Welcome to LookChem.com Sign In|Join Free

CAS

  • or
BENZYL 2-BROMOETHYL ETHER is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

1462-37-9 Suppliers

Post Buying Request

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier
  • 1462-37-9 Structure
  • Basic information

    1. Product Name: BENZYL 2-BROMOETHYL ETHER
    2. Synonyms: BENZYL 2-BROMOETHYL ETHER;1-BROMO-2-BENZYLOXYETHANE;1-BENZYLOXY-2-BROMOETHANE;2-BENZYLOXY-1-BROMOETHANE;Benzyl 2-bromoethyl ether, 97 % (GC);(2-Bromoethoxymethyl)benzene;Benzyloxyethyl Bromide;2-(Benzyloxy)ethyl bromide
    3. CAS NO:1462-37-9
    4. Molecular Formula: C9H11BrO
    5. Molecular Weight: 215.09
    6. EINECS: 1592732-453-0
    7. Product Categories: Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;C9;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;alkyl bromide
    8. Mol File: 1462-37-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 254 °C(lit.)
    3. Flash Point: >230 °F
    4. Appearance: Clear colorless to pale yellow liquid
    5. Density: 1.36 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.022mmHg at 25°C
    7. Refractive Index: n20/D 1.541(lit.)
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
    10. Water Solubility: Slightly soluble in water
    11. CAS DataBase Reference: BENZYL 2-BROMOETHYL ETHER(CAS DataBase Reference)
    12. NIST Chemistry Reference: BENZYL 2-BROMOETHYL ETHER(1462-37-9)
    13. EPA Substance Registry System: BENZYL 2-BROMOETHYL ETHER(1462-37-9)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22
    3. Safety Statements: 24/25
    4. RIDADR: UN 3334
    5. WGK Germany: 3
    6. RTECS:
    7. TSCA: No
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 1462-37-9(Hazardous Substances Data)

1462-37-9 Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 1462-37-9 differently. You can refer to the following data:
1. Alkylation reagent for synthesis of a macrocyclic antifungal antibiotic.1
2. Benzyl 2-broMoethyl ether is a reactant used in the preparation of muscarinic antagonist.
3. Building block used to prepare a copper phthalocyanine discotic liquid crystal.

General Description

Benzyl 2-bromoethyl ether is an organic building block. Its enthalpy of vaporization at boiling point (527.15K) has been reported to be 46.499kjoule/mol.

Check Digit Verification of cas no

The CAS Registry Mumber 1462-37-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,6 and 2 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1462-37:
(6*1)+(5*4)+(4*6)+(3*2)+(2*3)+(1*7)=69
69 % 10 = 9
So 1462-37-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H11BrO/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5H,6-8H2

1462-37-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (H56872)  Benzyl 2-bromoethyl ether, 97%   

  • 1462-37-9

  • 1g

  • 267.0CNY

  • Detail
  • Alfa Aesar

  • (H56872)  Benzyl 2-bromoethyl ether, 97%   

  • 1462-37-9

  • 5g

  • 925.0CNY

  • Detail
  • Alfa Aesar

  • (H56872)  Benzyl 2-bromoethyl ether, 97%   

  • 1462-37-9

  • 25g

  • 4416.0CNY

  • Detail

1462-37-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzyl 2-Bromoethyl Ether

1.2 Other means of identification

Product number -
Other names (2-Bromoethoxymethyl)benzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1462-37-9 SDS

1462-37-9Synthetic route

2-Benzyloxyethanol
622-08-2

2-Benzyloxyethanol

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃;98%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -78 - 20℃; Inert atmosphere; Darkness;98%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 13h;89%
2,4,6-tris(benzyloxy)-1,3,5-triazine
7285-83-8

2,4,6-tris(benzyloxy)-1,3,5-triazine

2-bromoethanol
540-51-2

2-bromoethanol

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 5h; Inert atmosphere;98%
2-bromoethanol
540-51-2

2-bromoethanol

benzyl alcohol
100-51-6

benzyl alcohol

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold (I) at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation;98%
2-(Benzyloxy)ethyl p-toluenesulfonate
4981-83-3

2-(Benzyloxy)ethyl p-toluenesulfonate

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With lithium bromide In acetonitrile at 70 - 80℃; for 2.5h; Reagent/catalyst; Solvent; Temperature;94.3%
Pyridine-2-sulfonic acid 2-benzyloxy-ethyl ester
123455-81-2

Pyridine-2-sulfonic acid 2-benzyloxy-ethyl ester

A

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

B

C5H4NO3S(1-)*Br(1-)*Mg(2+)

C5H4NO3S(1-)*Br(1-)*Mg(2+)

Conditions
ConditionsYield
With magnesium bromide ethyl etherate In diethyl ether; dichloromethane at 0℃; for 0.5h;A 94%
B n/a
2-(benzyloxy)ethyl methanesulfonate
58841-52-4

2-(benzyloxy)ethyl methanesulfonate

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With sodium bromide In dimethyl sulfoxide at 80 - 100℃; for 1h;93.5%
2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazine

2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazine

2-bromoethanol
540-51-2

2-bromoethanol

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 0.0166667h; Molecular sieve; Inert atmosphere;89%
2-Benzyloxyethanol
622-08-2

2-Benzyloxyethanol

triphenylphosphine
603-35-0

triphenylphosphine

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
In hexane; dichloromethane85%
In N-Bromosuccinimide; hexane; dichloromethane85%
2-Benzyloxyethanol
622-08-2

2-Benzyloxyethanol

A

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

B

benzyl bromide
100-39-0

benzyl bromide

Conditions
ConditionsYield
With bromine In acetonitrile at 0℃; for 0.5h; Bromination;A 77%
B n/a
carbon tetrabromide
558-13-4

carbon tetrabromide

2-Benzyloxyethanol
622-08-2

2-Benzyloxyethanol

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With pyridine; triphenylphosphine In methanol; dichloromethane; ethyl acetate76%
ethylene dibromide
106-93-4

ethylene dibromide

benzyl alcohol
100-51-6

benzyl alcohol

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With potassium hydroxide; tetrafluoroboric acid; mercury(II) oxide In dichloromethane 1.) room temp., 1 h;70%
oxirane
75-21-8

oxirane

benzyl bromide
100-39-0

benzyl bromide

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
With copper
1-bromo-2-(chloromethoxy)ethane
1462-35-7

1-bromo-2-(chloromethoxy)ethane

phenylmagnesium bromide

phenylmagnesium bromide

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

benzyl bromide
100-39-0

benzyl bromide

polymer-bound NMe3(1+)*SCN(1-)

polymer-bound NMe3(1+)*SCN(1-)

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / NaH / tetrahydrofuran / 3 h / Heating
2: 89 percent / NBS; PPh3 / CH2Cl2 / 13 h / 20 °C
View Scheme
benzyl bromide
100-39-0

benzyl bromide

sodium compound of cyclohexanol

sodium compound of cyclohexanol

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaH
2: Br2, Ph3P
View Scheme
benzyl bromide
100-39-0

benzyl bromide

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / 16 h / 0 - 23 °C
2: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 1 h / -10 - 23 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 - 20 °C
1.2: 12 h / 0 - 20 °C
2.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 1 h / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran
2: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 1 h / -78 - 20 °C
View Scheme
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

benzyl vinyl ether
935-04-6

benzyl vinyl ether

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 8h;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 8h;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 68℃; for 12h;97%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;70%
With potassium tert-butylate
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

benzyl iodoethyl ether
54555-84-9

benzyl iodoethyl ether

Conditions
ConditionsYield
With sodium iodide In acetone Reflux;100%
With sodium iodide In acetone for 48h; Reflux;85%
With sodium iodide In acetone for 3h; Reflux;73%
With sodium iodide In acetone for 16h; Reflux;60%
With sodium iodide In acetone for 6h; Reflux;
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

triethyl phosphite
122-52-1

triethyl phosphite

diethyl <2-(benzyloxy)ethyl>phosphonate
727-18-4

diethyl <2-(benzyloxy)ethyl>phosphonate

Conditions
ConditionsYield
at 200℃; for 3h; Arbuzov Reaction; Inert atmosphere;98%
at 165 - 170℃; for 3h;76%
at 165 - 170℃;76%
at 170℃; for 2h;71%
piperidin-2-one
675-20-7

piperidin-2-one

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

1-(2-(benzyloxy)ethyl)piperidin-2-one
157399-43-4

1-(2-(benzyloxy)ethyl)piperidin-2-one

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) 0 deg C; 2.) heating;97%
C27H24N2O3
1057644-00-4

C27H24N2O3

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

C36H34N2O4
1057644-06-0

C36H34N2O4

Conditions
ConditionsYield
With sodium hydroxide In water; acetone Reflux;97%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

2-fluoro-4-hydroxybenzonitrile
82380-18-5

2-fluoro-4-hydroxybenzonitrile

4-(2-benzyloxy-ethoxy)-2-fluoro-benzonitrile
1409990-80-2

4-(2-benzyloxy-ethoxy)-2-fluoro-benzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 6h;97%
3,5-dicarbomethoxypyrazole
4077-76-3

3,5-dicarbomethoxypyrazole

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

3,5-dimethyl 1-[2-(benzyloxy)ethyl]-1H-pyrazole-3,5-dicarboxylate
1200497-52-4

3,5-dimethyl 1-[2-(benzyloxy)ethyl]-1H-pyrazole-3,5-dicarboxylate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 90℃; for 4h; Inert atmosphere;96.22%
With potassium carbonate In acetonitrile at 90℃; for 4h; Inert atmosphere;96.22%
With potassium carbonate In acetonitrile at 85℃; for 1.5h;
With potassium carbonate In acetonitrile for 4.5h; Inert atmosphere; Reflux;
With potassium carbonate In acetonitrile for 4.5h; Reflux; Inert atmosphere;
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl 2-(2-(benzyloxy)ethyl)-2-methylmalonate
172644-58-5

diethyl 2-(2-(benzyloxy)ethyl)-2-methylmalonate

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran
Stage #2: bromoethyl-2-benzyl ether In tetrahydrofuran at 90℃; for 5h;
96%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

4-(5-(trifluoromethyl)-1H-imidazol-2-yl)benzonitrile
33469-11-3

4-(5-(trifluoromethyl)-1H-imidazol-2-yl)benzonitrile

4-(1-(2-(benzyloxy)ethyl)-4-(trifluoromethyl)-1H-imidazol-2-yl)benzonitrile

4-(1-(2-(benzyloxy)ethyl)-4-(trifluoromethyl)-1H-imidazol-2-yl)benzonitrile

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 18h;96%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

1-(ethoxymethyl)benzene
539-30-0

1-(ethoxymethyl)benzene

Conditions
ConditionsYield
With tris-(trimethylsilyl)silane In acetonitrile at 50℃; for 24h;95%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

2-bromo-4-fluoro-phenol
496-69-5

2-bromo-4-fluoro-phenol

1-(2-(benzyloxy)ethoxy)-2-bromo-4-fluorobenzene

1-(2-(benzyloxy)ethoxy)-2-bromo-4-fluorobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h;95%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrochloride

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrochloride

Umeclidinium bromide

Umeclidinium bromide

Conditions
ConditionsYield
In propan-1-ol; water for 2h; Solvent; Reflux;94.01%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrobromide

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrobromide

Umeclidinium bromide

Umeclidinium bromide

Conditions
ConditionsYield
In 2-methyltetrahydrofuran; water for 2.5h; Reflux;93.25%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

3-(2-(benzyloxy)ethoxy)benzaldehyde
1141781-75-0

3-(2-(benzyloxy)ethoxy)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Large scale;93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Large scale;93%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol sulfuric acid

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol sulfuric acid

Umeclidinium bromide

Umeclidinium bromide

Conditions
ConditionsYield
In water; acetonitrile for 3h; Reflux;92.87%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol formic acid

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol formic acid

Umeclidinium bromide

Umeclidinium bromide

Conditions
ConditionsYield
In isopropyl alcohol for 2.5h; Reflux;92.05%
(2-propenyl)propanedioic acid diethyl ester
2049-80-1

(2-propenyl)propanedioic acid diethyl ester

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

2-(2-benzyloxyethyl)-allylmalonate
188125-31-7

2-(2-benzyloxyethyl)-allylmalonate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 12h; Alkylation; Heating;92%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

2-nitro-4-phenylmethoxy-phenol
96315-18-3

2-nitro-4-phenylmethoxy-phenol

4-(benzyloxy)-1-[2-(benzyloxy)ethoxy]-2-nitrobenzene
1257408-27-7

4-(benzyloxy)-1-[2-(benzyloxy)ethoxy]-2-nitrobenzene

Conditions
ConditionsYield
Stage #1: 2-nitro-4-phenylmethoxy-phenol With potassium carbonate In N,N-dimethyl-formamide for 0.333333h; Williamson alkylation;
Stage #2: bromoethyl-2-benzyl ether In N,N-dimethyl-formamide at 110℃; for 14h; Williamson alkylation; Inert atmosphere;
92%
4-iodopyrazole
3469-69-0

4-iodopyrazole

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

1-(2-(benzyloxy)ethyl)-4-iodo-1H-pyrazole
1562305-17-2

1-(2-(benzyloxy)ethyl)-4-iodo-1H-pyrazole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;91.7%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;91.7%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;20 g
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol nitric acid

(1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol nitric acid

Umeclidinium bromide

Umeclidinium bromide

Conditions
ConditionsYield
In 1,4-dioxane for 2h; Reflux;90.85%
diethyl <1-14C>malonate
23178-23-6

diethyl <1-14C>malonate

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

diethyl <2-(benzyloxy)ethyl><1-14C>malonate

diethyl <2-(benzyloxy)ethyl><1-14C>malonate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 9h; Heating;90%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

4,5-bis(hydroxy)phthalic acid dimethyl ester
66323-03-3

4,5-bis(hydroxy)phthalic acid dimethyl ester

4,5-bis(benzyloxyethoxy)phthalic acid dimethyl ester
264871-01-4

4,5-bis(benzyloxyethoxy)phthalic acid dimethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone for 48h; Etherification; Heating;90%
C25H20N2O3
263141-91-9

C25H20N2O3

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

C34H30N2O4
263141-92-0

C34H30N2O4

Conditions
ConditionsYield
With sodium hydroxide In water; acetone for 14h; Reflux;90%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

3-hydroxy-5-methoxy-benzoic acid methyl ester
19520-74-2

3-hydroxy-5-methoxy-benzoic acid methyl ester

methyl 3-(2-(benzyloxy)ethoxy)-5-methoxybenzoate
203803-61-6

methyl 3-(2-(benzyloxy)ethoxy)-5-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide90%
With potassium carbonate In N,N-dimethyl-formamide90%
Stage #1: 3-hydroxy-5-methoxy-benzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: bromoethyl-2-benzyl ether In N,N-dimethyl-formamide at 160℃; for 2h;

1462-37-9Relevant articles and documents

4-Acyl Pyrrole Capped HDAC Inhibitors: A New Scaffold for Hybrid Inhibitors of BET Proteins and Histone Deacetylases as Antileukemia Drug Leads

Ahlert, Heinz,Bhatia, Sanil,Borkhardt, Arndt,Breit, Bernhard,Gunther, Stefan,Hansen, Finn K.,Hugle, Martin,Kraft, Fabian B.,Mishra, Pankaj,Schaker-Hubner, Linda,Schliehe-Diecks, Julian,Scholer, Andrea,Warstat, Robin

, p. 14620 - 14646 (2021/10/20)

Multitarget drugs are an emerging alternative to combination therapies. In three iterative cycles of design, synthesis, and biological evaluation, we developed a novel type of potent hybrid inhibitors of bromodomain, and extra-terminal (BET) proteins and histone deacetylases (HDACs) based on the BET inhibitor XD14 and well-established HDAC inhibitors. The most promising new hybrids, 49 and 61, displayed submicromolar inhibitory activity against HDAC1-3 and 6, and BRD4(1), and possess potent antileukemia activity. 49 induced apoptosis more effectively than the combination of ricolinostat and birabresib (1:1). The most balanced dual inhibitor, 61, induced significantly more apoptosis than the related control compounds 62 (no BRD4(1) affinity) and 63 (no HDAC inhibition) as well as the 1:1 combination of both. Additionally, 61 was well tolerated in an in vivo zebrafish toxicity model. Overall, our data suggest an advantage of dual HDAC/BET inhibitors over the combination of two single targeted compounds.

CONDENSED PYRROLES AS NOVEL BROMODOMAIN INHIBITORS

-

Paragraph 0098-00100; 00103-00104, (2020/07/14)

Compounds of formula (1) or (2) and their use in the treatment of diseases or conditions for which a bromodomain inhibitor is indicated.

4-Acyl Pyrroles as Dual BET-BRD7/9 Bromodomain Inhibitors Address BETi Insensitive Human Cancer Cell Lines

Hügle, Martin,Regenass, Pierre,Warstat, Robin,Hau, Mirjam,Schmidtkunz, Karin,Lucas, Xavier,Wohlwend, Daniel,Einsle, Oliver,Jung, Manfred,Breit, Bernhard,Günther, Stefan

, p. 15603 - 15620 (2020/12/23)

Various malignant human diseases show disturbed signaling pathways due to increased activity of proteins within the epigenetic machinery. Recently, various novel inhibitors for epigenetic regulation have been introduced which promise a great therapeutic benefit. Inhibitors for the bromo- and extra-terminal domain (BET) family were of particular interest after inhibitors had shown a strong antiproliferative effect. More recently, the focus has increasingly shifted to bromodomains (BDs) outside the BET family. Based on previously developed inhibitors, we have optimized a small series of 4-acyl pyrroles, which we further analyzed by ITC, X-ray crystallography, selectivity studies, the NCI60 cell-panel, and GI50 determinations for several cancer cell lines. The inhibitors address both, BET and BRD7/9 BDs, with very high affinity and show a strong antiproliferative effect on various cancer cell lines that could not be observed for BD family selective inhibitors. Furthermore, a synergistic effect on breast cancer (MCF-7) and melanoma (SK-MEL-5) was proven.

Preparation method of high purity 2-benzyloxy bromoethane

-

, (2019/07/11)

The invention relates to a preparation method of an important intermediate 2-benzyloxy bromoethane (formula I) of umeclidinium bromide. The conditions of the preparation method are mild and controllable; post-treatment is simple; yield is high; and the purity of prepared 2-benzyloxy bromoethane is high.

Triazine-Based Cationic Leaving Group: Synergistic Driving Forces for Rapid Formation of Carbocation Species

Fujita, Hikaru,Kakuyama, Satoshi,Fukuyoshi, Shuichi,Hayakawa, Naoko,Oda, Akifumi,Kunishima, Munetaka

, p. 4568 - 4580 (2018/04/26)

A new triazine-based cationic leaving group has been developed for the acid-catalyzed alkylation of O- and C-nucleophiles. There are two synergistic driving forces, namely, stable C=O bond formation and charge-charge repulsive effects, involved in the rapid generation of the carbocation species in the presence of trifluoromethanesulfonic acid (~200 mol %). Considerable rate acceleration of benzylation, allylation, and p-nitrobenzylation was observed as compared to the reactions with less than 100 mol % of the acid catalyst. The triazine-based leaving group showed superior p-nitrobenzylation yield and stability in comparison to common leaving groups, trichloroacetimidate and bromide. A plausible reaction mechanism (the cationic leaving group pathway) was proposed on the basis of mechanistic and kinetic studies, NMR experiments, and calculations.

Synthesis, antiproliferative and pro-apoptotic activity of 2-phenylindoles

Kelly, Patrick M.,Bright, Sandra A.,Fayne, Darren,Pollock, Jade K.,Zisterer, Daniela M.,Williams, D. Clive,Meegan, Mary J.

, p. 4075 - 4099 (2016/08/23)

Breast cancer is the second most common cancer worldwide after lung cancer with the vast majority of early stage breast cancers being hormone-dependent. One of the major therapeutic advances in the clinical treatment of breast cancer has been the introduction of selective estrogen receptor modulators (SERMs). We describe the design and synthesis of novel SERM type ligands based on the 2-arylindole scaffold to selectively target the estrogen receptor in hormone dependent breast cancers. Some of these novel compounds are designed as bisindole type structures, while others are conjugated to a cytotoxic agent based on combretastatin A4 (CA4) which is a potent inhibitor of tubulin polymerisation. The indole compounds synthesised within this project such as 31 and 86 demonstrate estrogen receptor (ER) binding and strong antiproliferative activity in the ER positive MCF-7 breast cancer cell line with IC50values of 2.71?μM and 1.86?μM respectively. These active compounds induce apoptotic activity in MCF-7 cells with minimal effects on normal peripheral blood cells. Their strong anti-cancer effect is likely mediated by the presence of two ER binding ligands for 31 and an ER binding ligand combined with a cytotoxic agent for 86.

Gold(I)-catalyzed synthesis of unsymmetrical ethers using alcohols as alkylating reagents

Liu, Yongxiang,Wang, Xiaoyu,Wang, Yanshi,Du, Chuan,Shi, Hui,Jin, Shengfei,Jiang, Chongguo,Xiao, Jianyong,Cheng, Maosheng

, p. 1029 - 1036 (2015/03/30)

A microwave-irradiated alcohol-protecting strategy based on gold catalysis utilizing benzyl alcohol, tert-butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen-18 isotope labelled alcohols assisted by GC-MS techniques and chemical kinetic experiments. This strategy provides an efficient, straightforward and alternative approach to the preparation of benzyl, tert-butyl and trityl ethers in organic synthesis.

SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN O-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS

-

Page/Page column 118, (2013/05/23)

The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (Q) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure

Yamada, Kohei,Fujita, Hikaru,Kunishima, Munetaka

, p. 5026 - 5029,4 (2012/12/12)

Formal trimerization of the smallest unit of benzyl imidate leads to 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT), which can be used as an acid-catalyzed O-benzylating reagent. The reaction of various functionalized alcohols with 0.4 equiv of TriBOT in the presence of trifluoromethanesulfonic acid afforded the benzyl ethers in good yields. TriBOT is an inexpensive stable crystalline solid with high atom economy.

A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure

Yamada, Kohei,Fujita, Hikaru,Kunishima, Munetaka

, p. 5026 - 5029 (2013/01/15)

Formal trimerization of the smallest unit of benzyl imidate leads to 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT), which can be used as an acid-catalyzed O-benzylating reagent. The reaction of various functionalized alcohols with 0.4 equiv of TriBOT in the presence of trifluoromethanesulfonic acid afforded the benzyl ethers in good yields. TriBOT is an inexpensive stable crystalline solid with high atom economy.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 1462-37-9