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Basic Information
CAS No.: 123-42-2
Name: 4-Hydroxy-4-methyl-2-pentanone
Article Data: 161
Molecular Structure:
Molecular Structure of 123-42-2 (4-Hydroxy-4-methyl-2-pentanone)
Formula: C6H12O2
Molecular Weight: 116.16
Synonyms: 2-Hydroxy-2-methyl-4-pentanone;2-Methyl-2-pentanol-4-one;2-Methyl-4-oxo-2-pentanol;2-Methyl-4-oxopentan-2-ol;4-Hydroxy-2-keto-4-methylpentane;4-Hydroxy-4-methyl-2-oxopentane;4-Methyl-4-hydroxy-2-pentanone;Acetonyldimethylcarbinol;Diacetone alcohol;
EINECS: 204-626-7
Density: 0.95 g/cm3
Melting Point: -42.8 °C
Boiling Point: 168.1 °C at 760 mmHg
Flash Point: 61.7 °C
Solubility: miscible with water
Appearance: Clear, colorless liquid
Hazard Symbols: IrritantXi
Risk Codes: 36
Safety: 24/25
Transport Information: UN 1148 3/PG 3
PSA: 37.30000
LogP: 0.73640
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Synthetic route
67-64-1

acetone

123-42-2

4-Hydroxy-4-methyl-2-pentanone

Conditions
ConditionsYield
at 2 - 100℃; for 168h; Temperature;99.85%
ruthenium trichloride for 24h; Condensation; Heating;90%
With 1-bromomagnesio-1-bromo-2,2-diphenylcyclopropane In tetrahydrofuran at -60℃; for 0.5h;80%
116997-41-2

4-(1-Methoxy-2-methylprop-1-enyl)-1,1'-biphenyl

A

123-42-2

4-Hydroxy-4-methyl-2-pentanone

B

720-75-2

methyl 4-phenylbenzoate

C

7472-38-0

1-[(1,1'-biphenyl)-4-yl]-2-hydroxy-2-methylpropan-1-on

D

β,β-Dimethoxy-α,α-dimethyl(1,1'-biphenyl)-4-ethanol

Conditions
ConditionsYield
With ozone In trichlorofluoromethane at -70℃; for 0.15h; Further byproducts given;A n/a
B 86%
C n/a
D n/a
...Expand
67-64-1

acetone

A

141-79-7

4-methyl-pent-3-en-2-one

B

504-20-1

phorone

C

123-42-2

4-Hydroxy-4-methyl-2-pentanone

Conditions
ConditionsYield
With titanium tetrachloride; NCNMe2 In benzene at 25℃;A 82%
B 2%
C 8%
With sodium hydroxide In benzene at 40℃; Mechanism; Kinetics; benzyltriethylammonium chloride presence;
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In benzene at 40℃; reaction order, effect of concentration on the initial rate;
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In benzene at 40℃; Mechanism; effect concentrations, initial rate;
With MgO/ZrO2 mixed oxides at 249.84℃;
...Expand
29882-07-3

4-chlorobutanal dimethyl acetal

A

123-42-2

4-Hydroxy-4-methyl-2-pentanone

B

91988-32-8

4-iodobutyraldehyde dimethyl acetal

C

77406-93-0

4-iodobutyraldehyde

Conditions
ConditionsYield
With sodium iodide In acetone at 56℃; for 10h;A n/a
B 80%
C n/a
...Expand
100-44-7

benzyl chloride

67-64-1

acetone

A

123-42-2

4-Hydroxy-4-methyl-2-pentanone

B

100-86-7

2-Methyl-1-phenyl-2-propanol

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide for 5h; electrolysis;A n/a
B 75%
...Expand
57283-21-3

4-(tetrahydropyranyl-2-oxy)-4-methyl-2-pentanone

123-42-2

4-Hydroxy-4-methyl-2-pentanone

Conditions
ConditionsYield
With poly-p-styryl-acetonyltriphenylphosphonium bromide In methanol at 20℃; for 12h;74%
67-64-1

acetone

cis/trans-1,1,2-tribromo-3-phenylcyclopropane

A

123-42-2

4-Hydroxy-4-methyl-2-pentanone

B

2-(3-phenylcyclopropenyl)-propan-2-ol

Conditions
ConditionsYield
Stage #1: cis/trans-1,1,2-tribromo-3-phenylcyclopropane With methyllithium at -80 - 20℃; for 0.5h;
Stage #2: acetone		A n/a
B 73%
Stage #1: cis/trans-1,1,2-tribromo-3-phenylcyclopropane With methyllithium In diethyl ether at -82 - 20℃; for 0.966667h; Inert atmosphere;
Stage #2: acetone In diethyl ether at -60 - 20℃; Inert atmosphere;		A n/a
B 106 mg
...Expand

4-(1-ethoxyethoxy)-4-methyl-2-pentanone

123-42-2

4-Hydroxy-4-methyl-2-pentanone

Conditions
ConditionsYield
With poly-p-styryl-acetonyltriphenylphosphonium bromide In methanol at 20℃; for 10h;70%

4-(tetrahydrofuranyl-2-oxy)-4-methyl-2-pentanone

123-42-2

4-Hydroxy-4-methyl-2-pentanone

Conditions
ConditionsYield
With poly-p-styryl-acetonyltriphenylphosphonium bromide In methanol at 20℃; for 12h;70%
123934-62-3

5-(trifluoroacetamido)pentyl trifluoroacetate

74-88-4

methyl iodide

A

123-42-2

4-Hydroxy-4-methyl-2-pentanone

B

123934-63-4

N-methyl-N-(5-hydroxy-1-pentyl)trifluoroacetamide

Conditions
ConditionsYield
With potassium hydroxide In acetone for 0.0833333h; Heating;A n/a
B 63%
...Expand
Raw Materials
75-16-1
1833-53-0
93-91-4
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Downstream Products
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Chemistry

IUPAC Name: 4-hydroxy-4-methylpentan-2-one
Synonyms of Diacetone alcohol (CAS NO.123-42-2): 2-Methyl-2-pentanol-4-one ; 4-Hydroxy-2-keto-4-methylpentane ; Diacetonalcohol ; Dimethyl acetonyl carbinol ; 2-Pentanone, 4-hydroxy-4-methyl-
CAS NO: 123-42-2
Molecular Formula: C6H12O2
Molecular Weight: 116.16
Molecular Structure:
EINECS: 204-626-7
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 3
Polar Surface Area: 37.3 Å2
Index of Refraction: 1.426
Molar Refractivity: 31.37 cm3
Molar Volume: 122.2 cm3
Surface Tension: 30.6 dyne/cm
Density: 0.95 g/cm3
Flash Point: 61.7 °C
Enthalpy of Vaporization: 47.1 kJ/mol
Boiling Point: 168.1 °C at 760 mmHg
Vapour Pressure: 0.539 mmHg at 25°C 
Melting Point: -42.8 °C
Water Solubility: Miscible
Appearance: Clear, colorless liquid
Product Categories of Diacetone alcohol (CAS NO.123-42-2): Industrial/Fine Chemicals
Stability: Stable. Flammable. Incompatible with strong oxidizing agents, amines, ammonia, strong acids, strong bases, alkalies, aluminium

Uses

Uses of  Diacetone alcohol (CAS NO.123-42-2) :
 Diacetone alcohol is used in cellulose ester lacquers, particularly of the brushing type, where it produces brilliant gloss and hard film and where its lack of odor is desirable. Besides Diacetone alcohol is also used in lacquer thinners, dopes, wood stains, wood preservatives and printing pastes; in coating compositions for paper and textiles; in making artificial silk and leather; in imitation gold leaf; in celluloid cements; as a preservative for animal tissue; in metal cleaning compounds; in the manufacture of photographic film; and in hydraulic brake fluids, where it is usually mixed with an equal volume of castor oil.

Production

 Preparation of Diacetone alcohol (CAS NO.123-42-2) entails the Ba(OH)2-catalyzed condensation of two molecules of acetone. It undergoes dehydration to give the α,β-unsaturated ketone, mesityl oxide: Hydrogenation of mesityl oxide gives the industrial solvent, methyl isobutyl ketone .
                    

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TCLo inhalation 100ppm (100ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: HEADACHE

GASTROINTESTINAL: NAUSEA OR VOMITING		 Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 21, 1974.
human TCLo inhalation 400ppm (400ppm) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 21, 1974.
mouse LD50 intraperitoneal 933mg/kg (933mg/kg)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 3, 1961.
mouse LD50 oral 3950mg/kg (3950mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 669, 1956.
rabbit LD50 skin 13500mg/kg (13500mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 21, 1974.
rabbit LDLo intramuscular 2792mg/kg (2792mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Journal of Pharmacology and Experimental Therapeutics. Vol. 33, Pg. 175, 1928.
rabbit LDLo intravenous 2792mg/kg (2792mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacology and Experimental Therapeutics. Vol. 33, Pg. 175, 1928.
rabbit LDLo oral 4653mg/kg (4653mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacology and Experimental Therapeutics. Vol. 33, Pg. 175, 1928.
rat LCLo inhalation 1000ppm/4H (1000ppm)   National Technical Information Service. Vol. OTS0557741,
rat LD50 oral 2520mg/kg (2520mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LIVER: OTHER CHANGES		 National Technical Information Service. Vol. OTS0557732,
rat LDLo intravenous 3024mg/kg (3024mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA		 Journal of Pharmacology and Experimental Therapeutics. Vol. 33, Pg. 175, 1928.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information for Diacetone alcohol(123-42-2)
Hazard Codes: IrritantXi
Risk Statements: 36
36: Irritating to eyes
Safety Statements: 24/25
S24/25: Avoid contact with skin and eyes.
RIDADR: UN 1148 3/PG 3
WGK: Germany 1
RTECS: SA9100000
F: 9
HazardClass: 3
PackingGroup: III
Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by skin contact. Human systemic effects by inhalation: headache, nausea or vomiting, eye and pulmonary changes. A skin, mucous membrane, and severe eye irritant. Can cause anemia and damage to liver and kidneys. Narcotic in high concentration. Flammable liquid when exposed to heat or flame; can react with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Standards and Recommendations

OSHA PEL: TWA 50 ppm
ACGIH TLV: TWA 50 ppm
DFG MAK: 50 ppm (240 mg/m3)
NIOSH REL: (Ketones) TWA 240 mg/m3
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: Alcohols III, 1402.

Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Vapors can travel to a source of ignition and flash back. Will burn if involved in a fire. Containers may explode in the heat of a fire. Combustible liquid.
Extinguishing Media: Use water spray to cool fire-exposed containers. Use dry chemical, carbon dioxide, or alcohol-resistant foam. 
Handling: Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.