3670-15-3

Basic information

• Product Name: 2-(2-CHLOROPHENYL)PROPAN-2-OL
• Synonyms: 2-(2-CHLOROPHENYL)PROPAN-2-OL
• CAS NO: 3670-15-3
• Molecular Formula: C₉H₁₁ClO
• Molecular Weight: 170.638
• Mol File: 3670-15-3.mol

Chemical Properties

• Melting Point: 23.7 °C
• Boiling Point: 94 °C(Press: 8 Torr)
• Appearance: /
• Density: 1.144±0.06 g/cm3(Predicted)
• PKA: 14.12±0.29(Predicted)
• CAS DataBase Reference: 2-(2-CHLOROPHENYL)PROPAN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-CHLOROPHENYL)PROPAN-2-OL(3670-15-3)
• EPA Substance Registry System: 2-(2-CHLOROPHENYL)PROPAN-2-OL(3670-15-3)

Safety Data

• Hazardous Substances Data: 3670-15-3(Hazardous Substances Data)

Usage

Classification

Derivative of phenethylamine
It belongs to a group of chemical compounds derived from phenethylamine.

Use

Medication and antihistamine
It is primarily used as a medication to relieve allergy symptoms by acting as an antihistamine.

Symptom relief

Sneezing, itching, and watery eyes
The specific symptoms that chlorpheniramine helps alleviate are sneezing, itching, and watery eyes.

Mechanism

Blocks the action of histamine
It works by inhibiting the effects of histamine, a substance in the body responsible for causing allergic symptoms.

Availability

Over-the-counter cold and allergy medications
Chlorpheniramine can be found in many over-the-counter medications designed to treat cold and allergy symptoms.

Additional uses

Treats hives, itching, and insect bites
Apart from its primary use, chlorpheniramine can also be used to treat hives, itching, and insect bites.

Side effect

Drowsiness
One of the side effects of taking chlorpheniramine is drowsiness, which may cause impaired alertness.

Precaution

Avoid driving or operating heavy machinery
Due to the potential for drowsiness, it is recommended to avoid driving or operating heavy machinery while taking this medication.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 610-96-8 methyl chlorobenzoate 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 15842-76-9 (2-chloro-phenyl)-trimethyl-silane 
• 67-64-1 acetone 
• 74-88-4 methyl iodide 
• 609-65-4 o-chlorobenzoyl chloride 
• 7335-25-3 ethyl 2-chlorobenzoate 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 2077-13-6 2-chlorocumene 

Downstream Products

• 99846-68-1 1-chloro-2-(α-chloro-isopropyl)-benzene 
• 3609-45-8 1-chloro-2-(prop-1-en-2-yl)benzene 
• 854649-68-6 2-(2-chloro-phenyl)-2-phenyl-propane 
• 64946-66-3 1-Chloro-2-(1-isocyanato-1-methyl-ethyl)-benzene 
• 82466-13-5 2-chlorocumyl acetate 
• 26106-09-2 Benzyl-<1-(2-chlorophenyl)-1-methylethyl>-sulfid 
• 50481-48-6 2-chloro-α,α-dimethylbenzenemethanamine 
• 3425-72-7 cumyl acetate 
• 739-45-7 9,9-dimethyl-10-phenyl-9,10-dihydro-anthracene 
• 855290-80-1 2-(1-methyl-1-phenyl-ethyl)-benzonitrile 
• 217-59-4 triphenylene 
• 21190-34-1 (2-isopropylphenyl)methanol 
• 180092-32-4 [2-(1-methylethenyl)phenyl]methyl alcohol 
• 15582-48-6 o-1-menthene 

Relevant articles and documents

Stepwise benzylic oxygenation via uranyl-photocatalysis

Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.

Room temperature C(sp2)-H oxidative chlorination: Via photoredox catalysis

Photoredox catalysis has been developed to achieve oxidative C-H chlorination of aromatic compounds using NaCl as the chlorine source and Na2S2O8 as the oxidant. The reactions occur at room temperature and exhibit exclusive selectivity for C(sp2)-H bonds over C(sp3)-H bonds. The method has been used for the chlorination of a diverse set of substrates, including the expedited synthesis of key intermediates to bioactive compounds and a drug.

Compounds of the menthane series. Synthesis of unsaturated primary alcohols with the o- and p-menthane skeletons

Precursors to terpene alcohols of the o- and p-menthane series (o-cimen-7-ol and o- and p-cimen-9-ols) were synthesized, and their reduction with lithium in ethylenediamine was studied. The reduction of o- and p-cimen-9-ols in the presence of isopropyl alcohol selectively afforded the corresponding 1,4-dihydro derivatives. Under analogous conditions, o-cimen-7-ol was converted into a mixture of unsaturated hydrocarbons. The reduction with lithium in ethylenediamine in the absence of isopropyl alcohol in all cases gave mixtures of menthene alcohols.

Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of o-Iodobiphenyls or (Z)-β-Halostyrenes with o-Bromobenzyl Alcohols through Two Sequential C-C Bond Formations Catalyzed by a Palladium Complex

o-Bromobenzyl alcohol has been developed as a novel annulating reagent, bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular cyclization. An array of experimental data suggest that the reaction mechanism involves the equilibrium of 1,4-palladium migration.

Palladium-catalyzed annulation of o-iodobiphenyls with o-bromobenzyl alcohols: Synthesis of functionalized triphenylenes via C-C and C-H bond cleavages

Treatment of o-iodobiphenyls with o-bromobenzyl alcohols in the presence of cesium carbonate under palladium catalysis affords a series of highly substituted triphenylenes. The reaction involves two C-C bond formations and C-C and C-H bond cleavages. A combination of palladium and an electron-deficient phosphine ligand proves to be effective for both decarbonylative cross-coupling and intramolecular cyclization.

ortho-Effect on the acid-catalyzed hydration of 2-substituted α-methylstyrenes

α-Methylstyrene and nine ortho-substituted analogs have been synthesized and the kinetics of their acid-catalyzed hydration in aqueous solutions of sulfuric acid at 25°C have been investigated. The kinetic acidity function HS has been constructed from the dependence of the observed rate constants kobs on the sulfuric acid concentration. The catalytic rate constants of the acid-catalyzed hydration kortho have been calculated as well. The identical shape of the kinetic acidity functions for ortho- and para-derivatives confirms what the consistent mechanism A-SE2 of the acid-catalyzed hydration has already proved for the corresponding paraderivatives. The A-SE2 mechanism involves a rate-determining proton transfer of the hydrated proton to the substrate. From the dependence of the catalytic rate constants of the ortho-derivatives on the catalytic rate constants of the para-derivatives, it is seen that the logarithm of the catalytic rate constant for hydrogen as a substituent is markedly out of the range of the other substituents and, simultaneously, that the ortho-derivatives react significantly slower than the corresponding para-derivatives. In correlation with the substitent constants σp+, a reaction constant of ρ+= -1.45 have been found. The constant is, in absolute value, considerably smaller than that for para-derivatives (ρ+ = -3.07). In parallel, the steric effects are enforced more significantly for the monoatomic substituents (slope of the Charton's constants 3.92) than for substituents including more atoms (slope of the Charton's constants 2.09). A small value of the reaction constant ρ+ has been elucidated due to the lower conjugation between the reaction centre and the benzene ring as a consequence of the geometric twist of the reaction centre out of the main aromatic plane accompanied by fading mesomeric interaction between the reaction centre and the substituents attached to the benzene ring. The isopropyl group in the carbocation is twisted less out of the aromatic plane for the monoatomic substituents and, therefore, also a small difference in the bulk of substituents has considerable steric influence on the conjugation between the carbocation and the benzene ring bearing substituents. On the contrary, the isopropyl group in the carbocations with polyatomic substituents is twisted to such a degree that changes in the bulk of substituents affect the resonant stabilization negligibly. Similar conclusions were also deduced from the correlations of the substitution constants σI and σR+.

Improved preparative route toward 3-arylcyclopropenes

A convenient preparative protocol for the synthesis of various 3-arylcyclopropenes in a multigram scale is disclosed. Optimization of the reaction conditions and isolation procedures allowed for significant improvement of the chemical yields of these strained products. The described protocol was used for efficient preparation of a series of 3-methyl-3-arylcyclopropenes possessing different substituents in the aromatic ring. The effect of substitution in the aryl group on the stability of 3-arylcyclopropenes, as well as the corresponding precursors, is discussed.

Hydroxyalkylation, Acylation, Formylation, and Carboxylation of 2-Nitro- and 2-Chloro-1-(trimethylsilyl)benzene

The synthetic application of base-catalyzed carbodesilylation of aryltrimethylsilanes is demonstrated in the reactions of 2-nitro- (1a) and 2-chloro-1-(trimethylsilyl)benzene (1b) with aldehydes, ketones, acyl fluorides and carboxylic anhydrides, respectively, dimethylformamide, and carbon dioxide.The corresponding benzenes 3 and 8, (hydroxyalkyl)benzenes 4, 6, and 9, the benzophenones 12, the benzaldehydes 14, and the benzoic acids 17 are obtained in good yields.The new method is a useful alternative to the normal electrophilic substitution or the application of organometallic compounds, respectively, for the synthesis of polysubstituted benzenes.

Synthesis and Herbicidal Activities of 1,2-Benzisoxazole-3-acetamide Derivatives

Many 1,2-benzisoxazole-3-acetamides were synthesized and their herbicidal activities in the paddy field were studied.Of the compounds tested, N-α,α-dimethylbenzyl-2-bromo-(1,2-benzisoxazol-3-yl)acetamide 10a was the most effective.Details of the synthesis and the results of herbicidal evaluations are given.