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111-16-0

Basic Information
CAS No.: 111-16-0
Name: Pimelic acid
Article Data: 210
Cas Database
Molecular Structure:
Molecular Structure of 111-16-0 (Pimelic acid)
Formula: C7H12O4
Molecular Weight: 160.17
Synonyms: Pimelicacid (8CI);1,5-Pentanedicarboxylic acid;1,7-Heptanedioic acid;NSC 30112;Pileric acid;Heptanedioic Acid;
EINECS: 203-840-8
Density: 1.201 g/cm3
Melting Point: 103-105 °C(lit.)
Boiling Point: 212 °C10 mm Hg(lit.)
Flash Point: 181.9 °C
Solubility: ethanol: 0.1 g/mL, clear to very faintly hazy
Appearance: white crystal or crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: N/A
PSA: 74.60000
LogP: 1.10610
Synthetic route
502-42-1

cycloheptanone

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%
629-30-1

1,7-heptandiol

111-16-0

heptanedioic acid

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

formic acid

1577-22-6

5-hexenoic 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%
628-92-2

Cycloheptene

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%
616-25-1

1-Penten-3-ol

201230-82-2

carbon monoxide

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%
1569-50-2

3-penten-2-ol

201230-82-2

carbon monoxide

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%
13154-27-3

2-nitrocycloheptanone

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;
13553-19-0

trans-cycloheptane-1,2-diol

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%
14112-98-2

7-oxooctanoic acid

111-16-0

heptanedioic acid

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

8-oxabicyclo[5.1.0]octane

111-16-0

heptanedioic acid

Conditions
ConditionsYield
With dodecyltrimethylammonium phosphotungstate; water; dihydrogen peroxide In toluene at 80℃; for 12h; chemoselective reaction;84%
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    Product name: pimelic acid Synonyms: heptanedioic acid;1,7-Heptanediacid;1,5-Pentane-1,5-dicarboxylic acid; CAS No:111-16-0 Molecular formula: C7H12O4 Molecular Weight: 160.16800 Appearance:White crystal or crystal powder Assay:99% Annual Capacity:5M

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Chemistry

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

Uses

 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.

Toxicity Data With Reference

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.

 
 

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

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 Irritant
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

Specification

 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.