118647-53-3

Basic information

• Product Name: 3-(Bromomethyl)phenylacetic acid
• Synonyms: 2-(3-(Bromomethyl)phenyl)acetic acid;BENZENEACETIC ACID, 3-(BROMOMETHYL)-
• CAS NO: 118647-53-3
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229
• Mol File: 118647-53-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 341℃
• Flash Point: 160℃
• Appearance: /
• Density: 1.565
• PKA: 4.22±0.10(Predicted)
• CAS DataBase Reference: 3-(Bromomethyl)phenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Bromomethyl)phenylacetic acid(118647-53-3)
• EPA Substance Registry System: 3-(Bromomethyl)phenylacetic acid(118647-53-3)

Safety Data

• Hazardous Substances Data: 118647-53-3(Hazardous Substances Data)

Synthetic route

m-methylphenylacetic acid (621-36-3) → (3-bromomethyl-phenyl)-acetic acid (118647-53-3)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 16h; Reflux; Inert atmosphere;	95%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 16h; Reflux;	79.3%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 16h; Reflux;	79.3%

methanol (67-56-1) + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 3-methoxymethylphenylacetic acid (256382-37-3)

Conditions	Yield
With sodium methylate Inert atmosphere; Reflux;	99%

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 2-(3-(bromomethyl)phenyl)ethanol (141337-05-5)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 20℃; for 2h;	94%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	94%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 13h;	85%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 13h;	71%
With borane-THF at 0℃;	66%

sodium acetate (127-09-3) + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → (3-acetoxymethyl-phenyl)-acetic acid methyl ester (1046492-41-4)

Conditions	Yield
In DMA at 120℃; for 4h; Irradiation;	93%

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) + triphenylphosphine (603-35-0) → [3-(carboxymethyl)benzyl](triphenyl)phosphonium bromide (1030893-55-0)

Conditions	Yield
In acetonitrile for 16h; Heating / reflux;	92.4%

methanol (67-56-1) + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → methyl 2-(3-(bromomethyl)phenyl)acetate (104508-22-7)

Conditions	Yield
With thionyl chloride In toluene at 0℃; for 3h;	72%
With hydrogenchloride at 0℃;
With thionyl chloride In toluene at 0℃;

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 2-(3-formylphenyl)acetic acid (34956-29-1)

Conditions	Yield
Stage #1: (3-bromomethyl-phenyl)-acetic acid With hexamethylenetetramine; water In ethanol for 4h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol; water for 0.5h; Reflux; Inert atmosphere;	72%
Stage #1: (3-bromomethyl-phenyl)-acetic acid With hexamethylenetetramine In ethanol; water for 10h; Reflux; Stage #2: With hydrogenchloride In ethanol; water for 0.5h; Reflux;	66%

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 2-(3-((nitrooxy)methyl)phenyl)acetic acid

Conditions	Yield
With silver nitrate In acetonitrile at 20℃; for 48h; Darkness;	70%

sodium 6-oxo-4-(trifluoromethyl)-1,6-dihydropyrimidine-2-thiolate + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃;	45%

2-mercapto-6-oxo-4-(thiophen-2-yl)-1,6-dihydropyridine-3-carbonitrile + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(3-cyano-6-oxo-4-thiophen-2-yl-1,6-dihydropyridin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; acetone at 20℃;	42%

4-benzyl-2-mercapto-6-oxo-1,6-dihydropyridine-3-carbonitrile + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(4-benzyl-3-cyano-6-oxo-1,6-dihydropyridin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone at 20℃;	40%

2-mercapto-6-oxo-4-phenyl-1,6-dihydropyridine-3-carbonitrile + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(3-cyano-6-oxo-4-phenyl-1,6-dihydropyridin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone at 20℃;	37%

potassium 3-cyano-6-oxo-4-trifluoromethyl-1,6-dihydropyridine-2-thiolate + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(3-cyano-6-oxo-4-trifluoromethyl-1,6-dihydropyridin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃;	37%

6-mercapto-2-oxo-4-thiophen-2-yl-1,2-dihydropyridine-3,5-dicarbonitrile + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(3,5-dicyano-6-oxo-4-thiophen-2-yl-1,6-dihydropyridin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone at 20℃;	35%

4-benzyl-2-mercapto-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(4-benzyl-5-cyano-6-oxo-1,6-dihydropyrimidin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone Reflux;	33%

4-oxo-6-(thiophen-2-yl)-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (109532-65-2) + (3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(5-cyano-6-oxo-4-thiophen-2-yl-1,6-dihydropyrimidin-2-ylsulfanylmethyl)phenyl]acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃;	25%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃;	25%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃;	25%

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 3-bromomethylphenylacetic acid chloride (1026167-99-6)

Conditions	Yield
With oxalyl dichloride In dichloromethane at 25℃;
With oxalyl dichloride; N,N-dimethyl-formamide In chloroform at 20℃; for 0.166667h;

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) + [Imino-(4-piperazin-1-yl-phenyl)-methyl]-carbamic acid tert-butyl ester → (3-{4-[4-(tert-Butoxycarbonylamino-imino-methyl)-phenyl]-piperazin-1-ylmethyl}-phenyl)-acetic acid

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → {3-[4-(4-Carbamimidoyl-phenyl)-piperazin-1-ylmethyl]-phenyl}-acetic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide 2: CF3CO2H / CH2Cl2 View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → methyl 3-formylphenylacetate (142327-44-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 0 °C 2: Me3NO / dimethylsulfoxide / 0 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → (3-Thiophen-3-ylmethyl-phenyl)-acetic acid (155172-84-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: HCl / 0 °C 2: Me3NO / dimethylsulfoxide / 0 °C 3: tetrahydrofuran / -78 °C 4: Et3SiH, TFA / CH2Cl2 / 0 °C 5: LiOH / tetrahydrofuran / 25 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → (3-Thiophen-3-ylmethyl-phenyl)-acetyl chloride (1026038-84-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: HCl / 0 °C 2: Me3NO / dimethylsulfoxide / 0 °C 3: tetrahydrofuran / -78 °C 4: Et3SiH, TFA / CH2Cl2 / 0 °C 5: LiOH / tetrahydrofuran / 25 °C 6: (COCl)2 / CH2Cl2 / 25 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → (3-Thiophen-3-ylmethyl-phenyl)-acetic acid methyl ester (142327-17-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: HCl / 0 °C 2: Me3NO / dimethylsulfoxide / 0 °C 3: tetrahydrofuran / -78 °C 4: Et3SiH, TFA / CH2Cl2 / 0 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → [3-(Hydroxy-thiophen-3-yl-methyl)-phenyl]-acetic acid methyl ester (142327-16-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl / 0 °C 2: Me3NO / dimethylsulfoxide / 0 °C 3: tetrahydrofuran / -78 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → methyl 4-chloro-2-(3-(bromomethyl)phenylacetamido)benzoate (142327-14-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2 / CH2Cl2 / 25 °C 2: 1,2-dichloro-ethane / 80 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 3-(3-benzylphenyl)-7-chloro-4-hydroxy-2(1H)-quinolone

Conditions	Yield
Multi-step reaction with 4 steps 1: (COCl)2 / CH2Cl2 / 25 °C 2: 1,2-dichloro-ethane / 80 °C 3: tetrahydrofuran / -78 °C 4: 1.) KHMDS, 2.) TFA / tetrahydrofuran / 25 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 7-chloro-4-hydroxy-3-[3-(3-thienylmethyl)phenyl]-2(1H)-quinolone

Conditions	Yield
Multi-step reaction with 8 steps 1: HCl / 0 °C 2: Me3NO / dimethylsulfoxide / 0 °C 3: tetrahydrofuran / -78 °C 4: Et3SiH, TFA / CH2Cl2 / 0 °C 5: LiOH / tetrahydrofuran / 25 °C 6: (COCl)2 / CH2Cl2 / 25 °C 7: 1,2-dichloro-ethane / 80 °C 8: 1.) KHMDS, 2.) TFA / tetrahydrofuran / 25 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → 2-[2-(3-Benzyl-phenyl)-acetylamino]-4-chloro-benzoic acid methyl ester (155172-81-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: (COCl)2 / CH2Cl2 / 25 °C 2: 1,2-dichloro-ethane / 80 °C 3: tetrahydrofuran / -78 °C View Scheme

(3-bromomethyl-phenyl)-acetic acid (118647-53-3) → L 703717 (142326-92-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: (COCl)2 / CH2Cl2 / 25 °C 2: 1,2-dichloro-ethane / 80 °C 3: tetrahydrofuran / -78 °C 4: 1.) KHMDS, 2.) TFA / tetrahydrofuran / 25 °C View Scheme

Upstream product

• 621-36-3 m-methylphenylacetic acid 

Downstream Products

• 1030893-55-0 [3-(carboxymethyl)benzyl](triphenyl)phosphonium bromide 
• 1571022-82-6 1-(3-(2-hydroxyethyl)benzyl)-5-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)pyridin-2(1H)-one 
• 1404375-21-8 C₂₄H₃₀N₄O₂ 

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