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  2. 95-71-6
Methylhydroquinone | 95-71-6

Nome del prodotto:Methylhydroquinone

Numero CAS:95-71-6
MF:C7H8O2
MW:124.137222290039
MDL:MFCD00002345
CID:34812
ID PubChem:7253
Nomi e identificatori
  • 2-Methylbenzene-1,4-diol
  • 3-METHYL-1,4-DIHYDROXYBENZENE
  • METHYLHYDROQUINONE
  • P-TOLUHYDROQUINOL
  • 1,4-Dihydroxy-2-methylbenzene
  • 2,5-Toluenediol
  • 2-Methyl-1,4-benzenediol (2-methylhydroquinone)
  • 2-methyl-1,4-hydroquinone
  • 2-methyl-4-benzenediol
  • 2-Methyl-p-hydroquinone
  • 4-Benzenediol,2-methyl-1
  • Hydroquinone, methyl-
  • methyl-hydroquinon
  • Methyl-p-hydroquinone
  • p-Toluquinol
  • Toluquinol
  • THQ
  • 2,5-Dihydroxytoluene
  • p-Toluhydroquinone
  • 2-Methyl-1,4-benzenediol
  • Toluhydroquinone
  • 2-Methylhydroquinone
  • Tolylhydroquinone
  • 1,4-Benzenediol, 2-methyl-
  • METHYL HYDROQUINONE
  • Pyrolin
  • Hydroquinone, tolyl-
  • THQ (VAN)
  • NSC496
  • 2-Methyl-1,4-benzenediol (ACI)
  • Hydroquinone, methyl- (6CI, 8CI)
  • 2-Methyl-1,4-dihydroxybenzene
  • 2-Methyl-1,4-hydroquinone
  • 4-Hydroxy-2-methylphenol
  • M-HQ
  • m-Methylhydroquinone
  • Methyl 1,4-dihydroxybenzene
  • Methylhydroquinone
  • NSC 4962
  • o-Methylhydroquinone
  • p-Toluhydroquinol
  • p-toluhydroquinone
  • methyl-p-hydroquinone
  • tolylhydroquinone
  • methylhydroquinone
  • Speciosin G
  • p-toluquinol
  • 2,5-dihydroxytoluene
  • toluhydroquinone
  • 1,4-dihydroxy-2-methylbenzene
  • 2,5-toluenediol
  • p-toluhydroquinol
  • 2-methylhydroquinone
  • MDL:MFCD00002345
  • InChIKey:CNHDIAIOKMXOLK-UHFFFAOYSA-N
  • Inchi:1S/C7H8O2/c1-5-4-6(8)2-3-7(5)9/h2-4,8-9H,1H3
  • SMILES:OC1C=C(C)C(O)=CC=1
  • BRN:2041489
Proprietà chimiche e fisiche

Proprietà calcolate

  • Massa esatta: 124.05243
  • Conta donatori di obbligazioni idrogeno: 2
  • Conta accettatore di obbligazioni idrogeno: 2
  • Conta legami ruotabili: 0
  • Massa monoisotopica: 124.05243
  • Conta atomi pesanti: 9
  • Complessità: 92.9
  • Conta atomi isotopi: 0
  • Conto di stereocentri atomici definito: 0
  • Conta stereocentri atomici non definiti: 0
  • Conto stereocentrico definito delle obbligazioni: 0
  • Conto stereocenter di bond non definito: 0
  • Conteggio di unità legate in modo Covalent: 1
  • XLogP3: 1
  • Conta Tautomer: 13
  • Carica superficiale: 0
  • Superficie polare topologica: 40.5

Proprietà sperimentali

  • LogP: 1.40620
  • PSA: 40.46000
  • Indice di rifrazione: 1.4922 (estimate)
  • Coefficiente di ripartizione dell'acqua: 77G/L(25ºC)
  • Punto di ebollizione: 285°C
  • Punto di fusione: 128-130 °C (lit.)
  • Punto di infiammabilità: Fahrenheit: 341,6 ° f< br / >Celsius: 172 ° C< br / >
  • FEMA: 3596
  • Solubilità: 77g/l
  • Colore/forma: Powder
  • Stabilità/Periodo di validità: Stable. Combustible. Incompatible with oxidizing agents, strong bases.
  • Solubilità: Non determinato
  • Densità: 1.1006 (rough estimate)
Informazioni sulla sicurezza
  • Simbolo: GHS07
  • RTECS:MX6700000
  • WGK Germania:2
  • Istruzioni di sicurezza:26-36
  • Segno di merci pericolose: Xn Xn
  • Numero di trasporto dei materiali pericolosi:NONH for all modes of transport
  • Dichiarazione di pericolo:H302,H315,H319,H335
  • Dichiarazione di avvertimento:P261,P305+P351+P338
  • Prompt:avviso
  • Condizioni di conservazione:Conservare in contenitori ben chiusi. Conservare in un luogo fresco, asciutto e ben ventilato lontano da sostanze incompatibili.
  • PackingGroup:III
  • Codice categoria di pericolo:22-36/37/38
  • Parola segnale:Warning
  • TSCA:Yes
  • Classe di pericolo:6.1(b)
Dati doganali
  • CODICE SA:29072900
Circuito sintetico

Circuito sintetico 1

Condizioni di reazione
1.1 Reagents: Sulfuric acid Solvents: Ethanol
Riferimento
Action of Dilute Sulfuric Acid on Phenyl- and p-Tolylhydroxylamine (in the Presence and Absence of Phenol)
Bamberger, Eug., Annalen der Chemie, 1912, 390, 131-90

Circuito sintetico 2

Condizioni di reazione
1.1 Reagents: Acetic acid ,  N-Methyl-2-pyrrolidone ,  Oxygen Catalysts: Cuprate(1-), trichloro-, lithium, dihydrate Solvents: Methyl isobutyl ketone ,  Water ;  24 h, 700 kPa, 50 °C
1.2 Reagents: Hydrogen Catalysts: Nickel Solvents: Water ;  5.5 h, 630 kPa, 80 °C
Riferimento
Processes for production of benzoquinones by oxidation of aromatic hydroxy compounds over copper catalyst followed by reduction to hydroquinones
, United States, , ,

Circuito sintetico 3

Condizioni di reazione
1.1 Catalysts: Palladium (diphenyl-2-pyridylphosphine complex, porous organic polymer supported) ,  Pyridine, 2-[bis(4-ethenylphenyl)phosphino]-, homopolymer (palladium complex) Solvents: Dimethylacetamide ;  rt → 140 °C; 12 h, 1 atm, 140 °C
Riferimento
Pd0-PyPPh2@porous organic polymer: Efficient heterogeneous nanoparticle catalyst for dehydrogenation of 3-methyl-2-cyclohexen-1-one without extra oxidants and hydrogen acceptors
Chen, Xingkun; Wang, Wenlong; Zhu, Hejun; Yang, Wenshao; Ding, Yunjie, Molecular Catalysis, 2018, 456, 49-56

Circuito sintetico 4

Condizioni di reazione
1.1 Reagents: Sulfuric acid Catalysts: Aluminum Solvents: Water ;  rt → 86 °C; 30 min, 86 °C; 60 min, 86 °C; 86 °C → 25 °C
Riferimento
Synthesis process for 2-methyl-1,4-dihydroxybenzene
Sun, Xiaobo; Jiang, Denggao; Liu, Guoji; Ren, Ke, Huagong Shikan, 2005, 19(10), 24-26

Circuito sintetico 5

Condizioni di reazione
1.1 Reagents: Sulfuric acid Solvents: Water ;  30 min, 86 °C; 1 h, 86 °C
Riferimento
Improvement of the synthesis process of methyhydroquinone
Sun, Xiaobo; Jiang, Denggao; Wang, Xunqiu; Zhou, Cairong; Ren, Ke, Henan Huagong, 2003, (2), 15-16

Circuito sintetico 6

Condizioni di reazione
1.1 Reagents: 1-Methyl-1,4-cyclohexadiene Catalysts: Trifluoroacetic acid Solvents: Toluene ;  2 h, 30 °C
Riferimento
1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones
Baschieri, Andrea ; Amorati, Riccardo ; Valgimigli, Luca ; Sambri, Letizia, Journal of Organic Chemistry, 2019, 84(21), 13655-13664

Circuito sintetico 7

Condizioni di reazione
1.1 Reagents: Sodium bisulfite
Riferimento
Synthesis of 4,7-dimethoxyindoles bearing substituents at the C-5 and C-6 positions and studies on their demethylation products
Malesani, Giorgio; Galiano, Fabio; Ferlin, Maria Grazia; Masiero, Sergio, Journal of Heterocyclic Chemistry, 1980, 17(3), 563-9

Circuito sintetico 8

Condizioni di reazione
1.1 Reagents: Potassium carbonate Solvents: Ethanol ,  Water ;  reflux; 1 h, reflux; 3 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  neutralized, reflux
Riferimento
Green, lithium salt-free synthesis of 2-alkylated 1,4-benzenediols in hydroalcoholic media
Peixoto de Abreu Lima, Alejandro; Graziano, Natali; Pandolfi, Enrique, Green Chemistry Letters and Reviews, 2016, 9(4), 210-215

Circuito sintetico 9

Condizioni di reazione
1.1 Reagents: Ammonium formate Catalysts: Palladium Solvents: Methanol ;  5 min, reflux
Riferimento
An efficient reduction of quinones by formate-palladium/carbon system
Pande, Poorn Prakash, Asian Journal of Chemistry, 2010, 22(4), 2549-2553

Circuito sintetico 10

Condizioni di reazione
1.1 Reagents: Triethylamine ,  Ethyl chloroformate Solvents: Tetrahydrofuran ;  0 °C; 3 h, 0 °C
1.2 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ,  Water ;  0 °C; 3 h, rt; 0 °C → rt; 1 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  neutralized, rt
Riferimento
An easy two-step reduction of salicylic acids and alcohols to 2-methylphenols
Mazzini, Francesco; Salvadori, Piero, Synthesis, 2005, (15), 2479-2481

Circuito sintetico 11

Condizioni di reazione
1.1 Reagents: Sulfuric acid Solvents: Water
Riferimento
Synthesis of methylhydroquinone
Zhang, Li-yang; Jiang, Deng-gao; Zhou, Cai-rong; Liu, Qi-yu; Jiang, Xue-gen, Jingxi Huagong, 2000, 17(12), 735-737

Circuito sintetico 12

Condizioni di reazione
1.1 Reagents: Sulfuric acid ,  Hydrogen peroxide Solvents: Water ;  6 h, rt
1.2 Reagents: Sodium carbonate Solvents: Water ;  neutralized, rt
Riferimento
Selective electro-oxidation of phenol to 1,4-hydroquinone employing carbonaceous electrodes: surface modification is the key
Baravkar, Mayur D.; Prasad, Bhagavatula L. V., New Journal of Chemistry, 2022, 46(5), 2518-2525

Circuito sintetico 13

Condizioni di reazione
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl acetate
Riferimento
Synthesis of (±)-6-hydroxy-3,4-dihydro-4,7-dimethylbenzo-1-pyran-2(H)-one, a tetranorsesquiterpenoid
Nadkarni, K. K.; Kamat, S. P.; Paknikar, S. K., Indian Journal of Chemistry, 1994, (5), 432-5

Circuito sintetico 14

Condizioni di reazione
1.1 Reagents: Chlorotrimethylsilane ,  1,1,3,3-Tetramethyldisiloxane ,  Sodium iodide Solvents: Dichloromethane
Riferimento
Ionic and organometallic-catalyzed organosilane reductions
Larson, Gerald L.; Fry, James L., Organic Reactions (Hoboken, 2008, 71, 1-737

Circuito sintetico 15

Condizioni di reazione
1.1 Reagents: Chlorotrimethylsilane ,  1,1,3,3-Tetramethyldisiloxane ,  Sodium iodide Solvents: Acetonitrile ,  Dichloromethane
Riferimento
Reagents and synthetic methods. 57. Reduction of carbonyl compounds promoted by silicon hydrides under the influence of trimethylsilyl-based reagents
Aizpurua, Jesus M.; Lecea, Begona; Palomo, Claudio, Canadian Journal of Chemistry, 1986, 64(12), 2342-7

Circuito sintetico 16

Condizioni di reazione
1.1 Reagents: Sodium azide Solvents: Acetone ,  Water ;  5 - 12 h, rt
Riferimento
Simple, mild, and efficient method for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3
Algi, Fatih; Balci, Metin, Synthetic Communications, 2006, 36(16), 2293-2297

Circuito sintetico 17

Condizioni di reazione
1.1 Reagents: Sodium hydroxide ,  Sodium persulfate Solvents: Water
Riferimento
Supported metalated phthalocyanine as catalyst for oxidation by molecular oxygen. Synthesis of quinones and carbonyl compounds
Villemin, Didier; Hammadi, Mohamed; Hachemi, Messaoud, Synthetic Communications, 2002, 32(10), 1501-1515

Circuito sintetico 18

Condizioni di reazione
1.1 Reagents: Hydrogen peroxide Catalysts: Benzyltriethylammonium chloride ,  Titanium superoxide (Ti(O2)2) Solvents: Water ;  rt → 60 °C; 50 - 60 °C; 1 h, 50 - 60 °C; 60 °C → rt
1.2 Reagents: Hydrogen Catalysts: Nickel ;  > 10 h, 0.6 MPa, 100 °C; 5 min, reflux
Riferimento
Method for preparation of 2-methylhydroquinone
, China, , ,

Circuito sintetico 19

Condizioni di reazione
1.1 Reagents: Sodium dodecyl sulfate ,  Ceric ammonium nitrate Solvents: Acetic acid ,  Water
1.2 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water
Riferimento
Hydroxylation of alkylphenols by cerium(IV) in conjunction with hydrogen peroxide and sodium dodecyl sulfate
Chawla, H. Mohindra; Sharma, S. Kumar; Chakrabarty, K.; Bhanumati, S., Journal of the Chemical Society, 1988, (2), 128-9

Circuito sintetico 20

Condizioni di reazione
1.1 Reagents: Butyllithium ,  N,N,N′,N′-Tetramethylethylenediamine
Riferimento
The generation of C,O,O-trilithiated derivatives of dihydric phenols
Saa, Jose M.; Morey, Jeroni; Suner, Guillem; Frontera, Antoni; Costa, Antoni, Tetrahedron Letters, 1991, 32(49), 7313-16
Letteratura correlata
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