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Basic Information
CAS No.: 78-59-1
Name: Isophoron
Article Data: 198
Molecular Structure:
Molecular Structure of 78-59-1 (Isophoron)
Formula: C9H14O
Molecular Weight: 138.21
Synonyms: 3,5,5-Trimethyl-2-cyclohexen-1-one;3,5,5-Trimethyl-2-cyclohexene-1-one;3,5,5-Trimethyl-2-cyclohexenone;Isoacetophorone;Isoforon;Isophoron;NSC 403657;NSC 4881;a-Isophoron;a-Isophorone;iso-phorone;2-Cyclohexen-1-one,3,5,5-trimethyl-;1,1,3-Trimethyl-3-cyclohexene-5-one;1,5,5-Trimethyl-3-oxocyclohexene;1-Cyclohexen-3-one, 1,5,5-trimethyl-;
EINECS: 201-126-0
Density: 0.905 g/cm3
Melting Point: -8 °C(lit.)
Boiling Point: 215.2 °C at 760 mmHg
Flash Point: 84.4 °C
Appearance: light yellow liquid
Hazard Symbols: HarmfulXn
Risk Codes: 21/22-36/37-40
Safety: 13-23-36/37/39-46
PSA: 17.07000
LogP: 2.32180
Synthetic route
470-99-5

isophorol

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 2,4-dichlorotoluene at 25℃; for 2h; Inert atmosphere;99%
With pyridine; oxygen; Pd(II)-hydrotalcite In toluene at 80℃; for 3h;96%
With iodosylbenzene; N,N-ethylenebis(3,5-dichlorosalicylideneiminato)Cr(III)Cl In dichloromethane at 20℃; for 0.666667h;95%
10276-21-8

isophorone oxide

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With iodine; triphenylphosphine In acetonitrile at 20℃; for 0.25h;98%
With sodium hydroxide; thiourea dioxide; tetrabutylammomium bromide In tetrahydrofuran at 50℃; for 0.5h;95%
Stage #1: isophorone oxide With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran; acetonitrile for 0.5h; Inert atmosphere;
Stage #2: With sodium dihydrogenphosphate; water In tetrahydrofuran; acetonitrile for 0.333333h; Inert atmosphere;
88%
136116-41-1

Trimethyl-(3,5,5-trimethyl-cyclohex-2-enyloxy)-silane

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With chromium(VI) oxide; tert.-butylhydroperoxide; triphenylhydroxysilane In dichloromethane for 17h; Ambient temperature;98%
107742-85-8

6-Benzenesulfinyl-3,5,5-trimethyl-cyclohex-2-enone

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran at 25℃; for 2h;98%
107742-84-7

3,5,5-Trimethyl-6-phenylsulfanyl-cyclohex-2-enone

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran at 25℃; for 3h;95%
13271-49-3

3-bromo-5,5-dimethlycyclohex-2-en-1-one

917-54-4

methyllithium

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With copper(I) thiophenolate In tetrahydrofuran; diethyl ether at 0℃; for 2.5h;94%
78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
In chloroform for 25h; Ambient temperature; Irradiation;90%
With oxygen; methylene blue In chloroform for 24h; Irradiation; Yield given;
175602-66-1

(3,5,5-trimethyl-2-cyclohexenyl) ethyl ether

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 8h; Heating;90%
207395-09-3

(3,5,5-trimethyl-cyclohex-2-enyloxymethyl)-benzene

A

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

B

100-52-7

benzaldehyde

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 8h; Heating;A 87%
B 60%
81036-85-3

7-Bromo-9,9-dimethyl-1,4-dioxa-spiro[4.5]dec-7-ene

74-88-4

methyl iodide

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran86%
With n-butyllithium 1.) THF, -78 deg C, 2 h, 2.) a) -78 deg C, 1 h, b) RT, 1 h; Yield given. Multistep reaction;
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Chemistry

Molecular Structure of Isophorone (CAS NO.78-59-1):

IUPAC Name: 3,5,5-Trimethylcyclohex-2-en-1-one
Molecular Weight: 138.20686 [g/mol]
Molecular Formula: C9H14O
XLogP3-AA: 1.6
H-Bond Donor: 0
H-Bond Acceptor: 1 
Index of Refraction: 1.455
Molar Refractivity: 41.43 cm3
Molar Volume: 152.6 cm3
Surface Tension: 26.4 dyne/cm
Density: 0.905 g/cm3
Flash Point: 84.4 °C
Enthalpy of Vaporization: 45.15 kJ/mol
Boiling Point: 215.2 °C at 760 mmHg
Vapour Pressure: 0.15 mmHg at 25 °C
Appearance: light yellow liquid
Melting Point: −8 °C(lit.)
storage temp.: 2-8 °C
Stability: Stable. Substances to be avoided include strong bases, strong acids and strong oxidizing agents.
Classification Code: Human Data; Mutation data; Skin / Eye Irritant; TSCA Flag T [Subject to the Section 4 test rule under TSCA]; Tumor data

History

The use of Isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which is a waste product of phenol synthesis by the Hock method.

Uses

 Isophorone (CAS NO.78-59-1) is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides.[2] It is also used as a chemical intermediate and as an ingredient in wood preservatives and floor sealants.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD intravenous > 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
National Technical Information Service. Vol. OTS0535380,
guinea pig LC50 inhalation 4600ppm/8H (4600ppm)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 290, 1986.
guinea pig LD50 oral 700mg/kg (700mg/kg)   National Technical Information Service. Vol. OTS0535380,
human TCLo inhalation 25ppm (25ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 28, Pg. 262, 1946.
mouse LC inhalation > 3500mg/kg/6H (3500mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA National Technical Information Service. Vol. OTS0535380,
mouse LD50 oral 2690mg/kg (2690mg/kg)   Toxicology and Applied Pharmacology. Vol. 17, Pg. 498, 1970.
rabbit LD50 oral 1420mg/kg (1420mg/kg)   National Technical Information Service. Vol. OTS0535380,
rabbit LD50 skin 1500uL/kg (1.5mL/kg)   Union Carbide Data Sheet. Vol. 11/15/1971,
rat LC50 inhalation 7gm/m3 (7000mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0572861,
rat LD50 oral 1870mg/kg (1870mg/kg)   Union Carbide Data Sheet. Vol. 11/15/1971,
rat LD50 skin 1390mg/kg (1390mg/kg)   National Technical Information Service. Vol. OTS0526403,

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. Human systemic effects by inhalation: olfactory changes, conjunctiva irritation, and respiratory changes. Human systemic irritant by inhalation. A skin and severe eye irritant. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Considered to be more toxic than mesityl oxide. However, due to its low volatility, it is not a dangerous industrial hazard. The response of guinea pigs and rats to repeated inhalation of the vapors indicates that it is one of the most toxic of the ketones. It is chiefly a kidney poison. It can cause irritation, lachrymation, possible opacity of the cornea, and necrosis of the cornea (experimental). It is irritating at the level of 25 ppm to humans. In animal experiments death during exposure was usually due to narcosis, but occasionally due to irritation of the lungs. Flammable and explosive when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical.
Safety Information of Isophorone (CAS NO.78-59-1):
Hazard Codes: HarmfulXn
Risk Statements: 21/22-36/37-40 
R21/22:Harmful in contact with skin and if swallowed. 
R36/37:Irritating to eyes and respiratory system. 
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 13-23-36/37/39-46 
S13:Keep away from food, drink and animal foodstuffs. 
S23:Do not breathe vapour. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S46:If swallowed, seek medical advice immediately and show this container or label.
WGK Germany: 1
RTECS: GW7700000

Standards and Recommendations

OSHA PEL: TWA 4 ppm
ACGIH TLV: CL 5 ppm
DFG MAK: 2 ppm (11 mg/m3)
NIOSH REL: TWA (Ketones) 23 mg/m3

Analytical Methods

For occupational chemical analysis use NIOSH: Isophorone, 2508.

Specification

 Isophorone (CAS NO.78-59-1), its Synonyms are 3,5,5-Trimethyl-2-cyclohexen-1-one ; 3,5,5-Trimethyl-2-cyclohexenone ; 3,5,5-Trimetil-2-cicloesen-1-one ; 1,1,3-Trimethyl-3-cyclohexene-5-one ; 2-Cyclohexen-1-one, 3,5,5-trimethyl- ; 3,5,5-Trimethyl-2-cyclohexen-1-on ; Isoacetophorone ; Isoforon ; Isoforone .