4272-02-0

Basic information

• Product Name: undecane-1,4-diol
• Synonyms: undecane-1,4-diol;Einecs 224-263-8;1,4-Undecanediol
• CAS NO: 4272-02-0
• Molecular Formula: C₁₁H₂₄O₂
• Molecular Weight: 188.30706
• EINECS: 224-263-8
• Mol File: 4272-02-0.mol

Chemical Properties

• Melting Point: 52°C (estimate)
• Boiling Point: 156-158℃ (5 Torr)
• Flash Point: 130.7 °C
• Appearance: /
• Density: 0.9314 (rough estimate)
• Vapor Pressure: 0.000188mmHg at 25°C
• Refractive Index: 1.495 (589.3 nm 20℃)
• PKA: 15.10±0.10(Predicted)
• CAS DataBase Reference: undecane-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: undecane-1,4-diol(4272-02-0)
• EPA Substance Registry System: undecane-1,4-diol(4272-02-0)

Safety Data

• Hazardous Substances Data: 4272-02-0(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
Undecane-1,4-diol is used as a crosslinking agent for the production of polymers, such as polyurethane and polyester resins. Its diol functionality allows it to react with other monomers to form a network of polymer chains, enhancing the mechanical properties and durability of the final product.
Used in Chemical and Pharmaceutical Synthesis:
Undecane-1,4-diol is utilized as a precursor in the synthesis of various chemicals and pharmaceutical intermediates. Its two hydroxyl groups can be further modified or used as starting points for the creation of more complex molecules, making it a versatile building block in the chemical industry.
Used in Cosmetic and Personal Care Industry:
In the cosmetic and personal care industry, undecane-1,4-diol is used as a moisturizing and conditioning agent in skincare and haircare products. Its ability to form hydrogen bonds with water molecules helps to retain moisture, providing hydration and improving the texture and appearance of the skin and hair.
While undecane-1,4-diol is considered to be a relatively low-toxicity compound, it is important to follow proper handling and usage precautions to ensure safety and effectiveness in its various applications.

InChI:InChI=1/C11H24O2/c1-2-3-4-5-6-8-11(13)9-7-10-12/h11-13H,2-10H2,1H3

Upstream product

• 96-48-0 4-butanolide 
• 13125-66-1 n-heptylmagnesium bromide 
• 104-67-6 5-heptyldihydro-2(3H)-furanone 
• 2146-67-0 (dichloromethyl)lithium 
• 112630-62-3 2-Heptyl-[1,2]oxaborolane 

Downstream Products

• 111-14-8 oenanthic acid 
• 110-15-6 succinic acid 
• 104-67-6 5-heptyldihydro-2(3H)-furanone 

Relevant articles and documents

Redox-active ligand based Mn(i)-catalyst for hydrosilylative ester reduction

Herein a Mn(i) catalyst bearing a redox-active phenalenyl (PLY) based ligand is reported for the efficient hydrosilylation of esters to alcohols using the inexpensive silane source polymethylhydrosiloxane (PMHS) under mild conditions. Mechanistic investigations suggest a strong ligand-metal cooperation where a ligand-based single electron transfer (SET) process initiates the reaction through Si-H bond activation.

An efficient oxidative lactonization of 1,4-diols catalyzed by Cp*Ru(PN) complexes

An efficient oxidative lactonization of 1,4-diols in acetone is accomplished by the well-defined ruthenium catalyst, whose bifunctional nature underlies the high efficiency as well as unique chemo- and regioselectivity of the reaction which provides a rapid access to γ-butyrolactones including flavor lactones hinokinin, and muricatacin.

Reduction of carboxylic acid derivatives using diphenylsilane in the presence of a Rh-PPh3 complex

Reductions of carboxylic acid derivatives by silanes in the presence of rhodium complexes were studied. Carboxylic esters were reduced to alcohols by diphenylsilane catalyzed by [RhCl(cod)]2/4PPh3 or [RhCl(PPh3)3] at room temperature in up to 99% yields. For example, ethyl decanoate and ethyl phenylacetate were converted to decanol and 2-phenylethanol in 98 and 92% yields, respectively. Carboxylic acids were also reduced by this reducing system to the corresponding alcohols in high yields. Furthermore, N-monosubstituted amides were reduced to secondary amines in moderate to good yields. For sterically hindered amides, the yields were moderate, and imines were produced in competitive yields.

Rhodium-catalyzed reduction of esters to alcohols using diphenylsilane

Carboxylic esters were reduced to alcohols by diphenylsilane catalyzed by a Rh complex at room temperature. For example, ethyl decanoate and ethyl phenylacetate were converted to decanol and 2-phenylethanol by [RhCl(cod)]2 / 4PPh3 for 72 hours in 98 and 92% yields, respectively. Wilkinson's catalyst is also usable, and the reduction of ethyl decanoate finished in 6 hours at room temperature. The bromo-substituent on ethyl 7-bromoheptanoate remained intact through this reduction.

REACTIONS OF 2-ALKYL-, 2-PHENYL- AND 2-ALKOXY-1,2-OXABOROLANES WITH (DICHLOROMETHYL)LITHIUM. A NOVEL SYNTHESIS OF 1,4-ALKANEDIOLS.

Two novel alternative procedures for the synthesis of 1,4-alkanediols were described by involving the reactions of (dichloromethyl)lithium with some 1,2-oxaborolane derivatives readily obtainable from allyl alcohol.

PRACTICAL PROCEDURE FOR THE CHEMOSELECTIVE REDUCTION OF ESTERS BY SODIUM BOROHYDRIDE. EFFECT OF THE SLOW ADDITION OF METHANOL.

The effect of solvents on the reduction of esters was examined with readily available sodium borohydride which is known to be incapable of reducing such functional groups. In mixed solvents of t-butyl alcohol-methanol or tetrahydrofuran-methanol, various carboxylic esters and lactones were found to be reduced by sodium borohydride to the corresponding alcohols or diols in high yields. Slow addition of methanol to the refluxing mixture of ester and sodium borohydride in t-butyl alcohol or tetrahydrofuran was essential to achieve effective reduction. On the other hand, each individual solvent, methanol or t-butyl alcohol, was not effective for the reduction.