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616-55-7 Usage

General Description

4,6-Di-tert-butyl-2-methylphenol is a synthetic chemical compound known for its antioxidant properties. It falls under the class of organic compounds known as methoxyphenols, which are phenols substituted with a methoxy group. It is most commonly used in industrial products and processes due to its ability to prevent or slow down the process of oxidation. This makes it useful in the manufacturing of rubber and plastic products, as it can extend their life by protecting them against deterioration caused by heat, light, and oxygen exposure. The compound is generally stable but may cause irritation on contact with the skin or eyes and can be harmful if ingested or inhaled.

Check Digit Verification of cas no

The CAS Registry Mumber 616-55-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 6 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 616-55:
(5*6)+(4*1)+(3*6)+(2*5)+(1*5)=67
67 % 10 = 7
So 616-55-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H24O/c1-10-8-11(14(2,3)4)9-12(13(10)16)15(5,6)7/h8-9,16H,1-7H3

616-55-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,4-ditert-butyl-6-methylphenol

1.2 Other means of identification

Product number -
Other names 4,6-DI-TERT-BUTYL-2-METHYLPHENOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:616-55-7 SDS

616-55-7Synthetic route

2,4-di-tert-butyl-6-hydroxymethylphenol
16373-02-7

2,4-di-tert-butyl-6-hydroxymethylphenol

A

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

B

6,6'-(ethane-1,2-diyl)bis(2,4-di-tert-butylphenol)
37758-52-4

6,6'-(ethane-1,2-diyl)bis(2,4-di-tert-butylphenol)

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene for 4h; Heating;A 68%
B 16%
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene for 4h; Heating;A 10%
B 66%
ortho-cresol
95-48-7

ortho-cresol

tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

2-Methyl-4-t-butylphenol
98-27-1

2-Methyl-4-t-butylphenol

B

2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

C

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
With carbon tetrabromide at 175℃; for 6h; Sealed tube;A 68%
B 3%
C 27%
With carbon tetrabromide at 175℃; for 6h; Sealed tube;A 39%
B 8%
C 51%
2,4-di-tert-butyl-6-methylaniline hydrochloride
108715-85-1

2,4-di-tert-butyl-6-methylaniline hydrochloride

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite
tertiary butyl chloride
507-20-0

tertiary butyl chloride

ortho-cresol
95-48-7

ortho-cresol

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
With aluminium trichloride at 105℃;
ortho-cresol
95-48-7

ortho-cresol

isobutene
115-11-7

isobutene

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
With sulfuric acid
With sulfuric acid In benzene
ortho-cresol
95-48-7

ortho-cresol

tert-butyl alcohol
75-65-0

tert-butyl alcohol

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
With sulfuric acid
t-butyl bromide
507-19-7

t-butyl bromide

6-acetoxy-2-tert-butyl-6-methyl-cyclohexa-2,4-dienone
51067-62-0

6-acetoxy-2-tert-butyl-6-methyl-cyclohexa-2,4-dienone

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
In diethyl ether
ortho-cresol
95-48-7

ortho-cresol

isobutene
115-11-7

isobutene

A

2-Methyl-4-t-butylphenol
98-27-1

2-Methyl-4-t-butylphenol

B

2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

C

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
With aluminium(III) phenoxide at 100℃; for 2h;
2-Methyl-4-t-butylphenol
98-27-1

2-Methyl-4-t-butylphenol

2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

A

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

B

ortho-cresol
95-48-7

ortho-cresol

Conditions
ConditionsYield
In neat (no solvent) at 79.9 - 179.9℃; Equilibrium constant; effect of temperature;
2,6-di-tert-butyl-4-methyl-phenol
128-37-0

2,6-di-tert-butyl-4-methyl-phenol

ortho-cresol
95-48-7

ortho-cresol

A

p-cresol
106-44-5

p-cresol

B

2-tert-Butyl-4-methylphenol
2409-55-4

2-tert-Butyl-4-methylphenol

C

2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

D

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
sulfuric acid at 80℃; for 8h; Yield given. Further byproducts given. Yields of byproduct given;
2,6-di-tert-butyl-4-methyl-phenol
128-37-0

2,6-di-tert-butyl-4-methyl-phenol

ortho-cresol
95-48-7

ortho-cresol

A

2-Methyl-4-t-butylphenol
98-27-1

2-Methyl-4-t-butylphenol

B

2-tert-Butyl-4-methylphenol
2409-55-4

2-tert-Butyl-4-methylphenol

C

2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

D

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
sulfuric acid at 80℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given;
sulfuric acid at 80℃; for 2h; Yield given. Further byproducts given. Yields of byproduct given;
aluminium trichloride
7446-70-0

aluminium trichloride

tertiary butyl chloride
507-20-0

tertiary butyl chloride

ortho-cresol
95-48-7

ortho-cresol

A

2-Methyl-4-t-butylphenol
98-27-1

2-Methyl-4-t-butylphenol

B

2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

C

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
at 105℃;
sulfuric acid
7664-93-9

sulfuric acid

ortho-cresol
95-48-7

ortho-cresol

isobutene
115-11-7

isobutene

A

2-Methyl-4-t-butylphenol
98-27-1

2-Methyl-4-t-butylphenol

B

2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

C

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

pentacarbonyl(methoxymethylcarbene)molybdemum

pentacarbonyl(methoxymethylcarbene)molybdemum

A

(3E)-5,5-dimethylhex-3-en-2-one
20859-11-4

(3E)-5,5-dimethylhex-3-en-2-one

B

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
In hexane at 70 - 80℃; Yield given. Yields of byproduct given;
2-tert-Butyl-6-methylphenol
2219-82-1

2-tert-Butyl-6-methylphenol

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CHCl3
2: diethyl ether
View Scheme
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2-bromo-1,5-di-tert-butyl-3-methyl-benzene
16358-71-7

2-bromo-1,5-di-tert-butyl-3-methyl-benzene

Conditions
ConditionsYield
With trimethyl phosphite; bromine at 60 - 65℃; for 11h;95%
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,6-Naphthalenedicarboxylic acid
1141-38-4

2,6-Naphthalenedicarboxylic acid

C42H52O4

C42H52O4

Conditions
ConditionsYield
With titanium(IV) isopropylate at 80℃; for 6h;84.4%
furan
110-00-9

furan

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,4-di-tert-butyl-6-(2-furyl)-6-methylcyclohexa-2,4-dien-1-one
1127942-82-8

2,4-di-tert-butyl-6-(2-furyl)-6-methylcyclohexa-2,4-dien-1-one

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In 1,1,1,3',3',3'-hexafluoro-propanol at 0℃; for 0.0388889h; oxidative Friedel Crafts reaction; regioselective reaction;72%
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

methoxybenzene
100-66-3

methoxybenzene

4,6-di-tert-butyl-4'-methoxy-2-methylbiphenyl-3-ol
1127943-03-6

4,6-di-tert-butyl-4'-methoxy-2-methylbiphenyl-3-ol

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In 1,1,1,3',3',3'-hexafluoro-propanol at 0℃; for 0.0388889h; oxidative Friedel Crafts reaction;67%
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

(1R*,2S*,6R*)‐4,6‐di‐tert‐butyl‐2‐hydroxy‐2‐methyl‐7‐oxabicyclo[4.1.0]hept‐4‐en‐3‐one

(1R*,2S*,6R*)‐4,6‐di‐tert‐butyl‐2‐hydroxy‐2‐methyl‐7‐oxabicyclo[4.1.0]hept‐4‐en‐3‐one

Conditions
ConditionsYield
With Oxone; sodium hydrogencarbonate In water; acetone at 20℃; for 1h;67%
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

5,7-di-t-butyl-1-oxaspiro<2.5>octa-5,7-dien-4-one
39117-89-0

5,7-di-t-butyl-1-oxaspiro<2.5>octa-5,7-dien-4-one

Conditions
ConditionsYield
With sodium hypochlorite pentahydrate; tetra-(n-butyl)ammonium iodide In ethyl acetate at 25℃; for 0.5h; Green chemistry; chemoselective reaction;63%
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

A

3,5-di-tert-butyl-2-hydroxybenzaldehyde
37942-07-7

3,5-di-tert-butyl-2-hydroxybenzaldehyde

B

3,5-di-tert-butyl-2-hydroxybenzyl bromide
194734-57-1

3,5-di-tert-butyl-2-hydroxybenzyl bromide

Conditions
ConditionsYield
With N-Bromosuccinimide In dimethyl sulfoxide at 120℃; Oxidation;A 54%
B n/a
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

C18H28O
1131688-01-1

C18H28O

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol; [bis(acetoxy)iodo]benzene at 20℃; for 0.25h; Hosomi-Sakurai reaction;42%
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,4-di-t-butyl-6-methyl-4-nitrocyclohexa-2,5-dienone
92727-16-7

2,4-di-t-butyl-6-methyl-4-nitrocyclohexa-2,5-dienone

Conditions
ConditionsYield
With nitric acid In acetic acid at 5℃;40%
With nitric acid In acetic acid577 mg
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

A

2,4-di-tert-butyl-6-tert-butylperoxy-6-methyl-cyclohexa-2,4-dienone
64756-81-6

2,4-di-tert-butyl-6-tert-butylperoxy-6-methyl-cyclohexa-2,4-dienone

B

2,4-di-tert-butyl-4-tert-butylperoxy-6-methyl-cyclohexa-2,5-dienone

2,4-di-tert-butyl-4-tert-butylperoxy-6-methyl-cyclohexa-2,5-dienone

Conditions
ConditionsYield
With cobalt naphthenate; benzene
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,4-di-tert-butyl-6-methyl-cyclohexanone
35606-11-2

2,4-di-tert-butyl-6-methyl-cyclohexanone

Conditions
ConditionsYield
With nickel at 160 - 180℃; under 110326 Torr; Hydrogenation;
(i) H2, Raney-Ni, (ii) Na2Cr2O7; Multistep reaction;
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

Opt.-inakt. 2-Hydroxy-1-methyl-3.5-di-tert.-butyl-cyclohexan

Opt.-inakt. 2-Hydroxy-1-methyl-3.5-di-tert.-butyl-cyclohexan

Conditions
ConditionsYield
With nickel at 185 - 220℃; under 110326 - 117681 Torr; Hydrogenation;
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

benzoic acid-(2,4-di-tert-butyl-6-methyl-phenyl ester)

benzoic acid-(2,4-di-tert-butyl-6-methyl-phenyl ester)

2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

6,8,3',5'-tetra-tert-butyl-spiro[chroman-2,1'-cyclohexa-3',5'-dien]-2'-one
107423-28-9

6,8,3',5'-tetra-tert-butyl-spiro[chroman-2,1'-cyclohexa-3',5'-dien]-2'-one

Conditions
ConditionsYield
With silver(l) oxide; benzene
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

phenyl isocyanate
103-71-9

phenyl isocyanate

phenyl-carbamic acid-(2,4-di-tert-butyl-6-methyl-phenyl ester)
66018-94-8

phenyl-carbamic acid-(2,4-di-tert-butyl-6-methyl-phenyl ester)

Conditions
ConditionsYield
With Petroleum ether
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

allyl bromide
106-95-6

allyl bromide

allyl-(2,4-di-tert-butyl-6-methyl-phenyl)-ether

allyl-(2,4-di-tert-butyl-6-methyl-phenyl)-ether

Conditions
ConditionsYield
With ethanol; sodium methylate
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2-chloro-ethanol
107-07-3

2-chloro-ethanol

2-(2,4-di-tert-butyl-6-methyl-phenoxy)-ethanol

2-(2,4-di-tert-butyl-6-methyl-phenoxy)-ethanol

Conditions
ConditionsYield
With sodium hydroxide at 80 - 85℃;
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,4-Di-tert-butyl-4,5,6-trihydroxy-6-methyl-cyclohex-2-enone

2,4-Di-tert-butyl-4,5,6-trihydroxy-6-methyl-cyclohex-2-enone

Conditions
ConditionsYield
With potassium tert-butylate; oxygen
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

(15N)-2,4-di-t-butyl-6-methyl-4-nitrocyclohexa-2,5-dienone
125259-57-6

(15N)-2,4-di-t-butyl-6-methyl-4-nitrocyclohexa-2,5-dienone

Conditions
ConditionsYield
With [15N]-nitric acid In acetic acid at 5℃; Yield given;
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,4-di-t-butyl-c-6-hydroxy-6-methyl-r-2,c-5-dinitrocyclohex-3-enone
96540-08-8, 125354-57-6

2,4-di-t-butyl-c-6-hydroxy-6-methyl-r-2,c-5-dinitrocyclohex-3-enone

2,4-di-t-butyl-r-2-hydroxy-6-methyl-t-5,c-6-dinitrocyclohex-3-enone
96540-06-6, 96540-07-7, 125354-58-7

2,4-di-t-butyl-r-2-hydroxy-6-methyl-t-5,c-6-dinitrocyclohex-3-enone

2,4-di-t-butyl-6-methyl-r-2,c-5,t-6-trinitrocyclohex-3-enone
96540-02-2, 96540-03-3, 96540-04-4, 96540-05-5, 125211-89-4

2,4-di-t-butyl-6-methyl-r-2,c-5,t-6-trinitrocyclohex-3-enone

2,4-di-t-butyl-6-methyl-r-2,t-5,c-6-trinitrocyclohex-3-enone
96540-02-2, 96540-03-3, 96540-04-4, 96540-05-5, 125211-89-4

2,4-di-t-butyl-6-methyl-r-2,t-5,c-6-trinitrocyclohex-3-enone

Conditions
ConditionsYield
With Nitrogen dioxide In benzene at 20℃; for 5h; Yield given. Further byproducts given. Yields of byproduct given;
2,4-di-tert-butyl-6-methylphenol
616-55-7

2,4-di-tert-butyl-6-methylphenol

2,4-di-t-butyl-r-2-hydroxy-6-methyl-t-5,c-6-dinitrocyclohex-3-enone
96540-06-6, 96540-07-7, 125354-58-7

2,4-di-t-butyl-r-2-hydroxy-6-methyl-t-5,c-6-dinitrocyclohex-3-enone

2,4-di-t-butyl-r-2-hydroxy-6-methyl-t-5,t-6-dinitrocyclohex-3-enone
96540-06-6, 96540-07-7, 125354-58-7

2,4-di-t-butyl-r-2-hydroxy-6-methyl-t-5,t-6-dinitrocyclohex-3-enone

2,4-di-t-butyl-6-methyl-r-2,c-5,t-6-trinitrocyclohex-3-enone
96540-02-2, 96540-03-3, 96540-04-4, 96540-05-5, 125211-89-4

2,4-di-t-butyl-6-methyl-r-2,c-5,t-6-trinitrocyclohex-3-enone

2,4-di-t-butyl-6-methyl-r-2,t-5,c-6-trinitrocyclohex-3-enone
96540-02-2, 96540-03-3, 96540-04-4, 96540-05-5, 125211-89-4

2,4-di-t-butyl-6-methyl-r-2,t-5,c-6-trinitrocyclohex-3-enone

Conditions
ConditionsYield
With Nitrogen dioxide In benzene at 20℃; for 5h; Yield given. Further byproducts given. Yields of byproduct given;

616-55-7Relevant articles and documents

Alkylation of Phenols with tert-Butanol Catalyzed by H-Form of Y Zeolites with a Hierarchical Porous Structure

Bayguzina,Makhiyanova,Khazipova,Khusnutdinov

, p. 1554 - 1559 (2019/10/14)

tert-Butyl-substituted phenols have been synthesized via the reaction of phenol, o-, m-, and p-cresols with tert-butanol under the action of CBr4-promoted Y-zeolites in the H-form with a hierarchical porous structure.

Cyclopentenone formation via hydrogen activation in the reactions of chromium carbene complexes with alkynes

Challener, Cynthia A.,Wulff, William D.,Anderson, Benjamin A.,Chamberlin, Steve,Faron, Katherine L.,Kim, Oak K.,Murray, Christopher K.,Xu, Yao-Chang,Yang, Dominic C.,Darling, Stephen D.

, p. 1359 - 1376 (2007/10/02)

The reactions of alkyl chromium carbene complexes with alkynes have been found to give cyclopentenones. Mechanisms are proposed to account for the formation of these products that involve metal hydride intermediates. As has been previously reported for tungsten, molybdenum alkyl complexes have been found to give 1,3-dienes rather than cyclopentenones. The difference between chromium and molybdenum and tungsten may be that a metal hydride intermediate can re-add to an olefin in the case of chromium rather than undergo reductive elimination. A mechanism for the formation of cyclopentenones involving a free vinylketene was ruled out on the basis of an experiment in which the free vinylketene was generated via thermolysis of a cyclobutenone and found not to give a cyclopentenone product but rather an intramolecular [2 + 2] cycloadduct.

Trans-substitution and equilibration of phenols. Part IV. The influence of various catalysts on the trans-tert-butylation reaction of phenols; mechanistic aspects

Willemse, F. R. J.,Kooyman, E. C.,Lamoen, H. B. van,Vos, D. de,Wolters, J.

, p. 206 - 209 (2007/10/02)

The trans-tert-butylation reaction by 2,6-di-tert-butyl-4-methylphenol has been studied for a number of phenols in the presence of different catalysts.Equilibria, as well as reaction kinetics, have been investigated.The mechanism involves the intermediacy of a tert-butyl ether.This mechanism is supported both by the kinetics and the initially high ortho/para ratio as well as by the reversed substituent effect.

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