Description

Lawesson’s Reagent (CAS 19172-47-5) is a highly versatile and widely used organosulfur compound with the molecular formula C₁₄H₁₄O₂P₂S₄. This yellow crystalline solid is renowned for its role as a thionation agent, efficiently converting carbonyl groups (C=O) into thiocarbonyl groups (C=S) in ketones, amides, esters, and lactams. Its IUPAC name is 2,4-bis(4-methoxyphenyl)-2,4-bis(sulfanylidene)-1,3,2λ⁵,4λ⁵-dithiadiphosphetane. With a purity of ≥95%, it is ideal for organic synthesis, pharmaceutical research, and material science applications. Packaged under inert gas to ensure stability, this reagent is moisture-sensitive and should be stored in a cool, dry place. Suitable for use by professional chemists in controlled laboratory environments.

Properties

• CAS Number: 19172-47-5
• Complexity: 425
• IUPAC Name: 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2lambda5,4lambda5-dithiadiphosphetane
• 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
• InChI Key: CFHGBZLNZZVTAY-UHFFFAOYSA-N
• Exact Mass: 403.93518837
• Molecular Formula: C14H14O2P2S4
• Molecular Weight: 404.5
• SMILES: COC1=CC=C(C=C1)P2(=S)SP(=S)(S2)C3=CC=C(C=C3)OC
• Topological: 133
• Monoisotopic Mass: 403.93518837
• Physical Description: Off-white, light yellow, or light brown powder with a stench;
• Synonyms: Lawesson’s reagent, 19172-47-5, Lawesson reagent, 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane, 1,3,2,4-Dithiadiphosphetane, 2,4-bis(4-methoxyphenyl)-, 2,4-disulfide, P-Anisyldithiophosphonic anhydride, 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide, EINECS 242-855-4, NSC 150550, NSC-150550, 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, DTXSID4066460, LAWESSON’S REAGENT [MI], 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulphide, 2,4-DI(P-METHOXYPHENYL)-1,3-DITHIADIPHOSPHETANE DISULFIDE, 2,4-BIS(P-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE 2,4-DISULFIDE, PHOSPHONOTRITHIOIC ACID, (P-METHOXYPHENYL)-, BIMOL. CYCLIC ANHYDROSULFIDE, 2,4-bis[4-methoxyphenyl]-1,3-dithia-2,4-diphosphetane 2,4-disulphide, 2,4BMP-DTDPDS, DTXCID8036023, 4Methoxyphenylthiophosphoric cyclic di(thioanhydride), 2,4Bis(4methoxyphenyl)1,3,2,4dithiadiphosphetane2,4disulfide, 2,4Bis(4methoxyphenyl)1,3dithia2,4diphosphetane 2,4disulfide, 2,4Bis(4methoxyphenyl)1,3dithia2,4diphosphetane 2,4disulphide, 2,4Bis(4methoxyphenyl)2,4dithioxo1,3,2,4dithiadiphosphetane, 1,3,2,4Dithiadiphosphetane, 2,4bis(4methoxyphenyl), 2,4disulfide, 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, Lawesson’ reagent, MFCD00005171, A4125MQ8RX, NSC150550, 4-Methoxyphenylthiophosphoric cyclic di(thioanhydride), 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione, 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide, 2,4-Bis-(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane, Lawessons reagent, 2,4-Bis-(4-methoxy-phenyl)-[1,3,2,4]dithiadiphosphetane 2,4-disulfide, 2,4-Bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide, 2,4-Bis-[4-methoxyphenyl]-1,3-dithia-2,4-diphosphetane 2,4-disulfide, C14H14O2P2S4, UNII-A4125MQ8RX, Lawesson’s Reagent, Lawesson reagent, 97%, SCHEMBL7961, SCHEMBL12999906, 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide, AC-547, BBL010078, SBB056186, STL145901, AKOS005716277, CS-W013865, FL32202, 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2^{5},4^{5}-dithiadiphosphetane, 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide; p-Methoxyphenylthionophosphine sulfide dimer; Lawesson’s Reagent;, AC-16496, AS-17360, BP-21250, p-Methoxyphenylthionophosphine sulfide dimer, B1133, NS00026251, ST51007175, EN300-26784, A813513, Q419324, F0001-0690, 2,4-bis(4-Methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfide, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane2,4-disulfide, 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetan, 2,4-bis(4methoxyphenyl)1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo1,3,2,4-dithiadiphosphetane, 2,4bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4disulfide, 2,4bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane2,4-disulfide, bis(4-methoxyphenyl)-1,3,2??,4??-dithiadiphosphetane-2,4-dithione, [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide], 1,3,2,4-dithiadiphosphetane,2,4-bis(4-methoxyphenyl)-,2,4-disulfide, 2,4 bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide, 2,4-bis (4-methoxyphenyl) -1,3 -dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis (4-methoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide, 2,4-bis (4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis (4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide, 2,4-bis(4- methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4- disulfide, 2,4-bis(4- methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis(4-methoxyphenyl) -1, 3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis(4-methoxyphenyl)- 1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide #, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide, 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide, 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide, 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane2,4-disulfide, 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithia-diphosphetan, 2,4-bis(4-methoxyphenyl)-l,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide, 2,4-bis(p-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis- (4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis-(4-methoxy-phenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide, 2,4-bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, 2,4-bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide, 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulphide, 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphos phetane, 2,4-bis-(4-methoxyphenyl)-l,3-dithia-2,4-diphosphetan-2,4-disulphide, 2,4-Bis-(p-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide, 1,3,2,4-DITHIADIPHOSPHETANE, 2,4-BIS(4-METHOXYPHENYL)-, 2,4- DISULFIDE, 2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2,4- DISULFIDE, 2,4-bis(4-methoxyphenyl)-2,4-bis(sulfanylidene)-1,3,2|E5,4|E5-dithiadiphosphetane, 2,4-bis(4-methoxyphenyl)-2,4-bis(sulfanylidene)-1,3,2lambda5,4lambda5-dithiadiphosphetane, 2,4-BIS(4-METHOXYPHENYL)-2,4-DISULFANYLENE-1,3,2,4-DITHIADIPHOSPHETANE, 2,4-Di(4-methoxyphenyl)-1,3,2lambda5,4lambda5-dithiadiphosphetane-2,4-dithione, bis(4-methoxyphenyl)-1,3,2lambda5,4lambda5-dithiadiphosphetane-2,4-dithione, 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide;2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithion e

Application

Lawesson’s Reagent is primarily used for the thionation of carbonyl compounds to their corresponding thio-analogs, a critical step in synthesizing thioketones, thioamides, and thioesters. It is widely applied in medicinal chemistry for the preparation of sulfur-containing bioactive molecules and heterocycles. Additionally, it serves as a key reagent in the synthesis of organosulfur compounds for agrochemicals and materials science research.

Safety and Hazards

GHS Hazard Statements

• H261 (86.2%): In contact with water releases flammable gas [Danger Substances and mixtures which in contact with water, emit flammable gases]
• H302 (24.1%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (15.5%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H332 (24.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

• P231+P232, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P370+P378, P402+P404, and P501

Hazard Classes and Categories

• Water-react. 2 (86.2%)
• Acute Tox. 4 (24.1%)
• Acute Tox. 4 (15.5%)
• Acute Tox. 4 (24.1%)

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