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Cas Database |
| Name |
2,6-Dimethylhydroquinone |
EINECS | 211-505-2 |
| CAS No. | 654-42-2 | Density | 1.162 g/cm3 |
| PSA | 40.46000 | LogP | 1.71460 |
| Solubility | N/A | Melting Point |
154°C |
| Formula | C8H10O2 | Boiling Point | 284.6 °C at 760 mmHg |
| Molecular Weight | 138.166 | Flash Point | 141.1 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | 26-36/37/39 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols | Xi,T |
| Synonyms |
Hydroquinone,2,6-dimethyl- (7CI,8CI);1,4-Dihydroxy-2,6-dimethylbenzene;2,6-Dimethyl-1,4-benzenediol;2,6-Dimethyl-1,4-hydroquinone;2,6-Dimethyl-p-benzohydroquinone;2,6-Dimethylhydroquinone;2,6-Xylohydroquinone;2,6-Xyloquinol;3,5-Dimethylhydroquinone;NSC 36868;m-XHQ;m-Xylene-2,5-diol;m-Xylohydroquinone; |
Article Data | 83 |
2,6-Dimethylhydroquinone Synthetic route
| Conditions | Yield |
|---|---|
| With sodium dithionite In diethyl ether; water | 100% |
| With sodium dithionite In diethyl ether; water at 20℃; | 100% |
| With isopropyl alcohol; zirconium(IV) oxide for 2h; Heating; | 99% |
| Conditions | Yield |
|---|---|
| With 2-Ethylhexanoic acid; [Fe(CF3SO3)2((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)]; dihydrogen peroxide In acetonitrile at 0℃; for 2.5h; | 99% |
| Conditions | Yield |
|---|---|
| With cis-bisglycinato copper(II) monohydrate; dihydrogen peroxide at 70℃; for 4h; Oxidation; | 98% |
| With <(Ce2(p-tert-butylcalix(8)arene))(Me2SO)5>*2Me2SO; dihydrogen peroxide In acetonitrile for 5h; Ambient temperature; | 56% |
| With sodium hydroxide; dipotassium peroxodisulfate Erhitzen des mit wss. HCl angesaeuerten Reaktionsgemisches; |
| Conditions | Yield |
|---|---|
| With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; | A 2% B 98% |
- 576-26-1
2.6-dimethylphenol
A
- 654-42-2
1,4-dihydroxy-2,6-dimethylbenzene
B
- 527-61-7
2,6-dimethyl-1,4-benzoquinone
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide; Ti-superoxide In water; acetic acid at 50 - 60℃; for 1.25h; Product distribution / selectivity; | A 2% B 97% |
- 527-61-7
2,6-dimethyl-1,4-benzoquinone
- 103-49-1
dibenzylamine
A
- 654-42-2
1,4-dihydroxy-2,6-dimethylbenzene
| Conditions | Yield |
|---|---|
| With triethylamine In isopropyl alcohol at 70℃; for 2h; Solvent; Reagent/catalyst; Inert atmosphere; | A 6% B 94% |
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide at 20℃; for 1h; Dakin Phenol Oxidation; Green chemistry; | 92% |
| With 7,8-difluoro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; dihydrogen peroxide; sodium hydrogencarbonate In methanol; water at 20℃; for 0.333333h; Dakin oxidation; | 91% |
| With dihydrogen peroxide In water at 20℃; for 3h; Dakin Phenol Oxidation; Green chemistry; | 88% |
| Conditions | Yield |
|---|---|
| With tetrabutylammonium tricarbonylnitrosylferrate In ethanol at 40℃; for 1h; Michael Addition; Inert atmosphere; Microwave irradiation; | A 10% B 80% |
- 187873-55-8
2,6-dimethyl-cyclohex-3-ene-1,2-diol
A
- 654-42-2
1,4-dihydroxy-2,6-dimethylbenzene
B
- 527-61-7
2,6-dimethyl-1,4-benzoquinone
| Conditions | Yield |
|---|---|
| With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 1h; | A 71% B 6% |
- 2233-18-3
4-hydroxy-3,5-dimethylbenzaldehyde
A
- 654-42-2
1,4-dihydroxy-2,6-dimethylbenzene
B
- 527-61-7
2,6-dimethyl-1,4-benzoquinone
| Conditions | Yield |
|---|---|
| With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; oxygen; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 3h; Dakin Phenol Oxidation; | A 23% B 65% |
2,6-Dimethylhydroquinone Specification
The 2,6-Dimethylhydroquinone with cas registry number of 654-42-2 is also known as MXHQ; m-Xhq; Metaxylohydroquinone. It belongs to the categories of Industrial/Fine Chemicals; Anthraquinones, Hydroquinones and Quinones. Its EINECS registry number is 211-505-2. It has an IUPAC name which is 2,6-dimethylbenzene-1,4-diol.
Physical properties about this chemical are: (1)ACD/LogP: 1.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.56; (4)ACD/LogD (pH 7.4): 1.56; (5)ACD/BCF (pH 5.5): 9.1; (6)ACD/BCF (pH 7.4): 9.1; (7)ACD/KOC (pH 5.5): 169.07; (8)ACD/KOC (pH 7.4): 169; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2 ; (12)Index of Refraction: 1.582; (13)Molar Refractivity: 39.66 cm3; (14)Molar Volume: 118.8 cm3; (15)Surface Tension: 47.8 dyne/cm; (16)Density: 1.162 g/cm3; (17)Flash Point: 141.1 °C; (18)Enthalpy of Vaporization: 54.46 kJ/mol; (19)Boiling Point: 284.6 °C at 760 mmHg; (20)Vapour Pressure: 0.00172 mmHg at 25°C.
Preparation of 2,6-Dimethylhydroquinone: this chemical can be made by 2,6-dimethyl-phenol using reagents cis-bisglycinato copper (II) monohydrate and H2O2. This reaction is a kind of Oxidation. Its reaction time is 4 hours. And its reaction temperature is 70 ℃. The yield is 98%.
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Uses of 2,6-Dimethylhydroquinone: it can react with methanol to give 4-Methoxy-2,6-dimethyl-phenol using reagent conc. H2SO4. The yield is about 87%.
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When you are using this chemical, please be cautious about it as the following:
Poison by ingestion and intraperitoneal routes. An experimental teratogen. Human reproductive effects by ingestion: impaired spermatogenesis in men and changes in fertility in women. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. Wear suitable protective clothing, gloves and eye/face protection during using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)InChI: InChI=1/C8H10O2/c1-5-3-7(9)4-6(2)8(5)10/h3-4,9-10H,1-2H3;
(2)Smiles: Cc1c(O)c(C)cc(O)c1
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | intraperitoneal | 20mg/kg (20mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Indian Journal of Experimental Biology. Vol. 2, Pg. 23, 1964. |
| mouse | LD50 | intraperitoneal | 117mg/kg (117mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR | Indian Journal of Experimental Biology. Vol. 2, Pg. 23, 1964. |
| mouse | LD50 | oral | 186mg/kg (186mg/kg) | Indian Journal of Experimental Biology. Vol. 2, Pg. 23, 1964. |
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