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  • 75-66-1 Structure
  • Basic information

    1. Product Name: 2-Methyl-2-propanethiol
    2. Synonyms: 1,1-Dimethylethanethiol;2-Isobutanethiol;2-methyl-2-propanethio;2-methyl-propane-2-thiol;mercaptantert-butyliquebutanethiol(non-specificname);methylpropanethiol(non-specificname);tert-Butyl hydrosulfide;tert-Butylthiol
    3. CAS NO:75-66-1
    4. Molecular Formula: C4H10S
    5. Molecular Weight: 90.19
    6. EINECS: 200-890-2
    7. Product Categories: N/A
    8. Mol File: 75-66-1.mol
    9. Article Data: 27
  • Chemical Properties

    1. Melting Point: -1.1 °C
    2. Boiling Point: 62-65 °C(lit.)
    3. Flash Point: −12 °F
    4. Appearance: Clear colorless/Liquid
    5. Density: 0.8 g/mL at 25 °C(lit.)
    6. Vapor Density: 3.1 (vs air)
    7. Vapor Pressure: 303.5 mm Hg ( 37.7 °C)
    8. Refractive Index: n20/D 1.423(lit.)
    9. Storage Temp.: Flammables area
    10. Solubility: 1.47g/l slightly soluble
    11. PKA: pK1:11.22 (25°C,μ=0.1)
    12. Water Solubility: Slightly soluble in water
    13. Stability: Stable. Flammable - note low flashpoint. Incompatible with strong oxidizing agents.
    14. Merck: 14,1579
    15. BRN: 505947
    16. CAS DataBase Reference: 2-Methyl-2-propanethiol(CAS DataBase Reference)
    17. NIST Chemistry Reference: 2-Methyl-2-propanethiol(75-66-1)
    18. EPA Substance Registry System: 2-Methyl-2-propanethiol(75-66-1)
  • Safety Data

    1. Hazard Codes: F,Xi,Xn,N
    2. Statements: 11-41-65-43-36-51/53
    3. Safety Statements: 3-16-26-39-38-36/37-61
    4. RIDADR: UN 2347 3/PG 2
    5. WGK Germany: 3
    6. RTECS: TZ7660000
    7. F: 13
    8. HazardClass: 3.1
    9. PackingGroup: II
    10. Hazardous Substances Data: 75-66-1(Hazardous Substances Data)

75-66-1 Usage

Description

tert-Butylthiol, also known as 2-methyl propane-2-thiol, 2- methyl-2-propane thiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organo sulfur compound with the formula (CH3)3CSH. This thiol may have been used as a flavoring agent, as an odorant for natural gas (which is odorless), and also in a wide range of organic reactions.

Uses

Different sources of media describe the Uses of 75-66-1 differently. You can refer to the following data:
1. 2-Methyl-2-propanethiol was used in reaction of 2-methyl-2-propanethiol on Mo(110) using temperature programmed reaction, high resolution electron enegy loss and X-ray photoelectron spectroscopies. It was used in the synthesis of chain-transfer agents for reversible addition-fragmentation chain-transfer copolymerization of vinylidene chloride and methyl acrylate.
2. Tert-Butylthiol is the main ingredient in many gas odorant blends. It is always utilized as a blend of other compounds, typically dimethyl sulfide, methyl ethyl sulfide, tetrahydrothiophene or other mercaptans (isopropyl mercaptan, sec-butyl mercaptan and/or n-butyl mercaptan, due to its rather high melting point of 273 K. These blends are used only with natural gas and not propane, as the boiling points of these blends and propane are quite different. As propane is delivered as a liquid and vaporizes to gas when being delivered to the appliance, the vapor liquid equilibrium would substantially reduce the amount of odorant blend in the vapor. Tert - Butyl thiol has been listed on the European Food Safety Authority (FL-no: 12.174) as a flavor additive. There is no indication of what flavor or flavors it may have been used in. It has been removed from this list.

Preparation

tert-Butyl thiol likely does not occur naturally, but at least one publication has listed it as a very minor component of cooked potatoes. The compound was first prepared in 1890 by Leonard Dobbin by the reaction of zinc sulfide and t-butyl chloride. The compound was later prepared in 1932 by the reaction of the Grignard reagent, t-BuMgCl, with sulfur to give the corresponding thiolate, followed by hydrolysis. This preparation is shown below: t-BuMgCl + S → t-BuSMgCl t-BuSMgCl + H2O → t-BuSH + Mg(OH)Cl It is currently prepared industrially by the reaction of isobutylene with hydrogen sulfide over a clay (silica alumina) catalyst.

Reactions

tert-Butylthiol can react with metal alkoxides and acyl chlorides to form thiol esters, as shown in the equation : In the reaction above, thallium (I) ethoxide converts to thallium (I) t-butyl thiolate. In the presence of diethyl ether, thallium (I) tbutylthiolate reacts with acyl chlorides to give the corresponding tertbutyl thioesters. Like other thio esters, it reverts back to tert-butylthiol by hydrolysis. Lithium 2-methyl propane-2-thiolate can be prepared by treatment of tert-butyl thiol with lithium hydride in an aprotic solvent such as hexa methyl phosphorous triamide (HMPT). The resulting thiolate salt is a useful demethylating reagent. For example, treatment with 7- methyl guanosine gives guanosine. Other N-methylated nucleosides in tRNA are not demethylated by this reagent .

General Description

2-Methyl-2-propanethiol undergoes ring opening nucleophilic reaction with 3-isothiazolones and reaction kinetics studies suggested reaction was second order in thiol and third order overall.

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. An eye irritant. A very dangerous fire hazard when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use alcohol foam, dry chemical, mist, fog. When heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of SOx.

Safety

Even in well ventilated areas, extreme caution must be made when handling tert-butylthiol as it is a highly odorous chemical with an odor threshold of < 0.33 ppb. Extreme caution is not due to toxicity, but due to the significant odor and concerns that this odor would cause to the many individuals that might be exposed. The PEL for thiols of most types is 500 ppb, primarily due to reaction of nausea at levels of 2–3 ppm. The LC50 of tert-butylthiol is much, much higher.

Purification Methods

Dry the thiol for several days over CaO, then distil it from CaO. Purify it as for 2-methylpropane-1-thiol above. [Beilstein 1 H 383, 1 II 416, 1 III 1589, 1 IV 1634.]

Metal complexes

The anion derived from tert – butyl thiol forms complexes with various metals. One example is tetra kis (tert-butyl thiolato ) molybdenum (IV), Mo(t-BuS)4. This complex was prepared by treating MoCl4 with t-BuSLi : Mo Cl4 + 4t-Bu S Li → Mo (t-BuS)4 + 4LiCl Mo(t-BuS)4 is a dark red diamagnetic complex that is sensitive to air and moisture. The molybdenum center has a distorted tetra hedral coordination to four sulfur atoms, with overall D2 symmetry.

Check Digit Verification of cas no

The CAS Registry Mumber 75-66-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 75-66:
(4*7)+(3*5)+(2*6)+(1*6)=61
61 % 10 = 1
So 75-66-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H10S/c1-4(2,3)5/h5H,1-3H3

75-66-1 Well-known Company Product Price

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  • Aldrich

  • (109207)  2-Methyl-2-propanethiol  99%

  • 75-66-1

  • 109207-100ML

  • 314.73CNY

  • Detail
  • Aldrich

  • (109207)  2-Methyl-2-propanethiol  99%

  • 75-66-1

  • 109207-500ML

  • 366.21CNY

  • Detail
  • Aldrich

  • (109207)  2-Methyl-2-propanethiol  99%

  • 75-66-1

  • 109207-2L

  • 1,154.79CNY

  • Detail

75-66-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methyl-2-Propanethiol

1.2 Other means of identification

Product number -
Other names 2-Methyl-2-propanethiol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Odor agents
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:75-66-1 SDS

75-66-1Synthetic route

t-butyl bromide
507-19-7

t-butyl bromide

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With hydrosulfide exchange resin In acetonitrile at 25℃; for 0.25h;96%
Stage #1: t-butyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: With sulfur In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
tertiary butyl chloride
507-20-0

tertiary butyl chloride

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With hydrosulfide exchange resin In acetonitrile at 25℃; for 0.25h;95%
With hydrogen sulfide; boron trifluoride
With hydrogen sulfide; tin(IV) chloride
1-chloro-3-phenylpropan-2-one
937-38-2

1-chloro-3-phenylpropan-2-one

t-butyl thionitrite
15459-95-7

t-butyl thionitrite

A

C9H8ClNO2
78946-49-3

C9H8ClNO2

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A 95%
B n/a
t-butyl thionitrite
15459-95-7

t-butyl thionitrite

1-chlorohexan-2-one
20261-68-1

1-chlorohexan-2-one

A

C6H10ClNO2
78946-52-8

C6H10ClNO2

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A 95%
B n/a
t-butyl thionitrite
15459-95-7

t-butyl thionitrite

1-chloro-3-phenoxyacetone
940-47-6

1-chloro-3-phenoxyacetone

A

C9H8ClNO3
78946-50-6

C9H8ClNO3

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A 95%
B n/a
t-butyl thionitrite
15459-95-7

t-butyl thionitrite

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

A

(1Z)-N-hydroxy-3,3-dimethyl-2-oxobutanimidoyl chloride
96759-10-3

(1Z)-N-hydroxy-3,3-dimethyl-2-oxobutanimidoyl chloride

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A 85%
B n/a
t-butyl thionitrite
15459-95-7

t-butyl thionitrite

chloroacetone
78-95-5

chloroacetone

A

N-hydroxy-2-oxo-propionimidoyl chloride
17019-27-1

N-hydroxy-2-oxo-propionimidoyl chloride

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A 82%
B n/a
tert-butyl alcohol
75-65-0

tert-butyl alcohol

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With polymer supported thiol; trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h;75%
With hydrogen sulfide at 180℃; under 6251820 Torr;
t-butyl thionitrite
15459-95-7

t-butyl thionitrite

1-bromoacetone
598-31-2

1-bromoacetone

A

(Z)-pyruvohydroximoyl bromide
30822-62-9

(Z)-pyruvohydroximoyl bromide

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A 43%
B n/a
methanol
67-56-1

methanol

2-(2-tert-Butylsulfanyl-2-methoxy-ethyl)-benzo[de]isoquinoline-1,3-dione

2-(2-tert-Butylsulfanyl-2-methoxy-ethyl)-benzo[de]isoquinoline-1,3-dione

A

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

B

2-(2,2-dimethoxyethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione
153721-06-3

2-(2,2-dimethoxyethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
In dichloromethane Irradiation;A 30%
B 34%
t-butyl thionitrite
15459-95-7

t-butyl thionitrite

1-chloroacetophenone
532-27-4

1-chloroacetophenone

A

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

B

(Z)-N-hydroxy-α-oxobenzeneethanimidoyl chloride
17019-28-2

(Z)-N-hydroxy-α-oxobenzeneethanimidoyl chloride

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A n/a
B 20%
t-butyl thionitrite
15459-95-7

t-butyl thionitrite

α-bromoacetophenone
70-11-1

α-bromoacetophenone

A

C8H6BrNO2
14450-97-6

C8H6BrNO2

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;A 10%
B n/a
O,O-di-t-butyl dithiophosphoric acid
92799-96-7

O,O-di-t-butyl dithiophosphoric acid

A

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

B

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
at 70℃;
Isobutyl bromide
78-77-3

Isobutyl bromide

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With sodium hydrogensulfide; ethanol
sulfure de di tert-butyle
107-47-1

sulfure de di tert-butyle

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With iron sulfide; hydrogen sulfide at 190℃; unter Druck;
With hydrogen sulfide; propionic acid anhydride at 190℃; unter Druck;
3-tert-Butyl-2,4,4-trimethyl-pent-2-ene
2437-52-7

3-tert-Butyl-2,4,4-trimethyl-pent-2-ene

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With hydrogen sulfide at 200℃; under 36775.4 Torr;
tert-butylmagnesium chloride
677-22-5

tert-butylmagnesium chloride

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With diethyl ether; sulfur Zersetzen mit Eiswasser und verd.H2SO4;
S-tert-butyl isothiouronium bromide
53243-22-4

S-tert-butyl isothiouronium bromide

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With potassium hydroxide
tert-Butyl iodide
558-17-8

tert-Butyl iodide

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With ethanol; zinc sulfide
isobutene
115-11-7

isobutene

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With sulfuric acid; hydrogen sulfide
With hydrogen sulfide; benzenesulfonic acid
With phosphoric acid; hydrogen sulfide; pyrographite
thiophene
110-01-0

thiophene

A

thiophene
188290-36-0

thiophene

B

trans-2-Butene
624-64-6

trans-2-Butene

C

Isobutane
75-28-5

Isobutane

D

Dibutyl sulfide
544-40-1

Dibutyl sulfide

E

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

F

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
aluminum oxide; cobalt molybdenum In n-heptane at 290℃; under 21280 Torr; Product distribution; Mechanism; effect of temperature, pressure and contact time;
thiophene
188290-36-0

thiophene

A

thiophene
110-01-0

thiophene

B

trans-2-Butene
624-64-6

trans-2-Butene

C

Isobutane
75-28-5

Isobutane

D

Dibutyl sulfide
544-40-1

Dibutyl sulfide

E

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

F

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
aluminum oxide; cobalt molybdenum In n-heptane at 290℃; under 21280 Torr; Product distribution; Mechanism; effect of temperature, pressure and contact time;
di-tert-butyl disulfide
110-06-5

di-tert-butyl disulfide

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With n-butanethiol Equilibrium constant;
t-butyl bromide
507-19-7

t-butyl bromide

Potassium N-<(2-vinyloxy)ethyl>dithiocarbamate
97006-62-7

Potassium N-<(2-vinyloxy)ethyl>dithiocarbamate

A

tert-butyl N-(2-vinyloxyethyl)dithiocarbamate
126560-48-3

tert-butyl N-(2-vinyloxyethyl)dithiocarbamate

B

2-(vinyloxy)ethyl isothiocyanate
59565-09-2

2-(vinyloxy)ethyl isothiocyanate

C

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In ethanol at 60℃; for 1h;A 36 % Spectr.
B n/a
C n/a
S-tert-butyl acetothioacetate
15925-47-0

S-tert-butyl acetothioacetate

A

2-acetoacetic acid
541-50-4

2-acetoacetic acid

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
With water at 23.3 - 49℃; Rate constant; Thermodynamic data; 0.8percent (v/v) acetonitrile, ionic strength 0.1M. ΔH(excit.), ΔS(excit.), study of rate constant at different temperatures.;
With sodium hydroxide at 25℃; Rate constant; ionic strength 0.1M, 0.8percent (v/v) acetonitrile;
di-tert-butyl sulfoxide
2211-92-9

di-tert-butyl sulfoxide

A

2-methyl-2-propanesulfenic acid
4719-19-1

2-methyl-2-propanesulfenic acid

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
at 350℃;
C16H17O2S3(1-)

C16H17O2S3(1-)

A

dibenzo<1,2>dithiin 5,5-dioxide
25331-82-2

dibenzo<1,2>dithiin 5,5-dioxide

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In 1,4-dioxane; water at 25℃; Rate constant; var. pH;
selenium(II) bis(2-methyl-2-propanethiolate)
75272-63-8

selenium(II) bis(2-methyl-2-propanethiolate)

35S-2-methyl-2-propanethiol
58204-98-1

35S-2-methyl-2-propanethiol

A

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

B

C8H18(35)S2Se

C8H18(35)S2Se

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 25℃; Rate constant; Kinetics; exchange of 35S labeled thiols with bis(alkylthio) selenides reactions of bis(alkylthio) selenides with various nucleophiles, reactivity and site of nucleophilic attack;
2-methylpropane-2-thiol-d1
32259-07-7

2-methylpropane-2-thiol-d1

2-propanethiol
75-33-2

2-propanethiol

A

isopropylthiol-d
41782-40-5

isopropylthiol-d

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Conditions
ConditionsYield
In Cyclohexane-d12 at 29.9℃; Rate constant; Equilibrium constant; Thermodynamic data; EA (Arrhenius activation energy); ΔH<*> (enthalpy for isotopic exchange); ΔS<*> (entropy for isotopic exchange); various solvents investigated;
sulfure de di tert-butyle
107-47-1

sulfure de di tert-butyle

chlorobenzene
108-90-7

chlorobenzene

A

diphenyl sulfide
139-66-2

diphenyl sulfide

B

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

C

thiophenol
108-98-5

thiophenol

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 650℃; Product distribution; Mechanism;
at 650℃; Product distribution; Mechanism; 600 deg C;
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

2-methyl-2-propanethiosulfenyl chloride
6009-05-8

2-methyl-2-propanethiosulfenyl chloride

Conditions
ConditionsYield
With pyridine; sulfur dichloride In diethyl ether at -78℃; for 0.5h;100%
With chlorine In tetrachloromethane
With sulfur dichloride; pentane
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

1,1-dimethylethanesulfenyl chloride
52322-55-1

1,1-dimethylethanesulfenyl chloride

Conditions
ConditionsYield
With pyridine; sulfuryl dichloride In diethyl ether at -78℃; for 0.5h;100%
With methylbutane; chlorine
With hexane; chlorine
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

bis(2-methyl-2-propyl)tetrasulfide
5943-35-1

bis(2-methyl-2-propyl)tetrasulfide

Conditions
ConditionsYield
With disulfur dichloride100%
With disulfur dichloride; benzene
With propylamine; sulfur In dichloromethane
With disulfur dichloride In tetrachloromethane Ambient temperature;
With disulfur dichloride
2-methyl-2-propanethiosulfenyl chloride
6009-05-8

2-methyl-2-propanethiosulfenyl chloride

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

di-tert-butyl trisulfide
4253-90-1

di-tert-butyl trisulfide

Conditions
ConditionsYield
With pyridine In diethyl ether for 0.5h;100%
1,1-dimethylethanesulfenyl chloride
52322-55-1

1,1-dimethylethanesulfenyl chloride

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

di-tert-butyl disulfide
110-06-5

di-tert-butyl disulfide

Conditions
ConditionsYield
With pyridine In diethyl ether for 0.5h;100%
<(E)-3,3-dimethyl-1-butenyl>mercuric chloride
36525-02-7, 79178-05-5

<(E)-3,3-dimethyl-1-butenyl>mercuric chloride

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

(E)-1-tert-Butylsulfanyl-3,3-dimethyl-but-1-ene
75924-71-9

(E)-1-tert-Butylsulfanyl-3,3-dimethyl-but-1-ene

Conditions
ConditionsYield
With sodium hydrogencarbonate In benzene at 35 - 45℃; for 15h; Irradiation;100%
(p-cymene)osmium bis(t-butyloxide)
134654-70-9

(p-cymene)osmium bis(t-butyloxide)

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

A

(p-cymene)osmium bis(t-butylthiolate)
134654-72-1

(p-cymene)osmium bis(t-butylthiolate)

B

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
In benzene-d6 soln. of CymOs(O-t-Bu)2 in C6D6 is degassed, t-BuSH is added at -196°C; (1)H-NMR;A 92%
B 100%
monomethylgallium di-iodide
95050-66-1

monomethylgallium di-iodide

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

diiodomethyl(tert-butylthiol)gallane

diiodomethyl(tert-butylthiol)gallane

Conditions
ConditionsYield
In benzene byproducts: CH4; (under N2); the thiol is introduced into a soln. of MeGaI2 in benzene; the solvent is evapd., the residue is washed, dried; elem. anal.;100%
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

4-chlorobenzoylmethyl bromide
536-38-9

4-chlorobenzoylmethyl bromide

C12H15ClOS
88577-88-2

C12H15ClOS

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 16h;100%
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

1-(1,1-dimethylethyl)sulfanyl-4-nitrobenzene
7205-66-5

1-(1,1-dimethylethyl)sulfanyl-4-nitrobenzene

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide Inert atmosphere;100%
Stage #1: 2-methylpropan-2-thiol; 4-Fluoronitrobenzene With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃;
Stage #2: With water In N,N-dimethyl-formamide; mineral oil for 0.25h;
91%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h;
methyl 2-(3-(2-bromomethyl-4-nitrophenoxy)-4-methoxyphenyl)acetate
1313757-49-1

methyl 2-(3-(2-bromomethyl-4-nitrophenoxy)-4-methoxyphenyl)acetate

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

methyl 2-(3-(2-(tert-butylthiomethyl)-4-nitrophenoxy)-4-methoxyphenyl)acetate
1313757-50-4

methyl 2-(3-(2-(tert-butylthiomethyl)-4-nitrophenoxy)-4-methoxyphenyl)acetate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 15℃; for 5h;100%
bis(acetonitrile)(5,10,15,20-tetra-p-tolylporphyrinato)ruthenium(II)
114550-41-3

bis(acetonitrile)(5,10,15,20-tetra-p-tolylporphyrinato)ruthenium(II)

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

Ru(meso-tetrakis(4-methylphenyl)porphyrin)(t-BuSH)2
1357363-80-4

Ru(meso-tetrakis(4-methylphenyl)porphyrin)(t-BuSH)2

Conditions
ConditionsYield
In benzene at 20℃; for 24h;100%
In benzene-d6 identified by NMR;
4-fluorophenylpyridine
58861-53-3

4-fluorophenylpyridine

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

2-(4-tbutylsulfanylphenyl)pyridine
1580547-38-1

2-(4-tbutylsulfanylphenyl)pyridine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 120℃; for 24h; Inert atmosphere;100%
8-fluoroquinoline-3-carboxylic acid
71082-53-6

8-fluoroquinoline-3-carboxylic acid

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

8-(tert-butylthio)quinoline-3-carboxylic acid
1414882-17-9

8-(tert-butylthio)quinoline-3-carboxylic acid

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 140℃; for 18h; Inert atmosphere;100%
With sodium hydride In N,N-dimethyl-formamide at 140℃; for 18h; Inert atmosphere;100%
2,6-dichloro-4-phenylpyridine
25297-51-2

2,6-dichloro-4-phenylpyridine

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

2-(tert-butylthio)-6-chloro-4-phenylpyridine

2-(tert-butylthio)-6-chloro-4-phenylpyridine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;100%
acetic anhydride
108-24-7

acetic anhydride

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

S-tert-butyl thioacetate
999-90-6

S-tert-butyl thioacetate

Conditions
ConditionsYield
With vanadyl triflate In dichloromethane at 20℃; for 12h;99%
Stage #1: acetic anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: 2-methylpropan-2-thiol In dichloromethane at 20℃; for 18h;
98%
With pyridine
With perchloric acid; acetic acid
With triethylamine
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

di-tert-butyl disulfide
110-06-5

di-tert-butyl disulfide

Conditions
ConditionsYield
With nanophase manganese (VII) oxide coated clay (NM7O coated clay) In toluene at 40℃; for 2h;99%
With potassium permanganate at 20℃; for 8h;99%
With water; dihydrogen peroxide In various solvent(s) at 20℃; for 0.166667h; Oxidation; Dimerization;98%
1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

1,3-bis(tert-butylthio)propan-2-ol
101855-82-7

1,3-bis(tert-butylthio)propan-2-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;99%
With sodium 1) EtOH, 50 deg C, 30 min, 2) 6 h, reflux; Yield given. Multistep reaction;
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

1-bromo-2-[(tert-butylsulfanyl)methyl]benzene
259136-26-0

1-bromo-2-[(tert-butylsulfanyl)methyl]benzene

Conditions
ConditionsYield
With potassium hydride In tetrahydrofuran at 0 - 20℃; for 24h; Substitution;99%
Stage #1: 2-methylpropan-2-thiol With sodium hydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;
Stage #2: 1-Bromo-2-bromomethyl-benzene In tetrahydrofuran for 18h; Inert atmosphere; Reflux;
97%
Stage #1: 2-methylpropan-2-thiol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: 1-Bromo-2-bromomethyl-benzene In tetrahydrofuran for 16h; Inert atmosphere; Reflux;
94%
With sodium hydroxide In methanol; water at 20 - 40℃; for 0.5h;
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

1-[(1,1-dimethylethyl)thio]-4-methoxybenzene
7205-64-3

1-[(1,1-dimethylethyl)thio]-4-methoxybenzene

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate In 1,4-dioxane at 100℃; for 18h;99%
2-Bromo-m-xylene
576-22-7

2-Bromo-m-xylene

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

2,6-dimethylphenyl 2-methyl-2-propyl sulfide
16463-11-9

2,6-dimethylphenyl 2-methyl-2-propyl sulfide

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate In 1,4-dioxane at 100℃; for 18h;99%
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; sodium t-butanolate In 1,2-dimethoxyethane at 110℃; for 4h; Inert atmosphere;92%
Stage #1: 2-Bromo-m-xylene With dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II); lithium isopropoxide In toluene at 80℃; for 0.5h; Inert atmosphere;
Stage #2: 2-methylpropan-2-thiol With potassium tert-butylate In toluene at 40℃; for 24h; Inert atmosphere;
73%

75-66-1Relevant articles and documents

Photoactivatable Odorants for Chemosensory Research

Gore, Sangram,Ukhanov, Kirill,Herbivo, Cyril,Asad, Naeem,Bobkov, Yuriy V.,Martens, Jeffrey R.,Dore, Timothy M.

, p. 2516 - 2528 (2020/10/02)

The chemosensory system of any animal relies on a vast array of detectors tuned to distinct chemical cues. Odorant receptors and the ion channels of the TRP family are all uniquely expressed in olfactory tissues in a species-specific manner. Great effort has been made to characterize the molecular and pharmacological properties of these proteins. Nevertheless, most of the natural ligands are highly hydrophobic molecules that are not amenable to controlled delivery. We sought to develop photoreleasable, biologically inactive odorants that could be delivered to the target receptor or ion channel and effectively activated by a short light pulse. Chemically distinct ligands eugenol, benzaldehyde, 2-phenethylamine, ethanethiol, butane-1-thiol, and 2,2-dimethylethane-1-thiol were modified by covalently attaching the photoremovable protecting group (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ). The CyHQ derivatives were shown to release the active odorant upon illumination with 365 and 405 nm light. We characterized their bioactivity by measuring activation of recombinant TRPV1 and TRPA1 ion channels expressed in HEK 293 cells and the electroolfactogram (EOG) response from intact mouse olfactory epithelium (OE). Illumination with 405 nm light was sufficient to robustly activate TRP channels within milliseconds of the light pulse. Photoactivation of channels was superior to activation by conventional bath application of the ligands. Photolysis of the CyHQ-protected odorants efficiently activated an EOG response in a dose-dependent manner with kinetics similar to that evoked by the vaporized odorant amyl acetate (AAc). We conclude that CyHQ-based, photoreleasable odorants can be successfully implemented in chemosensory research.

Quantitative Reactivity Scales for Dynamic Covalent and Systems Chemistry

Zhou, Yuntao,Li, Lijie,Ye, Hebo,Zhang, Ling,You, Lei

supporting information, p. 381 - 389 (2016/01/26)

Dynamic covalent chemistry (DCC) has become a powerful tool for the creation of molecular assemblies and complex systems in chemistry and materials science. Herein we developed for the first time quantitative reactivity scales capable of correlation and prediction of the equilibrium of dynamic covalent reactions (DCRs). The reference reactions are based upon universal DCRs between imines, one of the most utilized structural motifs in DCC, and a series of O-, N-, and S- mononucleophiles. Aromatic imines derived from pyridine-2-carboxyaldehyde exhibit capability for controlling the equilibrium through distinct substituent effects. Electron-donating groups (EDGs) stabilize the imine through quinoidal resonance, while electron-withdrawing groups (EWGs) stabilize the adduct by enhancing intramolecular hydrogen bonding, resulting in curvature in Hammett analysis. Notably, unique nonlinearity induced by both EDGs and EWGs emerged in Hammett plot when cyclic secondary amines were used. This is the first time such a behavior is observed in a thermodynamically controlled system, to the best of our knowledge. Unified quantitative reactivity scales were proposed for DCC and defined by the correlation log K = SN (RN + RE). Nucleophilicity parameters (RN and SN) and electrophilicity parameters (RE) were then developed from DCRs discovered. Furthermore, the predictive power of those parameters was verified by successful correlation of other DCRs, validating our reactivity scales as a general and useful tool for the evaluation and modeling of DCRs. The reactivity parameters proposed here should be complementary to well-established kinetics based parameters and find applications in many aspects, such as DCR discovery, bioconjugation, and catalysis.

C-S bond cleavage by a polyketide synthase domain

Ma, Ming,Lohman, Jeremy R.,Liu, Tao,Shen, Ben

, p. 10359 - 10364 (2015/09/01)

Leinamycin (LNM) is a sulfur-containing antitumor antibiotic featuring an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro-fused to a thiazole-containing 18-membered lactam ring. The 1,3-dioxo-1,2- dithiolane moiety is essential for LNM's antitumor activity, by virtue of its ability to generate an episulfonium ion intermediate capable of alkylating DNA. We have previously cloned and sequenced the lnm gene cluster from Streptomyces atroolivaceus S-140. In vivo and in vitro characterizations of the LNM biosynthetic machinery have since established that: (i) the 18-membered macrolactam backbone is synthesized by LnmP, LnmQ, LnmJ, LnmI, and LnmG, (ii) the alkyl branch at C-3 of LNM is installed by LnmK, LnmL, LnmM, and LnmF, and (iii) leinamycin E1 (LNM E1), bearing a thiol moiety at C-3, is the nascent product of the LNM hybrid nonribosomal peptide synthetase (NRPS)-acyltransferase (AT)-less type I polyketide synthase (PKS). Sulfur incorporation at C-3 of LNM E1, however, has not been addressed. Here we report that: (i) the bioinformatics analysis reveals a pyridoxal phosphate (PLP)-dependent domain, we termed cysteine lyase (SH) domain (LnmJ-SH), within PKS module-8 of LnmJ; (ii) the LnmJ-SH domain catalyzes C-S bond cleavage by using L-cysteine and L-cysteine S-modified analogs as substrates through a PLP-dependent β-elimination reaction, establishing L-cysteine as the origin of sulfur at C-3 of LNM; and (iii) the LnmJ-SH domain, sharing no sequence homology with any other enzymes catalyzing C-S bond cleavage, represents a new family of PKS domains that expands the chemistry and enzymology of PKSs and might be exploited to incorporate sulfur into polyketide natural products by PKS engineering.

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