top-grade coatings, painting materials, corrosion inhibitor, surfactant, and engineering plastics.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
HS Code: 29171990
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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