3312-96-7

Basic information

• Product Name: 3-(phenyldisulfanyl)propanoic acid
• CAS NO: 3312-96-7
• Molecular Formula: C₉H₁₀O₂S₂
• Molecular Weight: 214.3045
• Mol File: 3312-96-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 361.4°C at 760 mmHg
• Flash Point: 172.3°C
• Density: 1.32g/cm³
• Vapor Pressure: 7.47E-06mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: 3-(phenyldisulfanyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(phenyldisulfanyl)propanoic acid(3312-96-7)
• EPA Substance Registry System: 3-(phenyldisulfanyl)propanoic acid(3312-96-7)

Safety Data

• Hazardous Substances Data: 3312-96-7(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 107-96-0 3-mercaptopropionic acid 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 3312-97-8 N-(2-Tritylthio-ethyl)-5-phenyl-4,5-dithiapentansaeureamid 
• 382599-34-0 N-methyl-N-(3-phenyldithio-propanoyl)-L-alanine 
• 15515-60-3 N-(2-Benzhydrylthio-ethyl)-(5-phenyl-4,5-dithia-pentan)-saeureamid 
• 1119-62-6 3,3'-dithiobis(propionic acid) 
• 123861-58-5 NHS-DTP 
• 3312-99-0 N-<3-Thiapropyl>-5-phenyl-4,5-dithiapentanamid-disulfid 
• 3313-02-8 N-[2-(4-Nitro-benzyldisulfanyl)-ethyl]-3-phenyldisulfanyl-propionamide 
• 3313-01-7 N-(6-Carboxy-3.4-dithiahexyl)-5-phenyl-4.5-dithiapentan-saeureamid 

Relevant articles and documents

Photochemical metal-free aerobic oxidation of thiols to disulfides

Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is

Process for the preparation and purification of thiol-containing maytansinoids

The present invention provides a process for the preparation and purification of thiol-containing maytansinoids comprising the steps of: (1) reductive hydrolysis of a maytansinoid C-3 ester with a reducing agent selected from the group consisting lithium trimethoxyaluminum hydride (LiAl(OMe)3H), lithium triethoxyaluminum hydride (LiAl(OEt)3H), lithium tripropoxyaluminum hydride (LiAl(OPr)3H), sodium trimethoxyaluminum hydride (NaAl(OMe)3H), sodium triethoxyaluminum hydride (NaAl(OEt)3H) and sodium tripropoxyaluminum hydride (NaAl(OPr)3H) to yield a maytansinol; (2) purifying the maytansinol to remove side products when present; (3) esterifying the purified maytansinol with a carboxylic acid to yield a mixture of an L- and a D-aminoacyl ester of maytansinol; (4) separating the L-aminoacyl ester of maytansinol from the reaction mixture in (3); (5) reducing the L-aminoacyl ester of maytansinol to yield a thiol-containing maytansinoid; and (6) purifying the thiol-containing maytansinoid.

Conversion of Thiols into Disulfides with Diethyl Bromomalonate

Reaction of aliphatic, aromatic and heterocyclic thiols (2 and 5a-h) with diethyl bromomalonate (1a) gave the corresponding symmetrical disulfides (3 and 6a-h) in high yields.In the case of L-cysteine (5i), glutathione (5j) or thiamine (5k), the reaction also gave L-cystine (6i), oxidized glutathione (6j) or thiamine disulfide (6k) in high yields regardless of the presence of other functional groups.Dithiols (11) were converted into cyclic disulfides (12) by this method.In particular, N-(2-mercapto-2-methylpropionyl)-L-cysteine (9) was converted into (4R)-tetrahydro-7,7-dimethyl-6-oxo-3H-1,2,5-dithiazepine-4-carboxylic acid (10) (obtained in poor yields by general oxidation methods) in good yields.The intermediate in the reaction was considered to be sulfenyl bromide (8).Keywords-diethyl bromomalonate; thiol; dithiol; disulfide; cyclic disulfide; thiol oxidation; disulfide formation; N-(2-mercapto-2-methylpropionyl)-L-cysteine; (4R)-tetrahydro-7,7-dimethyl-6-oxo-3H-1,2,5-dithiazepine-4-carboxylic acid