999-90-6

Basic information

• Product Name: S-TERT-BUTYL THIOACETATE
• Synonyms: S-TERT-BUTYL THIOACETATE;CH3C(O)SC(CH3)3;Ethanethioic acid S-tert-butyl ester;S-(tert-Butyl) ethanethioate;Thioacetic acid S-(tert-butyl) ester;Thioacetic acid S-tert-butyl ester;S-tert-Butyl thioacetate 98%;Ethanethioic acid, S-(1,1-dimethylethyl) ester
• CAS NO: 999-90-6
• Molecular Formula: C₆H₁₂OS
• Molecular Weight: 132.22
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiol Esters;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thiol Esters
• Mol File: 999-90-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 135-136 °C(lit.)
• Flash Point: 93 °F
• Appearance: /
• Density: 0.927 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.68mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• BRN: 1740436
• CAS DataBase Reference: S-TERT-BUTYL THIOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: S-TERT-BUTYL THIOACETATE(999-90-6)
• EPA Substance Registry System: S-TERT-BUTYL THIOACETATE(999-90-6)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 9-13
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 999-90-6(Hazardous Substances Data)

Usage

Uses

S-tert-Butyl thioacetate may be used for the preparation of vinyloxyborane derivative.

General Description

S-tert-Butyl thioacetate is a thioester.

Purification Methods

Dissolve it in CHCl3 (EtOH-free), wash with H2O, 10% H2SO4, saturated aqueous NaHCO3 (care CO2 liberated), H2O again, dry over Drierite and anhydrous K2CO3, and fractionate under reduced pressure. [Rylander & Tarbell J Am Chem Soc 72 3021 1950, Beilstein 2 IV 546.]

InChI:InChI=1/C6H12OS/c1-5(7)8-6(2,3)4/h1-4H3

Upstream product

• 463-51-4 Ketene 
• 75-66-1 2-methylpropan-2-thiol 
• 75-36-5 acetyl chloride 
• 75-05-8 acetonitrile 
• 507-20-0 tertiary butyl chloride 
• 507-19-7 t-butyl bromide 
• 631-61-8 ammonium acetate 
• 34832-35-4 sodium thioacetate 
• 507-09-5 tiolacetic acid 
• 23728-82-7 Tributylstannyl tert-butyl sulfide 
• 108-24-7 acetic anhydride 
• 41463-35-8 1-(t-butylthio)acetylene 

Downstream Products

• 15925-47-0 S-tert-butyl acetothioacetate 
• 128806-22-4 S-tert-butyl (3S)-3-hydroxy-5-phenylpentanethioate 
• 121534-53-0 tert-butyl (3S,4S)-3-hydroxy-4-(benzyloxy)thiopentanoate 
• 157945-01-2 (S)-tert-butyl (3S,4R)-5-(benzyloxy)-3-hydroxy-4-methylpentanethioate 
• 110-06-5 di-tert-butyl disulfide 
• 507-20-0 tertiary butyl chloride 
• 52322-55-1 1,1-dimethylethanesulfenyl chloride 
• 75-36-5 acetyl chloride 
• 104805-25-6 (S)-S-tert-butyl 3-hydroxy-5-phenylpropanethioate 
• 112303-67-0 S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate 
• 189328-22-1 (3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 
• 121534-56-3 tert-butyl (3S,4S)-3-hydroxy-4-methyl-5-(benzyloxy)thiopentanoate 
• 121571-38-8 tert-butyl (3R,4S)-3-hydroxy-4-methyl-5-(benzyloxy)thiopentanoate 
• 98-86-2 acetophenone 

Relevant articles and documents

Structure-Proving Syntheses of the Polyenoyltetramic Acids Pyranonigrin J and I

The polyenoyltetramic acids pyranonigrin J (3) and pyranonigrin I (4) had been isolated from Aspergillus niger. Their origins from and roles in biosynthesis as well as the S-configurations of their stereocenter had been deduced from expression experiments with modifications of the corresponding gene cluster. We corroborated this stereochemical assignment after executing the first total syntheses of both compounds because they had essentially the same specific rotations as their natural counterparts. Our syntheses used the β-ketothioester 18 as a conjunctive reagent. It was combined with the l-serine derivatives (S)-19 or (S)-21 (“Western building blocks”), respectively, through aminolyses. Stille couplings with the stannane 13 (“Eastern building block”) followed. The resulting β-ketoamides (S)-11 and (S)-12 underwent desilylative Lacey-Dieckmann cyclizations when exposed to 8 equiv. of Bu4NF. They rendered the polyenoyltetramic acids (S)-26 [acidolysis: → (S)-3] and (S)-4, respectively.

Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C §

The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8′ and C-10′ were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.

CELL-PROTECTIVE COMPOUNDS AND THEIR USE

The present invention is directed to cell-protective, in particular, cardio- and renal-protective organic compounds, preferably to organic compounds that inhibit substrate phosphorylation by the G-protein-coupled receptor kinase 2 (GRK2, ADRBK1). Preferably, the organic compounds inhibit the GRK2-mediated phosphorylation of serine/arginine-rich splicing factor 1 (SRSF1, ASF- 1, SF2) and/or phosducin for treating hypertension, heart diseases, heart dysfunction or failure and heart disease-associated pathologies, e.g. cardiomyocyte necrosis, ischemic cardiac disease and/or ischemic heart damage or ageing. Furthermore, the present invention is directed to a method for the identification of inhibitors of the (GRK2)-mediated phosphorylation of (SRSF1) and/or phosducin.