Benzyl alcohol

Benzyl alcohol

Chembox new
Name = Benzyl alcohol
ImageFile = Benzyl-alcohol-2D-skeletal.png ImageSize = 150px
ImageName = Benzyl alcohol
ImageFile1 = Benzyl-alcohol-3D-vdW.png ImageSize1 = 100px
ImageName1 = Benzyl alcohol
IUPACName = Benzyl alcohol
OtherNames = Phenylmethanol
Phenylcarbinol
Section1 = Chembox Identifiers
CASNo = 100-51-6
SMILES = OCc1ccccc1

Section2 = Chembox Properties
C=7|H=8|O=1
Density = 1.044 g/cm3
MeltingPt = -15 °C
BoilingPt = 205 °C

Section7 = Chembox Hazards
ExternalMSDS = [http://www.sciencelab.com/msds.php?msdsId=9927099 ScienceLab.com]

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapor pressure. Benzyl alcohol is partially soluble in water (4 g/100 mL) and completely miscible in alcohols and ether. It is prepared by the hydrolysis of benzyl chloride using sodium hydroxide::C6H5CH2Cl + NaOH → C6H5CH2OH + NaClIt can also be prepared via a Grignard reaction by reacting phenylmagnesium bromide (C6H5MgBr) with formaldehyde, followed by acidification. Like most alcohols, it reacts with carboxylic acids to form esters. Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is also found in a variety of essential oils including jasmine, hyacinth, and y _yl. flavor industries. It is often added to intravenous medication solutions as a preservative due to its bacteriostatic and antipruritic properties. It is also used as a photographic developer.

Illustrative organic synthetic uses

In organic synthesis, benzyl esters are popular protecting groups because they can be removed by mild hydrogenolysis. [OrgSynth | author = Furuta, K.; Gao, Q.-Z.; Yamamoto, H. | title = Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde | collvol = 9 | collvolpages = 722 | year = 1998 | prep = cv9p0722]

BnOH reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction: [OrgSynth | author = Parris, C. L. | title = N-benzylacrylamide | collvol = 5 | collvolpages = 73 | year = 1973 | prep = cv5p0073] :C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2

Nanotechnological uses

Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic reconfiguration of nanowires. [cite journal | title = Nanowires get reconfigured | author = Alexander Wissner-Gross | date = 19 Oct 2006 | url = http://nanotechweb.org/articles/journal/5/10/2/1 | publisher = Nanotechweb.org]

Use in Health Care

Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications. It is oxidized rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. High concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis. Newborns, especially if critically ill, may not metabolize benzyl alcohol as readily as adults. Reports in the early 1980's of sixteen neonatal deaths associated with the use of saline flush solutions containing benzyl alcohol preservative led to recommendations to avoid its use in neonates. [cite journal | url = http://www.cdc.gov/MMWR/preview/mmwrhtml/00001109.htm | title = Neonatal Deaths Associated With Use Of Benzyl Alcohol — United States | journal = Morbidity and Mortality Weekly Report | date = 11 Jun 1982 | volume = 31 | issue = 22 | pages = 290–1]

Other uses

Benzyl alcohol has nearly the same refraction index of quartz and wool fibre. If a clear quartz object is immersed in benzyl alcohol therefore it becomes almost invisible. This has been used as a method to non-destructively recognize if an object is made of true quartz or not (see Crystal skulls). Similarly, white wool immersed in benzyl alcohol also becomes almost invisible clearly revealing contaminants such as dark & medullated fibres and vegetable matter.

References


Wikimedia Foundation. 2010.

Игры ⚽ Нужно сделать НИР?

Look at other dictionaries:

  • benzyl alcohol — Chem. a colorless, faintly aromatic, slightly water soluble liquid, C7H8O, used chiefly as a solvent in the manufacture of perfumes and flavorings, and as an intermediate in the synthesis of benzyl esters and ethers. Also called phenylcarbinol. * …   Universalium

  • benzyl alcohol — benzilo alkoholis statusas T sritis chemija formulė C₆H₅CH₂OH atitikmenys: angl. benzyl alcohol rus. бензиловый спирт ryšiai: sinonimas – fenilmetanolis …   Chemijos terminų aiškinamasis žodynas

  • benzyl alcohol — noun : a colorless liquid primary alcohol C6H5CH2OH occurring free and in the form of esters in many essential oils, made usually by hydrolysis of benzyl chloride, and used chiefly as a solvent and in making esters * * * Chem. a colorless,… …   Useful english dictionary

  • benzyl alcohol — noun The aromatic alcohol phenylmethanol …   Wiktionary

  • benzyl alcohol — [NF] a clear colorless oily liquid used as a bacteriostatic in solutions for injection and topically as a local anesthetic. Called also benzenemethanol, phenylcarbinol, and phenylmethanol …   Medical dictionary

  • hydroxy-benzyl alcohol — Saligenin Sa*lig e*nin, n. [Salicin + gen.] (Chem.) A phenol alcohol obtained, by the decomposition of salicin, as a white crystalline substance; called also {hydroxy benzyl alcohol}. [1913 Webster] …   The Collaborative International Dictionary of English

  • Benzyl benzoate — Identifiers CAS number 120 51 4  …   Wikipedia

  • Alcohol bencílico — Alcohol bencílico …   Wikipedia Español

  • Benzyl — In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2 . The abbreviation Bn is frequently used to denote benzyl moieties in nomenclature and structural depictions of… …   Wikipedia

  • Benzyl chloride — Not to be confused with benzoyl chloride. Benzyl chloride …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”