111-16-0

Basic information

• Product Name: Pimelic acid
• Synonyms: PEMILIC ACID;Pimelic acid, Heptanedioic acid;Dimelic acid;Pimelic acid, 98+%;(Heptanedioic acid)dianion;Pimelate;NSC-30112;Heptanedioic acid 1,5-Pentanedicarboxylic acid
• CAS NO: 111-16-0
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• EINECS: 203-840-8
• Product Categories: Miscellaneous Natural Products;BUILDING BLOCKS;alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes
• Mol File: 111-16-0.mol
• Article Data: 210

Chemical Properties

• Melting Point: 103-105 °C(lit.)
• Boiling Point: 212 °C10 mm Hg(lit.)
• Flash Point: 212°C/10mm
• Appearance: White to slightly beige/Powder
• Density: 1,329 g/cm3
• Vapor Pressure: 5.92E-06mmHg at 25°C
• Refractive Index: 1.4352 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: ethanol: 0.1 g/mL, clear to very faintly hazy
• PKA: 4.71(at 25℃)
• Water Solubility: 25 g/L (13 ºC)
• Stability: Stable. Incompatible with oxidizing agents, bases. Combustible.
• Merck: 14,7431
• BRN: 1210024
• CAS DataBase Reference: Pimelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Pimelic acid(111-16-0)
• EPA Substance Registry System: Pimelic acid(111-16-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: TK3677000
• TSCA: Yes
• Hazardous Substances Data: 111-16-0(Hazardous Substances Data)

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.

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

Uses

The major uses of pimelic acid are in plasticizers and polymers.

Chemical Properties

white solid

Purification Methods

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

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

Synthetic route

cycloheptanone (502-42-1) → heptanedioic acid (111-16-0)

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%

1,7-heptandiol (629-30-1) → heptanedioic acid (111-16-0)

Conditions	Yield
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux;	97%

formic acid (64-18-6) + 5-hexenoic acid (1577-22-6) → heptanedioic acid (111-16-0)

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%

Cycloheptene (628-92-2) → heptanedioic acid (111-16-0)

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%

1-Penten-3-ol (616-25-1) + carbon monoxide (201230-82-2) → heptanedioic acid (111-16-0)

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%

3-penten-2-ol (1569-50-2) + carbon monoxide (201230-82-2) → heptanedioic acid (111-16-0)

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 (13154-27-3) → heptanedioic acid (111-16-0)

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 (13553-19-0) → heptanedioic acid (111-16-0)

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 (14112-98-2) → heptanedioic acid (111-16-0)

Conditions	Yield
With ethanol; potassium bromide; sodium hydroxide In dimethyl sulfoxide at 140℃; pH=7;	87%

8-oxabicyclo[5.1.0]octane (286-45-3) → heptanedioic acid (111-16-0)

Conditions	Yield
With dodecyltrimethylammonium phosphotungstate; water; dihydrogen peroxide In toluene at 80℃; for 12h; chemoselective reaction;	84%

cycloheptanol (502-41-0) → heptanedioic acid (111-16-0)

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 (13553-19-0, 65678-03-7, 90970-69-7, 108268-27-5, 108268-28-6, 42114-72-7) → heptanedioic acid (111-16-0)

Conditions	Yield
With potassium carbonate for 2.7h; Ambient temperature; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A;	81%

cycloheptanol (502-41-0) → heptanedioic acid (111-16-0) + cycloheptanone (502-42-1)

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 (22081-48-7) → heptanedioic acid (111-16-0) + 2-hydroxycyloheptanone (4436-58-2)

Conditions	Yield
With tert.-butylhydroperoxide; titanium silicate for 24h; Heating;	A 78% B 6%

1,6-dioxaspiro[4.4]nonane-2,7-dione (3505-67-7) → heptanedioic acid (111-16-0)

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%

pimelonitrile (646-20-8) → heptanedioic acid (111-16-0)

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;

carbon monoxide (201230-82-2) + pent-2-en-1-ol (20273-24-9) → heptanedioic acid (111-16-0)

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 (4747-15-3) + (E)-2-benzylidenecycloheptanone (88356-04-1) → heptanedioic acid (111-16-0) + benzaldehyde (100-52-7)

Conditions	Yield
With ozone In diethyl ether at -70℃;	A 17% B 65%

cycloheptane (291-64-5) → heptanedioic acid (111-16-0) + cycloheptanone (502-42-1)

Conditions	Yield
With ozone In neat (no solvent) at 20℃; for 15h; UV-irradiation;	A 65% B 8%

1-(2-methoxyvinyl)benzene (4747-15-3) + 2-[1-(2-Trifluoromethyl-phenyl)-meth-(E)-ylidene]-cycloheptanone (138955-59-6) → heptanedioic acid (111-16-0) + benzaldehyde (100-52-7)

Conditions	Yield
With ozone In diethyl ether at -70℃;	A 17% B 60%

pimelonitrile (646-20-8) → heptanedioic acid (111-16-0) + 6-cyanohexanaoic acid (5602-19-7)

Conditions	Yield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 2h;	A 35% B 60%

μ-(1,5)-pentanediyl-bis(pentacarbonyl manganese) → heptanedioic acid (111-16-0)

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%

cycloheptanone (502-42-1) → heptanedioic acid (111-16-0) + cycloheptanedione

Conditions	Yield
With potassium permanganate; water; aluminum oxide for 0.25h; Heating; microwave;	A 58.5% B n/a

Cyclohexanone-2-carbaldehyde (1193-63-1) → heptanedioic acid (111-16-0) + cyclopentanecarboxylic acid (3400-45-1)

Conditions	Yield
With dihydrogen peroxide In tert-butyl alcohol at 50℃; regioselective reaction;	A 41% B 26%

cycloheptane (291-64-5) → heptanedioic acid (111-16-0)

Conditions	Yield
With N-hydroxyphthalimide; nitric acid; trifluoroacetic acid at 20℃; under 760.051 Torr; for 18h;	41%

methyl 5-bromohexanoate (41796-82-1) + carbon dioxide (124-38-9) → heptanedioic acid (111-16-0)

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 (112-62-9) → azelaic acid (123-99-9) + heptanedioic acid (111-16-0) + octane-1,8-dioic acid (505-48-6) + Octanoic acid (124-07-2) + nonanoic acid (112-05-0)

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 (112-62-9) → azelaic acid (123-99-9) + heptanedioic acid (111-16-0) + octane-1,8-dioic acid (505-48-6) + oenanthic acid (111-14-8) + Octanoic acid (124-07-2) + nonanoic acid (112-05-0)

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 (291-64-5) → heptanedioic acid (111-16-0) + cycloheptanol (502-41-0) + cycloheptanone (502-42-1)

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%

methanol (67-56-1) + heptanedioic acid (111-16-0) → dimethyl 1,7-heptanedioate (1732-08-7)

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 (6066-82-6) + heptanedioic acid (111-16-0) → 1-({7-[(2,5-dioxo-1-pyrrolidinyl)oxy]-7-oxoheptanoyl}-oxy)-2,5-pyrrolidine-dione (74648-14-9)

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 (111-16-0) + 2-(vinyloxy)ethyl isothiocyanate (59565-09-2) → heptanedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

Conditions	Yield
trifluoroacetic acid at 60 - 65℃; for 0.5h;	100%

heptanedioic acid (111-16-0) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) + (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine (151433-25-9) → [(1-RR)-(Pimelic acid)]

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%

heptanedioic acid (111-16-0) + benzyl bromide (100-39-0) → dibenzyl pimelate (84743-98-6)

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%

heptanedioic acid (111-16-0) + 2,2-dimethoxy-propane (77-76-9) → dimethyl 1,7-heptanedioate (1732-08-7)

Conditions	Yield
With chloro-trimethyl-silane In methanol at 20℃;	100%

heptanedioic acid (111-16-0) + ethanol (64-17-5) → diethyl pimelate (2050-20-6)

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%

heptanedioic acid (111-16-0) → pimeloyl chloride (142-79-0)

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%

heptanedioic acid (111-16-0) + allyl alcohol (107-18-6) → pimelic acid diallyl ester (91906-66-0)

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 (111-16-0) + 3-tert-butyl-2,5-dihydroxybenzaldehyde (192803-37-5) → heptanedioic acid bis-(3-tert-butyl-5-formyl-4-hydroxy-phenyl) ester

Conditions	Yield
With dmap; diisopropyl-carbodiimide	99%

heptanedioic acid (111-16-0) + 1,1'-bis(4-pyridinyl)ferrocene (459142-93-9) → [(Fe(η5-C5H4-1-(4-C5H4N))2)(1-pimelic acid)] (914645-93-5)

Conditions	Yield
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.;	99%

heptanedioic acid (111-16-0) + carbonic acid dimethyl ester (616-38-6) → dimethyl 1,7-heptanedioate (1732-08-7)

Conditions	Yield
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry;	98%

heptanedioic acid (111-16-0) + manganese (II) acetate tetrahydrate (6156-78-1) → manganese(II) pimelate (50962-31-7)

Conditions	Yield
In ethanol refluxing (2 h); cooling, filtn., washing (EtOH), drying; elem. anal.;	97%

heptanedioic acid (111-16-0) + (R)-1-phenyl-ethyl-amine (3886-69-9) → heptanedioic acid bis[(1-phenylethyl)amide]

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	95%

heptanedioic acid (111-16-0) + C14H24N4(2+)*2HO(1-) → 1,6-bis(3-methylimidazol-1-yl)hexane pimelate

Conditions	Yield
In ethanol at 25℃; for 24h;	94%
In ethanol at 25℃; for 24h;

heptanedioic acid (111-16-0) + butan-1-ol (71-36-3) → dibutyl heptanedioate (51238-94-9)

Conditions	Yield
With sulfuric acid at 20℃; for 0.0541667h;	92%

heptanedioic acid (111-16-0) + 1,4-bis(1-methylimidazolium-3-yl)butane hydroxide → 1,4-bis(3-methylimidazol-1-yl)butane pimelate

Conditions	Yield
In ethanol at 25℃; for 24h;	92%
In ethanol at 25℃; for 24h;

heptanedioic acid (111-16-0) + sulfanilamide (63-74-1) → C19H24N4O6S2 (123351-06-4)

Conditions	Yield
With sulfuric acid at 30 - 40℃; for 0.5h;	91%

heptanedioic acid (111-16-0) + 4-amino-5-chloro-2-methoxy-benzoic acid 2-piperazin-1-yl-ethyl ester (307973-17-7) → C35H48Cl2N6O8

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 20℃; for 24h;	91%

heptanedioic acid (111-16-0) + menthol (89-78-1) → heptanedioic acid dimenthyl ester (67714-15-2)

Conditions	Yield
With tetrabutoxytitanium In toluene at 110℃; for 33h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	90.7%

heptanedioic acid (111-16-0) → pimelic acid anhydride (10521-07-0)

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%

heptanedioic acid (111-16-0) + aniline (62-53-3) → 7-oxo-7-(phenylamino)heptanoic acid (160777-08-2)

Conditions	Yield
at 185℃; for 7h;	90%
at 180℃; for 1h;	49%
at 180℃;	43%
at 180℃;

heptanedioic acid (111-16-0) + cobalt(II) nitrate hexahydrate + hydrazine hydrate (7803-57-8) → cobalt(II)pimelate*2(hydrazine) monohydrate

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%

Upstream product

• 123-51-3 3-Methyl-1-butanol 

Downstream Products

• 1732-08-7 DIMETHYL PIMELATE 
• 657-27-2 L-Lysine hydrochloride 
• 2050-20-6 Diethyl pimelate 

Recommend Products

• 10297-09-3  oct-7-ynoic acid 
• 64-19-7  acetic acid 
• 14047-60-0  sodium nonanoate 
• 110-94-1  1,5-pentanedioic acid 
• 636-82-8  cyclohexene-1-carboxylic acid 
• 935-12-6  3-(tetrahydrofuran-2-yl)propanoic acid 
• 124-04-9  Adipic acid 
• 646-07-1  4-Methylpentanoic acid 
• 7732-18-5  water 
• 67-64-1  acetone 
• 61771-76-4  1-(but-3-enyl)-2-oxocyclohexanecarboxylic acid ethyl ester 
• 505-48-6  octane-1,8-dioic acid 
• 3128-07-2  6-oxoheptanoic acid 
• 931-88-4  cis-Cyclooctene 

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