2209-86-1

Basic information

• Product Name: loprodiol
• Synonyms: loprodiol;2,2-Bis(chloromethyl)-1,3-propanediol;Dispranol;2,2-bis(chloromethyl)propane-1,3-diol
• CAS NO: 2209-86-1
• Molecular Formula: C₅H₁₀Cl₂O₂
• Molecular Weight: 173.038
• EINECS: 218-635-9
• Mol File: 2209-86-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 79-80° (uncorr), 83° (corr), also reported as 65° and 95°
• Boiling Point: bp12 158.5-160°
• Flash Point: 156.3°C
• Appearance: /
• Density: 1.2950 (rough estimate)
• Vapor Pressure: 8.73E-06mmHg at 25°C
• Refractive Index: 1.4595 (estimate)
• PKA: 13.63±0.10(Predicted)
• CAS DataBase Reference: loprodiol(CAS DataBase Reference)
• NIST Chemistry Reference: loprodiol(2209-86-1)
• EPA Substance Registry System: loprodiol(2209-86-1)

Safety Data

• Hazardous Substances Data: 2209-86-1(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic by ingestion,intraperitoneal, and possibly other routes. When heated todecomposition it emits toxic fumes of Cl-.

InChI:InChI=1/C5H10Cl2O2/c6-1-5(2-7,3-8)4-9/h8-9H,1-4H2

Upstream product

• 78-71-7 3,3-bis(chloromethyl)oxetane 
• 115-77-5 Pentaerythritol 
• 110-86-1 pyridine 
• 7719-09-7 thionyl chloride 
• 770-74-1 2,2-dimethyl-5,5-bis(hydroxymethyl)-1,3-dioxane 
• 2210-05-1 5,5-dichloromethyl-2-thia-1,3-dioxane 2-oxide 
• 2425-41-4 5,5-dihydroxymethyl-2-phenyl-1,3-dioxane 

Downstream Products

• 174-79-8 2,6-dioxaspiro<3.3>heptane 
• 4351-76-2 3-ethoxymethyl-3-hydroxymethyl-oxetane 
• 4351-77-3 3-(hydroxymethyl)-3-chloromethyl oxetane 
• 26344-43-4 2-Benzyl-5,5-bischlormethyl-2-oxo-1,3,2-dioxaphosphorinan 
• 38578-33-5 5,5-Bis-chloromethyl-2-(4-chloro-phenoxy)-[1,3,2]dioxaphosphinane 2-oxide 
• 38578-32-4 5,5-Bis-chloromethyl-2-phenoxy-[1,3,2]dioxaphosphinane 2-oxide 
• 38578-34-6 2-(4-Bromo-phenoxy)-5,5-bis-chloromethyl-[1,3,2]dioxaphosphinane 2-oxide 
• 38578-43-7 (5,5-Bis-chloromethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-(2,4,6-tribromo-phenyl)-amine 
• 38578-42-6 (5,5-Bis-chloromethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-(2,4-dibromo-phenyl)-amine 
• 38578-45-9 (5,5-Bis-chloromethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-(4-chloro-phenyl)-amine 
• 38598-38-8 (5,5-Bis-chloromethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-(4-bromo-phenyl)-amine 
• 38578-29-9 5,5-Bis-chloromethyl-2-pentachlorophenyloxy-[1,3,2]dioxaphosphinane 2-oxide 
• 38578-35-7 5,5-Bis-chloromethyl-2-(2,4,6-tribromo-phenoxy)-[1,3,2]dioxaphosphinane 2-oxide 
• 6103-09-9 2-phenyl-5,5-bis(chloromethyl)-1,3-dioxane 

Relevant articles and documents

Synthesis and antibacterial activity of new dimeric pyridinium chlorides based on 2,2-bis(hydroxymethyl)propane-1,3-diyl spacer

New bispyridinium dichlorides based on 2,2-bis(hydroxymethyl)propane-1,3-diyl spacer were synthesized from pentaerythritol, 4-aminopyridine, and carboxylic acids. The resulting biocides possess a high antibacterial effect. The minimal inhibitory concentration (MIC) of these compounds against pathogenic bacteria, namely, gram-positive Methicillin-resistant Staphylococcus aureus (strain ATCC 25923) and gram-negative Escherichia coli (ATCC 25922) and Pseudomonas aeruginosa (ATCC 27853), was established. The influence of the alkyl substituent length in salts on their microbiological activity was studied.

The mixed diol-dithiol 2,2-bis-(sulfanylmethyl)propane-1,3-diol: Characterization of key intermediates on a new synthetic pathway

A new synthetic route to 2,2-bis(sulfanylmethyl)propane-1,3-diol, (II), is described starting from the commercially available 2,2-bis(hydroxymethyl) propane-1,3-diol. The structures of two intermediates on this route are described. 5,5-Dimethenyl-2,2-dimethyl-1,3-dioxane bis(thiocyanate) (systematic name: {[5-(cyanosulfanyl)-2,2-dimethyl-1,3-dioxan-5-yl]sulfan-yl}formo-nitrile), C10H14N2O2S2, (X), crystallizes in the space group P21/c with no symmetry relationship between the two thio-cyanate groups. There is a short intra-molecular N...S contact for one thio-cyanate group, while the second group is positioned such that this type of interaction is not possible. 1,3-(Hydroxymethyl)propane-1,3- diyl bis(thiocyanate), C7H10N2O 2S2, (XI), also features a single short N...S contact in the solid state. Hydrogen bonding between two mol-ecules of compound (XI) results in the formation of dimers in the crystal, which are then linked together by a second hydrogen-bond interaction between the dimers. In addition, the structures of two inter-mediates from an unsuccessful alternative synthesis of (II) are reported. 2,2-Bis(chloromethyl)propane-1,3-diol, C5H 10Cl2O2, (VI), crystallized as an inversion twin with a minor twin fraction of 0.43 (6). It forms a zigzag structure as a result of intermolecular hydrogen bonding. The structure of 9,9-di-methyl-2,4,8, 10-tetraoxa-3λ4-thiaspiro-[5.5]undecan-3-one, C 8H14O5S, (VII), shows evidence for a weak S...O contact with a distance of 3.2529 (11) A.

SYNTHESIS AND BRONCHOLYTIC ACTIVITY OF 3,3-DISUBSTITUTED OXETANES

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