111128-12-2

Basic information

• Product Name: 2-(4-Bromomethyl)phenylpropionic acid
• Synonyms: 4-(BROMOMETHYL)HYDRATROPIC ACID;2-[4-(BROMOMETHYL)PHENYL]PROPANOIC ACID;2-[4-(BROMOMETHYL)PHENYL]PROPIONIC ACID;2-[(P-BROMOMETHYL)PHENYL]PROPIONIC ACID;BMPPA;2-[4-(Bromomethyl)phenyl]propinic acid;Loxoprofen Intermediate;2-((4-Bromomethyl)phenyl)propanic acid
• CAS NO: 111128-12-2
• Molecular Formula: C₁₀H₁₁BrO₂
• Molecular Weight: 243.09714
• EINECS: 2017-001-1
• Product Categories: Aromatic Propionic Acids;Organic acids;(intermediate of loxoprofen);C10;Carbonyl Compounds;Carboxylic Acids;Pharmaceutical intermediate
• Mol File: 111128-12-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 126-130 °C(lit.)
• Boiling Point: 148°C (rough estimate)
• Flash Point: 162 °C
• Appearance: Beige-cream crystalline powder
• Density: 1.4557 (rough estimate)
• Vapor Pressure: 2.54E-05mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.29±0.10(Predicted)
• CAS DataBase Reference: 2-(4-Bromomethyl)phenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Bromomethyl)phenylpropionic acid(111128-12-2)
• EPA Substance Registry System: 2-(4-Bromomethyl)phenylpropionic acid(111128-12-2)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-27-36/37/39-45-37/39
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 111128-12-2(Hazardous Substances Data)

Usage

Description

2-(4-Bromomethyl)phenylpropionic acid is a propionic acid derivative characterized by its beige-cream crystalline powder appearance. It exhibits unique chemical properties, with an enthalpy of vaporization at boiling point (421.15K) of 36.363 kJ/mol and a density of 1.4212 g/ml at 25°C.

Uses

Used in Pharmaceutical Industry:
2-(4-Bromomethyl)phenylpropionic acid is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific receptors or enzymes in the body.
Used in Chemical Research:
In the field of chemical research, 2-(4-Bromomethyl)phenylpropionic acid serves as a valuable compound for studying the properties and reactions of propionic acid derivatives. Its distinct characteristics make it an important subject for understanding the behavior of similar compounds and their potential applications in various industries.
Used in Material Science:
2-(4-Bromomethyl)phenylpropionic acid can be utilized in material science as a component in the development of new materials with specific properties. Its unique chemical structure may contribute to the creation of materials with enhanced characteristics, such as improved stability, reactivity, or selectivity in various applications.
Used in Agrochemical Industry:
2-(4-Bromomethyl)phenylpropionic acid is used as a building block for the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties make it a suitable candidate for the development of new compounds that can effectively control pests and weeds in agriculture, thus contributing to increased crop yields and food security.

InChI:InChI=1/C10H11BrO2/c1-7(10(12)13)9-4-2-8(6-11)3-5-9/h2-5,7H,6H2,1H3,(H,12,13)/p-1/t7-/m1/s1

Synthetic route

formaldehyd (50-00-0) + hydratropic acid (492-37-5, 2328-24-7) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
With sulfuric acid; hydrogen bromide at 35 - 70℃; for 11h; Temperature;	99%
With sulfuric acid; hydrogen bromide at 35 - 90℃; for 11.5h; Temperature;	96%
Stage #1: formaldehyd; hydratropic acid With hydrogen bromide at 55 - 65℃; Stage #2: With sulfuric acid at 20 - 65℃;	96%

(R,S)-2-(4'-methylphenyl) propionic acid (938-94-3) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
With bromine; dibenzoyl peroxide In dichloromethane Reflux;	92%
With bromine; dibenzoyl peroxide In dichloromethane at 40℃; for 0.0416667h; Temperature;	90%
With hydrogen bromide; bromine In ethyl acetate at 20℃; for 2h;	79%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane Solvent; Reflux;	42.05 g
With hydrogen bromide; dihydrogen peroxide; dibenzoyl peroxide In dichloromethane at 10 - 15℃; Irradiation;

C10H10Br2O2 → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; phosphonic acid diethyl ester In water; toluene at 5 - 85℃; for 6h; Reagent/catalyst; Inert atmosphere;	85.3%

trioxane (188680-60-6) + hydratropic acid (492-37-5, 2328-24-7) + cetyltrimethylammonim bromide (57-09-0) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
With hydrogen bromide; acetic acid
With hydrogen bromide; acetic acid

sodium 2-phenyl-2-cyanopropionate → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene / 3 h / 35 - 75 °C 2.1: sodium hydroxide / 1 h / 80 °C 3.1: sodium hydroxide / 12.5 h / 105 °C / Reflux 3.2: 0.58 h / pH 3 4.1: sulfuric acid; hydrogen bromide / 11.5 h / 35 - 90 °C View Scheme

phenylacetonitrile (140-29-4) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium methylate / methanol; toluene / 10 h / 20 °C 2.1: toluene / 3 h / 35 - 75 °C 3.1: sodium hydroxide / 1 h / 80 °C 4.1: sodium hydroxide / 12.5 h / 105 °C / Reflux 4.2: 0.58 h / pH 3 5.1: sulfuric acid; hydrogen bromide / 11.5 h / 35 - 90 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / 15 h / 250 °C / 30003 Torr / Autoclave 2: sodium hydroxide; water / 8 h / 40 °C 3: sulfuric acid; hydrogen bromide / 11 h / 35 - 70 °C View Scheme

2-methoxycarbonyl-2-phenylpropionitrile (79341-72-3) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / 1 h / 80 °C 2.1: sodium hydroxide / 12.5 h / 105 °C / Reflux 2.2: 0.58 h / pH 3 3.1: sulfuric acid; hydrogen bromide / 11.5 h / 35 - 90 °C View Scheme

CH3C6H4CH(CH3)OH (536-50-5) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine; calcium chloride / dichloromethane / 40 h 2: dimethyl sulfoxide / 18 h / 90 °C / Reflux 3: hydrogenchloride / 1 h / Reflux 4: hydrogen bromide; bromine / ethyl acetate / 2 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: thionyl chloride / toluene / Reflux 2: tetrabutylammomium bromide / toluene; water / 8 h / 60 - 70 °C 3: sodium hydroxide / 100 - 105 °C 4: dibenzoyl peroxide; bromine / dichloromethane / Reflux View Scheme

1-(4-methylphenyl)ethyl 4-methylbenzenesulfonate (82925-34-6) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethyl sulfoxide / 18 h / 90 °C / Reflux 2: hydrogenchloride / 1 h / Reflux 3: hydrogen bromide; bromine / ethyl acetate / 2 h / 20 °C View Scheme

para-methylacetophenone (122-00-9) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol 2: triethylamine; calcium chloride / dichloromethane / 40 h 3: dimethyl sulfoxide / 18 h / 90 °C / Reflux 4: hydrogenchloride / 1 h / Reflux 5: hydrogen bromide; bromine / ethyl acetate / 2 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol / 15 - 35 °C 2: thionyl chloride / toluene / Reflux 3: tetrabutylammomium bromide / toluene; water / 8 h / 60 - 70 °C 4: sodium hydroxide / 100 - 105 °C 5: dibenzoyl peroxide; bromine / dichloromethane / Reflux View Scheme

(+/-)-2-(4'-methylphenyl)-propionitrile (75920-45-5) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / 1 h / Reflux 2: hydrogen bromide; bromine / ethyl acetate / 2 h / 20 °C View Scheme

1-(1-chloroethyl)-4-methylbenzene (2362-36-9) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / 1.5 h / 20 - 30 °C / Inert atmosphere 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / dichloromethane / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran; ethylene dibromide / 13 h / 60 - 65 °C / Inert atmosphere 1.2: 20 - 25 °C 2.1: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran; ethylene dibromide / 13 h / 60 - 65 °C / Inert atmosphere 1.2: 20 - 25 °C 2.1: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere 3.1: tetra-(n-butyl)ammonium iodide; phosphonic acid diethyl ester / water; toluene / 6 h / 5 - 85 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: tetrabutylammomium bromide / toluene; water / 8 h / 60 - 70 °C 2: sodium hydroxide / 100 - 105 °C 3: dibenzoyl peroxide; bromine / dichloromethane / Reflux View Scheme

1-ethenyl-4-methylbenzene (622-97-9) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water / 6 h / 65 - 70 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran; ethylene dibromide / 13 h / 60 - 65 °C / Inert atmosphere 2.2: 20 - 25 °C 3.1: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: hydrogen bromide / 5 h / 60 - 65 °C / Inert atmosphere 2: magnesium / tetrahydrofuran; ethylene dibromide / 55 - 65 °C 3: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water / 6 h / 65 - 70 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran; ethylene dibromide / 13 h / 60 - 65 °C / Inert atmosphere 2.2: 20 - 25 °C 3.1: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere 4.1: tetra-(n-butyl)ammonium iodide; phosphonic acid diethyl ester / water; toluene / 6 h / 5 - 85 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: hydrogen bromide / 5 h / 60 - 65 °C / Inert atmosphere 2: magnesium / tetrahydrofuran; ethylene dibromide / 55 - 65 °C 3: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere 4: tetra-(n-butyl)ammonium iodide; phosphonic acid diethyl ester / water; toluene / 6 h / 5 - 85 °C / Inert atmosphere View Scheme

1-(1-bromoethyl)-4-methylbenzene (159755-12-1) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran; ethylene dibromide / 55 - 65 °C 2: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran; ethylene dibromide / 55 - 65 °C 2: bromine; 2,2'-azobis(isobutyronitrile) / dichloromethane / 40 - 55 °C / Inert atmosphere 3: tetra-(n-butyl)ammonium iodide; phosphonic acid diethyl ester / water; toluene / 6 h / 5 - 85 °C / Inert atmosphere View Scheme

(R,S)-2-(4'-methylphenyl) propionic acid (938-94-3) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + C10H10Br2O2

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); bromine In dichloromethane at 40 - 55℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;

styrene (292638-84-7) → 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / dichloromethane / 5 h / 10 - 20 °C 2.1: magnesium / 2-methyltetrahydrofuran / 5 h / 20 - 30 °C 2.2: 5 h / 20 - 30 °C 3.1: sulfuric acid; hydrogen bromide / 3 h / 50 - 120 °C View Scheme

methanol (67-56-1) + 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) → 2-(4-bromomethylphenyl)propionic acid methyl ester (99807-54-2)

Conditions	Yield
In 2,2,4-trimethylpentane at 65℃; for 0.5h; Solvent; Temperature;	99.7%
Stage #1: methanol With sulfuric acid In toluene at 35℃; Stage #2: 2-[4-(bromomethyl)phenyl]propanoic acid In toluene at 281℃; for 5h;	98.7%
With sulfuric acid at 0 - 5℃; for 6h;	98%

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + ethanol (64-17-5) → ethyl 2-(4-bromomethylphenyl)propanoate

Conditions	Yield
In toluene at 79℃; for 0.333333h; Time;	97.8%

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) → 2-(4-(azidomethyl)phenyl)propanoic acid

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	96%
With sodium azide; 15-crown-5 In 1,4-dioxane at 80℃; for 16h;
With sodium azide In N,N-dimethyl-formamide at 100℃; for 12h; Temperature; Inert atmosphere;
With sodium azide In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + triphenylphosphine (603-35-0) → [4-(methyl)phenyl-2-propionyl-N-succinimido]-triphenylphosphonium bromide

Conditions	Yield
With dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 16h;	94.9%

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate (80382-23-6)

Conditions	Yield
Stage #1: 2-[4-(bromomethyl)phenyl]propanoic acid; 2-ethoxycarbonyl-1-cyclopentanone With sodium hydroxide In N,N-dimethyl-formamide under 760.051 Torr; for 8h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=5 - 6; Further stages;	92%

2-methyl-1-buten-4-ol (763-32-6) + 2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) → C15H19BrO2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 23℃; Inert atmosphere;	87%

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + dimethylmonochlorosilane (1066-35-9) + diethyl ether (60-29-7) + hexane I ethyl acetate → 2-[(4-dimethylsilylmethyl)phenyl]propionic acid (1096356-08-9)

Conditions	Yield
With triethylamine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate	85%

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 2-(4-(((1H-1,2,4-triazol-3-yl)thio)methyl)phenyl)propanoic acid

Conditions	Yield
In acetone at 40℃; for 12h; Reflux;	85%

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + 5-chloro-2-mercaptobenzothiazole (5331-91-9) → 2-(4-(((5-chlorobenzo[d]thiazol-2-yl)thio)methyl)phenyl)propanoic acid

Conditions	Yield
In acetone at 40℃; for 12h; Reflux;	85%

Upstream product

• 43153-04-4 ethyl 2-(4-formylphenyl)propionate 
• 2510-99-8 ethyl 2-phenylpropanoate 
• 492-37-5 hydratropic acid 
• 938-94-3 (R,S)-2-(4'-methylphenyl) propionic acid 
• 159755-12-1 1-(1-bromoethyl)-4-methylbenzene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 2362-36-9 1-(1-chloroethyl)-4-methylbenzene 
• 75920-45-5 (+/-)-2-(4'-methylphenyl)-propionitrile 
• 122-00-9 para-methylacetophenone 
• 82925-34-6 1-(4-methylphenyl)ethyl 4-methylbenzenesulfonate 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 79341-72-3 2-methoxycarbonyl-2-phenylpropionitrile 
• 140-29-4 phenylacetonitrile 
• 50-00-0 formaldehyd 

Downstream Products

• 63476-54-0 2-(4-formylphenyl)propionic acid methyl ester 
• 81762-92-7 loxoprofen methyl ester 
• 80382-23-6 sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate 
• 861080-59-3 2-(4-carboxymethyl-phenyl)-propionic acid 

Relevant articles and documents

Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

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Production method of 2-(4-bromomethyl phenyl)propionic acid

The invention discloses a production method of 2-(4-bromomethyl phenyl)propionic acid. An adopted ionic liquid catalyst can be recycled and used, no molten aluminum trichloride is generated, a material does not need to be washed for multiple times, only layered extraction needs to be conducted, then a required product can be obtained, aluminum trichloride and triethanolamine salt ionic liquid is used, thus environmentally friendliness is achieved, the cost is also saved, and that is, an original cumbersome process is simplified. An original bromination reaction in a glass kettle is changed toa cooling glass pipeline circulation-type bromination reaction in the kettle, through the glass pipeline type reaction, the contact area of the material and light is increased, through circulation, the situation that the material is gathered on the illumination surface, and consequently light illumination is affected is avoided, thus the reaction efficiency is higher, the reaction time is shortened, the occurrence of a side reaction is controlled, and the product purity is higher.

Novel synthesizing method of 2-(4-bromomethyl)phenylpropionic acid

The invention belongs to the field of preparation of intermediates in chemical engineering, and particularly relates to a novel synthesizing method of 2-(4-bromomethyl)phenylpropionic acid. The novelsynthesizing method comprises the following steps of using 4-methyl acetophenone as the raw material; performing reduction, chlorinating and cyaniding, so as to obtain 2-(4-methyl)phenylpropionitrile;hydrolyzing, and brominating, so as to obtain the 2-(4-bromomethyl)phenylpropionic acid. The novel synthesizing method has the advantages that the yield rate is increased, and the cost of raw material is low; the novel synthesizing method is suitable for industrialized production.