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75-98-9

Basic Information
CAS No.: 75-98-9
Name: Pivalic acid
Molecular Structure:
Molecular Structure of 75-98-9 (Pivalic acid)
Formula: C5H10O2
Molecular Weight: 102.13
Synonyms: Pivalicacid (7CI,8CI);2,2,2-Trimethylacetic acid;2,2-Dimethylpropanoic acid;2,2-Dimethylpropionic acid;NSC 65449;Neopentanoic acid;Neovaleric acid;Trimethylacetic acid;Trimethylmethanecarboxylic acid;Versatic 5 acid;tert-Pentanoic acid;a,a-Dimethylpropionic acid;Propanoic acid,2,2-dimethyl-;
EINECS: 200-922-5
Density: 0.965 g/cm3
Melting Point: 32-35 °C
Boiling Point: 166.2 °C at 760 mmHg
Flash Point: 68.3 °C
Solubility: 25 g/L (20 °C) in water
Appearance: white crystalline low melting mass
Hazard Symbols: CorrosiveC
Risk Codes: 21/22-34
Safety: 26-36/37/39-45
Transport Information: UN 3261 8/PG 2
PSA: 37.30000
LogP: 1.11710
Synthetic route
598-98-1

Methyl pivalate

A

4346-64-9

selenoanisole

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With benzeneselenolate ion Mechanism; reaction of esters with phenyl selenide anion;A 100%
B 98%
With Benzeneselenol; sodium hydride 1.) THF, 2.) HMPA, 6 h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
630-19-3

pivalaldehyde

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With C22H42CoN4O4(1+)*C4H10O*C24H20B(1-) In methanol; acetonitrile at 25℃;94%
75-97-8

3,3-dimethyl-butan-2-one

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With tetrachloromethane; sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 2h;96%
With sodium hypochlorite; lithium hypochlorite In ethanol at 77℃; for 8h;84%
With sodium hypochlorite; sulfuric acid In water83.8%
754-10-9

2,2-dimethylpropionamide

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.25h; microwave irradiation;96%
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 0.583333h; Hydrolysis;91%
With niobium(V) oxide; water In neat (no solvent) for 20h; Reflux; Inert atmosphere;91%
With sulfuric acid; cis-nitrous acid at 25℃; Thermodynamic data; E; other aliphatic and aromatic primary amides;
75-84-3

2,2-dimethyl-propanol-1

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 100℃; for 24h; Green chemistry; chemoselective reaction;93%
With sodium hypochlorite; nickel dichloride In dichloromethane; water at 0 - 20℃; for 4h;88%
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In water; acetonitrile at 20℃; for 480h;88%

2,2-dimethylpropionic acid, 4-methoxybenzyl ester

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 24h; Inert atmosphere; Glovebox; UV-irradiation;83%

(4R-cis)-6-(2-aminoethyl)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxane pivalate salt

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
In toluene for 27h; Heating / reflux;80.1%
120-72-9

indole

1538-75-6

2,2-dimethylpropanoic anhydride

A

69622-35-1

1-(1H-indol-3-yl)-2,2-dimethyl-1-propanone

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With Cl(1-)*C5H14NO(1+)*3ZnCl2 at 120℃; for 0.166667h; Friedel-Crafts Acylation; Microwave irradiation; Green chemistry; regioselective reaction;A 79%
B n/a
157843-81-7

3,5-Dimethoxybenzyl pivalate

A

4179-19-5

1,3-dimethoxy-5-methylbenzene

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 24h; Inert atmosphere; Glovebox; UV-irradiation;A 9%
B 78%
157843-82-8

3,4,5-Trimethoxybenzyl pivalate

A

6443-69-2

3,4,5-trimethoxytoluene

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 24h; Inert atmosphere; Glovebox; UV-irradiation;A 11%
B 73%
67-56-1

methanol

72681-59-5

1-naphthylmethyl 2,2-dimethylpropanoate

A

20411-45-4

1-neopentylnaphthalene

B

5903-23-1

1-(methoxymethyl)naphthalene

C

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
at 20℃; Rate constant; Quantum yield; Irradiation;A 9%
B 71%
C n/a
630-18-2

tert-butyl isocyanide

A

652-11-9

3,4,5,6-tetrafluorophthalimide

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With 3,4,5,6-tetrafluorophthalic acid at 180℃; for 120h;A n/a
B 70%
75-84-3

2,2-dimethyl-propanol-1

A

5340-26-1

neopentyl pivalate

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite for 2h; Ambient temperature;A 70%
B 4%
754-10-9

2,2-dimethylpropionamide

A

652-11-9

3,4,5,6-tetrafluorophthalimide

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With 4,5,6,7-tetrafluoroisobenzofuran-1,3-dione at 155℃; for 120h;A n/a
B 68%
7210-81-3

N-neopentylaniline

A

26029-60-7

N-(neopentylidene)aniline

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With iron(III) porphyrin(1+); iodosylbenzene In dichloromethane at 0℃; for 4h;A 65%
B 9%
75-84-3

2,2-dimethyl-propanol-1

A

630-19-3

pivalaldehyde

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; chromium tetra(tert-butoxide) In benzene at 20℃; for 24h;A 15%
B 61%
815-17-8

trimethylpyruvic acid

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With quinoline; oxygen; cobalt(II) acetate; copper at 110 - 120℃; for 1.25h;60%
With quinoline; oxygen; cobalt(II) acetate; copper at 110 - 120℃; for 1.25h; Product distribution; var. cat. syst.;
With silver(l) oxide
With chromic acid
With dihydrogen peroxide

t-Bu-oxycarbonylcobalt tetracarbonyl

B

15041-50-6

tetracobaltdodecacarbonyl

C

124-38-9

carbon dioxide

D

75-65-0

tert-butyl alcohol

E

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With carbon monoxide thermal decompn. of alkoxycarbonylcobalt tetracarbonyl at 60°C at 1 bar of CO, further products;A n/a
B 60-70
C n/a
D 60%
E 30%
630-19-3

pivalaldehyde

A

75-65-0

tert-butyl alcohol

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With dihydrogen peroxide; 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride In water; acetonitrile at 85℃; for 18h;A 40 %Spectr.
B 60%
1426824-99-8

2-phenylpropane-1,2-diyl bis(2,2-dimethylpropanoate)

A

98-83-9

isopropenylbenzene

B

75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; Inert atmosphere; Glovebox; UV-irradiation;A 21%
B 59%
62-53-3

aniline

75-98-9

Trimethylacetic acid

6625-74-7

N-pivaloylaniline

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
With TEA; diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate In various solvent(s) for 2h; Ambient temperature;99%
With triethylamine; Phenyl N-phenylphosphoramidochloridate In dichloromethane for 1.5h; Ambient temperature;91%
108-69-0

3,5-dimethylaminoaniline

75-98-9

Trimethylacetic acid

86489-67-0

N-(3,5-dimethylphenyl)pivalamide

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
87-62-7

2,6-dimethylaniline

75-98-9

Trimethylacetic acid

39627-97-9

2,2-dimethyl-N-(2,6-dimethylphenyl)propionamide

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
100-46-9

benzylamine

75-98-9

Trimethylacetic acid

26209-45-0

N-benzyl-2,2-dimethylpropanamide

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
With tetramethylorthosilicate In toluene at 110℃; for 20h; Inert atmosphere;99%
With 4,5,6,7-tetrachlorobenzo[d][1,3,2]dioxaborole In o-xylene for 15h; Heating;94%
96-53-7

2-mercaptothiazoline

75-98-9

Trimethylacetic acid

138459-91-3

3-pivaloyl-1,3-thiazolidine-2-thione

Conditions
ConditionsYield
With 2,6-dimethylpyridine; 2-chloro-1,3-dimethylimidazolinium chloride In dichloromethane at 20℃; for 72h; Acylation;100%
75-98-9

Trimethylacetic acid

14271-99-9

lithium trimethylacetate

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran; diethyl ether at 0℃; for 0.75h; Inert atmosphere;100%
With lithium hydroxide monohydrate In methanol at 40℃; for 1h;89%
With lithium hydroxide monohydrate In water at 140℃; Heating;88%
With lithium hydroxide In water
557-20-0

diethylzinc

75-98-9

Trimethylacetic acid

zinc trimethylacetate

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 1.5h; Inert atmosphere;100%
In tetrahydrofuran at 0 - 22℃; Inert atmosphere; Schlenk technique;100%
In tetrahydrofuran at 0 - 25℃; for 1.5h; Inert atmosphere;100%
855743-28-1

2-(2-nitrophenyl)but-3-en-1-ol

75-98-9

Trimethylacetic acid

1441228-44-9

2-(2-nitrophenyl)but-3-en-1-yl pivalate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 4h; Inert atmosphere; Reflux;100%
75-98-9

Trimethylacetic acid

123133-75-5

magnesium trimethylacetate

Conditions
ConditionsYield
With dibutylmagnesium In tetrahydrofuran; hexane at 0 - 25℃; for 6.5h; Inert atmosphere; Schlenk technique;100%
With dibutylmagnesium In tetrahydrofuran; hexane at 0 - 25℃; for 6.5h; Inert atmosphere; Schlenk technique;100%
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

75-98-9

Trimethylacetic acid

PivOBpin

Conditions
ConditionsYield
In toluene at 20℃; for 3.25h; Glovebox;100%
100-51-6

benzyl alcohol

75-98-9

Trimethylacetic acid

2094-69-1

benzyl pivalate

Conditions
ConditionsYield
With diphenylphosphinopolystyrene; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 4h;99%
With pyridine; 2,4,6-trinitrochlorobenzene for 3h;95%
With triethylamine In dichloromethane 1.) 0 deg C; 2.) to room temperature and 1 h;79%
524-38-9

N-hydroxyphthalimide

75-98-9

Trimethylacetic acid

84379-72-6

1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate

Conditions
ConditionsYield
Stage #1: Trimethylacetic acid With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.0166667h; Schlenk technique; Inert atmosphere;
Stage #2: N-hydroxyphthalimide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique;
99%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 5h;98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;95%
497233-85-9

N4-{3-[4-(3-aminopropyl)piperazino]propyl}-7-chloroquinolin-4-amine

75-98-9

Trimethylacetic acid

N-(3-{4-[3-(7-chloro-quinolin-4-ylamino)-propyl]-piperazin-1-yl}-propyl)-2,2-dimethyl-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;99%
532976-84-4

(1S,4aR,5S,7aS)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,4a,5,7a-tetrahydro-5-hydroxycyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside

75-98-9

Trimethylacetic acid

532976-86-6

(1S,4aR,5R,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 1.91667h; modified Mitsunobu reaction;99%
874910-51-7

2-chloro-3-(4-tetrahydropyranyl)-3-oxopropanoic acid methyl ester

75-98-9

Trimethylacetic acid

2-pivaloyloxy-3-(4-tetrahydropyranyl)-3-oxopropanoic acid methyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;99%

bis(η-cyclopentadienyl)hydridophenyltungsten

75-98-9

Trimethylacetic acid

bis(cyclopentadienyl)(hydrido)(pivalato)tungsten(IV)

Conditions
ConditionsYield
In diethyl ether byproducts: C6H6; addn. of diethyl ether to a mixture of the starting complex and the carboxylic acid, stirring at room temp. for 48 h, all steps under N2 or Ar; filtn. of ppt.;99%
67-51-6

3,5-dimethyl-1H-pyrazole

75-98-9

Trimethylacetic acid

615251-39-3

bis(3,5-dimethylpyrazole)bis(trimethylacetato)bis(μ-N,N'-3,5-dimethylpyrazolato)dicobalt(II)

Conditions
ConditionsYield
With triethylamine In hexane byproducts: (C2H5)3NHOOCC(CH3)3; under Ar atm.; aq. cobalt acetate and pivalic acid were fused at 165°C; cooled; excess of ligand, Et3N added; 22°C; suspn. dissolved in hexane; allowed to stand for 1 d at 5°C; crystals washed (hexane); dried in flowing Ar; elem. anal.;99%
21205-91-4

9-borabicyclo[3.3.1]nonane dimer

75-98-9

Trimethylacetic acid

169695-35-6

9-pivaloyloxy-9-borabicyclo[3.3.1]nonane, dimer

Conditions
ConditionsYield
In 1,2-dimethoxyethane byproducts: H2; (inert atmosphere); 40°C, 2 d; evapn. (20°C/0.01 Torr); elem. anal.;99%
110-86-1

pyridine

950990-97-3

[Ce(o-(tert-butyl)phenol(-H))3(tetrahydrofuran)3]

75-98-9

Trimethylacetic acid

950991-05-6

[Ce(o-(tert-butyl)phenol(-H))(μ-trimethylacetate)(μC-trimethylacetate)(pyridine)2]2

Conditions
ConditionsYield
In pyridine under inert atm., Schlenk techniques; soln. of Ce compd. (0.32 mmol) andacid (0.65 mmol) stirred for 12 h; crystd. on storage, elem. anal.;99%
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    Trimethylacetic acid Product Name: Trimethylacetic acid Molecular Weight: 102.13 CAS NO: 75-98-9 EC NO: 200-922-5 Molecular Formula: C5H1

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    CAS No.: 75-98-9 Other Names: Trimethylacetic acid MF: C5H10O2 EINECS No.: 200-922-5 Place of Origin: Anhui, China (Mainland) Type: Agrochemical Intermediates, Pharmaceutical Intermediates Purity: 99% Brand Name: TNJ

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Chemistry

Molecular Structure of Pivalic acid (CAS NO.75-98-9):

IUPAC Name: 2,2-Dimethylpropanoic acid
Canonical SMILES: CC(C)(C)C(=O)O
InChI: InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)
InChIKey: IUGYQRQAERSCNH-UHFFFAOYSA-N
Molecular Weight: 102.1317 [g/mol]
Molecular Formula: C5H10O2
XLogP3: 1.5
H-Bond Donor: 1
H-Bond Acceptor: 2 
EINECS: 200-922-5
Product Categories: Intermediates
Appearance: white crystalline low melting mass
Melting Point: 32-35 °C(lit.)
Index of Refraction: 1.419
Molar Refractivity: 26.74 cm3
Molar Volume: 105.7 cm3
Surface Tension: 30.2 dyne/cm
Density: 0.965 g/cm3
Flash Point: 68.3 °C
Enthalpy of Vaporization: 44.41 kJ/mol
Boiling Point: 166.2 °C at 760 mmHg
Vapour Pressure: 0.907 mmHg at 25 °C
storage temp.: 2-8°C
Water Solubility: 25 g/L (20 °C)
Classification Code: Tumor data 

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 900mg/kg (900mg/kg)   "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds. New York, John Wiley & Sons, Inc., 1978Vol. 4, Pg. 863, 1978.
rat LD50 skin 1900mg/kg (1900mg/kg)   "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds. New York, John Wiley & Sons, Inc., 1978Vol. 4, Pg. 863, 1978.

Safety Profile

Safety Information of Pivalic acid (CAS NO.75-98-9):
Hazard Codes: CorrosiveC
Risk Statements: 21/22-34 
R21/22:Harmful in contact with skin and if swallowed. 
R34:Causes burns.
Safety Statements: 26-36/37/39-45 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3261 8/PG 2
WGK Germany: 1
RTECS: TO7700000
HazardClass: 8
PackingGroup: II

Specification

 Pivalic acid (CAS NO.75-98-9), its Synonyms are 2,2-Dimethylpropanoic acid ; 2,2-Dimethylpropionic acid ; Acetic acid, trimethyl- ; Kyselina 2,2-dimethylpropionova ; Neopentanoic acid ; Propanoic acid, 2,2-dimethyl- ; Propionic acid, 2,2-dimethyl- ; Trimethylacetic acid ; Versatic 5 ; alpha,alpha-Dimethylpropionic acid ; tert-Pentanoic acid .