701-70-2

Basic information

• Product Name: 1-PHENYL-2-BUTANOL
• Synonyms: 1-PHENYL-2-BUTANOL;AURORA KA-6967;2-Butanol, 1-phenyl-;alpha-ethyl-benzeneethano;alpha-Ethylbenzeneethanol;Benzyl ethyl carbinol;Phenethyl alcohol, alpha-ethyl-;1-phenylbutan-2-ol
• CAS NO: 701-70-2
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 211-858-2
• Product Categories: Alcohols;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 701-70-2.mol

Chemical Properties

• Boiling Point: 124-127 °C25 mm Hg(lit.)
• Flash Point: 212 °F
• Appearance: /
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0459mmHg at 25°C
• Refractive Index: n20/D 1.516(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.24±0.20(Predicted)
• CAS DataBase Reference: 1-PHENYL-2-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-2-BUTANOL(701-70-2)
• EPA Substance Registry System: 1-PHENYL-2-BUTANOL(701-70-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 701-70-2(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
1-PHENYL-2-BUTANOL is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for a wide range of reactions, making it a valuable building block in the chemical industry.
2. Used in Flavor and Fragrance Industry:
1-PHENYL-2-BUTANOL is used as a component in the creation of artificial flavors and fragrances, particularly those with a floral or fruity scent. Its pleasant aroma and stability make it a popular choice for use in the perfumery and flavoring agents.
3. Used in the Cosmetics Industry:
1-PHENYL-2-BUTANOL is employed as a solvent and fixative in the formulation of cosmetics, such as perfumes, colognes, and other personal care products. Its ability to dissolve a variety of substances and enhance the longevity of fragrances makes it an essential ingredient in the cosmetics sector.
4. Used in the Plastics and Polymer Industry:
1-PHENYL-2-BUTANOL is utilized as a monomer in the production of certain types of polymers and plastics. Its chemical properties allow it to be copolymerized with other monomers, resulting in materials with specific characteristics, such as improved strength, flexibility, or durability.
5. Used in the Dyes and Pigments Industry:
1-PHENYL-2-BUTANOL is used as a starting material in the synthesis of various dyes and pigments, particularly those with vibrant colors and high stability. Its versatility in chemical reactions enables the production of a wide range of colorants for use in various applications, such as textiles, paints, and inks.

InChI:InChI=1/C10H14O/c1-2-10(11)8-9-6-4-3-5-7-9/h3-7,10-11H,2,8H2,1H3/t10-/m1/s1

Upstream product

• 123-38-6 propionaldehyde 
• 6921-34-2 benzylmagnesium chloride 
• 71-23-8 propan-1-ol 
• 108-88-3 toluene 
• 96-09-3 styrene oxide 
• 97-93-8 triethylaluminum 
• 27846-25-9 1-phenyl-2-(phenylsulfonyl)ethane 
• 97-94-9 triethyl borane 
• 1202-32-0 2-Nitro-1-phenyl-1-butene 
• 33603-06-4 (+)-1-amino-2-phenylbutane 
• 557-20-0 diethylzinc 
• 122-78-1 phenylacetaldehyde 
• 75-16-1 methylmagnesium bromide 
• 86527-08-4 (R,S)-1-phenyl-2-butyl acetate 

Downstream Products

• 128126-07-8 (3,5-Dinitro-phenyl)-carbamic acid (R)-1-benzyl-propyl ester 
• 128126-07-8 (3,5-Dinitro-phenyl)-carbamic acid (S)-1-benzyl-propyl ester 
• 1007-32-5 benzyl ethyl ketone 
• 24767-68-8 1-chloro-1-phenylbutan-2-one 
• 24767-67-7 3-chloro-1-phenyl-2-butanone 
• 1217293-62-3 (+/-)-[2-[(2-methoxyethoxy)methoxy]butyl]benzene 
• 29393-19-9 (2R)-1-phenylbutan-2-ol 
• 701-70-2 (S)-1-phenylbutan-2-ol 
• 30543-89-6 (R)-1-Benzyl-propylamine 
• 1271984-17-8 C₁₁H₁₄O₂ 
• 81012-82-0 (2-bromobutyl)benzene 
• 851317-57-2 3-(1-cyclohexylmethyl-propoxycarbonylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Direct and Unified Access to Carbon Radicals from Aliphatic Alcohols by Cost-Efficient Titanium-Mediated Homolytic C?OH Bond Cleavage

Low-valent Ti-mediated homolytic C?O bond cleavage offers unified access to carbon radicals from ubiquitous non-activated tertiary, secondary, and even primary alcohols. In contrast to the representative Ti reagents, which were ineffective for this purpos

Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus

We developed a one-pot sequential two-step deracemization approach to chiral alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of TeSADH with poor and good stereoselectivities, respectively. More specifically, W110G TeSADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V TeSADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure (S)-configured alcohols in up to > 99 percent enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G TeSADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G TeSADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of (R)-configured alcohols, and (S)-configured alcohols with up to > 99 percent enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.

Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation

A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.

Ligand-Enabled β-Methylene C(sp3)?H Arylation of Masked Aliphatic Alcohols

Despite recent advances, reactivity and site-selectivity remain significant obstacles for the practical application of C(sp3)?H bond functionalization methods. Here, we describe a system that combines a salicylic-aldehyde-derived L,X-type directing group with an electron-deficient 2-pyridone ligand to enable the β-methylene C(sp3)?H arylation of aliphatic alcohols, which has not been possible previously. Notably, this protocol is compatible with heterocycles embedded in both alcohol substrates and aryl coupling partners. A site- and stereo-specific annulation of dihydrocholesterol and the synthesis of a key intermediate of englitazone illustrate the practicality of this method.

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

Transfer hydrogenation of ketones catalyzed by a trinuclear Ni(II) complex of a Schiff base functionalized N-heterocyclic carbene ligand

A new Schiff base-functionalized N-heterocyclic carbene ligand precursor 3-benzyl-1-[2-((2-hydroxy-benzylidene)-amino]-ethyl-3H-imidazol-1-ium bromide (3), and its trinuclear Ni(II) complex [LNiL-Ni-LNiL].2Br (4) where L = 2-[2-(3-benzylimidazol-1-yl) ethyliminomethyl]phenol, were synthesized via the solventless and free carbene routes respectively. Both compounds were characterized by spectroscopic and X-ray diffraction techniques. Single crystal XRD analysis of 4 showed that it is composed of a central square planar Ni(II) ion symmetrically linked to two distorted square planar Ni(II) ions via two bridging ligands. The central Ni(II) ion is only bound to the Schiff base moieties of the bridging ligands via the phenolate oxygen donor (O1) and imine nitrogen donor (N1) atoms in a trans [N^O^(Ni2+)^N^O] mode, whilst the carbene moieties of each bridging ligand and a tridentate L are coordinated in a distorted square planar CNHC-(Ni2+)^N^O^CNHC mode to stabilise each of the terminal Ni(II) ions. Complex 4 showed significant activity as a catalyst in the transfer hydrogenation of a range of aliphatic and aromatic ketones, at a catalyst concentration of 0.1 mol%. An excellent conversion up to 100% was achieved for aromatic ketones after 4 h.

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation

Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.

Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations

Four (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds were synthesized, and their activities in transfer hydrogenations of carbonyl compounds and transfer dehydrogenations of alcohols were explored and compared to those of the well-established [2,5-(SiMe3)2-3,4-(CH2)4(η4-C4C=O)]Fe(CO)3 (3). A new compound, [2,5-bis(3,5-dimethylphenyl)-3,4-diphenylcyclopentadienone]iron tricarbonyl (7), was the most active catalyst in both transfer hydrogenations and dehydrogenations, and compound 3 was the least active catalyst in transfer hydrogenations. Evidence was found for product inhibition of both 3 and 7 in a transfer dehydrogenation reaction, with the activity of 3 being more heavily affected. A monomeric iron hydride derived from 7 was spectroscopically observed during a transfer hydrogenation, and no diiron bridging hydrides were found under reductive or oxidative conditions. Initial results in the transfer hydrogenation of N-benzylideneaniline showed that 3 was a significantly less active catalyst in comparison to the (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds.

Application of Ni(II) complexes of air stable Schiff base functionalized N-heterocyclic carbene ligands as catalysts for the transfer hydrogenation of aliphatic ketones

New air stable N-heterocyclic carbene functionalized Schiff base ligands (L) of the type 2-[-2-[3-(R)imidazol-1-yl]ethyliminomethyl]phenol [R = methyl (2), 2-pyridylmethyl (3)] were synthesized and characterized by NMR, IR, MS, and CHN analysis. Single crystal X-ray structural analysis of their Ni(II) complexes revealed square planar arrangement of the chelating ligands coordinated in tridentate (2, C^N^O) and tetradentate (3, N^C^N^O) modes around the metal. The three new isolated and fully characterized complexes were utilized as catalysts for the catalytic transfer hydrogenation of aliphatic ketones in 2-propanol as solvent and source of hydrogen. Based on 0.2 mol% catalyst concentration, the complexes showed activity for aliphatic ketones and 100% conversion (turnover number of 500) for cyclohexanone and all the aromatic ketones tested.