1,2-Octanediol

Base Information

• Chemical Name: 1,2-Octanediol
• CAS No.: 1117-86-8
• Deprecated CAS: 87720-89-6,2205885-37-4
• Molecular Formula: C8H18O2
• Molecular Weight: 146.23
• Hs Code.: 29053990
• European Community (EC) Number: 214-254-7
• NSC Number: 71546
• UNII: 00YIU5438U
• DSSTox Substance ID: DTXSID9036646
• Nikkaji Number: J103.154F
• Wikipedia: 1,2-Octanediol
• Wikidata: Q27115777
• RXCUI: 1363571
• Metabolomics Workbench ID: 3180
• ChEMBL ID: CHEMBL3186864
• Mol file: 1117-86-8.mol

Synonyms:1,2-dihydroxyoctane;1,2-octanediol;caprylyl glycol

Chemical Property of 1,2-Octanediol

Chemical Property:

• Appearance/Colour: colorless to white low melting solid
• Vapor Pressure: 0.00559mmHg at 25°C
• Melting Point: 36-38 °C(lit.)
• Refractive Index: 1.452
• Boiling Point: 243 °C at 760 mmHg
• PKA: 14.60±0.10(Predicted)
• Flash Point: 109.1 °C
• PSA: 40.46000
• Density: 0.914 g/cm³
• LogP: 1.31000
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: 3 g/L (20°C)
• Water Solubility.: 3 g/L (20 ºC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 146.130679813
• Heavy Atom Count: 10
• Complexity: 64.3

Purity/Quality:

98% ^*data from raw suppliers

1,2-Octanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 37/39-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CCCCCCC(CO)O
• Recent EU Clinical Trials: A Multicentre Phase III trial of 1,2-octanediol at 5%(w/v (KindaPed?) compared with Malathion 0.5% (w/v) (Derbac-M Liquid) in the treatment of head lice
• Uses: 1,2-Octanediol has a variety of applications. It is used to improve HPLC separation of organic acids and bases and to synthesize halohydrin palmitates. Additionally, it is studied for its potential use as a pediculicide and has been shown to be effective against louse infestations. caprylyl glycol (1,2-Octanediol) is an emollient with moisturizing properties that may also be used as a cosmetic stabilizer. When found in combination with phenoxyethanol these two ingredients work together as an anti-microbial. 1,2-Octanediol is a novel surfactant used in the treatment of head louse. Also used in the cosmetics industry in the formulations of sunscreen gels and eye make-up.

Technology Process of 1,2-Octanediol

There total 165 articles about 1,2-Octanediol 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: 28.0%

2-hexylboriran-1-ol → octanol (111-87-5) + rac-octan-2-ol (4128-31-8,113301-48-7,4128-32-9) + 1,2-octandiol (1117-86-8)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; at 0 ℃;

DOI:10.1016/j.mencom.2018.11.003

Reference yield: 16.0%

oct-1-ene (111-66-0,25068-25-1) → 1,2-octandiol (1117-86-8) + 2-oxooctanoic acid (328-51-8)

Guidance literature:

With oxygen; In acetonitrile; at 25 ℃; for 24h; Sealed tube; Irradiation; Green chemistry;

DOI:10.1039/d0cy02352c

Reference yield:

exo-2-norbornyldichloroborane-dimethyl sulfide → octanol (111-87-5) + rac-octan-2-ol (4128-31-8,113301-48-7,4128-32-9) + 1,2-octandiol (1117-86-8) + Norborneol (497-36-9,497-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: bis(cyclopentadienyl)titanium dichloride; magnesium / tetrahydrofuran / 21 h / 0 - 60 °C / Inert atmosphere

2: dihydrogen peroxide; sodium hydroxide / 0 °C

With bis(cyclopentadienyl)titanium dichloride; dihydrogen peroxide; magnesium; sodium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.jorganchem.2018.08.005

upstream raw materials:

oct-1-ene

trifluoroacetyl peroxide

2,2,2-trifluoroethanol

(2R,3S)-3-pentyloxiranemethanol

Downstream raw materials:

C₂₂H₂₄N₆O₁₂

C₂₂H₂₄N₆O₁₂

oenanthic acid

(S)-octane-1,2-diol

Refernces

• 1、 Ottenbacher, Roman V.,Bryliakov, Konstantin P.,Talsi, Evgenii P.. "Nonheme manganese-catalyzed asymmetric oxidation. A lewis acid activation versus oxygen rebound mechanism: Evidence for the "third oxidant"". . p. 8620 - 8628. Retrieved 2010.
• 2、 Marko, Istvan E.,Ates, Ali,Gautier, Arnaud,Leroy, Bernard,Plancher, Jean-Marc,Quesnel, Yannick,Vanherck, Jean-Christophe. "Cerium(IV)-catalyzed deprotection of acetals and ketals under mildly basic conditions". . p. 3207 - 3209. Retrieved 1999.
• 3、 Barchi,J.J.,Moore,R.E.,Patterson,G.M.. "-". . p. 8193. Retrieved 1984.
• 4、 Mas-Balleste, Ruben,Costas, Miquel,Van Den Berg, Tieme,Que Jr., Lawrence. "Ligand topology effects on olefin oxidations by bio-inspired [Fe II(N2Py2)] catalysts". . p. 7489 - 7500. Retrieved 2006.
• 5、 Kaduskar, Rahul D.,Dhavan, Atul A.,Dallavalle, Sabrina,Scaglioni, Leonardo,Musso, Loana. "Total synthesis of the salicyldehydroproline-containing antibiotic promysalin". . p. 2034 - 2041. Retrieved 2016.
• 6、 Bizzarri, Bruno Mattia,Botta, Lorenzo,Crucianelli, Marcello,Fanelli, Angelica,Ferella, Francesco,Gontrani, Lorenzo,Sadun, Claudia,Saladino, Raffaele. "Dendrimer crown-ether tethered multi-wall carbon nanotubes support methyltrioxorhenium in the selective oxidation of olefins to epoxides". . p. 17185 - 17194. Retrieved 2020.
• 7、 Kejriwal, Ambica,Biswas, Sachidulal,Biswas, Achintesh N.,Bandyopadhyay, Pinaki. "Cis-Dihydroxylation of electron deficient olefins catalysed by an oxo-bridged diiron(III) complex with H2O2". . p. 77 - 84. Retrieved 2016.
• 8、 Yanada, Reiko,Takemoto, Yoshiji. "OsO4-catalyzed dihydroxylation of olefins in ionic liquid [emim]BF4: A recoverable and reusable osmium". . p. 6849 - 6851. Retrieved 2002.
• 9、 Khafizova, Leila O.,Khusainova, Liliya I.,Tyumkina, Tat'yana V.,Ryazanov, Kirill S.,Popod'ko, Natal'ya R.,Dzhemilev, Usein M.. "An original catalytic synthesis of boriran-1-ols". . p. 577 - 578. Retrieved 2018.
• 10、 Rubinstein, Amir,Carmeli, Raanan,Neumann, Ronny. "Formation of persulphate from sodium sulphite and molecular oxygen catalysed by H5PV2Mo10O40-aerobic epoxidation and hydrolysis". . p. 13247 - 13249. Retrieved 2014.