Lawesson's Reagent

The Lawesson's reagent, with the CAS registry number 19172-47-5, is also known as 2,4-Di(p-methoxyphenyl)-1,3-dithiadiphosphetane disulfide. It belongs to the product categories of Dithietanes; Simple 4-Membered Ring Compounds; Sulfur Compounds (for Synthesis); Synthetic Organic Chemistry; Ring Systems. Its EINECS number is 242-855-4. This chemical's molecular formula is C₁₄H₁₄O₂P₂S₄ and molecular weight is 404.47. What's more, its systematic name is 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide. Its classification code is TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. It is stable at common pressure and temperature, and it should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from water, moisture and oxides. It is a chemical compound used in organic synthesis as a thiation agent. The main use of Lawesson's reagent is the thionation of carbonyl compounds. Additionally, Lawesson's reagent has been used to thionate enones, esters, lactones, amides, lactams and quinones.

Physical properties of Lawesson's reagent are: (1)ACD/LogP: 9.343 # of Rule of 5 Violations: 1; (2)ACD/LogD (pH 5.5): 9.34; (3)ACD/LogD (pH 7.4): 9.34; (4)ACD/BCF (pH 5.5): 1000000.00; (5)ACD/BCF (pH 7.4): 1000000.00; (6)ACD/KOC (pH 5.5): 2880933.00; (7)ACD/KOC (pH 7.4): 2880933.00; (8)#H bond acceptors: 2; (9)#H bond donors: 0; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 152.86 Å²; (12)Index of Refraction: 1.706; (13)Molar Refractivity: 105.655 cm³; (14)Molar Volume: 271.569 cm³; (15)Polarizability: 41.885×10^-24cm³; (16)Surface Tension: 73.68 dyne/cm; (17)Density: 1.489 g/cm³; (18)Flash Point: 271.782 °C; (19)Enthalpy of Vaporization: 76.988 kJ/mol; (20)Boiling Point: 525.779 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by methoxybenzene by heating. This reaction will need reagent P₄S₁₀ with the reaction time of 6 hours. The yield is about 88%.

Uses of Lawesson's reagent: it can be used to produce 3-methyl-2-cyclohexenethione at the temperature of 60 °C. It will need solvents benzene, toluene with the reaction time of 1 hour. The yield is about 86%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. If contact with water, it will liberate toxic, extremely flammable gases, so you should keep the container dry. It is irritating to respiratory system. You should not breathe dust. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water).

You can still convert the following datas into molecular structure:
(1)SMILES: S=P1(SP(=S)(S1)c2ccc(OC)cc2)c3ccc(OC)cc3
(2)Std. InChI: InChI=1S/C14H14O2P2S4/c1-15-11-3-7-13(8-4-11)17(19)21-18(20,22-17)14-9-5-12(16-2)6-10-14/h3-10H,1-2H3
(3)Std. InChIKey: CFHGBZLNZZVTAY-UHFFFAOYSA-N