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CAS Number : 75-66-1
EC Number : 200-890-2
Molecular Formula : C4H10S
Molecular Weight : 90.19
Appearance : Colorless, clear liquid
ECHA InfoCard : 100.000.810
Melting point : −0.50 °C
Boiling point : 62 to 65 °C
Other names :
-t-BuSH
-2-Methylpropane-2-thiol
-2-Methyl-2-propanethiol
-2-Methylpropane-2-thiol
tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH.
tert-Butyl Mercaptan is used as an odorant for natural gas, which is otherwise odorless.
tert-Butyl Mercaptan may also have been used as a flavoring agent.
Preparation of tert-Butyl Mercaptan
At least one publication has listed tert-butylthiol as a very minor component of cooked potatoes,but because the tert-butyl moiety is very rare in natural products, other sources doubt the existence of natural sources of the compound.
tert-Butyl Mercaptan 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
tert-Butyl Mercaptan is currently prepared industrially by the reaction of isobutylene with hydrogen sulfide over a clay (silica alumina) catalyst.
Commercial use of tert-Butyl Mercaptan
tert-Butyl Mercaptan is the main ingredient in many gas odorant blends.
tert-Butyl Mercaptan is always utilized as a blend of other compounds, typically dimethyl sulfide, methyl ethyl sulfide, tetrahydrothiophene or other mercaptans such as isopropyl mercaptan, sec-butyl mercaptan and/or n-butyl mercaptan, due to its rather high melting point of −0.5 °C (31.1 °F).
These blends are used only with natural gas and not propane, as the boiling points of these blends and propane are quite different.
Because propane is delivered as a liquid and vaporizes to gas when it is delivered to the appliance, the vapor liquid equilibrium would substantially reduce the amount of odorant blend in the vapor.
tert-Butyl Mercaptan has been listed on the European Food Safety Authority (FL-no: 12.174) as a flavor additive.
There is no indication of what flavor(s) it may have been used in.
tert-Butyl Mercaptan has been removed from this list.
Application of tert-Butyl Mercaptan
tert-Butyl Mercaptan 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.
tert-Butyl Mercaptan was used in the synthesis of chain-transfer agents for reversible addition-fragmentation chain-transfer copolymerization of vinylidene chloride and methyl acrylate.
Tert-Butyl mercaptan (2-methyl-2-propanethiol, CAS # 75-66-1) is a highly odorous material, with an odor threshold of < 1ppb.
Tert-Butyl mercaptan is a component in several Scentinel Gas Odorants for use in odorizing natural gas so that leaks can be detected by smell before explosive levels are reached.
Tert-Butyl mercaptan is also used as a chemical intermediate for synthesis of agrichemicals and other chemical substances.
tert-Butyl Mercaptan belongs to the class of organic compounds known as alkylthiols.
These are organic compounds containing the thiol functional group linked to an alkyl chain.
tert-Butyl Mercaptan is a cooked, mustard, and vegetable tasting compound.
tert-Butyl Mercaptan has been detected, but not quantified in, several different foods, such as alcoholic beverages, fruits, guavas (Psidium guajava), and milk and milk products.
This could make tert-Butyl Mercaptan a potential biomarker for the consumption of these foods.
Based on a literature review a small amount of articles have been published on tert-Butyl Mercaptan.
Uses of tert-Butyl Mercaptan
tert-Butyl Mercaptan is the main ingredient in many gas odorant blends.
tert-Butyl Mercaptan 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 Mercaptan, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH.
tert-Butyl Mercaptan is used as an odorant for natural gas, which is otherwise odorless.
tert-Butyl Mercaptan may also have been used as a flavoring agent.
Applications of tert-Butyl Mercaptan
tert-Butyl Mercaptan was used in reaction of 2-methyl-2-propanethiol.
tert-Butyl Mercaptan was also used in the synthesis of chain-transfer agents for reversible addition-fragmentation chain-transfer copolymerization of vinylidene chloride and methyl acrylate.
Physico-chemical Properties of tert-Butyl Mercaptan
Molecular Formula : C4H10S
Molar Mass : 90.19
Density : 0.8g/mLat 25°C(lit.)
Melting Point : -1.1 °C
Boling Point : 62-65°C(lit.)
Flash Point : −12°F
Water Solubility : Slightly soluble in water
Solubility : 1.47g/l slightly soluble
Vapor Presure : 303.5 mm Hg ( 37.7 °C)
Vapor Density : 3.1 (vs air)
Appearance : Liquid
Color : Clear colorless
Merck : 14,1579
BRN : 505947
pKa : pK1:11.22 (25°C,μ=0.1)
Storage Condition : Flammables area
Stability : Stable. Flammable - note low flashpoint. Incompatible with strong oxidizing agents.
Refractive Index : n20/D 1.423(lit.)
First aid measures of Tert-Butyl mercaptan
General advice :
Move out of dangerous area.
Show this material safety data sheet to the doctor in attendance.
Symptoms of poisoning may appear several hours later.
Do not leave the victim unattended.
If inhaled :
If unconscious, place in recovery position and seek medical advice.
If symptoms persist, call a physician.
In case of skin contact :
If on skin, rinse well with water.
If on clothes, remove clothes.
In case of eye contact :
Flush eyes with water as a precaution.
Remove contact lenses.
Protect unharmed eye.
Keep eye wide open while rinsing.
If eye irritation persists, consult a specialist.
If swallowed :
Keep respiratory tract clear.
Do NOT induce vomiting.
Do not give milk or alcoholic beverages.
Never give anything by mouth to an unconscious person.
If symptoms persist, call a physician.
Take victim immediately to hospital.
Substance identity
EC / List no.: 200-890-2
CAS no.: 75-66-1
Mol. formula: C4H10S
Hazard classification & labelling of tert-Butyl Mercaptan
Danger! According to the classification provided by companies to ECHA in REACH registrations this substance is toxic to aquatic life with long lasting effects, is a highly flammable liquid and vapour, causes serious eye irritation and may cause an allergic skin reaction.
About tert-Butyl Mercaptan
tert-Butyl Mercaptan is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
tert-Butyl Mercaptan is used by consumers, in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of tert-Butyl Mercaptan
tert-Butyl Mercaptan is used in the following products: perfumes and fragrances.
Other release to the environment of tert-Butyl Mercaptan is likely to occur from: indoor use as reactive substance.
Article service life of tert-Butyl Mercaptan
ECHA has no public registered data on the routes by which tert-Butyl Mercaptan is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers of tert-Butyl Mercaptan
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
ECHA has no public registered data on the types of manufacture using this substance.
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Formulation or re-packing of tert-Butyl Mercaptan
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
Release to the environment of tert-Butyl Mercaptan can occur from industrial use: formulation of mixtures.
Uses at industrial sites of tert-Butyl Mercaptan
tert-Butyl Mercaptan is used in the following products: perfumes and fragrances.
tert-Butyl Mercaptan is used in the following areas: municipal supply (e.g. electricity, steam, gas, water) and sewage treatment and scientific research and development.
tert-Butyl Mercaptan is used for the manufacture of: chemicals and .
Release to the environment of tert-Butyl Mercaptan can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates) and of substances in closed systems with minimal release.
Manufacture of tert-Butyl Mercaptan
Release to the environment of tert-Butyl Mercaptan can occur from industrial use: manufacturing of the substance.
Synonyms:
2-methylpropane-2-thiol
2-methylpropane-2-thiol
2-Propanethiol, 2-methyl-
2-Propanethiol, 2-methyl-
2-methylpropane-2-thiol
2-Propanethiol, 2-methyl
tert-Butyl Mercaptan
Tertiobutylmercaptan
75-66-1
2-Methyl-2-propanethiol
tert-Butyl mercaptan
75-66-1
2-Methylpropane-2-thiol
tert-Butylthiol
tert-Butanethiol
2-Propanethiol, 2-methyl-
T-BUTYL MERCAPTAN
tert-Butylmercaptan
1,1-Dimethylethanethiol
t-Butylmercaptan
2-Isobutanethiol
tertiary-Butyl mercaptan
tert-butyl thiol
2-methyl-propane-2-thiol
489PW92WIV
3374-16-1
TBM
t-BuSH
HSDB 1611
EINECS 200-890-2
BRN 0505947
tertbutanethiol
UNII-489PW92WIV
t-butanethiol
terbutyl mercaptan
tBuSH
tert.-butylmercaptan
tert-C4H9SH
tert. butyl mercaptan
tert.-butyl mercaptan
HS-t-Bu
tert-Butyl hydrosulfide
2-methyl-2propanethiol
2-methylpropan-2-thiol
2-Methyl-2-propylthiol
DSSTox_CID_6418
BUTANETHIOL, TERT-
EC 200-890-2
DSSTox_RID_78108
DSSTox_GSID_26418
4-01-00-01634 (Beilstein Handbook Reference)
CHEMBL3182458
DTXSID0026418
2-Methyl-2-propanethiol, 99%
TERT-BUTYL MERCAPTAN [MI]
AMY28695
ZINC4706566
Tox21_200874
MFCD00004857
NSC229569
STL264247
AKOS000121277
AT13962
NSC-229569
CAS-75-66-1
NCGC00248858-01
NCGC00258428-01
DB-000158
FT-0612928
M0405
Q973473
W-109267
F0001-1902
16528-55-5
1,1-Dimethylethanethiol
200-890-2 [EINECS]
2-Methyl-2-propanethiol [ACD/IUPAC Name]
2-Méthyl-2-propanethiol [French] [ACD/IUPAC Name]
2-Methyl-2-propanthiol [German] [ACD/IUPAC Name]
2-Methylpropane-2-thiol
2-Propanethiol, 2-methyl- [ACD/Index Name]
75-66-1 [RN]
MFCD00004857
propane-2-thiol, 2-methyl-
TBM
t-Butyl mercaptan
t-Butylmercaptan
t-butylthiol
tert.-Butanethiol
TERT-BUTANETHIOL
tert-Butyl Mercaptan
tert-butyl thiol
tert-Butylmercaptan
Tert-Butylthiol [Wiki]
tertiary-Butyl mercaptan
TZ7660000
[75-66-1] [RN]
15800-78-9 [RN]
16528-55-5 [RN]
2-ISOBUTANETHIOL
2-METHYL-2-PROPANETHIOL|2-METHYLPROPANE-2-THIOL
2-Methyl-2-propylthiol
3374-16-1 [RN]
4-01-00-01634 (Beilstein Handbook Reference) [Beilstein]
99224-24-5 [RN]
EINECS 200-890-2
ETHYLTHIO, 1,1-DIMETHYL-
hydrogen tert-butylsulfanide
tert-Butyl hydrosulfide
tert-C4H9SH
489PW92WIV [DBID]
505947 [DBID]
109207_ALDRICH [DBID]
20230_FLUKA [DBID]
519499_ALDRICH [DBID]
BRN 0505947 [DBID]
HSDB 1611 [DBID]
NSC229569 [DBID]
NSC229612 [DBID]
NSC3903 [DBID]
NSC61733 [DBID]
UNII:489PW92WIV [DBID]
UNII-489PW92WIV [DBID]
ZINC04706566 [DBID]
