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2,2'-Methylenebis(6-tert-butyl-4-methylphenol)
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Name

2,2'-Methylenebis(6-tert-butyl-4-methylphenol)

 EINECS 204-327-1
CAS No. 119-47-1 Density 1.026 g/cm3
PSA 40.46000 LogP 5.90040
Solubility 7μg/L at 20℃ Melting Point 123-127 °C(lit.)
Formula C23H32O2 Boiling Point 428.6 °C at 760 mmHg
Molecular Weight 340.506 Flash Point 181.2 °C
Transport Information N/A Appearance white to pale creamy crystalline powder
Safety 26-36 Risk Codes 36
Molecular Structure Molecular Structure of 119-47-1 (2,2'-Methylenebis(6-tert-butyl-4-methylphenol)) Hazard Symbols IrritantXi
Synonyms

p-Cresol,2,2'-methylenebis[6-tert-butyl- (8CI);2,2'-Bis(4-methyl-6-tert-butylphenol)methane;2,2'-Methylenebis[4-methyl-6-t-butylphenol];2,2'-Methylenebis[4-methyl-6-tert-butylphenol];2,2'-Methylenebis[6-(1,1-dimethylethyl)-4-methyl)phenol;2,2'-Methylenebis[6-tert-butyl-p-cresol];Advastab 405;Agidol 2;Antage W 400;Anti Ox;Antioxidant 1;Antioxidant 2246;Antioxidant BKF;Antioxidant NG 2246;Antioxidant OMB;BKF;Baynox Plus;Bisalkofen BP;CAO 14;CAO5;Calco 2246;Catolin 14;Chemanox 21;Cyanox 2246;Lowinox 22M48;MBP 5;MDP;NG 2246;NS 6;NSC 7781;Naftonox 22M46;Noclizer NS 6;Nocrac NS 6;Nonflex MBP;Nonflex MPP;Ongrostab 2246;Plastanox 2246;Product 2246;

Article Data 64

2,2'-Methylenebis(6-tert-butyl-4-methylphenol) Synthetic route

50-00-0

formaldehyd

106-44-5

p-cresol

1634-04-4

tert-butyl methyl ether

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

Conditions
ConditionsYield
With sulfonated multi-walled carbon nanotubes In neat (no solvent) at 100℃; for 2.5h; Catalytic behavior; regiospecific reaction;100%
109-87-5

Dimethoxymethane

2409-55-4

2-tert-Butyl-4-methylphenol

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

Conditions
ConditionsYield
With acid clay at 170℃; for 2h; Reagent/catalyst; Temperature;97%
With sulfuric acid at 60 - 70℃; for 2h;70%
With cation exchanger KU-2; sulfuric acid at 100℃; for 3h; Kinetics; Mechanism; Rate constant; other time, other temperature;
50-00-0

formaldehyd

2409-55-4

2-tert-Butyl-4-methylphenol

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

Conditions
ConditionsYield
With sodium tetramethoxyborate In dimethyl sulfoxide at 150℃; for 0.5h; Reagent/catalyst; Temperature; Solvent;95%
In xylene at 175℃; for 10h;85%
With montmorillonite KSF In octane for 2h; Reflux;79%
50-00-0

formaldehyd

96-76-4

2,4-di-tert-Butylphenol

A

14362-12-0

2,2'-methylenebis(4,6-di-tert-butylphenol)

B

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

Conditions
ConditionsYield
With montmorillonite KSF In n-heptane for 2h; Reflux;A 85%
B 77%
50-00-0

formaldehyd

2409-55-4

2-tert-Butyl-4-methylphenol

A

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

B

8-tert-butyl-6-methyl-4H-benzo[1,3]dioxine

Conditions
ConditionsYield
In toluene at 100℃; for 1h; Condensation; acetalisation;A 35%
B 48%
109-87-5

Dimethoxymethane

2409-55-4

2-tert-Butyl-4-methylphenol

A

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

B

4103-77-9

2-(tert-butyl)-6-(methoxymethyl)-4-methylphenol

Conditions
ConditionsYield
With ion-exchange resin at 100℃; Product distribution;
462-95-3

formaldehyde diethyl acetal

2409-55-4

2-tert-Butyl-4-methylphenol

A

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

B

2-ethoxymethyl-4-methyl-6-tert-butylphenol

Conditions
ConditionsYield
With ion-exchange resin at 100℃; Product distribution;
2409-55-4

2-tert-Butyl-4-methylphenol

4103-77-9

2-(tert-butyl)-6-(methoxymethyl)-4-methylphenol

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

Conditions
ConditionsYield
With cation exchanger KU-2; sulfuric acid at 100℃; for 3h; Kinetics; Mechanism; Rate constant; other time, other temperature;
106-44-5

p-cresol

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / 60 °C
2: aq.-ethanolic HCl
View Scheme
109-87-5

Dimethoxymethane

2409-55-4

2-tert-Butyl-4-methylphenol

7664-93-9

sulfuric acid

119-47-1

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane

2,2'-Methylenebis(6-tert-butyl-4-methylphenol) Consensus Reports

Reported in EPA TSCA Inventory.

2,2'-Methylenebis(6-tert-butyl-4-methylphenol) Specification

The CAS register number of 2,2'-Methylenebis(6-tert-butyl-4-methylphenol) is 119-47-1. It also can be called as 6,6'-Di-tert-butyl-2,2'-methylenedi-p-cresol and the IUPAC name about this chemical is 2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol. The molecular formula about this chemical is C23H32O2 and the molecular weight is 340.50. It belongs to the following product categories, such as Industrial/Fine Chemicals; Organics; Diphenylmethanes (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research; Polymer Additives; Polymer Science; Stabilizers and so on. This chemical can be used in styrenic and olefin polymers and polyoxymethylene homo and copolymers.

Physical properties about 2,2'-Methylenebis(6-tert-butyl-4-methylphenol) are: (1)ACD/LogP: 7.03; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.03; (4)ACD/LogD (pH 7.4): 7.03; (5)ACD/BCF (pH 5.5): 129927.87; (6)ACD/BCF (pH 7.4): 129912.6; (7)ACD/KOC (pH 5.5): 159208.34; (8)ACD/KOC (pH 7.4): 159189.64; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 18.46Å2; (13)Index of Refraction: 1.55; (14)Molar Refractivity: 105.75 cm3; (15)Molar Volume: 331.6 cm3; (16)Polarizability: 41.92x10-24cm3; (17)Surface Tension: 37.3 dyne/cm; (18)Enthalpy of Vaporization: 71.02 kJ/mol; (19)Boiling Point: 428.6 °C at 760 mmHg; (20)Vapour Pressure: 6E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by formaldehyde and 2-tert-butyl-4-methyl-phenol. This reaction will need reagent KOH.

Uses of 2,2'-Methylenebis(6-tert-butyl-4-methylphenol): it can be used to produce 2-(2-Hydroxy-5-methylbenzyl)-6-tert-butyl-4-methylphenol at temperature of 25 ℃. This reaction will need reagent AlCl3 and solvent toluene with reaction time of 2 hours. The yield is about 60%.

Antioxidant 264 can be produced by the reaction of P-cresol with Isobutylene, and this chemical can be used to produce the intermediate product of 2 - tert-Butyl -4-- cresol, this intermediate product can react with Formaldehyde to produce 2,2'-Methylenebis(6-tert-butyl-4-methylphenol).

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes. When you are using it, wear suitable protective clothing. 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)SMILES: Oc1c(cc(cc1C(C)(C)C)C)Cc2cc(cc(c2O)C(C)(C)C)C
(2)InChI: InChI=1/C23H32O2/c1-14-9-16(20(24)18(11-14)22(3,4)5)13-17-10-15(2)12-19(21(17)25)23(6,7)8/h9-12,24-25H,13H2,1-8H3
(3)InChIKey: KGRVJHAUYBGFFP-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C23H32O2/c1-14-9-16(20(24)18(11-14)22(3,4)5)13-17-10-15(2)12-19(21(17)25)23(6,7)8/h9-12,24-25H,13H2,1-8H3
(5)Std. InChIKey: KGRVJHAUYBGFFP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 11gm/kg (11000mg/kg)   Journal of Toxicological Sciences. Vol. 19, Pg. 77, 1994.
rat LDLo oral 10gm/kg (10000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(8), Pg. 28, 1973.

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