Pivalic acid

Iupac Name：2,2-dimethylpropanoic acid

CAS No.: 75-98-9

Molecular Weight：102.133

Modify Date.: 2022-11-05 03:16

Introduction: Pivalic acid is a colored crystalline solid of low toxicity that is soluble in water, ethyl alcohol and diethyl ether. View more+

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1. Names and Identifiers

1.1 Name: Pivalic acid
1.2 Synonyms: 2, 2-Dimethylpropanoic acid 2,2,2-trimethylacetic acid 2,2-Dimethylpropanoic acid 2,2-Dimethylpropansαure 2,2-Dimethylpropionic acid, Trimethylacetic acid 2,2-dimethylpropionic acid A,A-DIMETHYLPROPIONIC ACID Acetic acid,trimethyl EINECS 200-922-5 MFCD00004194 Neopentanoic acid PIVALIC ACID (TRIMETHYLACETIC ACID) PIVALIC ACID CRUDE Propanoic acid, 2,2-dimethyl- Propanoic acid,2,2-dimethyl tert-Pentanoic acid trimethylacetic acid trimethyl-acetic acid TRIMETHYLACETIC ACID (PIVALIC ACID) trimethyl-aceticaci

1.3 CAS No.: 75-98-9

1.4 CID: 6417

1.5 EINECS(EC#): 200-922-5

1.6 Molecular Formula: C5H10O2 (isomer)

1.7 Inchi: InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)

1.8 InChkey: IUGYQRQAERSCNH-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)(C)C(=O)O

1.10 Isomers Smiles: CC(C)(C)C(=O)O

2. Properties

2.1 Density: 0.905

2.1 Melting point: 33-36℃

2.1 Boiling point: 91 to 95° F (USCG, 1999)

2.1 Refractive index: 1.393

2.1 Flash Point: 147.2° F (USCG, 1999)

2.2 Precise Quality: 102.06800

2.2 PSA: 37.30000

2.2 logP: 1.11710

2.2 Solubility: 25g/l

2.3 VaporDensity: 3.6 (vs air)

2.4 Appearance: white crystalline low melting mass

2.5 Storage: Ambient temperatures.

2.6 Chemical Properties: white crystalline low melting mass

2.7 Color/Form: Colorless cyrstals
Needles

2.8 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.9 Physical: TRIMETHYLACETIC ACID; is a colored crystalline solid of low toxicity that is soluble in water;, ethyl alcohol; and diethyl ether;.

2.10 pKa: 5.03(at 25℃)

2.11 Water Solubility: 25 g/L (20 oC)

2.12 Spectral Properties: Index of refraction: 1.3931 at 36.5 deg C/D
IR: 6355 (Sadtler Research Laboratories Prism Collection)
NMR: 16038 (Sadtler Research Laboratories Spectral Collection)
MASS: 63363 (NIST/EPA/MSDC Mass Spectral database, 1990 version)

2.13 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 General Description: Pivalic acid is a colored crystalline solid of low toxicity that is soluble in water, ethyl alcohol and diethyl ether.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 135 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 135 companies. For more detailed information, please visit ECHA C&L website

Of the 8 notification(s) provided by 134 of 135 companies with hazard statement code(s):

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (20.15%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H314 (19.4%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H315 (80.6%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (79.85%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H331 (50%): Toxic if inhaled [Danger Acute toxicity, inhalation]
H332 (29.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501

3.3 Methods of Manufacturing: Prepared by the reaction of tert-butylmagnesium chloride; and carbon dioxide;.

3.4 Purification Methods: Fractionally distil the acid under reduced pressure, then fractionally crystallise it from its melt. Recrystallise it from *benzene. [Beilstein 2 IV 908.] Pivalic acid Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Symbol: GHS05;GHS07;

4.1 Hazard Codes: C

4.1 Signal Word: DANGER

4.1 Risk Statements: R21/22;R34

4.1 Safety Statements: S26;S36/37/39;S45

4.1 Packing Group: II

4.1 Octanol/Water Partition Coefficient: log Kow = 1.48

4.2 Fire Hazard: COMBUSTIBLE. Produces vapors irritating to eyes and skin. Decomposes to produce acrid smoke and fumes.

4.3 Other Preventative Measures: If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to disperse vapors and dilute standing pools of liquid..
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

4.4 Hazard Class: 8

4.4 Hazard Declaration: H302 + H312; H314

4.4 Cleanup Methods: Collect leaking liquid in sealable containers. If solid: sweep spilled substance into containers; if appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. (Extra personal protection: A/P2 filter respirator for organic vapour and harmful dust).
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors.

4.5 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.6 RIDADR: UN 3261 8/PG 2

4.6 Fire Fighting Procedures: Powder, alcohol-resistant foam, water spray, carbon dioxide.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical, or carbon dioxide.

4.7 FirePotential: Combustible.

4.8 Safety Profile: Moderately toxic byingestion and skin contact. Questionablecarcinogen with experimental tumorigenicdata. When heated to decomposition itemits acrid smoke and irritating fumes.

4.9 Caution Statement: P280-P305 + P351 + P338-P310

4.9 Formulations/Preparations: >99% pure

4.10 WGK Germany: 1

4.10 RTECS: TO7700000

4.10 Protective Equipment and Clothing: The substance irritates the eyes, the skin and the respiratory tract.

4.11 Skin, Eye, and Respiratory Irritations: The substance irritates the eyes, the skin and the respiratory tract.

4.12 Safety: Safety Information of Pivalic acid (CAS NO.75-98-9):
Hazard Codes:?C
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

4.13 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 .

4.14 Toxicity

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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H331 Toxic if inhaled
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P311 Call a POISON CENTER/doctor/\u2026
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : parameter in CDCl3

1H NMR : Predict

IR : CCl4 solution

IR : liquid film

Raman : 4880 A,200 M,

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

75-98-9Total: 66 Synthesis Route

98-54-4 95 Suppliers

815-17-8 126 Suppliers

75-98-9 219 Suppliers

Literatures:
Justus Liebigs Annalen der Chemie, , vol. 327, p. 207
Yield: null

75-97-8 99 Suppliers

815-17-8 126 Suppliers

75-98-9 219 Suppliers

Literatures:
Monatshefte fuer Chemie, , vol. 10, p. 779 Monatshefte fuer Chemie, , vol. 12, p. 356
Yield: null

75-84-3 93 Suppliers

77212-96-5

926-42-1

630-19-3 125 Suppliers

75-98-9 219 Suppliers

Literatures:
European Journal of Organic Chemistry, , # 3 p. 526 - 536
Yield: ~64%

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8. Other Information

8.0 Merck: 14,7511

8.1 BRN: 969480

8.2 Chemical Properties: white crystalline low melting mass

8.3 Uses: Pivalic Acid is a metabolite of oral cephem (β-lactam) antibiotics such as S-1108, containing pivaloyl moieties.

8.4 Uses

Pivalic acid can be employed:

As a co-catalyst with palladium for the arylation of unactivated arenes and N-heterocycles.
As an additive to facilitate the carbonylative suzuki reactions to synthesize biaryl ketones from aryl iodides and arylboronic acids by using palladium nanoparticles as catalyst.
In the cyclization reaction of benzamides with alkynes to synthesize isoquinolones in the presence of 8-aminoquinoline ligand and cobalt catalyst.

8.5 Usage: Trimethylacetic acid can be used as an internal chemical-shift standard for NMR of aqueous solutions. It is a metabolite of oral cephem (β-lactam) antibiotics such as S-1108, containing pivaloyl moieties.

9. Computational chemical data

Molecular Weight: 102.133g/mol
Molecular Formula: C₅H₁₀O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 102.068079557
Monoisotopic Mass: 102.068079557
Complexity: 78.6
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.3
Heavy Atom Count: 7
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAADgCAgAACCAAAAgAIAACQCAAAAAAAAAAAAAEAAAAAAAAAAAAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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