7340-90-1

Basic information

• Product Name: 5-TERT-BUTYL-2-METHYLTHIOPHENOL
• Synonyms: 2-METHYL-5-(1,1-DIMETHYLETHYL)THIOPHENOL;2-METHYL-5-TERT-BUTYLTHIOPHENOL;5-(1,1-DIMETHYLETHYL)-2-METHYLTHIOPHENOL;4-TERT-BUTYL-2-MERCAPTOTOLUENE;4-TERT-BUTYL-2-METHYLTHIOPHENOL;5-TERT-BUTYL-O-THIOCRESOL;5-TERT-BUTYL-2-METHYLTHIOPHENOL;5-TERT-BUTYL-2-METHYLBENZENETHIOL
• CAS NO: 7340-90-1
• Molecular Formula: C₁₁H₁₆S
• Molecular Weight: 180.31
• EINECS: 444-970-7
• Mol File: 7340-90-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: -10 °C
• Boiling Point: 260 °C
• Flash Point: 116°C
• Appearance: Clear colorless/Liquid
• Density: 0.98
• Vapor Pressure: 0.0387mmHg at 25°C
• Refractive Index: 1.5470
• PKA: 6.93±0.48(Predicted)
• Sensitive: Air Sensitive
• BRN: 7473482
• CAS DataBase Reference: 5-TERT-BUTYL-2-METHYLTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-TERT-BUTYL-2-METHYLTHIOPHENOL(7340-90-1)
• EPA Substance Registry System: 5-TERT-BUTYL-2-METHYLTHIOPHENOL(7340-90-1)

Safety Data

• Statements: 36/38-51/53
• Safety Statements: 26-37/39-61
• RIDADR: 3082
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 7340-90-1(Hazardous Substances Data)

Usage

Description

5-TERT-BUTYL-2-METHYLTHIOPHENOL is an organic compound characterized by its clear, colorless liquid appearance. It is known for its unique chemical properties that make it suitable for various applications across different industries.

Uses

Used in Chemical Synthesis:
5-TERT-BUTYL-2-METHYLTHIOPHENOL is used as a synthetic compound for the production of biotinylated tetra β(1→5) galactofuranoside. 5-TERT-BUTYL-2-METHYLTHIOPHENOL plays a crucial role in the in vitro diagnosis of aspergillosis, a fungal infection caused by Aspergillus species.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-TERT-BUTYL-2-METHYLTHIOPHENOL is utilized as an intermediate or building block for the development of new drugs. Its unique chemical structure allows for the creation of novel therapeutic agents that can target specific medical conditions.
Used in Research and Development:
5-TERT-BUTYL-2-METHYLTHIOPHENOL is also employed in research and development laboratories for the study of its chemical properties and potential applications. This includes exploring its reactivity, stability, and compatibility with other compounds to develop new materials or improve existing ones.
Used in Material Science:
In the field of material science, 5-TERT-BUTYL-2-METHYLTHIOPHENOL may be used as an additive or component in the development of new materials with specific properties. Its clear, colorless liquid form and unique chemical characteristics can contribute to the creation of materials with enhanced performance in various applications.
Used in Environmental Applications:
5-TERT-BUTYL-2-METHYLTHIOPHENOL could potentially be used in environmental applications, such as the treatment of contaminated water or soil. Its chemical properties may allow it to interact with pollutants or contaminants, facilitating their removal or neutralization.

InChI:InChI=1/C11H16S/c1-8-5-6-9(7-10(8)12)11(2,3)4/h5-7,12H,1-4H3/p-1

Synthetic route

1,2-bis(5-(tert-butyl)-2-methylphenyl)disulfane (34493-12-4) → 2-methyl-5-tert-butylthiophenol (7340-90-1)

Conditions	Yield
With sodium tetrahydroborate

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6, 31505-44-9, 81704-02-1, 116347-84-3, 131234-07-6, 144300-04-9, 79733-86-1) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-α-D-glucopyranoside (1011529-31-9)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane	98%

1,2,3,5,6-penta-O-benzoyl-D-galactofuranose (138811-45-7) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside (1269500-75-5)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	97%

2-chloropyridine (109-09-1) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → 2-(2-methyl-5-tert-butylphenylthio)pyridine

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating;	95%

2-methyl-5-tert-butylthiophenol (7340-90-1) + β-D-glucose pentaacetate (604-69-3) → (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-S-β-D-thioglucopyranoside (1334540-33-8)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane Inert atmosphere;	94%
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	92%
With boron trifluoride diethyl etherate In dichloromethane	85%

2-methyl-5-tert-butylthiophenol (7340-90-1) + ((2R,3S,4S,5R,6S)-6-(((1S,2S,3R,4S,6R)-4,6-bis((tert-butoxycarbonyl)amino)-3-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2Hpyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl 2,4,6-triisopropylbenzenesulfonate (220612-64-6) → C54H91N5O18S (1392113-84-6)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	94%

1,3,4,6-tetra-O-acetyl-2-(trifluoroacetamido)-2-deoxy-β-D-glucopyranoside (7139-63-1) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → 5-tert-butyl-2-methylphenyl 3,4,6-tri-O-acetyl-2-(trifluoroacetamido)-2-deoxy-1-thio-β-D-glucopyranoside (866823-12-3)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; Inert atmosphere;	93%

2-methyl-5-tert-butylthiophenol (7340-90-1) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside (1379519-57-9)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -78 - 20℃; Inert atmosphere;	93%

2-methyl-5-tert-butylthiophenol (7340-90-1) + β-D-galactose peracetate (4163-60-4) → (2-methyl-5-tert-butylphenyl) 1-thio-β-D-galactopyranoside

Conditions	Yield
Stage #1: 2-methyl-5-tert-butylthiophenol; β-D-galactose peracetate With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 1h; Stage #2: With sodium methylate In methanol for 0.5h;	93%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-α-D-glucopyranoside (1011529-31-9)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 8h; Inert atmosphere;	92%

C23H33NO14 + 2-methyl-5-tert-butylthiophenol (7340-90-1) → C32H45NO12S

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 3h; Inert atmosphere;	91%

2-methyl-5-tert-butylthiophenol (7340-90-1) → 5-(tert-butyl)-2-methylbenzenesulfonamide (7155-00-2)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 24h; Inert atmosphere; chemoselective reaction;	90%

C28H34Cl3F3N2O17 + 2-methyl-5-tert-butylthiophenol (7340-90-1) → C37H48F3NO16S

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -20 - -5℃; for 1.5h; Molecular sieve;	89.5%

2-methyl-5-tert-butylthiophenol (7340-90-1) → 1,2-bis(5-(tert-butyl)-2-methylphenyl)disulfane (34493-12-4)

Conditions	Yield
With (bis(2,1-phenylene)bis(azanediyl)bis(methylene)diphenol)diselenide In acetonitrile at 20℃; for 7h;	89%
With phosphoric acid; oxygen; methyl 2-N-salicylidene-3-hydroxypropanoate; manganese(ll) chloride In acetone at 20℃; under 760.051 Torr;

3-O-benzyl-1,2,4,6-tetra-O-acetyl-D-glucopyranose (39686-94-7, 56632-47-4, 65827-58-9, 99202-62-7, 99202-66-1, 103082-79-7, 103703-00-0, 103703-01-1, 118711-49-2, 127853-23-0, 139563-66-9) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranose

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	89%
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	89%

2-methyl-5-tert-butylthiophenol (7340-90-1) → 2-Methyl-5-t-butylbenzolsulfosaeure (25589-81-5)

Conditions	Yield
With sodium molybdate; dihydrogen peroxide; sodium dodecyl-sulfate In dichloromethane; water; butan-1-ol at 25℃; for 2h;	88%

C68H69Cl3N4O33 + 2-methyl-5-tert-butylthiophenol (7340-90-1) → C77H83N3O32S (945263-06-9)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -10℃;	86%

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (7404-35-5, 17081-04-8, 20853-37-6, 24332-95-4, 27821-10-9, 27821-11-0, 33947-15-8, 34371-40-9, 34371-41-0, 35521-79-0, 36807-81-5, 36807-82-6, 50615-78-6, 51921-33-6, 62182-03-0, 64913-16-2, 70004-81-8, 84622-47-9, 87303-56-8, 108942-32-1, 108942-33-2, 109430-94-6, 143394-72-3, 30021-94-4) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → 2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (1185741-87-0)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; Inert atmosphere;	86%

2-Fluorobenzaldehyde (446-52-6) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → C18H20OS

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 3h;	84%

Ethyl <2,4,5,7,8-penta-O-acetyl-3-deoxy-β-D-manno-octulopyranosid>onate (150885-36-2) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → ethyl (5-tert-butyl-2-methylbenzenethio 4,5,7,8-tetra-O-acetyl-3-deoxy-D-manno-oct-2-ulopyranoside)onate

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere;	83%

ethyl iodide (75-03-6) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → 1-methyl-2-ethylsulfonyl-4-(1,1-dimethylethyl)benzene

Conditions	Yield
Stage #1: 2-methyl-5-tert-butylthiophenol With methyllithium; N-(benzenesulfonyl)-3-phenyloxaziridine In tetrahydrofuran; N,N-dimethyl-formamide Stage #2: ethyl iodide In tetrahydrofuran; N,N-dimethyl-formamide Further stages.;	80%

3,4,6-tri-O-acetyl-1,2-dideoxy-2-iodo-1-[2-(trimethylsilyl)ethanesulfonamido]-α-D-mannopyranose (1293911-28-0) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → 3,4,6-tri-O-acetyl-1,2-dideoxy-1-(5-tert-butyl-2-methyl)phenylthio-2-[2-(trimethylsilyl)ethanesulfonamido]-β-D-glucopyranoside (1293911-40-6)

Conditions	Yield
Stage #1: 2-methyl-5-tert-butylthiophenol With lithium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; Inert atmosphere; Stage #2: 3,4,6-tri-O-acetyl-1,2-dideoxy-2-iodo-1-[2-(trimethylsilyl)ethanesulfonamido]-α-D-mannopyranose In tetrahydrofuran; N,N-dimethyl-formamide at -30 - 20℃; for 0.333333h; diastereoselective reaction;	77%

D-Mannose (3458-28-4) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 1-thia-α-D-mannopyranoside (1361016-58-1)

Conditions	Yield
Stage #1: D-Mannose With pyridine; acetic anhydride at 20℃; Inert atmosphere; Stage #2: 2-methyl-5-tert-butylthiophenol With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere;	75%

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranoside (55628-56-3, 68567-54-4, 77790-45-5, 77790-46-6, 81969-44-0, 99630-89-4, 125135-30-0, 137567-77-2, 65827-55-6) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-D-mannopyranoside

Conditions	Yield
With boron trifluoride diethyl etherate In toluene at 20℃; for 2h; Inert atmosphere; optical yield given as %de;	75%

O-{O-[(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)]-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)]-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)]-3-O-acetyl-α-D-mannopyranosyl}-trichloroacetimidate + 2-methyl-5-tert-butylthiophenol (7340-90-1) → C79H85N3O33S

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0℃;	69%

2,7-di-O-acetyl-3-O-levulinoyl-4-O-(para-bromobenzyl)-6-O-benzyl-L-glycero-D-manno-heptopyranosyl levulinoate + 2-methyl-5-tert-butylthiophenol (7340-90-1) → 5-tert-butyl-2-methylphenyl 2,7-di-O-acetyl-3-O-levulinoyl-4-O-para-bromobenzyl-6-O-benzyl-1-thio-L-glycero-D-manno-heptopyranoside

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere;	66%

2,7-di-O-acetyl-3-O-levulinoyl-4-O-para-bromobenzyl-6-O-benzyl-L-glycero-D-manno-heptopyranosyl levulinoate (1403362-05-9) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → 5-tert-butyl-2-methylphenyl 2,7-di-O-acetyl-3-O-levulinoyl-4-O-parabromobenzyl-6-O-benzyl-1-thio-L-glycero-D-manno-heptopyranoside (1403362-08-2)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere;	66%

1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose (53270-12-5) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (1011529-36-4)

Conditions	Yield
With mercury dibromide In toluene at 80℃;	64%

1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside (96996-90-6) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside (1011529-30-8)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;	56%

2-methyl-5-tert-butylthiophenol (7340-90-1) + 1,2,3,4,6-penta-O-benzoyl-α-D-galactopyranoside (2592-58-7, 3006-48-2, 3006-49-3, 13526-09-5, 14679-57-3, 22415-91-4, 29884-70-6, 41545-55-5, 41545-56-6, 41569-33-9, 96996-90-6, 121570-85-2, 121570-86-3) → (2-methyl-5-tert-butylphenyl) α-D-(2,3,4,6-tetra-O-benzoyl) thiogalactopyranoside

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;	56%

(E)-1,2-diphenyl-ethene (103-30-0) + 2-methyl-5-tert-butylthiophenol (7340-90-1) → S-(5-tert-butyl-2-methylphenyl)-S-(2-hydroxy-1,2-diphenylethyl)sulfoxide

Conditions	Yield
With oxygen In hexane; ethyl acetate for 2.5h; Irradiation;	55%

Upstream product

• 34493-12-4 1,2-bis(5-(tert-butyl)-2-methylphenyl)disulfane 

Downstream Products

• 25589-81-5 2-Methyl-5-t-butylbenzolsulfosaeure 
• 34493-12-4 1,2-bis(5-(tert-butyl)-2-methylphenyl)disulfane 
• 945263-06-9 C₇₇H₈₃N₃O₃₂S 
• 1011529-36-4 (2-methyl-5-tert-butylphenyl) 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 1011529-31-9 (2-methyl-5-tert-butylphenyl) 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-α-D-glucopyranoside 
• 1011529-55-7 (2-methyl-5-tert-butylphenyl) 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 1011529-38-6 (2-methyl-5-tert-butylphenyl) 2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranoside 
• 1011529-30-8 (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 1011529-29-5 (2-methyl-5-tert-butylphenyl) 2,3,4-tri-O-benzoyl-1-thio-β-D-xylopyranoside 
• 1185741-87-0 2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 1384442-62-9 2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 
• 1269500-76-6 (2-methyl-5-tert-butylphenyl) 1-thio-β-D-galactofuranoside 

Relevant articles and documents

Unexpected catalyzed C=C bond cleavage by molecular oxygen promoted by a thiyl radical

Olefin oxidation with molecular oxygen, promoted by a transition metal catalyst and a thiophenol, involved C=C bond cleavage into the corresponding carbonyl derivatives. This new reaction proceeds under one atmosphere of oxygen, at room temperature, in the presence of an excess of thiophenol and a catalyst such as MnL2 3a or VC1L2 3c. It was applied to aromatic and aliphatic olefins, as well as to functionalized or unfunctionalized acyclic compounds, providing the corresponding ketones and aldehydes in up to 98% yield. The synthetic interest of this catalytic oxidation was illustrated by a one-step preparation of the fragrance (-)-4-acetyl-1-methylcyclohexene 7e in 73% isolated yield. The C=C bond cleavage probably results from a catalyzed decomposition of the β-hydroperoxysulfide intermediate 12 that is formed by the radical addition of thiophenol to the olefin in the presence of oxygen. Although an excess of the thiophenol was used, it was transformed into the disulfide which could then be reduced without purification in 83% overall yield, thereby allowing for recycling. In addition, the C=C bond cleavage under oxygen could be promoted by catalytic quantities of the thiyl radical, generated by photolysis of the disulfide; thus, in the presence of 0.1 equiv of bis(4-chlorophenyl) disulfide 4b and 5% of the manganese complex 3a, trans-methylstilbene 1b gave, under radiation, benzaldehyde 6a and acetophenone 7a in up to 95% yield. This new reaction offers an alternative to the classical C=C bond cleavage procedures, and further developments in the fields of bioinorganic and environmental chemistry are likely.