10304-16-2

Basic information

• Product Name: 3-thietan-1-ol
• Synonyms: 3-thietan-1-ol;3-Hydroxythietane;3-Thietanol
• CAS NO: 10304-16-2
• Molecular Formula: C₃H₆OS
• Molecular Weight: 90.14414
• EINECS: 233-678-3
• Mol File: 10304-16-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 185.8 °C at 760 mmHg
• Flash Point: 91.3 °C
• Appearance: /
• Density: 1.336 g/cm³
• Vapor Pressure: 0.193mmHg at 25°C
• Refractive Index: 1.616
• PKA: 13.55±0.20(Predicted)
• CAS DataBase Reference: 3-thietan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-thietan-1-ol(10304-16-2)
• EPA Substance Registry System: 3-thietan-1-ol(10304-16-2)

Safety Data

• Hazardous Substances Data: 10304-16-2(Hazardous Substances Data)

Usage

Description

3-thietan-1-ol, with the molecular formula C4H8OS, is a colorless liquid thiol alcohol known for its strong odor reminiscent of fish and sulfur. It is a versatile compound that serves as a building block in the synthesis of various organic compounds, particularly in the pharmaceutical and fragrance industries, and is also used as a reagent in organic chemistry reactions.

Uses

Used in Pharmaceutical Industry:
3-thietan-1-ol is used as a building block for the synthesis of various organic compounds, contributing to the development of new pharmaceutical products. Its unique chemical properties make it a valuable component in the creation of novel drug molecules.
Used in Fragrance Industry:
In the fragrance industry, 3-thietan-1-ol is used as a building block for the synthesis of various scent compounds. Its distinctive fishy and sulfur-like odor makes it a key ingredient in the creation of realistic fish and seafood flavorings.
Used in Organic Chemistry:
3-thietan-1-ol is used as a reagent in organic chemistry reactions, facilitating the synthesis of a wide range of organic compounds. Its versatility in chemical reactions makes it an essential tool for researchers and chemists in the field.
Safety Considerations:
Despite its strong odor, 3-thietan-1-ol is considered relatively safe when handled and used properly. However, exposure to high concentrations can cause irritation to the eyes, skin, and respiratory system, necessitating proper safety measures during its use.

InChI:InChI=1/C3H6OS/c4-3-1-5-2-3/h3-4H,1-2H2

Synthetic route

epichlorohydrin (106-89-8) → 3-thietanol (10304-16-2)

Conditions	Yield
benzyltriethylammonium tetrathiomolybdate In ethanol; acetonitrile at 28℃; for 3h;	90%
With hydrogen sulfide; potassium hydroxide In water at 60℃; for 18h;	51%

1,3-Dichloro-2-propanol (96-23-1) → 3-thietanol (10304-16-2)

Conditions	Yield
With sodium sulfide; triethylhexadecylammonium chloride In dichloromethane; water for 3h;	81%

oxiranyl-methanol (556-52-5) → 3-thietanol (10304-16-2)

Conditions	Yield
Stage #1: oxiranyl-methanol With dicyclohexyl-carbodiimide; copper(l) chloride at 28℃; Stage #2: benzyltriethylammonium tetrathiomolybdate In ethanol; acetonitrile at 28℃; Further stages.;	73%

2-(chloromethyl)thiirane (3221-15-6) + ammonium thiocyanate (1147550-11-5) → 3-thietanol (10304-16-2) + 3-Thietanyl isothiocyanate (59288-36-7)

Conditions	Yield
In water; benzene at 50℃; for 2h;	A 30% B 51%

Phenethyl-thiocarbamic acid S-(3-chloro-2-hydroxy-propyl) ester → 3-thietanol (10304-16-2)

Conditions	Yield
With phenethylamine In dimethyl sulfoxide at 50℃; for 2h; Yield given;

Phenethyl-thiocarbamic acid S-(3-bromo-2-hydroxy-propyl) ester → 3-thietanol (10304-16-2)

Conditions	Yield
With phenethylamine In dimethyl sulfoxide at 50℃; for 2h; Yield given;

(+-)-1-chloro-3-mercapto-propan-2-ol → 3-thietanol (10304-16-2)

Conditions	Yield
With alkaline solution

(+-) epichlorohydrin → 3-thietanol (10304-16-2)

Conditions	Yield
With alkali hydrogensulfide solution at 50℃;

1,3-Dichloro-2-propanol (96-23-1) → 3-thietanol (10304-16-2) + 4-hydroxy-1,2-dithiolane (27550-66-9) + 1,2,3-trithian-5-ol (69337-13-9)

Conditions	Yield
Stage #1: With sulfur; ethanolamine; hydrazine In water at 65℃; for 2.5h; Stage #2: 1,3-Dichloro-2-propanol With ethanolamine; hydrazine In water at 27 - 35℃; for 2h; Stage #3: In chloroform-d1 for 18h; Inert atmosphere;

2-(chloromethyl)thiirane (3221-15-6) → 3-thietanol (10304-16-2) + N-hydroxythietan-3-amine (1418193-25-5)

Conditions	Yield
With hydroxylamine In hexane; water at 50℃; for 15h;	A n/a B 244 mg

3-thietanol (10304-16-2) + chloro-trimethyl-silane (75-77-4) → 3-trimethylsilatothietane

Conditions	Yield
In pyridine 1.) 0 deg C, 1h, 2.) room temperature, 1h;	83%

3-thietanol (10304-16-2) → 3-hydroxythietane 1-oxide (24446-67-1)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 18h; Ambient temperature;	64%

3-thietanol (10304-16-2) + 2,2'-dipyridyl carbonate (1659-31-0) → Carbonic acid pyridin-2-yl ester thietan-3-yl ester

Conditions	Yield
With triethylamine In dichloromethane at 24℃; for 12h;

3-thietanol (10304-16-2) → thioformaldehyde (865-36-1) + acetaldehyde (75-07-0)

Conditions	Yield
at 900℃; under 0.02 - 0.04 Torr;

3-thietanol (10304-16-2) + phthalimide (136918-14-4) + di-isopropyl ether (108-20-3) + diethylazodicarboxylate (1972-28-7) → 3-phthalimidoylthietane

Conditions	Yield
With triphenylphosphine In tetrahydrofuran

3-thietanol (10304-16-2) + 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H) pyrimidinyl]-benzoic acid (115784-94-6) → thietan-3-yl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate

Conditions	Yield
With pyridine; hydrogenchloride; thionyl chloride In 1,4-dioxane; N-methyl-acetamide; hexane; water; benzene

3-thietanol (10304-16-2) + 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic acid (120890-57-5) → thietan-3-yl 2-chloro-5-[3,6-dihydro-2 6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate

Conditions	Yield
With pyridine; hydrogenchloride; thionyl chloride In 1,4-dioxane; N-methyl-acetamide; hexane; water; benzene

3-thietanol (10304-16-2) + thiourea (17356-08-0) → 3-mercaptothietane (597580-25-1)

Conditions	Yield
Stage #1: 3-thietanol; thiourea With hydrogenchloride In water at 30℃; for 25h; Stage #2: With ammonia In water at 30℃; for 16h;

3-thietanol (10304-16-2) → 3-mercaptothietane (597580-25-1)

Conditions	Yield
Stage #1: 3-thietanol With hydrogenchloride; thiourea In water at 30℃; for 25h; Stage #2: With ammonia In water at 30℃; for 16h;
Stage #1: 3-thietanol With hydrogenchloride; thiourea In water at 30℃; Stage #2: With ammonia In water at 30℃;
Stage #1: 3-thietanol With hydrogenchloride; thiourea In water at 30℃; for 25h; Stage #2: With ammonia In water at 30℃; for 16h;

Upstream product

• 96-23-1 1,3-Dichloro-2-propanol 
• 3221-15-6 2-(chloromethyl)thiirane 
• 1147550-11-5 ammonium thiocyanate 
• 556-52-5 oxiranyl-methanol 
• 106-89-8 epichlorohydrin 

Downstream Products

• 865-36-1 thioformaldehyde 
• 75-07-0 acetaldehyde 
• 1418193-22-2 3-pyridinium-thietane p-toluenesulfonate 

Relevant articles and documents

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Efficient Syntheses of Thietanes and Thiete 1,1-Dioxide using Phase-Transfer Catalysis

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NOVEL ANTHRANILAMIDES, THEIR USE AS INSECTICIDE AND PROCESSES FOR PREPARING THE SAME.

The present invention relates to novel anthranilamides of Formula I, wherein, the definition of W1, W2, B1, B2, D, Z1, E, R1, R3, R4, m is as described in the description. The present invention also relates to the composition, combination, use and method of application of the anthranilamides of Formula I.

COMPOUND, POLYMERIZABLE COMPOSITION, RESIN, AND USE OF THE COMPOSITION AND THE RESIN

Disclosed is a compound represented by the following general formula (1), wherein, in the formula, M1 represents Sb or Bi; X1 and X2 each independently represent a sulfur atom or an oxygen atom; R1 represents a divalent organic group; Y1 represents a monovalent inorganic or organic group; a represents a number of 1 or 2; b represents a number of 0 or an integer of not less than 1; c represents an integer of not less than 1 and not more than d; d represents a valence of M1; when d-c is not less than 2, a plurality of Y1s each independently represent a monovalent inorganic or organic group and may be bonded to each other to form an M1-containing ring; and e represents a number of 0 or an integer of not less than 1.

Selective synthesis of isomeric dithioglycerols

Reactions of 2,3-dibromopropan-1-ol and 1,3-dichloropropan-2-ol with elemental sulfur activated in the system hydrazine hydrate-2-aminoethanol at 30-35°C gave oligomeric polysulfides which were subjected to reductive cleavage with formation of individual dithioglycerol isomers. Activation of sulfur with the use of alkali gives rise to mixtures of isomeric products.