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| CAS No.: | 136-77-6 |
|---|---|
| Name: | 4-Hexyl-1,3-benzenediol |
| Article Data: | 15 |
| Molecular Structure: | |
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|
|
| Formula: | C12H18O2 |
| Molecular Weight: | 194.274 |
| Synonyms: | Resorcinol,4-hexyl- (8CI);1,3-Dihydroxy-4-hexylbenzene;4-(1-Hexyl)resorcinol;4-Hexyl-1,3-dihydroxybenzene;4-Hexylresorcine;4-Hexylresorcinol;4-n-Hexylresorcinol;Adrover;Antascarin;Ascaricid;Ascarinol;Ascaryl; |
| EINECS: | 205-257-4 |
| Density: | 1.049 g/cm3 |
| Melting Point: | 65-67 °C(lit.) |
| Boiling Point: | 329.5 °C at 760 mmHg |
| Flash Point: | 155.2 °C |
| Solubility: | 0.05 g/100 mL (18 °C) in water |
| Appearance: | slightly red powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36/37/38-20/21/22 |
| Safety: | 22-36/37/38-20/21/22 |
| PSA: | 40.46000 |
| LogP: | 3.22060 |
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| Conditions | Yield |
|---|---|
| With palladium 10% on activated carbon; hydrogen In methanol at 80℃; under 11251.1 Torr; Reagent/catalyst; Autoclave; | 86.2% |
| With hydrogenchloride; amalgamated zinc In ethanol | 67% |
| With hydrogenchloride; amalgamated zinc In ethanol; water Heating; |
- 136-77-6
4-Hexylresorcinol
| Conditions | Yield |
|---|---|
| With ethanol; platinum Hydrogenation; |
- 136-77-6
4-Hexylresorcinol
| Conditions | Yield |
|---|---|
| With hydrogenchloride; amalgamated zinc | |
| With hydrogenchloride; amalgamated zinc |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: aluminum chloride / nitrobenzene / cooling 2: zinc amalgamate; conc. hydrochloric acid / ethanol; H2O / Heating View Scheme | |
| Multi-step reaction with 2 steps 1: 68 percent / aluminum chloride / nitrobenzene 2: 67 percent / zinc amalgame, hydrochloric acid / ethanol View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: aluminum chloride / nitrobenzene / cooling 2: zinc amalgamate; conc. hydrochloric acid / ethanol; H2O / Heating View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 68 percent / aluminum chloride / nitrobenzene 2: 67 percent / zinc amalgame, hydrochloric acid / ethanol View Scheme |
- 34686-76-5
1-bromo-2-hexene
- 136-77-6
4-Hexylresorcinol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: K2CO3; acetone 2: ethanol; platinum / Hydrogenation View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: K2CO3; acetone 2: ethanol; platinum / Hydrogenation View Scheme | |
| Multi-step reaction with 2 steps 1: zinc(II) chloride / 6 h / 95 - 100 °C 2: zinc; hydrogenchloride / ethanol View Scheme |
| Conditions | Yield |
|---|---|
| With sulfuric acid In di-isopropyl ether |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: zinc(II) chloride / 6 h / 95 - 100 °C 2: zinc; hydrogenchloride / ethanol View Scheme |
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Chemistry
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IUPAC Name: 4-Hexylbenzene-1,3-diol
Molecular Weight: 194.27012 [g/mol]
Molecular Formula: C12H18O2
XLogP3: 3.5
H-Bond Donor: 2
H-Bond Acceptor: 2
EINECS: 205-257-4
Product Categories: Miscellaneous
Solubility: chloroform: 50 mg/mL, clear
Water Solubility: 0.05 g/100 mL (18 ºC)
Stability: Stable. Incompatible with acid chlorides, acid anhydrides, oxidizing agents.
Index of Refraction: 1.54
Molar Refractivity: 58.09 cm3
Molar Volume: 185.1 cm3
Surface Tension: 42.6 dyne/cm
Density: 1.049 g/cm3
Flash Point: 155.2 °C
Enthalpy of Vaporization: 59.47 kJ/mol
Boiling Point: 329.5 °C at 760 mmHg
Vapour Pressure: 9.25E-05 mmHg at 25 °C
Appearance: slightly red powder
Melting Point: 65-67 °C(lit.)
Classification Code of 4-Hexylresorcinol (CAS NO.136-77-6): Anthelmintic; Anthelmintics; Anti-Infective Agents; Antiparasitic Agents; Drug / Therapeutic Agent; Mutation data; Reproductive Effect; Skin / Eye Irritant; Tumor data
Uses
4-Hexylresorcinol (CAS NO.136-77-6) is used as an antiseptic, commonly employed in a dilution of 1:1000. It commonly can be used on small skin infections, or as an ingredient in throat lozenges. It has the same lightening effect as 2% hydroquinone over an 8 week period in vivo studies conducted on Synovea HR 4-Hexylresorcinol.
Production
In the manutacture of 4-Hexylresorcinol (CAS NO.136-77-6), resorcinol and caproic acid are heated with a condensing agent, such as zinc chloride, and the intermediate ketone derivative is formed, which is purified by vacuum distillation. After reduction with zinc amalgam and hydrochloric acid, impure 4-Hexylresorcinol is formed, which can be purified by vacuum distillation.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LDLo | oral | 400mg/kg (400mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 28, Pg. 609, 1931. | |
| mouse | LD50 | intraperitoneal | 335mg/kg (335mg/kg) | Japanese Kokai Tokyo Koho Patents. Vol. #90-292213, | |
| mouse | LD50 | oral | 1040mg/kg (1040mg/kg) | Pharmazie. Vol. 30, Pg. 147, 1975. | |
| mouse | LDLo | subcutaneous | 750mg/kg (750mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 148, 1959. | |
| mouse | LDLo | unreported | 100mg/kg (100mg/kg) | Annals of Tropical Medicine and Parasitology. Vol. 32, Pg. 177, 1938. | |
| rat | LD50 | oral | 550mg/kg (550mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 53, Pg. 198, 1935. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
A poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. An eye irritant. Concentrated solutions can cause burns on the skin and mucous membranes in humans. An anthelmintic and topical antiseptic. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes: 
Xn
Risk Statements: 22-36/37/38-20/21/22
22: Harmful if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 26-36-24/25
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
24/25: Avoid contact with skin and eyes
WGK Germany: 3
RTECS: VH1575000
Specification
4-Hexylresorcinol (CAS NO.136-77-6), its Synonyms are 1,3-Dihydroxy-4-hexylbenzene ; 1,3-Dihydroxy-4-n-hexylbenzene ; 4-(1-Hexyl)resorcinol ; 4-Hexyl-1,3-benzenediol ; 4-Hexyl-1,3-dihydroxybenzene ; 4-Hexylresorcine ; 4-4-Hexylresorcinol ; 4-n-4-Hexylresorcinol ; Crystoids ; Cystoids anthelmintic ; Worm-agen ; p-4-Hexylresorcinol .
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