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111-16-0

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111-16-0 Usage

Description

Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H which has been synthesized from cyclohexanone and from salicylic acid. In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.This acid (heptanedioic acid), from the Greek pimelh (pimele fat), as adipic acid, was isolated from oxidized fats. It was obtained in 1884 by Ganttner F et al. as a product of ricinoleic acid (hydroxylated oleic acid) from castor oil.

Chemical Properties

white solid

Uses

Different sources of media describe the Uses of 111-16-0 differently. You can refer to the following data:
1. The major uses of pimelic acid are in plasticizers and polymers.
2. Pimelic Acid is a metabolite found in four biofluids from dairy cows that may be used as biomarkers of milk.

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is pentane with two carboxylic acid groups at positions C-1 and C-5.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 3425, 1956 DOI: 10.1021/ja01595a044Organic Syntheses, Coll. Vol. 2, p. 531, 1943Synthesis, p. 54, 1988

Purification Methods

Crystallise the acid from water or from *benzene containing 5% diethyl ether. [Beilstein 1 IV 2003.]

Check Digit Verification of cas no

The CAS Registry Mumber 111-16-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 111-16:
(5*1)+(4*1)+(3*1)+(2*1)+(1*6)=20
20 % 10 = 0
So 111-16-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)/p-2

111-16-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A18495)  Pimelic acid, 98+%   

  • 111-16-0

  • 25g

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A18495)  Pimelic acid, 98+%   

  • 111-16-0

  • 100g

  • 833.0CNY

  • Detail

111-16-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name pimelic acid

1.2 Other means of identification

Product number -
Other names Pimefilina [INN-Spanish]

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Lubricants and lubricant additives,Plasticizers
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:111-16-0 SDS

111-16-0Synthetic route

cycloheptanone
502-42-1

cycloheptanone

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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%
1,7-heptandiol
629-30-1

1,7-heptandiol

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux;97%
formic acid
64-18-6

formic acid

5-hexenoic acid
1577-22-6

5-hexenoic acid

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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%
Cycloheptene
628-92-2

Cycloheptene

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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%
1-Penten-3-ol
616-25-1

1-Penten-3-ol

carbon monoxide
201230-82-2

carbon monoxide

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;91%
3-penten-2-ol
1569-50-2

3-penten-2-ol

carbon monoxide
201230-82-2

carbon monoxide

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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
13154-27-3

2-nitrocycloheptanone

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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
13553-19-0

trans-cycloheptane-1,2-diol

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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
14112-98-2

7-oxooctanoic acid

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
With ethanol; potassium bromide; sodium hydroxide In dimethyl sulfoxide at 140℃; pH=7;87%
8-oxabicyclo[5.1.0]octane
286-45-3

8-oxabicyclo[5.1.0]octane

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
With dodecyltrimethylammonium phosphotungstate; water; dihydrogen peroxide In toluene at 80℃; for 12h; chemoselective reaction;84%
cycloheptanol
502-41-0

cycloheptanol

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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;
Conditions
ConditionsYield
With potassium carbonate for 2.7h; Ambient temperature; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A;81%
cycloheptanol
502-41-0

cycloheptanol

A

heptanedioic acid
111-16-0

heptanedioic acid

B

cycloheptanone
502-42-1

cycloheptanone

Conditions
ConditionsYield
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
22081-48-7

(cyclohept-1-en-1-yloxy)(trimethyl)silane

A

heptanedioic acid
111-16-0

heptanedioic acid

B

2-hydroxycyloheptanone
4436-58-2

2-hydroxycyloheptanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; titanium silicate for 24h; Heating;A 78%
B 6%
1,6-dioxaspiro[4.4]nonane-2,7-dione
3505-67-7

1,6-dioxaspiro[4.4]nonane-2,7-dione

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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%
pimelonitrile
646-20-8

pimelonitrile

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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;
carbon monoxide
201230-82-2

carbon monoxide

pent-2-en-1-ol
20273-24-9

pent-2-en-1-ol

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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
4747-15-3

1-(2-methoxyvinyl)benzene

(E)-2-benzylidenecycloheptanone
88356-04-1

(E)-2-benzylidenecycloheptanone

A

heptanedioic acid
111-16-0

heptanedioic acid

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With ozone In diethyl ether at -70℃;A 17%
B 65%
cycloheptane
291-64-5

cycloheptane

A

heptanedioic acid
111-16-0

heptanedioic acid

B

cycloheptanone
502-42-1

cycloheptanone

Conditions
ConditionsYield
With ozone In neat (no solvent) at 20℃; for 15h; UV-irradiation;A 65%
B 8%
1-(2-methoxyvinyl)benzene
4747-15-3

1-(2-methoxyvinyl)benzene

2-[1-(2-Trifluoromethyl-phenyl)-meth-(E)-ylidene]-cycloheptanone
138955-59-6

2-[1-(2-Trifluoromethyl-phenyl)-meth-(E)-ylidene]-cycloheptanone

A

heptanedioic acid
111-16-0

heptanedioic acid

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With ozone In diethyl ether at -70℃;A 17%
B 60%
pimelonitrile
646-20-8

pimelonitrile

A

heptanedioic acid
111-16-0

heptanedioic acid

B

6-cyanohexanaoic acid
5602-19-7

6-cyanohexanaoic acid

Conditions
ConditionsYield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 2h;A 35%
B 60%
μ-(1,5)-pentanediyl-bis(pentacarbonyl manganese)

μ-(1,5)-pentanediyl-bis(pentacarbonyl manganese)

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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%
cycloheptanone
502-42-1

cycloheptanone

A

heptanedioic acid
111-16-0

heptanedioic acid

B

cycloheptanedione

cycloheptanedione

Conditions
ConditionsYield
With potassium permanganate; water; aluminum oxide for 0.25h; Heating; microwave;A 58.5%
B n/a
Cyclohexanone-2-carbaldehyde
1193-63-1

Cyclohexanone-2-carbaldehyde

A

heptanedioic acid
111-16-0

heptanedioic acid

B

cyclopentanecarboxylic acid
3400-45-1

cyclopentanecarboxylic acid

Conditions
ConditionsYield
With dihydrogen peroxide In tert-butyl alcohol at 50℃; regioselective reaction;A 41%
B 26%
cycloheptane
291-64-5

cycloheptane

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; nitric acid; trifluoroacetic acid at 20℃; under 760.051 Torr; for 18h;41%
methyl 5-bromohexanoate
41796-82-1

methyl 5-bromohexanoate

carbon dioxide
124-38-9

carbon dioxide

heptanedioic acid
111-16-0

heptanedioic acid

Conditions
ConditionsYield
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
112-62-9

Methyl oleate

A

azelaic acid
123-99-9

azelaic acid

B

heptanedioic acid
111-16-0

heptanedioic acid

C

octane-1,8-dioic acid
505-48-6

octane-1,8-dioic acid

D

Octanoic acid
124-07-2

Octanoic acid

E

nonanoic acid
112-05-0

nonanoic acid

Conditions
ConditionsYield
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
112-62-9

Methyl oleate

A

azelaic acid
123-99-9

azelaic acid

B

heptanedioic acid
111-16-0

heptanedioic acid

C

octane-1,8-dioic acid
505-48-6

octane-1,8-dioic acid

D

oenanthic acid
111-14-8

oenanthic acid

E

Octanoic acid
124-07-2

Octanoic acid

F

nonanoic acid
112-05-0

nonanoic acid

Conditions
ConditionsYield
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
291-64-5

cycloheptane

A

heptanedioic acid
111-16-0

heptanedioic acid

B

cycloheptanol
502-41-0

cycloheptanol

C

cycloheptanone
502-42-1

cycloheptanone

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

heptanedioic acid
111-16-0

heptanedioic acid

dimethyl 1,7-heptanedioate
1732-08-7

dimethyl 1,7-heptanedioate

Conditions
ConditionsYield
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
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

heptanedioic acid
111-16-0

heptanedioic acid

1-({7-[(2,5-dioxo-1-pyrrolidinyl)oxy]-7-oxoheptanoyl}-oxy)-2,5-pyrrolidine-dione
74648-14-9

1-({7-[(2,5-dioxo-1-pyrrolidinyl)oxy]-7-oxoheptanoyl}-oxy)-2,5-pyrrolidine-dione

Conditions
ConditionsYield
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
111-16-0

heptanedioic acid

2-(vinyloxy)ethyl isothiocyanate
59565-09-2

2-(vinyloxy)ethyl isothiocyanate

heptanedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

heptanedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

Conditions
ConditionsYield
trifluoroacetic acid at 60 - 65℃; for 0.5h;100%
heptanedioic acid
111-16-0

heptanedioic acid

(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
151433-25-9

(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

[(1-RR)-(Pimelic acid)]

[(1-RR)-(Pimelic acid)]

Conditions
ConditionsYield
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%
heptanedioic acid
111-16-0

heptanedioic acid

benzyl bromide
100-39-0

benzyl bromide

dibenzyl pimelate
84743-98-6

dibenzyl pimelate

Conditions
ConditionsYield
Stage #1: heptanedioic acid With caesium carbonate In methanol; water
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 50℃; for 18h;
100%
heptanedioic acid
111-16-0

heptanedioic acid

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

dimethyl 1,7-heptanedioate
1732-08-7

dimethyl 1,7-heptanedioate

Conditions
ConditionsYield
With chloro-trimethyl-silane In methanol at 20℃;100%
heptanedioic acid
111-16-0

heptanedioic acid

ethanol
64-17-5

ethanol

diethyl pimelate
2050-20-6

diethyl pimelate

Conditions
ConditionsYield
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%
heptanedioic acid
111-16-0

heptanedioic acid

pimeloyl chloride
142-79-0

pimeloyl chloride

Conditions
ConditionsYield
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%
heptanedioic acid
111-16-0

heptanedioic acid

allyl alcohol
107-18-6

allyl alcohol

pimelic acid diallyl ester
91906-66-0

pimelic acid diallyl ester

Conditions
ConditionsYield
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
111-16-0

heptanedioic acid

3-tert-butyl-2,5-dihydroxybenzaldehyde
192803-37-5

3-tert-butyl-2,5-dihydroxybenzaldehyde

heptanedioic acid bis-(3-tert-butyl-5-formyl-4-hydroxy-phenyl) ester

heptanedioic acid bis-(3-tert-butyl-5-formyl-4-hydroxy-phenyl) ester

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide99%
heptanedioic acid
111-16-0

heptanedioic acid

1,1'-bis(4-pyridinyl)ferrocene
459142-93-9

1,1'-bis(4-pyridinyl)ferrocene

[(Fe(η5-C5H4-1-(4-C5H4N))2)(1-pimelic acid)]
914645-93-5

[(Fe(η5-C5H4-1-(4-C5H4N))2)(1-pimelic acid)]

Conditions
ConditionsYield
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.;99%
heptanedioic acid
111-16-0

heptanedioic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

dimethyl 1,7-heptanedioate
1732-08-7

dimethyl 1,7-heptanedioate

Conditions
ConditionsYield
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry;98%
heptanedioic acid
111-16-0

heptanedioic acid

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

manganese(II) pimelate
50962-31-7

manganese(II) pimelate

Conditions
ConditionsYield
In ethanol refluxing (2 h); cooling, filtn., washing (EtOH), drying; elem. anal.;97%
heptanedioic acid
111-16-0

heptanedioic acid

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

heptanedioic acid bis[(1-phenylethyl)amide]

heptanedioic acid bis[(1-phenylethyl)amide]

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;95%
heptanedioic acid
111-16-0

heptanedioic acid

C14H24N4(2+)*2HO(1-)

C14H24N4(2+)*2HO(1-)

1,6-bis(3-methylimidazol-1-yl)hexane pimelate

1,6-bis(3-methylimidazol-1-yl)hexane pimelate

Conditions
ConditionsYield
In ethanol at 25℃; for 24h;94%
In ethanol at 25℃; for 24h;
heptanedioic acid
111-16-0

heptanedioic acid

butan-1-ol
71-36-3

butan-1-ol

dibutyl heptanedioate
51238-94-9

dibutyl heptanedioate

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 0.0541667h;92%
heptanedioic acid
111-16-0

heptanedioic acid

1,4-bis(1-methylimidazolium-3-yl)butane hydroxide

1,4-bis(1-methylimidazolium-3-yl)butane hydroxide

1,4-bis(3-methylimidazol-1-yl)butane pimelate

1,4-bis(3-methylimidazol-1-yl)butane pimelate

Conditions
ConditionsYield
In ethanol at 25℃; for 24h;92%
In ethanol at 25℃; for 24h;
heptanedioic acid
111-16-0

heptanedioic acid

sulfanilamide
63-74-1

sulfanilamide

C19H24N4O6S2
123351-06-4

C19H24N4O6S2

Conditions
ConditionsYield
With sulfuric acid at 30 - 40℃; for 0.5h;91%
heptanedioic acid
111-16-0

heptanedioic acid

4-amino-5-chloro-2-methoxy-benzoic acid 2-piperazin-1-yl-ethyl ester
307973-17-7

4-amino-5-chloro-2-methoxy-benzoic acid 2-piperazin-1-yl-ethyl ester

C35H48Cl2N6O8

C35H48Cl2N6O8

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 20℃; for 24h;91%
heptanedioic acid
111-16-0

heptanedioic acid

menthol
89-78-1

menthol

heptanedioic acid dimenthyl ester
67714-15-2

heptanedioic acid dimenthyl ester

Conditions
ConditionsYield
With tetrabutoxytitanium In toluene at 110℃; for 33h; Reagent/catalyst; Solvent; Temperature; Green chemistry;90.7%
heptanedioic acid
111-16-0

heptanedioic acid

pimelic acid anhydride
10521-07-0

pimelic acid anhydride

Conditions
ConditionsYield
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%
heptanedioic acid
111-16-0

heptanedioic acid

aniline
62-53-3

aniline

7-oxo-7-(phenylamino)heptanoic acid
160777-08-2

7-oxo-7-(phenylamino)heptanoic acid

Conditions
ConditionsYield
at 185℃; for 7h;90%
at 180℃; for 1h;49%
at 180℃;43%
at 180℃;
heptanedioic acid
111-16-0

heptanedioic acid

cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

hydrazine hydrate
7803-57-8

hydrazine hydrate

cobalt(II)pimelate*2(hydrazine) monohydrate

cobalt(II)pimelate*2(hydrazine) monohydrate

Conditions
ConditionsYield
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%

111-16-0Related news

Material PropertiesEffect of calcium stearate and Pimelic acid (cas 111-16-0) addition on mechanical properties of heterophasic isotactic polypropylene/ethylene–propylene rubber blend08/25/2019

The effects of various heterogeneous nucleating agents (i.e. sodium benzoate, talcum, dimethyl dibenzylsorbitol, and a combination of calcium stearate and pimelic acid) on the mechanical properties of heterophasic copolymer of isotactic polypropylene and ethylene–propylene rubber (iPP/EPR blend...detailed

Three 2D complexes with helical chains constructed from Pimelic acid (cas 111-16-0) and rigid bis (imidazole) ligand: Syntheses, structures, thermal and photoluminescent properties08/23/2019

Three new complexes, namely, [M(Pim)(L)] (M = Co (1), Cd (2), Pim = Pimelic acid, L = 1,4-bis(1-imidazolyl)-benzene), [Zn(Pim)(L)]·H2O (3), have been synthesized hydrothermally from the self-assembly of the transtion metal ions (M2 +) with flexible aliphatic dicarboxylate ligand (Pim) and the r...detailed

Infrared spectra of the hydrogen bond in Pimelic acid (cas 111-16-0) crystals: polarization and temperature effects08/22/2019

This paper deals with the polarized IR spectra of the hydrogen bond in pimelic acid crystals and their quantitative interpretation. The spectra were measured for the νOH and νOD band frequency regions, at temperatures of 298 and 77 K, for the ‘alpha’ crystalline form of pimelic acid. Two...detailed

Effect of Pimelic acid (cas 111-16-0) on the crystallization, morphology and mechanical properties of polypropylene/wollastonite composites08/21/2019

The pimelic acid (PA) was used as a new surface modifier for wollastonite. The effects of PA treatment on the crystallization, morphology and mechanical properties of polypropylene/wollastonite composites were investigated. The Fourier transform infrared spectroscopy analysis revealed that the P...detailed

111-16-0Relevant articles and documents

-

Mueller

, p. 18 (1935)

-

Polymer supported vanadium complexes as catalysts for the oxidation of alkenes in water

Hsiao, Ming-Chieh,Liu, Shiuh-Tzung

, p. 61 - 66 (2010)

Polymer supported vanadium complexes (denoted as c-PMA n -V) were prepared by the complexation of vanadium ions onto a cross linked polyacrylate. c PMA n -V can catalyze the oxidative cleavage of olefins with a large excess of t-butyl hydroperoxide (TBHP) or bishydroxylation of olefins with 4 eq. of TBHP. Graphical Abstract: [Figure not available: see fulltext.].

Preparation and characterization of WO3 bonded imidazolium sulfonic acid chloride as a novel and green ionic liquid catalyst for the synthesis of adipic acid

Bhuyan, Bishal,Paul, Bappi,Vadivel, Sethumathavan,Dhar, Siddhartha Sankar

, p. 99044 - 99052 (2016)

A novel nano WO3-bonded imidazolium-sulfonic acid chloride (WO3-IL) was prepared, and characterized by FT-IR, XRD, SEM, TEM, EDX and BET. The as synthesized WO3 nanoparticle supported ionic liquid is studied as a heterogeneous catalyst for the liquid phase oxidation of cyclohexene to adipic acid. Apart from cyclohexene, a few other six-eight membered cyclic alcohols and ketones are converted into their dicarboxylic acids in high yields and in short reaction times employing the same reaction protocol. The synergy between the WO3 and ionic liquid is assumed to play a significant role towards its very high catalytic activity. The recyclability of the catalyst is proved to be noteworthy as the catalyst exhibits no significant change in its catalytic activity even after five cycles of reuse.

-

Schultz

, p. 1056 (1947)

-

-

Ackman et al.

, p. 1730 (1961)

-

Oxidative Cleavage of Vicinal Diols at the Nickel Hydroxide Electrode

Ruholl, Heinrich,Schaefer, Hans J.

, p. 54 - 56 (1988)

Vicinal diols are oxidatively cleaved with good yields by electrolysis at an oxide covered nickel electrode in an aqueous alkaline electrolyte and an undivided cell.The method is applied in the synthesis of optical pure derivatives of 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid.

-

Werber,Jansen,Gresham

, p. 532,534 (1952)

-

METHOD FOR PRODUCING DICARBOXYLIC ACID

-

Paragraph 0115, (2021/05/21)

A method for producing dicarboxylic acid. The method includes: subjecting a raw material system including a cyclic olefin and a lower monocarboxylic acid to an addition reaction in the presence of an addition reaction catalyst to generate an intermediate product system including cyclic carboxylic acid ester; and subjecting the intermediate product system including cyclic carboxylic acid ester to a ring-opening and oxidation reaction in the presence of an oxidant and an oxidation catalyst to generate a corresponding dicarboxylic acid product. The addition reaction in the dicarboxylic acid synthesis route achieves a high single-pass conversion rate, and the selectivity of the corresponding cyclic carboxylic acid ester is high. The addition-oxidation synthesis route achieves faster reaction rates for both the addition reaction and oxidation reaction, and high yield of corresponding dicarboxylic acid product. The addition-oxidation based synthesis route is suitable for continuous, stable and large-scale production of corresponding dicarboxylic acid product.

Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols

Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji

supporting information, p. 20394 - 20398 (2020/09/21)

A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.

Pd-Catalyzed Highly Chemo- And Regioselective Hydrocarboxylation of Terminal Alkyl Olefins with Formic Acid

Ren, Wenlong,Chu, Jianxiao,Sun, Fei,Shi, Yian

supporting information, p. 5967 - 5970 (2019/08/26)

An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.

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