Methyl 5-(bromoacetyl)salicylate supplier

Name
Benzoic acid, 5-(2-bromoacetyl)-2-hydroxy-, methyl ester
EINECS
CAS No. 36256-45-8
Article Data13
CAS DataBase
Density 1.602 g/cm³
Solubility
Melting Point 91-92℃
Formula C₁₀H₉BrO₄
Boiling Point 390.184 °C at 760 mmHg
Molecular Weight 273.083
Flash Point 189.777 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Benzoic acid, 5-(bromoacetyl)-2-hydroxy-, methyl ester (9CI);Salicylic acid, 5-(bromoacetyl)-, methyl ester (7CI);;Methyl 5-(bromoacetyl)-2-hydroxybenzoate;3-Carbomethoxy-4-hydroxy-α-bromoacetophenone;Methyl 5-(2-Bromoacetyl)-2-hydroxybenzoate;5-(2-Bromoacetyl)-2-hydroxybenzoic acid methyl ester;5-(Bromoacetyl)salicylic acid methyl ester;
PSA 63.60000
LogP 1.75640

Synthetic route

: 16475-90-4
estere metilico dell'acido 5-acetilsalicilico

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

Conditions

Conditions	Yield
With copper(ll) bromide In chloroform; ethyl acetate at 40 - 50℃; for 4h;	85%
With copper(ll) bromide In chloroform; ethyl acetate at 40 - 50℃; for 4h;	85%
With bromine In chloroform	81%

: 13110-96-8
5-acetylsalicylic acid

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / H2SO4 / 24 h / Heating 2: 76 percent / dioxane dibromide / dioxane; diethyl ether / 2 h / Ambient temperature View Scheme

: 50-78-2
aspirin

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / AlCl3 / nitrobenzene / 1 h 2: 96 percent / H2SO4 / 24 h / Heating 3: 76 percent / dioxane dibromide / dioxane; diethyl ether / 2 h / Ambient temperature View Scheme

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 97664-55-6
N-[6-(4-phenylbutoxy)hexyl]benzenemethanamine

: 497063-91-9
5-(2-{Benzyl-[6-(4-phenyl-butoxy)-hexyl]-amino}-acetyl)-2-hydroxy-benzoic acid methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃;	100%
With triethylamine In acetonitrile at 20℃; for 0.666667h; Inert atmosphere;

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: (R)-methyl 5-(2-bromo-1-hydroxyethyl)-2-hydroxybenzoate

Conditions

Conditions	Yield
With C31H33ClN2O8RhS3(2-)*2Na(1+); sodium formate In water at 40℃; for 6h; Inert atmosphere; enantioselective reaction;	91%

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: methyl 5-(2-bromo-1-hydroxy-ethyl)salicylate

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; Inert atmosphere;	91%

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 203854-47-1
Fmoc-(S)-β3-HLys(Boc)-OH

: methyl-5-(2-((3-((((8aH-fluoren-9-yl)methoxy)carbonyl)amino)-7-((tert-butoxycarbonyl)amino) heptanoyl)oxy)acetyl)-2-hydroxybenzoate

Conditions

Conditions	Yield
Stage #1: Fmoc-(S)-β3-HLys(Boc)-OH With potassium carbonate In acetonitrile for 0.166667h; Stage #2: 3-carbomethoxy-4-hydroxy-α-bromoacetophenone In acetonitrile at 20℃;	86%
Stage #1: Fmoc-(S)-β3-HLys(Boc)-OH With potassium carbonate In acetonitrile for 0.166667h; Stage #2: 3-carbomethoxy-4-hydroxy-α-bromoacetophenone In acetonitrile at 20℃;	86%

: 57294-38-9
N-(tert-butoxycarbonyl)-4-aminobutanoic acid

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 1292299-10-5
5-[4-(tert-butoxycarbonylaminobutyryloxy)acetyl]-2-hydroxybenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	46%

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 112233-74-6
N2-acetyl-O6-(diphenylcarbamoyl)guanine

: 1485770-54-4
2-N-acetyl-9-N’-(3’-carbmethoxy-4’-hydroxyphenyl)ketomethyl-6-O-diphenylcarbamoylguanine

Conditions

Conditions	Yield
Stage #1: N2-acetyl-O6-(diphenylcarbamoyl)guanine With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5h; Inert atmosphere; Stage #2: 3-carbomethoxy-4-hydroxy-α-bromoacetophenone In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;	32%

: 28151-46-4
trans-N-benzyl-4-phenylcyclohexan-1-amine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 5-{2-[Benzyl-(4-phenyl-cyclohexyl)-amino]-acetyl}-2-hydroxy-benzoic acid methyl ester

Conditions

Conditions	Yield
for 7h; Heating;	22%

: 136-95-8
2-amino-benzthiazole

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 99582-90-8
2-Hydroxy-5-[2-(2-imino-benzothiazol-3-yl)-acetyl]-benzoic acid methyl ester; hydrobromide

Conditions

Conditions	Yield
In butanone for 2h; Heating;

: 92-54-6
4-phenyl-1-piperazine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 2-Hydroxy-5-[2-(4-phenyl-piperazin-1-yl)-acetyl]-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;

: 34803-66-2
1-(2-pyridyl)piperazine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 2-Hydroxy-5-[2-(4-pyridin-2-yl-piperazin-1-yl)-acetyl]-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;

: 2759-28-6
1-phenylmethylpiperazine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 5-[2-(4-Benzyl-piperazin-1-yl)-acetyl]-2-hydroxy-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;

: 40742-32-3
α-methyl-1,3-benzodioxole-5-propanamine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 5-[2-(3-Benzo[1,3]dioxol-5-yl-1-methyl-propylamino)-acetyl]-2-hydroxy-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 2h;

: 4442-59-5
(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: methyl 5-<<<(2,3-dihydro-1,4-benzodioxan-2-yl)methyl>amino>acetyl>-2-hydroxybenzoate

Conditions

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h;

: 4764-17-4
3,4-methylenedioxyamphetamine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: methyl 5-<2-<<2-(1,3-benzodioxol-5-yl)-1-methylethyl>amino>acetyl>-2-hydroxybenzoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 2h;

: 38212-33-8
4-(4-chlorophenyl) piperazine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 5-{2-[4-(4-Chloro-phenyl)-piperazin-1-yl]-acetyl}-2-hydroxy-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;

: 39512-51-1
1-(o-toluyl)piperazine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: methyl 2-hydroxy-5-<2-<4-(2-methylphenyl)-1-piperazinyl>acetyl>benzoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;

: 38212-30-5
1-(4-methoxyphenyl)piperazine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 2-Hydroxy-5-{2-[4-(4-methoxy-phenyl)-piperazin-1-yl]-acetyl}-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;

: 35386-24-4
1-(2-Methoxyphenyl)piperazine

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 2-Hydroxy-5-{2-[4-(2-methoxy-phenyl)-piperazin-1-yl]-acetyl}-benzoic acid methyl ester; hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; triethylamine 1.) THF, RT, 4 h; Multistep reaction;

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 76310-64-0
α,α-dimethyl-1,3-benzodioxole-5-propanamine

: 5-[2-(3-Benzo[1,3]dioxol-5-yl-1,1-dimethyl-propylamino)-acetyl]-2-hydroxy-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 2h;

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 20662-53-7
4-(2-keto-1-benzimidazolinyl)piperidine

: 74971-65-6
methyl 5-<2-<4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidyl>acetyl>-2-hydroxybenzoate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 1h;	17.0 g

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 15532-75-9
1-(3-Trifluoromethylphenyl)piperazine

: 2-Hydroxy-5-{2-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-acetyl}-benzoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 40172-95-0
N-(furan-2-carbonyl)piperazine

: methyl 5-<2-<4-(2-furanylcarbonyl)-1-piperazinyl>acetyl>-2-hydroxybenzoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 4h;

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 103-49-1
dibenzylamine

: 24099-13-6
2-Hydroxy-5-[[bis(phenylmethyl)amino]acetyl]benzoic acid, methyl ester, hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In butanone for 12h; Ambient temperature;

: 102-97-6
Benzyl-isopropyl-amin

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 737695-76-0
methyl 2-hydroxy-5-<acetyl>benzoate hydrochloride

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 27566-05-8
4-(2-(benzylamino)propyl)phenol

: 5-(2-{Benzyl-[2-(4-hydroxy-phenyl)-1-methyl-ethyl]-amino}-acetyl)-2-hydroxy-benzoic acid methyl ester

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 29754-58-3
α,α-dihydroxy-4-hydroxy-3-methoxycarbonyl-acetophenone

Conditions

Conditions	Yield
With water; dimethyl sulfoxide

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 3378-72-1
N-tert-butylbenzylamine

: 5-[2-(Benzyl-tert-butyl-amino)-acetyl]-2-hydroxy-benzoic acid methyl ester

: 36256-45-8
3-carbomethoxy-4-hydroxy-α-bromoacetophenone

: 103-49-1
dibenzylamine

: 36270-04-9
methyl-5-(N,N-dibenzylglycyl) salicylate

Methyl 5-(bromoacetyl)salicylate Specification

The Methyl 5-(bromoacetyl)salicylate, with the CAS registry number 36256-45-8, is also known as 5-(2-Bromoacetyl)-2-hydroxybenzoic acid methyl ester. This chemical's molecular formula is C₁₀H₉BrO₄ and molecular weight is 273.08. What's more, its systematic name is Methyl 5-(bromoacetyl)-2-hydroxybenzoate.

Physical properties of Methyl 5-(bromoacetyl)salicylate are: (1)ACD/LogP: 3.206; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.20; (4)ACD/LogD (pH 7.4): 2.96; (5)ACD/BCF (pH 5.5): 159.47; (6)ACD/BCF (pH 7.4): 91.43; (7)ACD/KOC (pH 5.5): 1309.49; (8)ACD/KOC (pH 7.4): 750.82; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 63.6 Å²; (13)Index of Refraction: 1.592; (14)Molar Refractivity: 57.668 cm³; (15)Molar Volume: 170.468 cm³; (16)Polarizability: 22.861×10^-24cm³; (17)Surface Tension: 55.1 dyne/cm; (18)Density: 1.602 g/cm³; (19)Flash Point: 189.777 °C; (20)Enthalpy of Vaporization: 66.462 kJ/mol; (21)Boiling Point: 390.184 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation of Methyl 5-(bromoacetyl)salicylate: this chemical can be prepared by 5-acetyl-2-hydroxy-benzoic acid methyl ester at the ambient temperature. This reaction will need reagent dioxane dibromide and solvents dioxane, diethyl ether with the reaction time of 2 hours. The yield is about 76%.

Methyl 5-(bromoacetyl)salicylate can be prepared by 5-acetyl-2-hydroxy-benzoic acid methyl ester at the ambient temperature

Uses of Methyl 5-(bromoacetyl)salicylate: it can be used to produce 5-({benzyl-[6-(4-phenyl-butoxy)-hexyl]-amino}-acetyl)-2-hydroxy-benzoic acid methyl ester at the temperature of 60 °C. It will need reagent i-Pr₂EtN and solvent tetrahydrofuran. The yield is about 100%.

Methyl 5-(bromoacetyl)salicylate can be used to produce 5-({benzyl-[6-(4-phenyl-butoxy)-hexyl]-amino}-acetyl)-2-hydroxy-benzoic acid methyl ester at the temperature of 60 °C

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)c1cc(ccc1O)C(=O)CBr
(2)Std. InChI: InChI=1S/C10H9BrO4/c1-15-10(14)7-4-6(9(13)5-11)2-3-8(7)12/h2-4,12H,5H2,1H3
(3)Std. InChIKey: YRPHNSODVHXAOP-UHFFFAOYSA-N

Product Name

Benzoic acid, 5-(2-bromoacetyl)-2-hydroxy-, methyl ester

Synthetic route

Methyl 5-(bromoacetyl)salicylate Specification

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