3-Iodo-2-propynyl butylcarbamate

Base Information

• Chemical Name: 3-Iodo-2-propynyl butylcarbamate
• CAS No.: 55406-53-6
• Deprecated CAS: 104732-42-5,161849-41-8,84826-91-5,85045-09-6,1389329-45-6,84826-91-5,85045-09-6
• Molecular Formula: C8H12INO2
• Molecular Weight: 281.093
• Hs Code.: 29241990
• European Community (EC) Number: 259-627-5,617-662-7
• UN Number: 3077
• UNII: 603P14DHEB
• DSSTox Substance ID: DTXSID0028038
• Nikkaji Number: J94.789J
• Wikipedia: Iodopropynyl_butylcarbamate
• Wikidata: Q2928998
• RXCUI: 1426467
• Metabolomics Workbench ID: 155600
• ChEMBL ID: CHEMBL1893913
• Mol file: 55406-53-6.mol

Synonyms:3-iodo-2-propynyl-butylcarbamate;3-iodo-2-propynylbutylcarbamate;3-IPBC;iodopropynyl butylcarbamate

Chemical Property of 3-Iodo-2-propynyl butylcarbamate

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 0.005Pa at 25℃
• Melting Point: 64-68 °C(lit.)
• Refractive Index: 1.546
• Boiling Point: 321.8 °C at 760 mmHg
• PKA: 12.03±0.46(Predicted)
• Flash Point: 148.4 °C
• PSA: 38.33000
• Density: 1.606 g/cm³
• LogP: 2.29950
• Storage Temp.: Refrigerator
• Solubility.: soluble in Methanol
• Water Solubility.: 168mg/L at 20℃
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 280.99128
• Heavy Atom Count: 12
• Complexity: 192
• Transport DOT Label: Class 9

Purity/Quality:

≥99% ^*data from raw suppliers

3-Iodo-2-propynyl N-butylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53-50
• Safety Statements: 60-61-29

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: CCCCNC(=O)OCC#CI
• Recent ClinicalTrials: Treatment of Chronic Fatigue Syndrome (CFS) With Iodinated Activated Charcoal (IodoCarb?)
• Description: Iodopropynyl butylcarbamate is a preservative that has been used as an industrial fungicide since the 1970s and more recently has been combined with formaldehydereleasing agents for use in cosmetics. The North American Contact Dermatitis Group patch tested with 0.1%iodopropynyl butylcarbamate in petrolatum and found 0.2% of their patch test clinic patients had positive reactions to this chemical. Most cosmetic applications appear to require less than 0.012% of this preservative.
• Uses: Glycacil(R) 2000 is used as a preservative in personal care formulations. Glycacil(R) L is used as a preservative in personal care formulations. Glycacil(R) S is used as a preservative in personal care formulations. An antibacterial agent. Fungicide; mildewcide; preservative in cosmetics, paints and coatings, metal working fluids; wood protection. iodopropynyl butylcarbamate is a preservative with broad fungicidal activity used in skin care products. It is recommended for use in difficult formulation systems.
• Clinical Use: Iodopropynyl butylcarbamate (3-iodo-2-propynyl-butylcarbamate) is a highly effective fungicide as well as a bactericide. It was first used in the 1970s as a film fungicide for paint and then as a wood preservative, where final use concentration up to 4% was permitted. For paint and coatings usually no more than 0.5% iodopropynyl butylcarbamate is used. For metalworking fluids, adhesives, textiles, and paper, concentrations between 0.1%and 0.2% are common. The Cosmetic Ingredient Review Expert Panel concluded that iodopropynyl butylcarbamate is safe as a cosmetic ingredient in concentrations less than or equal to 0.1%and that it should not be used in products intended to be aerosolized. By 1996, iodopropynyl butylcarbamate was used in 122 formulations reported to the United States Food and Drug Administration. Iodopropynyl butylcarbamate is found in a wide variety of occupational and consumer products, including shampoos, lotions, powders, makeup, baby products, paints, coatings, metalworking fluids, household products, cooling water, building materials, and contact lenses. It is an irritant, although at low concentrations few problems have been reported.

Technology Process of 3-Iodo-2-propynyl butylcarbamate

There total 3 articles about 3-Iodo-2-propynyl butylcarbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.5%

butylcarbamic acid prop-2-ynyl ester (76114-73-3) → 3-iodo-2-propynyl butyl carbamate (55406-53-6)

Guidance literature:

butylcarbamic acid prop-2-ynyl ester; With sodium hydroxide; sodium hypochlorite; sodium iodide; In water; at 0 - 40 ℃; for 1.5h;

With acetic acid; In water; at 40 ℃; pH=6.9;

With sodium hydrogensulfite; In water; at 25 - 59 ℃; pH=6.6; Product distribution / selectivity;

Reference yield: 93.5%

→ 3-iodo-2-propynyl butyl carbamate (55406-53-6)

Guidance literature:

Reference yield: 91.0%

prop-2-yn-1-yl hydrogen carbonate (57272-05-6) + N-butylamine (109-73-9,85404-21-3) → 3-iodo-2-propynyl butyl carbamate (55406-53-6)

Guidance literature:

With hydrogenchloride; In Dimethyl ether; at 120 ℃; for 12h; Solvent; Industrial scale;

upstream raw materials:

butylcarbamic acid prop-2-ynyl ester

prop-2-yn-1-yl hydrogen carbonate

N-butylamine

Refernces

• 1、 -. "PROCESS FOR PREPARING IODOPROPARGYL COMPOUNDS". Page/Page column 2. . Retrieved 2013/02/28.
• 2、 -. "Process for the synthesis of iodopropynyl butylcarbamate in an aqueous solution of a suitable surfactant". Page/Page column 3-4. . Retrieved 2008/06/13.