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174265-12-4

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174265-12-4 Usage

General Description

2-Bromo-5-chlorobenzaldehyde, also known as 5-chloro-2-bromobenzaldehyde, is a chemical compound with the molecular formula C7H4BrClO. It is a white to off-white crystalline solid that is commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals and agrochemicals. 2-Bromo-5-chlorobenzaldehyde is also used as an intermediate in the manufacture of dyes, pigments, and other organic compounds. It is an important reagent in the production of various organic compounds due to its versatile chemical properties and functional groups. 2-Bromo-5-chlorobenzaldehyde is known for its strong and distinct odor, and it is considered to be a hazardous chemical that should be handled with care and caution.

Check Digit Verification of cas no

The CAS Registry Mumber 174265-12-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,4,2,6 and 5 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 174265-12:
(8*1)+(7*7)+(6*4)+(5*2)+(4*6)+(3*5)+(2*1)+(1*2)=134
134 % 10 = 4
So 174265-12-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H4BrClO/c8-7-2-1-6(9)3-5(7)4-10/h1-4H

174265-12-4 Well-known Company Product Price

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  • Alfa Aesar

  • (H64330)  2-Bromo-5-chlorobenzaldehyde, 97%   

  • 174265-12-4

  • 5g

  • 196.0CNY

  • Detail
  • Alfa Aesar

  • (H64330)  2-Bromo-5-chlorobenzaldehyde, 97%   

  • 174265-12-4

  • 25g

  • 647.0CNY

  • Detail
  • Alfa Aesar

  • (H64330)  2-Bromo-5-chlorobenzaldehyde, 97%   

  • 174265-12-4

  • 100g

  • 2587.0CNY

  • Detail

174265-12-4SDS

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 2-Bromo-5-chlorobenzaldehyde

1.2 Other means of identification

Product number -
Other names Benzaldehyde,2-bromo-5-chloro

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:174265-12-4 SDS

174265-12-4Synthetic route

2-bromo-5-chlorobenzyl alcohol
60666-70-8

2-bromo-5-chlorobenzyl alcohol

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
Stage #1: 2-bromo-5-chlorobenzyl alcohol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h;
Stage #2: With triethylamine In dichloromethane at -78 - 20℃;
96%
With triphenylmethyl alcohol; iron(III) chloride hexahydrate at 55℃; for 1h; Microwave irradiation;85%
With triphenylmethyl alcohol; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) at 140℃; for 1h; Microwave irradiation;85%
With Dess-Martin periodane In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #1: 2-bromo-5-chlorobenzyl alcohol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.0833333h;
Stage #2: With triethylamine In dichloromethane at 0 - 20℃; for 4h;
1-bromo-4-chloro-2-dibromomethylbenzene
1313762-49-0

1-bromo-4-chloro-2-dibromomethylbenzene

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
With sulfuric acid at 60℃; for 3h; Inert atmosphere;95%
2-bromo-5-chlorobenzyl bromide
66192-24-3

2-bromo-5-chlorobenzyl bromide

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide In acetonitrile at 0℃; for 2h; Molecular sieve;92%
With 4 A molecular sieve; 4-methylmorpholine N-oxide In acetonitrile at 0℃; for 2h;65%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfuric acid; iodine at 10 - 25℃; for 3h; Reagent/catalyst;90.1%
With N-Bromosuccinimide; 4-chloro-2-(trifluoromethyl)aniline; palladium diacetate In 1,2-dichloro-ethane; trifluoroacetic acid at 60℃; for 24h;88%
With N-Bromosuccinimide; palladium diacetate; silver trifluoroacetate; toluene-4-sulfonic acid; trifluoroacetic acid; 4-Nitroanthranilic acid In 1,2-dichloro-ethane at 90℃; for 24h; Sealed tube;80%
Multi-step reaction with 3 steps
1: pyridine / dichloromethane / 1 h / 20 °C
2: N-Bromosuccinimide; Ag(1-)*C2F3O2(1-); palladium diacetate / 1,2-dichloro-ethane / 24 h / 120 °C
3: formaldehyd; toluene-4-sulfonic acid / tetrahydrofuran; water / 0.25 h / 100 °C / Microwave irradiation
View Scheme
2-bromo-5-chlorobenzaldehyde O-methyloxime

2-bromo-5-chlorobenzaldehyde O-methyloxime

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
With formaldehyd; toluene-4-sulfonic acid In tetrahydrofuran; water at 100℃; for 0.25h; Microwave irradiation;86%
(2-bromo-5-chlorophenyl)methanediyl diacetate
882772-93-2

(2-bromo-5-chlorophenyl)methanediyl diacetate

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
With sulfuric acid In methanol; water for 0.5h; Reflux;83%
With hydrogenchloride; water In 1,4-dioxane for 2.5h; Reflux;
3N-HCl

3N-HCl

2-bromo-5-chlorotoluene
14495-51-3

2-bromo-5-chlorotoluene

chromium(VI) oxide
1333-82-0

chromium(VI) oxide

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
With sulfuric acid In ethanol; water; acetic anhydride77%
2-bromo-5-chlorotoluene
14495-51-3

2-bromo-5-chlorotoluene

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 16 h / Reflux; Inert atmosphere
2: sulfuric acid / 3 h / 60 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: chromium(VI) oxide; acetic acid; sulfuric acid / 2 h / 0 °C
2: sulfuric acid / methanol; water / 0.5 h / Reflux
View Scheme
2-bromo-5-chlorobenzoic acid
21739-93-5

2-bromo-5-chlorobenzoic acid

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: borane dimethyl sulphide complex / tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: borane-THF / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere
2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.25 h / -78 °C
2.2: -78 - 20 °C
View Scheme
3-chlorobenzaldehyde O-methyloxime
33499-36-4

3-chlorobenzaldehyde O-methyloxime

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; Ag(1-)*C2F3O2(1-); palladium diacetate / 1,2-dichloro-ethane / 24 h / 120 °C
2: formaldehyd; toluene-4-sulfonic acid / tetrahydrofuran; water / 0.25 h / 100 °C / Microwave irradiation
View Scheme
sodium metaborate
7775-19-1

sodium metaborate

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Conditions
ConditionsYield
bis(triphenylphosphine)palladium(II)-chloride In water
dihydroxyborane
13780-71-7

dihydroxyborane

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-bromo-5-chlorobenzyl alcohol
60666-70-8

2-bromo-5-chlorobenzyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;100%
With sodium hydride In methanol at 20℃;95%
With sodium borohydrid In methanol; water; acetone94%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

N'-(2-bromo-5-chlorobenzyl)-N,N-dimethylethane-1,2-diamine
886041-45-8

N'-(2-bromo-5-chlorobenzyl)-N,N-dimethylethane-1,2-diamine

Conditions
ConditionsYield
Stage #1: 2-bromo-5-chlorobenzaldehyde; N,N-dimethylethylenediamine With acetic acid In tetrahydrofuran at 20℃; for 1h; pH=5;
Stage #2: With sodium cyanoborohydride In methanol at 20℃; for 3h;
Stage #3: With water; sodium hydrogencarbonate In ethyl acetate
100%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

1-bromo-4-chloro-2-vinylbenzene

1-bromo-4-chloro-2-vinylbenzene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Wittig Olefination;
Stage #2: 2-bromo-5-chlorobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 12h; Wittig Olefination;
100%
With potassium carbonate In 1,4-dioxane at 110℃; for 10h; Inert atmosphere;79%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Inert atmosphere;
60%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

5-chloro-2-[2-(trimethylsilyl)ethynyl]benzaldehyde

5-chloro-2-[2-(trimethylsilyl)ethynyl]benzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 20 - 70℃; Sonogashira Cross-Coupling; Inert atmosphere;99%
Stage #1: 2-bromo-5-chlorobenzaldehyde With copper(l) iodide; triethylamine at 23℃; for 0.25h; Inert atmosphere;
Stage #2: trimethylsilylacetylene With tetrakis(triphenylphosphine) palladium(0) at 20℃; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 12h;
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

7-chloro-1,3-dimethoxyacridine

7-chloro-1,3-dimethoxyacridine

Conditions
ConditionsYield
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere;
99%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-(anthracene-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
676578-20-4

2-(anthracene-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C21H13ClO
1301205-51-5

C21H13ClO

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 11h; Suzuki-Miyaura Coupling; Reflux;98%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-bromo-5-chlorobenzaldehyde dimethyl acetal
959687-69-5

2-bromo-5-chlorobenzaldehyde dimethyl acetal

Conditions
ConditionsYield
With tropylium tetrafluoroborate In acetonitrile at 70℃; for 5h; Inert atmosphere; Green chemistry;98%
With Montmollironite clay K-10 at 20℃; for 1.5h; Inert atmosphere;77%
Stage #1: trimethyl orthoformate With montmorillonite clay k-10 at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde for 3h; Inert atmosphere;
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

ethylene glycol
107-21-1

ethylene glycol

2-(2-bromo-5-chlorophenyl)-1,3-dioxolane
1187647-98-8

2-(2-bromo-5-chlorophenyl)-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 12h; Inert atmosphere; Dean-Stark; Reflux;98%
With toluene-4-sulfonic acid In toluene Reflux;59%
With toluene-4-sulfonic acid In toluene for 18h; Reflux; Inert atmosphere;
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

trimethyleneglycol
504-63-2

trimethyleneglycol

2-(2-bromo-5-chlorophenyl)-1,3-dioxane

2-(2-bromo-5-chlorophenyl)-1,3-dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Reflux;97%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

(methoxymethyl)triphenylphosphonium chloride
4009-98-7

(methoxymethyl)triphenylphosphonium chloride

1-bromo-4-chloro-2-(2-methoxyvinyl)benzene

1-bromo-4-chloro-2-(2-methoxyvinyl)benzene

Conditions
ConditionsYield
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran at -25℃; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In tetrahydrofuran at -25℃; for 2h; Temperature;
97%
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium hexamethylsilazane In toluene at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In toluene at 0 - 20℃; for 7h; Inert atmosphere;
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In tetrahydrofuran at 20℃; for 3h; Wittig reaction; Inert atmosphere;
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In tetrahydrofuran at 0 - 24℃; for 24.5h; Inert atmosphere;
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-(2-hydroxy-3-methoxyphenyl)acetonitrile
42973-56-8

2-(2-hydroxy-3-methoxyphenyl)acetonitrile

2-chloro-6-methoxydibenzo[b,f]oxepine-10-carbonitrile
1446201-58-6

2-chloro-6-methoxydibenzo[b,f]oxepine-10-carbonitrile

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;97%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

4-chloro-aniline
106-47-8

4-chloro-aniline

2,7-dichloroacridine

2,7-dichloroacridine

Conditions
ConditionsYield
Stage #1: 4-chloro-aniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere;
Stage #3: With aluminum (III) chloride In toluene at 80℃; for 12h;
97%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

tert-butylamine
75-64-9

tert-butylamine

(E)-N-(2-bromo-5-chlorobenzylidene)-2-methylpropan-2-amine

(E)-N-(2-bromo-5-chlorobenzylidene)-2-methylpropan-2-amine

Conditions
ConditionsYield
at 80℃; for 17h; Sealed tube;97%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2,4-difluorophenylboronic acid
144025-03-6

2,4-difluorophenylboronic acid

4-chloro-2',4'-difluoro-[1,1'-biphenyl]-2-carbaldehyde

4-chloro-2',4'-difluoro-[1,1'-biphenyl]-2-carbaldehyde

Conditions
ConditionsYield
With potassium phosphate monohydrate; C66H84O10P2Pd In water; toluene at 45℃; for 3h; Reagent/catalyst; Solvent; Suzuki-Miyaura Coupling; Inert atmosphere;97%
With potassium phosphate monohydrate; C50H64NO6PPdS In water at 45℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

(methoxymethyl)triphenylphosphonium chloride
4009-98-7

(methoxymethyl)triphenylphosphonium chloride

1-bromo-4-chloro-2-(2-methoxyvinyl)benzene

1-bromo-4-chloro-2-(2-methoxyvinyl)benzene

Conditions
ConditionsYield
With potassium tert-butylate In Petroleum ether97%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

phenylboronic acid
98-80-6

phenylboronic acid

4-chloro-[1,1'-biphenyl]-2-carbaldehyde
1198208-10-4

4-chloro-[1,1'-biphenyl]-2-carbaldehyde

Conditions
ConditionsYield
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 24h; Suzuki-Miyaura Coupling;96%
Stage #1: 2-bromo-5-chlorobenzaldehyde; phenylboronic acid With sodium carbonate In water; N,N-dimethyl-formamide for 0.0833333h;
Stage #2: With palladium diacetate In water; N,N-dimethyl-formamide at 20℃;
91%
With C64H118O20; C54H72NO6PPdS; triethylamine In tetrahydrofuran; water at 45℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;90%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A

(1R)-6-chloro-2,3-dihydro-3-(methylene)inden-1-ol

(1R)-6-chloro-2,3-dihydro-3-(methylene)inden-1-ol

B

(1S)-6-chloro-2,3-dihydro-3-(methylene)inden-1-ol

(1S)-6-chloro-2,3-dihydro-3-(methylene)inden-1-ol

Conditions
ConditionsYield
Stage #1: 2-bromo-5-chlorobenzaldehyde; 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With (R)-3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate; potassium carbonate In water; toluene at -50 - 20℃; for 24h;
Stage #2: With bis-triphenylphosphine-palladium(II) chloride; hydrazine hydrate In water; toluene at 100℃; for 20h; enantioselective reaction;
A 96%
B n/a
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-(2′-bromo-5′-chlorophenyl)ethan-1-ol

1-(2′-bromo-5′-chlorophenyl)ethan-1-ol

Conditions
ConditionsYield
In diethyl ether; dibutyl ether at -78 - 0℃; Inert atmosphere;96%
In tetrahydrofuran at 0℃; Inert atmosphere;83%
In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;81%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

(S)-2-methylpropane-2-sulfinamide
343338-28-3

(S)-2-methylpropane-2-sulfinamide

S-N-(2-bromo-5-chlorobenzylidene)-2-methylpropane-2-sulfinamide

S-N-(2-bromo-5-chlorobenzylidene)-2-methylpropane-2-sulfinamide

Conditions
ConditionsYield
With caesium carbonate In toluene at 40℃; for 2h; Temperature; Concentration; Solvent;95.2%
With caesium carbonate In dichloromethane Reflux;
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-hydroxybenzyl cyanide
14714-50-2

2-hydroxybenzyl cyanide

2-chlorodibenzo[b,f]oxepine-10-carbonitrile
1400574-15-3

2-chlorodibenzo[b,f]oxepine-10-carbonitrile

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;95%
With caesium carbonate In toluene at 130℃; for 24h; Inert atmosphere; Molecular sieve;93%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

1-(2-bromo-5-chlorophenyl)methanamine
942400-60-4

1-(2-bromo-5-chlorophenyl)methanamine

Conditions
ConditionsYield
Stage #1: 2-bromo-5-chlorobenzaldehyde With hydroxylamine In methanol at 20℃; for 4h;
Stage #2: With acetic acid; zinc
95%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-(methylamino)-N’-phenylbenzohydrazide

2-(methylamino)-N’-phenylbenzohydrazide

2-(2-bromo-5-chlorophenyl)-1-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one
1437780-46-5

2-(2-bromo-5-chlorophenyl)-1-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With caesium carbonate; copper(I) bromide In 1,4-dioxane for 3h; Reflux;95%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

carbon monoxide
201230-82-2

carbon monoxide

3-hydroxy-5-chloroisobenzofuran-1(3H)-one
70097-46-0

3-hydroxy-5-chloroisobenzofuran-1(3H)-one

Conditions
ConditionsYield
With water; palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 65℃; for 2h; Inert atmosphere;95%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

4-dibenzofurylboronic acid
100124-06-9

4-dibenzofurylboronic acid

C19H11ClO2

C19H11ClO2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Inert atmosphere; Reflux;93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux; Inert atmosphere;77%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

phenylvinylboronic acid
14900-39-1

phenylvinylboronic acid

5-chloro-2-(1-phenylvinyl)benzaldehyde

5-chloro-2-(1-phenylvinyl)benzaldehyde

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;93%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-(5-bromo-2-hydroxyphenyl)acetonitrile
1261815-96-6

2-(5-bromo-2-hydroxyphenyl)acetonitrile

8-bromo-2-chlorodibenzo[b,f]oxepine-10-carbonitrile
1446201-66-6

8-bromo-2-chlorodibenzo[b,f]oxepine-10-carbonitrile

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;92%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

2-amino-N'-phenylbenzohydrazide
30086-49-8

2-amino-N'-phenylbenzohydrazide

2-chloro-5-phenylindazolo[3,2-b]quinazolin-7(5H)-one
1437780-33-0

2-chloro-5-phenylindazolo[3,2-b]quinazolin-7(5H)-one

Conditions
ConditionsYield
With caesium carbonate; copper(I) bromide In 1,4-dioxane for 15h; Reflux;92%
Multi-step reaction with 2 steps
1: citric acid / ethanol / Reflux
2: copper(l) chloride; L-proline; caesium carbonate / dimethyl sulfoxide / 12 h / 90 °C / Inert atmosphere; Schlenk technique
View Scheme

174265-12-4Relevant articles and documents

Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy

Yong, Qiyun,Sun, Bing,Zhang, Fang-Lin

supporting information, (2019/11/03)

A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.

Synthesis of functionalized helical BN-benzo[c] phenanthrenes

Abengózar, Alberto,García-García, Patricia,Sucunza, David,Pérez-Redondo, Adrián,Vaquero, Juan J.

supporting information, p. 2467 - 2470 (2018/03/21)

A novel parent BN-benzo[c]phenanthrene, with helical chirality and remarkable structural features, has been easily obtained in three steps with a global yield of 55%. Moreover, Cl-substituted derivatives have been prepared and these have served as useful starting materials for the development of palladium-catalyzed cross-coupling reactions.

A gold catalytic oxidation of benzyl alcohol synthesis method (by machine translation)

-

Paragraph 0034-0037; 0041; 0055-0057, (2017/08/25)

The present invention provides a kind of organic synthesis in the oxidation of benzyl alcohol synthesis method, the reaction formula is as follows, in the formula 1 containing different substituents is benzyl alcohol, in the formula 2 is triphenylcarbinol compound. The required reaction of gold catalyst is Ph3 PAuCl, Ph3 PAuNTf2 , HAuCl4 , NaAuCl4 , Ph3 PAuOTf, Ph3 PAuSbF6 , IPrAuCl, gold. The required reaction medium is: solvent-free, toluene, are three-toluene, 1, 2 - dichloroethane, tetrahydrofuran, acetonitrile, acetone. The reaction implementing microwave heating of reactor, the method of the invention the oxidizing agent triphenylcarbinol for commercial products, cheap, and simple experimental operation, substrate and wide range of application. (by machine translation)

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