2491-38-5

Basic information

• Product Name: 2-Bromo-4'-hydroxyacetophenone
• Synonyms: PTP INHIBITOR I;PROTEIN TYROSINE PHOSPHATASE INHIBITOR I;ALPHA-BROMO-4-HYDROXYACETOPHENONE;4-HYDROXYPHENACYL BR;4-HYDROXYPHENACYL BROMIDE;2-BROMO-1-(4-HYDROXY-PHENYL)-ETHANONE;2'-BROMO-4'-HYDROXYACETOPHENONE;2-BROMO-4'-HYDROXYACETOPHENONE
• CAS NO: 2491-38-5
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 219-655-0
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Aromatics;Inhibitors
• Mol File: 2491-38-5.mol
• Article Data: 81

Chemical Properties

• Melting Point: 123-126°C
• Boiling Point: 338.7 °C at 760 mmHg
• Flash Point: 158.6 °C
• Appearance: clear colorless to light yellow liquid
• Density: 1.622 g/cm³
• Refractive Index: 1.591
• Storage Temp.: -70°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 7.69±0.15(Predicted)
• Sensitive: Lachrymatory
• Stability: Hygroscopic
• BRN: 1865388
• CAS DataBase Reference: 2-Bromo-4'-hydroxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4'-hydroxyacetophenone(2491-38-5)
• EPA Substance Registry System: 2-Bromo-4'-hydroxyacetophenone(2491-38-5)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22-36
• Safety Statements: 26
• RIDADR: 1760
• WGK Germany: 1
• RTECS: AM5982000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2491-38-5(Hazardous Substances Data)

Usage

Description

PTP Inhibitor I is a cell-permeable, protein tyrosine phosphatase (PTP) inhibitor that covalently blocks the catalytic domain of the Src homology region 2 domain-containing phosphatase (SHP-1(ΔSH2)) with a Ki value of 43 μM and PTP1B with a Ki value of 42 μM. SHP-1 and PTP1B both have known roles in regulating insulin signaling as well as myeloid and lymphoid cell differentiation, making inhibitors of these phosphatases of interest in diabetes, cancer, allergy, and inflammation research.

Chemical Properties

Pale Beige Solid

Uses

A covalent inhibitor of protein tyrosine phosphatases (PTPs)

Preparation

Also obtained by reaction of pyridinium hydrobromide perbromide with 4-hydroxyacetophenone in THF at r.t. for 3 h.

in vitro

in previous study, the corresponding values of ptp inhibitor i against ptp1b were determined to be ki of 42 μm, kinact of 0.57 min-1, and kinact/ki of 1.4*104 m-1 min-1, respectively. this study also showed that α-bromoacetophenone such as ptp inhibitor i could provide an effective, neutral py mimetic inhibitor of ptps. while perturbation of the electronic properties of the phenyl ring did not significantly improve its potency against ptps, attachment of a proper peptidyl moiety to the para position could improve both the potency and the selectivity substantially. in addition, since the covalent ptp inhibitor complex could be cleaved to regenerate the ptp activity photolytically, ptp inhibitor i might provide a novel class of photolytic switch for controlling cellular signaling processes [1].

references

[1] arabaci g, yi t, fu h, porter me, beebe kd, pei d. alpha-bromoacetophenone derivatives as neutral protein tyrosine phosphatase inhibitors: structure-activity relationship. bioorg med chem lett. 2002 nov 4;12(21):3047-50.

InChI:InChI=1/C8H7BrO2/c1-5(10)7-3-2-6(11)4-8(7)9/h2-4,11H,1H3

Synthetic route

4-Hydroxyacetophenone (99-93-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
With copper(ll) bromide In ethanol; chloroform for 3.5h; Reflux;	99.3%
With copper(ll) bromide In ethyl acetate at 20℃; for 2h;	96%
With bromine; zinc In water at 20℃; for 0.25h;	94%

4-acetyloxyacetophenone (13031-43-1) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
With bis(dimethylacetamide)hydrogen tribromide In methanol at 20 - 45℃; for 0.25h;	96%
Multi-step reaction with 2 steps 1: CS2; bromine 2: aq.-ethanolic HBr View Scheme
Multi-step reaction with 2 steps 1: bromine / chloroform / 3 h 2: hydrogenchloride / water / 4 h / Reflux View Scheme

4-Hydroxyacetophenone (99-93-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 3-bromo-4-hydroxyacetophenone (1836-06-2)

Conditions	Yield
With phenyltrimethylammonium tribromide In methanol; chloroform for 0.5h; Product distribution; other reagent, var. solvents;	A 15% B 76%

acetic acid 4-(2-bromoacetyl)phenyl ester (41104-10-3) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
With hydrogenchloride In water for 4h; Reflux;	70%
With hydrogen bromide

methoxybenzene (100-66-3) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 2-(2-bromoacetyl)hydroxybenzene (2491-36-3)

Conditions	Yield
With aluminium trichloride; 1,2-Dichloropropane
With aluminium trichloride; 1,2-Dichloropropane

4-Hydroxyacetophenone (99-93-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 2,2-dibromo-4'-hydroxyacetophenone

Conditions	Yield
With bromine In 1,4-dioxane for 0.666667h; Ambient temperature;	A 10.3 g B 0.96 g
With bromine In 1,4-dioxane for 0.5h; Ambient temperature;	A 10.3 g B 0.96 g

phenyl 2-bromoacetate (620-72-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 2-bromo-1-<2-hydroxy-phenyl>-ethanone-(1)

Conditions	Yield
With aluminium trichloride at 140℃;

phenol (108-95-2) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 150 - 155 °C 2: AlCl3 / 140 °C View Scheme

C10H8Br2O3 → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
Stage #1: C10H8Br2O3 With sodium In methanol for 3h; Stage #2: With water In methanol

copper(II)bromide (7789-45-9) + 4-Hydroxyacetophenone (99-93-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
In chloroform; ethyl acetate
In chloroform; ethyl acetate

water (7732-18-5) + sodium hydrogensulfite + 4-Hydroxyacetophenone (99-93-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
With bromine In tetrahydrofuran

pyrographite (7440-44-0) + copper(II)bromide (7789-45-9) + 4-Hydroxyacetophenone (99-93-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 6-bromo-2-[4'-(2'-p-toluenesulfonyloxyethoxy)phenyl]imidazo[1,2-a]pyridine

Conditions	Yield
In chloroform; ethyl acetate

copper(II)bromide (7789-45-9) + 4-Hydroxyacetophenone (99-93-4) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 6-bromo-2-(4 - hydroxyphenyl)imidazo[1,2-a]pyridine (956499-75-5)

Conditions	Yield
In chloroform; ethyl acetate

4-hydroxypropiophenone (70-70-2) → 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5)

Conditions	Yield
With bromine In acetic acid Cooling;

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) → 2-bromo-1-(4-hydroxy-3-nitrophenyl)ethanone (5029-61-8)

Conditions	Yield
With nitric acid In methanol at 0 - 20℃; for 3h; Large scale;	100%
With trifluoromethylsulfonic anhydride; tetramethylammonium nitrate In dichloromethane for 27h;	93%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 2-methylpropan-2-thiol (75-66-1) → 2-tert-butylsulfanyl-1-(4-hydroxy-phenyl)-ethanone

Conditions	Yield
With sodium hydride In tetrahydrofuran	100%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + (R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)-acetate (1233329-45-7) → (R)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (1233330-73-8)

Conditions	Yield
With I2 In ethyl acetate	100%
In ethyl acetate at 20℃; for 15h;	100%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 4-(1H-imidazol-4-yl)phenol (68535-65-9)

Conditions	Yield
at 150℃; for 24h;	99%
at 170 - 180℃; Inert atmosphere;	52%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + ammonium thiocyanate (1147550-11-5) → 1-(4-hydroxyphenyl)-2-thiocyanato-1-ethanone (56430-88-7)

Conditions	Yield
Stage #1: ammonium thiocyanate With montmorillonite K10 clay In acetone at 20℃; for 0.666667h; Stage #2: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone at 20℃; for 0.00833333h; Neat (no solvent); Grinding;	98%
In dichloromethane at 20℃;

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + Boc-Trp-OH (13139-14-5) → N-tBOC-L-tryptophan 4-hydroxyphenacyl ester (1365571-06-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	98%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-(4-aminophenyl)ethylidenethiosemicarbazide (7410-53-9) → 4-(2-(2-(1-(4-aminophenyl)ethylidene)hydrazinyl)thiazol-4-yl)phenol

Conditions	Yield
In isopropyl alcohol Microwave irradiation; Green chemistry;	97.53%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + N-(3-hydroxyphenyl)thiourea (3394-05-6) → 3-(4-(4-hydroxyphenyl)thiazol-2-ylamino)phenol (758688-95-8)

Conditions	Yield
In ethanol at 71℃; for 0.0125h; Microwave irradiation;	96%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) → α,α-dimethyl-p-hydroxyphenacyl acetate (20816-46-0)

Conditions	Yield
With silver(I) acetate In N,N-dimethyl-formamide at 50℃; for 3h; Inert atmosphere; Darkness;	96%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + sodium benzenesulfonate (873-55-2) → 1-(4-hydroxyphenyl)-2-(phenylsulfonyl)ethanone (896109-70-9)

Conditions	Yield
With PEG-400 at 20℃; for 0.166667h;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 3-nitrophenylthiourea (709-72-8) → 4-(2-(3-nitrophenylamino)thiazol-4-yl)phenol (824945-93-9)

Conditions	Yield
In ethanol at 71℃; for 0.0125h; Microwave irradiation;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + p-nitrophenylthiourea (3696-22-8) → 4-(2-(4-nitrophenylamino)thiazol-4-yl)phenol (708280-53-9)

Conditions	Yield
In ethanol at 71℃; for 0.0125h; Microwave irradiation;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + thiourea (17356-08-0) → 4-(2-aminothiazol-4-yl)phenol (40353-60-4)

Conditions	Yield
In ethanol at 71℃; for 0.0125h; Microwave irradiation;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-(dibenzo[b,d]furan-2-yl(phenyl)methyl)-2-methyl-1H-imidazole (1449604-26-5) → 1-(dibenzo[b,d]furan-2-yl(phenyl)methyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide

Conditions	Yield
In acetone; toluene at 20℃; Reflux;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-(dibenzo[b,d]furan-2-yl(phenyl)methyl)-1H-benzo[d]imidazole (1449604-27-6) → 1-(dibenzo[b,d]furan-2-yl(phenyl)methyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-1H-benzo[d]imidazol-3-ium bromide (1449604-73-2)

Conditions	Yield
In acetone; toluene at 20℃; Reflux;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-(1-(dibenzo[b,d]furan-2-yl)ethyl)-1H-imidazole (1449604-22-1) → 1-(1-(dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-1H-imidazol-3-ium bromide (1449604-31-2)

Conditions	Yield
In acetone; toluene at 20℃; Reflux;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-(dibenzo[b,d]furan-2-yl(phenyl)methyl)-1H-imidazole (1449604-25-4) → 1-(dibenzo[b,d]furan-2-yl(phenyl)methyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-1H-imidazol-3-ium bromide (1449604-56-1)

Conditions	Yield
In acetone; toluene at 20℃; Reflux;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-(1-(dibenzo[b,d]furan-2-yl)ethyl)-2-methyl-1H-imidazole (1449604-23-2) → 1-(1-(dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide (1449604-39-0)

Conditions	Yield
In acetone; toluene at 20℃; Reflux;	95%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + benzoyl chloride (98-88-4) → 4'-benzoyloxy-2-bromoacetophenone (5324-15-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;	95%

d(4)-methanol (811-98-3) + 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) → C9H6(2)H3BrO2

Conditions	Yield
Stage #1: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone With triphenylphosphine In tetrahydrofuran for 0.166667h; Cooling with ice; Stage #2: d(4)-methanol With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 2h; Cooling with ice;	94.5%

2-hydroxyphenylthiourea (1520-26-9) + 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) → 2-(4-(4-hydroxyphenyl)thiazol-2-ylamino)phenol (1173282-18-2)

Conditions	Yield
In ethanol at 71℃; for 0.0125h; Microwave irradiation;	94%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + (4-aminosulfonylphenyl)thiourea (1718-39-4) → 4-(4-(4-hydroxyphenyl)thiazol-2-ylamino)benzenesulfonamide (708995-83-9)

Conditions	Yield
In ethanol at 71℃; for 0.0125h; Microwave irradiation;	94%
In ethanol; N,N-dimethyl-formamide at 80℃; for 5h;	84%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-(1-(dibenzo[b,d]furan-2-yl)ethyl)-1Hbenzo[d]imidazole (1449604-24-3) → 1-(1-(dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-1H-benzo[d]imidazol-3-ium bromide (1449604-47-0)

Conditions	Yield
In acetone; toluene at 20℃; Reflux;	94%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 1-((benzofuran-2-yl)methyl)-1H-benzo[d]imidazole (1422034-47-6) → 1-((benzofuran-2-yl)methyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-1H-benzo[d]imidazol-3-ium bromide (1454785-25-1)

Conditions	Yield
In toluene Reflux;	94%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + N4-methylpyrimidine-2,4-diamine (1004-18-8) → 4-(7-(methylamino)imidazo[1,2-a]pyrimidin-2-yl)phenol

Conditions	Yield
In acetone at 65℃; Inert atmosphere;	94%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 2-[2-(3,4-dimethoxy-phenyl)-ethylamino]-1-(4-hydroxy-phenyl)-ethanone hydrochloride

Conditions	Yield
Stage #1: 2-(3,4-dimethoxyphenyl)-ethylamine In acetonitrile for 0.166667h; Cooling with ice; Stage #2: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone In acetonitrile	94%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 4-(6-nitroquinoxalin-2-yl)phenol (1415328-10-7)

Conditions	Yield
In dimethyl sulfoxide at 20℃;	93.6%
In dimethyl sulfoxide at 20℃; for 10h;	58%
In dimethyl sulfoxide at 20℃; for 0.166667h;	58%

Upstream product

• 41104-10-3 acetic acid 4-(2-bromoacetyl)phenyl ester 
• 100-66-3 methoxybenzene 
• 598-21-0 2-Bromoacetyl bromide 
• 99-93-4 4-Hydroxyacetophenone 
• 13031-43-1 4-acetyloxyacetophenone 
• 620-72-4 phenyl 2-bromoacetate 
• 7789-45-9 copper(II)bromide 
• 70-70-2 4-hydroxypropiophenone 
• 7440-44-0 pyrographite 
• 7732-18-5 water 
• 108-95-2 phenol 

Downstream Products

• 7496-41-5 2-(4-hydroxyphenyl)indolizine 
• 87154-81-2 2-(diethylamino)-1-(4-hydroxyphenyl)ethanone 
• 130627-04-2 2-Nitrobenzoesaeure-(4-hydroxyphenacylester) 
• 770-39-8 4-methoxyphenylacetone 
• 98815-43-1 1-[(4-hydroxy)phenyl]-2-methyl-2-propanol 
• 32136-81-5 alpha-methoxy-4-hydroxyacetophenone 
• 41877-18-3 2,3-dibromo-4'-hydroxyacetophenone 
• 99-93-4 4-Hydroxyacetophenone 
• 139420-61-4 2-Amino-5-(4-hydroxyphenyl)-6H-1,3,4-thiadiazine 
• 139420-55-6 2-Hydrazino-4-(4-hydroxyphenyl)thiazole 
• 156897-31-3 4-(6,6-Dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)-phenol 
• 63735-77-3 6-(4-hydroxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazole-2-sulfonic acid amide 
• 270090-90-9 N-Boc-O-(4-hydroxyphenacyl)-Ala-Ala 
• 137618-45-2 2-Ethoxycarbonylmethylthio-5-(4-hydroxyphenyl)carbonylmethylthio-1,3,4-thiadiazole 

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