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3282-30-2

Basic Information
CAS No.: 3282-30-2
Name: Pivaloyl chloride
Article Data: 132
Cas Database
Molecular Structure:
Molecular Structure of 3282-30-2 (Pivaloyl chloride)
Formula: C5H9ClO
Molecular Weight: 120.579
Synonyms: Propanoyl chloride,2,2-dimethyl-;Trimethylacetyl chloride [UN2438] [Poison];Trimethylacetyl chloride;Propanoyl chloride, 2,2-dimethyl-;Trimethylacetychloride;
EINECS: 221-921-6
Density: 1.008 g/cm3
Melting Point: -56 °C
Boiling Point: 107.2 °C at 760 mmHg
Flash Point: 8.9 °C
Solubility: hydrolysis with water
Appearance: colorless to yellow liquid
Hazard Symbols: FlammableF, VeryT+, ToxicT
Risk Codes: 11-14-22-26-34-23
Safety: 16-26-36/37/39-45-38-28A
Transport Information: UN 2438 6.1/PG 1
PSA: 17.07000
LogP: 1.79790
Synthetic route
1634-04-4

tert-butyl methyl ether

106-47-8

4-chloro-aniline

A

65854-91-3

N-(4-chlorophenyl)-2,2-dimethylpropionamide

B

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
With sodium hydroxide In waterA 97%
B n/a
With sodium hydroxide In waterA 97%
B n/a
With sodium hydroxide In waterA 97%
B n/a
With sodium hydroxide In waterA 97%
B n/a
75-98-9

Trimethylacetic acid

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
With benzoyl chloride88%
With tetrachlorosilane at 50 - 55℃; for 5h;72%
With thionyl chloride for 24h; Ambient temperature;29%
78114-26-8, 114091-61-1, 63853-15-6

(2,2-dimethyl-1-(trimethylsiloxy)propylidene)-trimethylsilylphosphine

A

3282-30-2

pivaloyl chloride

B

PCl3

PCl3

Conditions
ConditionsYield
With sulfuryl dichlorideA 81%
B n/a
124-63-0

methanesulfonyl chloride

75-98-9

Trimethylacetic acid

A

3282-30-2

pivaloyl chloride

B

1538-75-6

2,2-dimethylpropanoic anhydride

C

C6H12O4S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;A 54%
B 5%
C 35%
75-98-9

Trimethylacetic acid

A

3282-30-2

pivaloyl chloride

B

1538-75-6

2,2-dimethylpropanoic anhydride

C

C6H12O4S

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃;A 54%
B 5%
C 35%
507-20-0

tertiary butyl chloride

201230-82-2

carbon monoxide

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In trichlorofluoromethane at -45℃; under 37503 Torr; for 1h; Product distribution;50%
507-20-0

tertiary butyl chloride

960

960

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In trichlorofluoromethane at -45℃; under 37503 Torr; for 1h;50%
507-20-0

tertiary butyl chloride

960

960

A

14705-30-7

2,2,5-trimethyl-hex-4-en-3-one

B

36967-88-1

Pivalinsaeure-trifluormethansulfonsaeure-anhydrid

C

3282-30-2

pivaloyl chloride

D

HCl

HCl

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In tetrachloromethane at -25℃; under 56254.5 Torr; for 1h;A n/a
B n/a
C 47%
D n/a
507-20-0

tertiary butyl chloride

1493-13-6

trifluorormethanesulfonic acid

960

960

A

14705-30-7

2,2,5-trimethyl-hex-4-en-3-one

B

36967-88-1

Pivalinsaeure-trifluormethansulfonsaeure-anhydrid

C

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
In tetrachloromethane at -25℃; under 56254.5 Torr; for 1h;A n/a
B n/a
C 47%
18243-80-6

trichloro-pivaloyloxy-silane

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
at 159 - 161℃;
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Chemistry

Molecule structure of Pivaloyl chloride (CAS NO.3282-30-2):
 
IUPAC Name: 2,2-Dimethylpropanoyl chloride 
Molecular Weight: 120.57736 g/mol
Molecular Formula: C5H9ClO 
Density: 1.008 g/cm3 
Melting Point: -56 °C
Boiling Point: 107.2 °C at 760 mmHg 
Flash Point: 8.9 °C
Index of Refraction: 1.416
Molar Refractivity: 30.05 cm3
Molar Volume: 119.6 cm3
Surface Tension: 25.8 dyne/cm 
Enthalpy of Vaporization: 34.6 kJ/mol
Vapour Pressure: 27.4 mmHg at 25 °C
Storage Temp.: store at RT.
Water Solubility: hydrolysis
Sensitive: moisture sensitive
XLogP3-AA: 2.2
H-Bond Acceptor: 1
Rotatable Bond Count: 1
Exact Mass: 120.034193
MonoIsotopic Mass: 120.034193
Topological Polar Surface Area: 17.1
Heavy Atom Count: 7
Canonical SMILES: CC(C)(C)C(=O)Cl
InChI: InChI=1S/C5H9ClO/c1-5(2,3)4(6)7/h1-3H3
InChIKey: JVSFQJZRHXAUGT-UHFFFAOYSA-N
EINECS: 221-921-6

Uses

 Pivaloyl chloride (CAS NO.3282-30-2) is used as acylating agent for the production of drugs such as ampicillin and cephalexin. It is also used for medicine and pesticide intermediates.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: FlammableF, VeryT+, ToxicT
Risk Statements: 11-14-22-26-34-23 
R11:Highly flammable. 
R14 :Reacts violently with water. 
R22:Harmful if swallowed. 
R26:Very toxic by inhalation. 
R34:Causes burns. 
R23 :Toxic by inhalation.
Safety Statements: 16-26-36/37/39-45-38-28A 
S16:Keep away from sources of ignition. 
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.) 
S38:In case of insufficient ventilation, wear suitable respiratory equipment. 
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 2438 6.1/PG 1
WGK Germany: 1
F: 9-19
HazardClass: 6.1
PackingGroup: I
HS Code: 29159080
A corrosive irritant to skin, eyes, and mucous membranes. The liquid is flammable when exposed to heat, flame, or oxidizers. When heated to decomposition it emits toxic fumes of Cl.

Standards and Recommendations

DOT Classification:  8; Label: Corrosive, Flammable Liquid, Poison

Specification

 Pivaloyl chloride (CAS NO.3282-30-2) is also named as 2,2-Dimethylpropanoyl chloride ; Propanoyl chloride, 2,2-dimethyl- ; Trimethylacetyl chloride ; UN2438 . Pivaloyl chloride (CAS NO.3282-30-2) is colorless to yellow liquid with a pungent odor. It is very toxic by inhalation, ingestion or skin absorption. Fumes irritate the eyes and mucous membranes. Corrosive to most metals and tissue. It is highly flammable. Reacts vigorously and exothermically with water to form trimethylacetic acid and corrosive hydrochloric acid; both acids corrode metals and tissue. Pivaloyl chloride is acidic and incompatible with bases (including amines), strong oxidizing agents, and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts. May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated.