Conditions | Yield |
---|---|
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity; | 98% |
With dihydrogen peroxide In water; acetonitrile at 90℃; for 9.5h; Green chemistry; | 89% |
With cerium(IV) sulphate; oxygen In acetic acid at 80℃; for 8h; Oxidation; | 86% |
Conditions | Yield |
---|---|
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux; | 97% |
Conditions | Yield |
---|---|
With palladium diacetate; acetic anhydride; P(p-C6H4F)3 In toluene at 80℃; for 48h; Sealed tube; Inert atmosphere; regioselective reaction; | 95% |
With palladium diacetate; acetic anhydride; P(p-C6H4F)3 In toluene at 80℃; for 48h; Inert atmosphere; Sealed tube; | 95% |
Conditions | Yield |
---|---|
With periodic acid; ruthenium trichloride In tetrachloromethane; water; acetonitrile at 20℃; for 2h; Ring cleavage; oxidation; | 94% |
With manganese (VII)-oxide In tetrachloromethane; acetone at -80℃; | 82% |
With periodic acid; ruthenium trichloride In cyclohexane; water; acetonitrile at 20℃; for 2h; | 77% |
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; | 91% |
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; | 91% |
2-nitrocycloheptanone
heptanedioic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In methanol for 10h; Ambient temperature; | 90% |
With Oxone; sodium hydroxide; disodium hydrogenphosphate; water 1.) MeOH, 70 deg C, 4 h, 2.) MeOH, r.t., 4 h; Yield given. Multistep reaction; |
trans-cycloheptane-1,2-diol
heptanedioic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium tungstate; phosphoric acid; dihydrogen peroxide at 90℃; for 5h; | 87% |
With potassium carbonate for 2.7h; Ambient temperature; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A; | 79% |
7-oxooctanoic acid
heptanedioic acid
Conditions | Yield |
---|---|
With ethanol; potassium bromide; sodium hydroxide In dimethyl sulfoxide at 140℃; pH=7; | 87% |
Conditions | Yield |
---|---|
With dodecyltrimethylammonium phosphotungstate; water; dihydrogen peroxide In toluene at 80℃; for 12h; chemoselective reaction; | 84% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 90℃; for 10h; Green chemistry; | 82% |
Stage #1: cycloheptanol With Oxone; ruthenium(III) chloride monohydrate In water at 70℃; for 8h; Stage #2: In ethanol Cooling; | 78% |
With hydrogenchloride; ruthenium trichloride; potassium hydrogensulfate; cerium (IV) sulfate; sulfuric acid; potassium chloride In water at 35℃; Mechanism; Rate constant; variation of concentration of reagents; |
cis-Cycloheptan-1,2-diol
heptanedioic acid
Conditions | Yield |
---|---|
With potassium carbonate for 2.7h; Ambient temperature; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A; | 81% |
Conditions | Yield |
---|---|
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 12.25h; Product distribution / selectivity; | A 80% B 18% |
With oxygen; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 12h; | A 73% B 18% |
(cyclohept-1-en-1-yloxy)(trimethyl)silane
A
heptanedioic acid
B
2-hydroxycyloheptanone
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; titanium silicate for 24h; Heating; | A 78% B 6% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid at 150℃; under 15001.5 Torr; for 12h; | 78% |
With palladium on activated carbon; W(OTf)6; hydrogen In acetic acid at 150℃; under 15201 Torr; for 12h; | 78% |
Conditions | Yield |
---|---|
With water for 48h; Rhodococcus rhodochrous AJ270; | 74% |
With potassium phosphate buffer; Rhodococcus sp. AJ270 at 30℃; for 48h; | 74% |
With hydrogenchloride | |
With hydrogenchloride at 110℃; im Rohr; | |
Durch Verseifen; |
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; | 70% |
1-(2-methoxyvinyl)benzene
(E)-2-benzylidenecycloheptanone
A
heptanedioic acid
B
benzaldehyde
Conditions | Yield |
---|---|
With ozone In diethyl ether at -70℃; | A 17% B 65% |
Conditions | Yield |
---|---|
With ozone In neat (no solvent) at 20℃; for 15h; UV-irradiation; | A 65% B 8% |
1-(2-methoxyvinyl)benzene
2-[1-(2-Trifluoromethyl-phenyl)-meth-(E)-ylidene]-cycloheptanone
A
heptanedioic acid
B
benzaldehyde
Conditions | Yield |
---|---|
With ozone In diethyl ether at -70℃; | A 17% B 60% |
Conditions | Yield |
---|---|
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 2h; | A 35% B 60% |
heptanedioic acid
Conditions | Yield |
---|---|
With bromine In tetrahydrofuran To a soln. of Mn-compd. a soln. of Br2 is added with rapid stirring, mixt. is stirred at room temp. for 1 h (N2).; Solvent is removed, addn. of CH2Cl2, ppt. is filtered off, washed with a minimum of CH2Cl2 and dried on the water pump.; | 60% |
Conditions | Yield |
---|---|
With potassium permanganate; water; aluminum oxide for 0.25h; Heating; microwave; | A 58.5% B n/a |
Cyclohexanone-2-carbaldehyde
A
heptanedioic acid
B
cyclopentanecarboxylic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In tert-butyl alcohol at 50℃; regioselective reaction; | A 41% B 26% |
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; nitric acid; trifluoroacetic acid at 20℃; under 760.051 Torr; for 18h; | 41% |
Conditions | Yield |
---|---|
With rubidium carbonate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 10℃; under 750.075 Torr; for 20h; Schlenk technique; Sealed tube; Irradiation; | 40% |
Methyl oleate
A
azelaic acid
B
heptanedioic acid
C
octane-1,8-dioic acid
D
Octanoic acid
E
nonanoic acid
Conditions | Yield |
---|---|
With 7CeO2*7Nb2O5*3La2O3*K2O*2Bi2O3; oxygen at 120℃; under 6750.68 Torr; for 15h; Autoclave; | A 27.5% B 6.8% C 17.5% D 11.4% E 17.6% |
Methyl oleate
A
azelaic acid
B
heptanedioic acid
C
octane-1,8-dioic acid
D
oenanthic acid
E
Octanoic acid
F
nonanoic acid
Conditions | Yield |
---|---|
With CeO2*Nb2O5; oxygen at 120℃; under 6750.68 Torr; for 15h; Catalytic behavior; Temperature; Autoclave; | A 20.7% B 5.9% C 13.7% D 5.1% E 9.3% F 19.3% |
cycloheptane
A
heptanedioic acid
B
cycloheptanol
C
cycloheptanone
Conditions | Yield |
---|---|
With polytetrafluoroethylene; cobalt(II) 5,10,15,20-tetra(4'-chlorophenyl)porphyrinate; oxygen at 20 - 120℃; under 7500.75 Torr; for 8h; Temperature; Pressure; Reagent/catalyst; Autoclave; Cooling with ice; | A 8.6% B 18.2% C 7.3% |
Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With sulfuric acid Heating; | 98% |
With toluene-4-sulfonic acid for 7h; Reflux; Large scale; | 98.08% |
1-hydroxy-pyrrolidine-2,5-dione
heptanedioic acid
1-({7-[(2,5-dioxo-1-pyrrolidinyl)oxy]-7-oxoheptanoyl}-oxy)-2,5-pyrrolidine-dione
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h; | 100% |
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h; | 71% |
With dicyclohexyl-carbodiimide | |
With dicyclohexyl-carbodiimide In tetrahydrofuran for 6h; |
heptanedioic acid
2-(vinyloxy)ethyl isothiocyanate
Conditions | Yield |
---|---|
trifluoroacetic acid at 60 - 65℃; for 0.5h; | 100% |
heptanedioic acid
cobalt(II) acetate
(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
Conditions | Yield |
---|---|
Stage #1: cobalt(II) acetate; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine In ethanol for 5h; Heating / reflux; Stage #2: heptanedioic acid With oxygen In dichloromethane; acetone at 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
Stage #1: heptanedioic acid With caesium carbonate In methanol; water Stage #2: benzyl bromide In N,N-dimethyl-formamide at 50℃; for 18h; | 100% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In methanol at 20℃; | 100% |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 85℃; for 10.5h; | 99% |
With 1-ethyl-3-methylimidazolium hydrogensulfate at 109.99℃; for 5h; | 96.37% |
With sulfuric acid at 20℃; for 0.0541667h; | 85% |
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide at 30℃; for 4h; | 99% |
With thionyl chloride at 75℃; for 3h; | 98% |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 4h; | 97% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 16h; Reflux; Inert atmosphere; | 99% |
With sulfuric acid; benzene | |
With chloro-trimethyl-silane at 0 - 20℃; Inert atmosphere; |
heptanedioic acid
3-tert-butyl-2,5-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide | 99% |
heptanedioic acid
1,1'-bis(4-pyridinyl)ferrocene
[(Fe(η5-C5H4-1-(4-C5H4N))2)(1-pimelic acid)]
Conditions | Yield |
---|---|
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.; | 99% |
heptanedioic acid
carbonic acid dimethyl ester
dimethyl 1,7-heptanedioate
Conditions | Yield |
---|---|
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry; | 98% |
heptanedioic acid
manganese (II) acetate tetrahydrate
manganese(II) pimelate
Conditions | Yield |
---|---|
In ethanol refluxing (2 h); cooling, filtn., washing (EtOH), drying; elem. anal.; | 97% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 95% |
Conditions | Yield |
---|---|
In ethanol at 25℃; for 24h; | 94% |
In ethanol at 25℃; for 24h; |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 0.0541667h; | 92% |
heptanedioic acid
Conditions | Yield |
---|---|
In ethanol at 25℃; for 24h; | 92% |
In ethanol at 25℃; for 24h; |
Conditions | Yield |
---|---|
With sulfuric acid at 30 - 40℃; for 0.5h; | 91% |
heptanedioic acid
4-amino-5-chloro-2-methoxy-benzoic acid 2-piperazin-1-yl-ethyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 20℃; for 24h; | 91% |
Conditions | Yield |
---|---|
With tetrabutoxytitanium In toluene at 110℃; for 33h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 90.7% |
heptanedioic acid
pimelic acid anhydride
Conditions | Yield |
---|---|
With acetic anhydride at 25℃; Inert atmosphere; | 90% |
With acetic anhydride for 1.5h; Reflux; | 80% |
With acetic anhydride for 4h; Inert atmosphere; Reflux; | 71% |
Conditions | Yield |
---|---|
at 185℃; for 7h; | 90% |
at 180℃; for 1h; | 49% |
at 180℃; | 43% |
at 180℃; |
Conditions | Yield |
---|---|
In water byproducts: HNO3; aq. soln. of pimelic acid and hydrazine hydrate added to metal nitrate soln.; ppt. collected, washed (water, ethanol, ether), air dried; elem. anal.; | 90% |
Product Name: Pimelic acid (CAS NO.111-16-0)
Molecular Formula: C7H12O4
Molecular Weight: 160.17
EINECS: 203-840-8
Melting point: 103-105 °C(lit.)
Boiling point: 212 °C10 mm Hg(lit.)
Density: 1.329 g/cm3
Flash point: 212°C/10mm
Solubility: ethanol: 0.1 g/mL, clear to very faintly hazy
Water Solubility: 25 g/L (13 °C)
Merck: 14,7431
BRN: 1210024
Index of Refraction: 1.476
Molar Refractivity: 37.6 cm3
Molar Volume: 133.3 cm3
Surface Tension: 49.8 dyne/cm
Enthalpy of Vaporization: 65.77 kJ/mol
Vapour Pressure: 5.92E-06 mmHg at 25°C
XLogP3-AA: 0.5
H-Bond Donor: 2
H-Bond Acceptor: 4
Structure Descriptors of Pimelic acid (CAS NO.111-16-0):
IUPAC Name: heptanedioic acid
Canonical SMILES: C(CCC(=O)O)CCC(=O)O
InChI: InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)
InChIKey: WLJVNTCWHIRURA-UHFFFAOYSA-N
Product Categories: Miscellaneous Natural Products; BUILDING BLOCKS; alpha,omega-Alkanedicarboxylic Acids; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes
Pimelic acid (CAS NO.111-16-0) is generally used in biochemical research, for the preparation of polymers,and can be used as raw material for plasticizers.
1. | orl-rat LD50:7000 mg/kg | 34ZIAG Toxicology of Drugs and Chemicals Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,477. | ||
2. | orl-mus LD50:4800 mg/kg | BIJOAK Biochemical Journal. 34 (1940),1196. |
Reported in EPA TSCA Inventory.
Mildly toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Pimelic acid (CAS NO.111-16-0):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and 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
Hazard Note: Irritant
HS Code: 29171990
Pimelic acid (CAS NO.111-16-0) is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. It has some synonyms like 1,5-Pentanedicarboxylic acid ; Heptanedioic acid ; Pentane-1,5-dicarboxylic acid ; Heptanedioic-2,2,6,6-d4 acid (Pimelic acid) ; 6-Carboxyhexanoate ,and so on.
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