Product Name

  • Name

    2-Bromobenzaldehyde

  • EINECS 229-622-2
  • CAS No. 6630-33-7
  • Article Data248
  • CAS DataBase
  • Density 1.58 g/cm3
  • Solubility Soluble in alcohol and benzene. Insoluble in water.
  • Melting Point 21-22 °C
  • Formula C7H5BrO
  • Boiling Point 230.8 °C at 760 mmHg
  • Molecular Weight 185.02
  • Flash Point 96.2 °C
  • Transport Information UN 2810 6.1/PG 3
  • Appearance clear yellow liquid after melting
  • Safety 26-36
  • Risk Codes 36/37/38-22
  • Molecular Structure Molecular Structure of 6630-33-7 (2-Bromobenzaldehyde)
  • Hazard Symbols IrritantXi,HarmfulXn
  • Synonyms Benzaldehyde,o-bromo- (6CI,7CI,8CI);1-Bromo-2-formylbenzene;2-Bromobenzenecarboxaldehyde;NSC 60390;o-Bromobenzaldehyde;
  • PSA 17.07000
  • LogP 2.26160

Synthetic route

o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With 1H-imidazole; sodium periodate; manganese(III)-porphyrin complex immobilized on polystyrene In water; acetonitrile at 20℃; for 1.16667h;100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 90℃; for 5h;100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; silica gel; potassium bromide In dichloromethane at 0℃; for 1h; pH=9.1; Anelli oxidation;99%
benzaldehyde
100-52-7

benzaldehyde

A

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

B

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With sulfuric acid; C18H16Br4N2O3V; dihydrogen peroxide; potassium bromide In methanol; water at 20℃; for 2.33333h; Catalytic behavior;A 100%
B n/a
2-(2-bromophenyl)-1,3-dioxolan
34824-58-3

2-(2-bromophenyl)-1,3-dioxolan

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With water at 90℃; for 2h; Green chemistry; chemoselective reaction;98%
With hyper-cross-linked polymer nanospheres with acid sites In nitromethane at 80℃; for 6h; Henry Nitro Aldol Condensation;97%
With trifluoroacetic acid In chloroform at 25℃; for 40h;93%
o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

methyllithium
917-54-4

methyllithium

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With oxygen; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(I) bromide dimethylsulfide complex; bis(3-(perfluorooctyl)butyl)-2,2'-bipyridine In chlorobenzene at 90℃; for 3h; Oxidation;96%
2-bromostyrene
2039-88-5

2-bromostyrene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 70℃; under 760.051 Torr; for 6h; Green chemistry; chemoselective reaction;96%
With eosin Y; oxygen In dimethyl sulfoxide at 20℃; for 11h; Irradiation; Green chemistry;86%
With tetrabutylammonium perchlorate; oxygen; platinum In acetonitrile at 20℃; Electrolysis;84%
With bismuth vanadate; oxygen In water at 20℃; Irradiation;82%
With dihydrogen peroxide; [Co4(SO4)3(F)3(2,4,6-tris-(4-pyridyl)-1,3,5-triazine)2(tatb)] In ethanethiol at 60℃;90 %Spectr.
2-bromo-(trimethylsilyloxymethyl)benzene
59184-20-2

2-bromo-(trimethylsilyloxymethyl)benzene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With silica chromate; silica gel In dichloromethane at 20℃; for 0.5h;95%
With trinitratocerium(IV) bromate for 0.7h; Heating;95%
With copper(II) nitrate trihydrate; water; silica gel; potassium bromide at 90℃; for 0.75h; Neat (no solvent);87%
2-bromobenzaldehyde diethyl acetal
35822-58-3

2-bromobenzaldehyde diethyl acetal

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
In(OSO2CF3)3 In acetone at 20℃; for 0.5h;94%
With iron(III) p-toluenesulfonate hexahydrate In water for 2.5h; Reflux;86%
With 1-diphenylphosphino-8-triphenylstibonium-naphthalene triflate; water In chloroform-d1 at 70℃; for 0.5h; Inert atmosphere; Schlenk technique; Green chemistry;
2-(2-bromophenyl)-1,3-oxathiolane
131496-49-6

2-(2-bromophenyl)-1,3-oxathiolane

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With t-butyl thionitrite In acetonitrile at 0℃; for 0.3h;93%
With Iron(III) nitrate nonahydrate at 90℃; for 0.05h;90%
With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Irradiation;80%
C6H4(2-Br)(CHSCH2CH2CH2S-cyclic)
130614-23-2

C6H4(2-Br)(CHSCH2CH2CH2S-cyclic)

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In neat (no solvent) at 20℃; for 1h; Milling;93%
With eosin y In water; acetonitrile at 20℃; for 3h; Irradiation;90%
2-(tetrahydropyranyloxy)methylbromobenzene
17100-66-2

2-(tetrahydropyranyloxy)methylbromobenzene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate; molybdenum trioxide In water; acetonitrile for 1.5h; Reflux;92%
With trichloroisocyanuric acid In acetonitrile Reflux;
2-bromobenzylchloride
578-51-8

2-bromobenzylchloride

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;91%
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;85%
With potassium carbonate; dimethyl sulfoxide at 90℃; Kornblum Aldehyd Synthesis;
2-bromobenzaldehyde oxime
34158-72-0, 52707-51-4, 52707-56-9

2-bromobenzaldehyde oxime

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With 2,6-dicarboxypyridinium fluorochromate for 0.283333h;90%
With chromium(VI) oxide; silica gel In dichloromethane for 0.0222222h; Irradiation;88%
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; toluene at 60℃; under 760.051 Torr; for 6h;82%
o-bromobenzaldehyde dimethyl acetal
35849-09-3

o-bromobenzaldehyde dimethyl acetal

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
perchloric acid In methanol; water at 25 - 30℃; for 0.166667h;90%
With water In methanol at 25 - 30℃; for 0.25h;90%
5-[(2-bromophenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
15795-61-6

5-[(2-bromophenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With oxone In water; acetonitrile at 45℃; for 1h;90%
1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;89%
With hydrogenchloride; ethanol; hexamethylenetetramine
With chloroform; hexamethylenetetramine Kochen des Reaktionsprodukts mit wss. Essigsaeure;
2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In hexane; dichloromethane for 4.5h; Ambient temperature;89%
With triethylsilane; iron(III)-acetylacetonate71%
With sodium tetrahydroborate; cadmium(II) chloride In N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile at -5℃; for 0.0833333h; Yield given;
Multi-step reaction with 4 steps
1.1: LDA / tetrahydrofuran / 0.5 h
1.2: 86 percent / tetrahydrofuran / -78 - 20 °C
2.1: 66 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
3.1: 47 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 96 h / 20 °C
4.1: TiCl4 / CH2Cl2 / -78 °C
View Scheme
2-bromostyrene
2039-88-5

2-bromostyrene

A

2,5-bis(2-bromophenyl)tetrahydrofuran

2,5-bis(2-bromophenyl)tetrahydrofuran

B

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With tetrabutylammonium perchlorate; oxygen; pyrographite In nitromethane at 20℃; Electrolysis; chemoselective reaction;A 89%
B 9%
1-allyl-2-bromobenzene
42918-20-7

1-allyl-2-bromobenzene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With iron(III) chloride; tetramethyldisiloxane In ethanol at 20℃; for 12h;86%
2-(2-bromophenyl)-1,3-dithiolane
113509-22-1

2-(2-bromophenyl)-1,3-dithiolane

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With iodosylbenzene In dichloromethane at 20℃; for 0.5h;85%
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h; Yield given;
(2-bromophenyl)methylene diacetate
60229-71-2

(2-bromophenyl)methylene diacetate

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With poly(4-vinylpyridinium) hydrogen sulfate solid acid In methanol at 20℃; for 0.75h; Irradiation;83%
With hydrogenchloride
With bismuth(III) nitrate In ethanol at 20℃; for 0.0833333h;
With water at 20℃; for 0.25h; Green chemistry;92 %Chromat.
[(2-bromo-phenyl)-methoxycarbonylmethanesulfonyl-methanesulfonyl]-acetic acid methyl ester

[(2-bromo-phenyl)-methoxycarbonylmethanesulfonyl-methanesulfonyl]-acetic acid methyl ester

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane for 4h; Heating;82%
o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

A

2-bromobenzyl 2'-bromobenzoate
1363569-70-3

2-bromobenzyl 2'-bromobenzoate

B

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,3,5-trimethyl-benzene at 157℃; for 48h;A 82%
B 9%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 3h; Irradiation; Green chemistry;81%
With Ag(Py)4S2O8 In acetonitrile for 7h; Heating;60%
With tetrakis(pyridine)silver(II) peroxodisulfate In acetonitrile for 7h; Heating;60%
2-(2-bromophenyl)-2-hydroxyacetonitrile
52923-21-4, 1269472-47-0, 548478-30-4

2-(2-bromophenyl)-2-hydroxyacetonitrile

A

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

B

2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
Stage #1: 2-(2-bromophenyl)-2-hydroxyacetonitrile With (η(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride In benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: With water In dichloromethane; ethyl acetate; benzene for 24h;		A 81%
B 17%
2-(2-bromophenyl)-2-hydroxyacetonitrile
52923-21-4, 1269472-47-0, 548478-30-4

2-(2-bromophenyl)-2-hydroxyacetonitrile

A

2-bromobenzoyl cyanide
88562-26-9

2-bromobenzoyl cyanide

B

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With (η(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride In benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;A n/a
B 81%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave;79%
formic acid
64-18-6

formic acid

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;78%
2-bromo-N-methoxy-N-methylbenzamide
899425-05-9

2-bromo-N-methoxy-N-methylbenzamide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
Stage #1: 2-bromo-N-methoxy-N-methylbenzamide With chloromagnesium dimethylaminoborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere;
Stage #2: With acetaldehyde; acetic acid In tetrahydrofuran; pentane for 0.25h; Inert atmosphere; Further stages;		74%
Stage #1: 2-bromo-N-methoxy-N-methylbenzamide With chloromagnesium dimethylaminoborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere;
Stage #2: With acetaldehyde; acetic acid In tetrahydrofuran; pentane for 0.25h; Inert atmosphere;
ortho-bromophenylacetic acid
18698-97-0

ortho-bromophenylacetic acid

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water at 90℃; for 12h; Green chemistry;72%
With copper(II) ferrite In dimethyl sulfoxide at 120℃; for 12h; Green chemistry;72%
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube;70%
With iron(III) chloride; oxygen In N,N-dimethyl-formamide at 110℃;58%
(electrolysis);
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

diethyl malonate
105-53-3

diethyl malonate

diethyl <(2-bromophenyl)methylene>propanedioate
93098-67-0

diethyl <(2-bromophenyl)methylene>propanedioate

Conditions
ConditionsYield
With piperidine; benzoic acid In toluene for 3h; Heating;100%
With piperidine; acetic acid In ethanol Reflux;77%
With iron(III) chloride; N-fluorobis(benzenesulfon)imide In neat (no solvent) at 60℃; for 24h; Knoevenagel Condensation; Inert atmosphere; Green chemistry;77%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

(E)-N-(2-bromobenzylidene)-4-methoxyaniline
38018-60-9

(E)-N-(2-bromobenzylidene)-4-methoxyaniline

Conditions
ConditionsYield
With sodium sulfate In dichloromethane for 0.5h;100%
toluene-4-sulfonic acid
With 3 A molecular sieve In benzene at 65℃;
With magnesium sulfate In dichloromethane for 12h;
ethylene glycol
107-21-1

ethylene glycol

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(2-bromophenyl)-1,3-dioxolan
34824-58-3

2-(2-bromophenyl)-1,3-dioxolan

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 4h; Heating / reflux;100%
With p-toluenesulfonic acid monohydrate In benzene Reflux;98%
With toluene-4-sulfonic acid In benzene Inert atmosphere; Reflux; Dean-Stark;98%
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

1-(2-bromophenyl)propan-1-ol
74532-85-7

1-(2-bromophenyl)propan-1-ol

Conditions
ConditionsYield
Stage #1: ethylmagnesium bromide; ortho-bromobenzaldehyde In tetrahydrofuran at -70 - 20℃; for 6h;
Stage #2: With water; ammonium chloride In tetrahydrofuran		100%
In diethyl ether at 0 - 20℃;95%
In tetrahydrofuran; diethyl ether at -78 - 0℃; Inert atmosphere;81%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-bromostyrene
2039-88-5

2-bromostyrene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Wittig Olefination;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 12h; Wittig Olefination;		100%
With n-butyllithium In tetrahydrofuran99%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
Stage #2: ortho-bromobenzaldehyde In diethyl ether at 0℃; for 15h; Inert atmosphere;		93%
phenylmagnesium bromide

phenylmagnesium bromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

(2-bromophenyl)phenylmethanol
59142-47-1

(2-bromophenyl)phenylmethanol

Conditions
ConditionsYield
In diethyl ether for 2h; Heating;100%
In diethyl ether at 0 - 20℃;91%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-[2-(trimethylsilyl)ethynyl]benzaldehyde
77123-58-1

2-[2-(trimethylsilyl)ethynyl]benzaldehyde

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;100%
Stage #1: ortho-bromobenzaldehyde; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.25h; Sonogashira coupling; Inert atmosphere;
Stage #2: With copper(l) iodide at 50℃; for 2.5h; Sonogashira coupling; Inert atmosphere;		99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere;99%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

o-bromobenzaldehyde dimethyl acetal
35849-09-3

o-bromobenzaldehyde dimethyl acetal

Conditions
ConditionsYield
Stage #1: trimethyl orthoformate With montmorillonite K10 Clay at 20℃; for 0.333333h;
Stage #2: ortho-bromobenzaldehyde at 20℃;		100%
With toluene-4-sulfonic acid In methanol at 20℃; for 2h; Inert atmosphere;96%
With p-toluenesulfonic acid monohydrate In methanol at 100℃; for 12h; Inert atmosphere;95%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

allylmagnesium bromide
1730-25-2

allylmagnesium bromide

1-(2-bromophenyl)but-3-en-1-ol
71787-51-4

1-(2-bromophenyl)but-3-en-1-ol

Conditions
ConditionsYield
In diethyl ether for 2h; Heating;100%
1-amino-2-propene
107-11-9

1-amino-2-propene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Allyl-[1-(2-bromo-phenyl)-meth-(Z)-ylidene]-amine
175853-25-5

Allyl-[1-(2-bromo-phenyl)-meth-(Z)-ylidene]-amine

Conditions
ConditionsYield
With molecular sieve In dichloromethane100%
With molecular sieve In dichloromethane76%
phenylhydrazine
100-63-0

phenylhydrazine

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-Brombenzaldehyd-Phenylhydrazon
10407-11-1

2-Brombenzaldehyd-Phenylhydrazon

Conditions
ConditionsYield
100%
toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

p-toluenesulfonylhydrazone of 2-bromobenzaldehyde

p-toluenesulfonylhydrazone of 2-bromobenzaldehyde

Conditions
ConditionsYield
100%
carbon tetrabromide
558-13-4

carbon tetrabromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

1-bromo-2-(2,2-dibromovinyl)benzene
213599-19-0

1-bromo-2-(2,2-dibromovinyl)benzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere;100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Wittig reaction;
Stage #2: ortho-bromobenzaldehyde In dichloromethane at 0 - 20℃;		97%
With triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;97%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

2-(4-methoxyphenylethynyl)benzaldehyde
176910-67-1

2-(4-methoxyphenylethynyl)benzaldehyde

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 6h; Sonogashira coupling;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Inert atmosphere; Schlenk technique;98%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

ethyl (2E)-3-(2-bromophenyl)prop-2-enoate
91047-77-7

ethyl (2E)-3-(2-bromophenyl)prop-2-enoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 1.33333h; Wadsworth-Emmons condensation;		100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; mineral oil Inert atmosphere; stereoselective reaction;		97%
With lithium hydroxide In tetrahydrofuran for 3h; Ambient temperature;94%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

1-bromo-2-(dibromomethyl)benzene
35849-08-2

1-bromo-2-(dibromomethyl)benzene

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃; for 24h; Substitution;100%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

urea
57-13-6

urea

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

ethyl 4-(2-bromophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ethyl 4-(2-bromophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In ethanol at 100℃; for 1h; Biginelli reaction; Microwave irradiation; Inert atmosphere;100%
With ytterbium(III) triflate at 100℃; for 0.666667h; Biginelli reaction;97%
With 2,2,2-trifluoroethanol at 80℃; Biginelli pyrimidine synthesis;94%
...Expand
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

phenylboronic acid
98-80-6

phenylboronic acid

2-Phenylbenzaldehyde
1203-68-5

2-Phenylbenzaldehyde

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethylene glycol at 80℃; for 3h; Suzuki-Miyaura Coupling;100%
With tetrabutylammomium bromide; potassium carbonate; cyclopalladated N-dodecylferrocenylimine In methanol; water at 20℃; for 5h; Suzuki-Miyaura cross-coupling reaction;99%
With potassium phosphate tribasic heptahydrate In tetrahydrofuran at 60℃; for 10h; Suzuki coupling; Inert atmosphere;99%
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(2-cyclohexylethynyl)benzaldehyde
396717-17-2

2-(2-cyclohexylethynyl)benzaldehyde

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere;100%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 50℃; for 2h;95%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; Sonogashira reaction;94%
1-propynylmagnesium bromide
16466-97-0, 13254-27-8

1-propynylmagnesium bromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

1-(2-bromo-phenyl)-but-2-yn-1-ol
429680-29-5

1-(2-bromo-phenyl)-but-2-yn-1-ol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;100%
In tetrahydrofuran at 20℃; for 2h;99%
99%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2,2-dimethoxyethylamine
22483-09-6

2,2-dimethoxyethylamine

(2-bromobenzylidene)(2,2-dimethoxyethyl)amine
405161-29-7

(2-bromobenzylidene)(2,2-dimethoxyethyl)amine

Conditions
ConditionsYield
In toluene for 0.5h; Heating;100%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

methylamine
74-89-5

methylamine

1-(2-bromophenyl)-N-methylmethanimine
95547-10-7

1-(2-bromophenyl)-N-methylmethanimine

Conditions
ConditionsYield
In methanol; water100%
In methanol; water at 20℃; for 0.25h;
at 20℃; for 1h;
at 20℃; for 1h;
With magnesium sulfate In dichloromethane for 2h; Reflux;
1-amino-2-propene
107-11-9

1-amino-2-propene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

N-[(2-bromophenyl)methylidene]-N-(2-propenyl)amine
183864-20-2

N-[(2-bromophenyl)methylidene]-N-(2-propenyl)amine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 20h;100%
In dichloromethane at 20℃; Inert atmosphere; Molecular sieve;100%
In methanol Inert atmosphere;99%
With magnesium sulfate In dichloromethane for 1h; Heating;98%
With trimethyl orthoformate
Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(2-cyclopropylethynyl)benzaldehyde
914220-97-6

2-(2-cyclopropylethynyl)benzaldehyde

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Sonogashira Cross-Coupling; Inert atmosphere;89%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Sonogashira Cross-Coupling;89%
phenylhydrazine
100-63-0

phenylhydrazine

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-Brom-benzaldehyd-phenylhydrazon
10407-11-1

2-Brom-benzaldehyd-phenylhydrazon

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 160℃; for 0.166667h; microwave irradiation;100%
In methanol at 20℃; for 2h;51%
With acetic acid In ethanol for 2h; Reflux;
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

7-chloro-4-piperazinylquinoline
837-52-5

7-chloro-4-piperazinylquinoline

4-[4-(2-bromo-benzyl)-piperazin-1-yl]-7-chloro-quinoline

4-[4-(2-bromo-benzyl)-piperazin-1-yl]-7-chloro-quinoline

Conditions
ConditionsYield
With sodium cyanoborohydride In methanol at 25℃; for 6h;100%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

1,4-dimethoxy-3-methyl-2-naphthylboronic acid
590401-48-2

1,4-dimethoxy-3-methyl-2-naphthylboronic acid

2-(1,4-dimethoxy-3-methyl-2-naphthyl)benzaldehyde
827347-02-4

2-(1,4-dimethoxy-3-methyl-2-naphthyl)benzaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol for 42h; Suzuki coupling; Heating;100%
phenylmagnesium bromide

phenylmagnesium bromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-Phenylbenzaldehyde
1203-68-5

2-Phenylbenzaldehyde

Conditions
ConditionsYield
Stage #1: phenylmagnesium bromide With indium(III) chloride In tetrahydrofuran at 25℃;
Stage #2: ortho-bromobenzaldehyde; tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane In tetrahydrofuran; water for 2h; Heating; Further stages.;		100%
Stage #1: phenylmagnesium bromide In tetrahydrofuran at -20℃; for 0.166667h;
Stage #2: ortho-bromobenzaldehyde With para-fluorostyrene; tetra-(n-butyl)ammonium iodide; cobalt acetylacetonate In tetrahydrofuran; 1,2-dimethoxyethane at 25℃; for 0.25h;		42%
isopropyltriphenylphosphonium iodide
24470-78-8

isopropyltriphenylphosphonium iodide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

1-bromo-2-(2-methylprop-1-en-1-yl)benzene
91388-25-9

1-bromo-2-(2-methylprop-1-en-1-yl)benzene

Conditions
ConditionsYield
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Wittig Olefination;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Wittig Olefination;		100%
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane at 0℃; for 2h;		89%
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane; cyclohexane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane; cyclohexane at 0 - 20℃; for 3.5h; Inert atmosphere;		88%
Stage #1: isopropyltriphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 20℃; Wittig reaction;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran Wittig reaction; Reflux;
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane for 2h;

2-Bromobenzaldehyde Specification

The IUPAC name of this chemical is 2-bromobenzaldehyde. With the CAS registry number 6630-33-7, it is also named as Benzaldehyde, o-bromo-. The product's categories are Aromatic Compounds; Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde; Adehydes, Acetals & Ketones; Bromine Compounds; Aldehydes; C7; Carbonyl Compounds. It is clear yellow liquid after melting which is sensitive to air.

 The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.45; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.45; (4)ACD/LogD (pH 7.4): 2.45; (5)#H bond acceptors: 1; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 1; (8)Index of Refraction: 1.61; (9)Molar Refractivity: 40.69 cm3; (10)Molar Volume: 117.2 cm3; (11)Polarizability: 16.13×10-24 cm3; (12)Surface Tension: 44.4 dyne/cm; (13)Enthalpy of Vaporization: 46.74 kJ/mol; (14)Vapour Pressure: 0.0646 mmHg at 25°C; (15)Rotatable Bond Count: 1; (16)Exact Mass: 183.952377; (17)MonoIsotopic Mass: 183.952377; (18)Topological Polar Surface Area: 17.1; (19)Heavy Atom Count: 9; (20)Complexity: 103.

Preparation of 2-Bromobenzaldehyde: It can be obtained by 1-bromo-2-methyl-benzene. This reaction needs reagent pyridinium chlorochromate and solvent acetonitrile by heating. The reaction time is 8 hours. The yield is 10%.

Uses of 2-Bromobenzaldehyde: It is used in organic synthesis. For example: it can react with trichloromethane to get 1-(2-bromo-phenyl)-2,2,2-trichloro-ethanol. This reaction needs reagent KOH and solvent dimethylformamide, methanol at temperature of -10 °C. The reaction time is 1 hours. The yield is 95%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=Cc1ccccc1Br
2. InChI:InChI=1/C7H5BrO/c8-7-4-2-1-3-6(7)5-9/h1-5H 
3. InChIKey:NDOPHXWIAZIXPR-UHFFFAOYAE

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