6630-33-7

Basic information

• Product Name: 2-Bromobenzaldehyde
• Synonyms: o-Bromobenzaldehyde 2-Bromobenzaldehyde;2-Bromobenzylaldehyde;2-Bromobenzaldehyde98%;Benzaldehyde, 2-bromo-;ORTHO-BROMOBENZALDEHYDE;1-Bromo-2-formylbenzene;2-Bromobenzenecarboxaldehyde;2-Bromobenzaldehyde,97%
• CAS NO: 6630-33-7
• Molecular Formula: C₇H₅BrO
• Molecular Weight: 185.02
• EINECS: 229-622-2
• Product Categories: Aromatic Compounds;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Adehydes, Acetals & Ketones;Bromine Compounds;Aldehydes;C7;Carbonyl Compounds
• Mol File: 6630-33-7.mol
• Article Data: 248

Chemical Properties

• Melting Point: 16-19 °C(lit.)
• Boiling Point: 230 °C(lit.)
• Flash Point: 203 °F
• Appearance: Clear yellow/Liquid After Melting
• Density: 1.585 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.27E-11mmHg at 25°C
• Refractive Index: n20/D 1.595(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Soluble in alcohol and benzene. Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 636132
• CAS DataBase Reference: 2-Bromobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobenzaldehyde(6630-33-7)
• EPA Substance Registry System: 2-Bromobenzaldehyde(6630-33-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 6630-33-7(Hazardous Substances Data)

Usage

Chemical Description

2-bromobenzaldehyde is an organic compound with a molecular formula C7H5BrO.

Chemical Properties

clear yellow liquid after melting

Uses

Different sources of media describe the Uses of 6630-33-7 differently. You can refer to the following data:
1. 2-Bromobenzaldehyde is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.
2. 2-Bromobenzaldehyde is used in L-threonine aldolase-catalyzed enantio and diastereoselective aldol reactions. Further, it reacts with trichloromethane to prepare 1-(2-bromo-phenyl)-2,2,2-trichloro-ethanol.

InChI:InChI=1/C17H15NO4S2/c1-20-12-5-6-14(21-2)11(8-12)9-15-16(19)18(17(23)24-15)10-13-4-3-7-22-13/h3-9H,10H2,1-2H3/b15-9+

Synthetic route

o-bromobenzyl alcohol (18982-54-2) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → 4-bromo-benzaldehyde (1122-91-4) + ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) + methyllithium (917-54-4) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With dipotassium peroxodisulfate; molybdenum trioxide In water; acetonitrile for 1.5h; Reflux;	92%
With trichloroisocyanuric acid In acetonitrile Reflux;

2-bromobenzylchloride (578-51-8) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With oxone In water; acetonitrile at 45℃; for 1h;	90%

1-Bromo-2-bromomethyl-benzene (3433-80-5) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In hexane; dichloromethane for 4.5h; Ambient temperature;	89%
With triethylsilane; iron(III)-acetylacetonate	71%
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) → 2,5-bis(2-bromophenyl)tetrahydrofuran + ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With tetrabutylammonium perchlorate; oxygen; pyrographite In nitromethane at 20℃; Electrolysis; chemoselective reaction;	A 89% B 9%

1-allyl-2-bromobenzene (42918-20-7) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With iron(III) chloride; tetramethyldisiloxane In ethanol at 20℃; for 12h;	86%

2-(2-bromophenyl)-1,3-dithiolane (113509-22-1) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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 → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 4h; Heating;	82%

o-bromobenzyl alcohol (18982-54-2) → 2-bromobenzyl 2'-bromobenzoate (1363569-70-3) + ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) → ortho-bromobenzaldehyde (6630-33-7) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
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-bromobenzoyl cyanide (88562-26-9) + ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) + carbon monoxide (201230-82-2) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) + 1-Bromo-2-iodobenzene (583-55-1) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;	78%

2-bromo-N-methoxy-N-methylbenzamide (899425-05-9) → ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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-bromobenzaldehyde (6630-33-7)

Conditions	Yield
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) + diethyl malonate (105-53-3) → diethyl <(2-bromophenyl)methylene>propanedioate (93098-67-0)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → (E)-N-(2-bromobenzylidene)-4-methoxyaniline (38018-60-9)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 2-(2-bromophenyl)-1,3-dioxolan (34824-58-3)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 1-(2-bromophenyl)propan-1-ol (74532-85-7)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 2-bromostyrene (2039-88-5)

Conditions	Yield
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 tetrahydrofuran	99%
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 + ortho-bromobenzaldehyde (6630-33-7) → (2-bromophenyl)phenylmethanol (59142-47-1)

Conditions	Yield
In diethyl ether for 2h; Heating;	100%
In diethyl ether at 0 - 20℃;	91%

ortho-bromobenzaldehyde (6630-33-7) + trimethylsilylacetylene (1066-54-2) → 2-[2-(trimethylsilyl)ethynyl]benzaldehyde (77123-58-1)

Conditions	Yield
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) + trimethyl orthoformate (149-73-5) → o-bromobenzaldehyde dimethyl acetal (35849-09-3)

Conditions	Yield
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) + allylmagnesium bromide (1730-25-2) → 1-(2-bromophenyl)but-3-en-1-ol (71787-51-4)

Conditions	Yield
In diethyl ether for 2h; Heating;	100%

1-amino-2-propene (107-11-9) + ortho-bromobenzaldehyde (6630-33-7) → Allyl-[1-(2-bromo-phenyl)-meth-(Z)-ylidene]-amine (175853-25-5)

Conditions	Yield
With molecular sieve In dichloromethane	100%
With molecular sieve In dichloromethane	76%

phenylhydrazine (100-63-0) + ortho-bromobenzaldehyde (6630-33-7) → 2-Brombenzaldehyd-Phenylhydrazon (10407-11-1)

Conditions	Yield
	100%

toluene-4-sulfonic acid hydrazide (1576-35-8) + ortho-bromobenzaldehyde (6630-33-7) → p-toluenesulfonylhydrazone of 2-bromobenzaldehyde

Conditions	Yield
	100%

carbon tetrabromide (558-13-4) + ortho-bromobenzaldehyde (6630-33-7) → 1-bromo-2-(2,2-dibromovinyl)benzene (213599-19-0)

Conditions	Yield
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) + 4-methoxyphenylacetylen (768-60-5) → 2-(4-methoxyphenylethynyl)benzaldehyde (176910-67-1)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → ethyl (2E)-3-(2-bromophenyl)prop-2-enoate (91047-77-7)

Conditions	Yield
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) → 1-bromo-2-(dibromomethyl)benzene (35849-08-2)

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 24h; Substitution;	100%

ethyl acetoacetate (141-97-9) + urea (57-13-6) + ortho-bromobenzaldehyde (6630-33-7) → ethyl 4-(2-bromophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions	Yield
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%

ortho-bromobenzaldehyde (6630-33-7) + phenylboronic acid (98-80-6) → 2-Phenylbenzaldehyde (1203-68-5)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 2-(2-cyclohexylethynyl)benzaldehyde (396717-17-2)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 1-(2-bromo-phenyl)-but-2-yn-1-ol (429680-29-5)

Conditions	Yield
In tetrahydrofuran at 20℃;	100%
In tetrahydrofuran at 20℃; for 2h;	99%
	99%

ortho-bromobenzaldehyde (6630-33-7) + 2,2-dimethoxyethylamine (22483-09-6) → (2-bromobenzylidene)(2,2-dimethoxyethyl)amine (405161-29-7)

Conditions	Yield
In toluene for 0.5h; Heating;	100%

ortho-bromobenzaldehyde (6630-33-7) + methylamine (74-89-5) → 1-(2-bromophenyl)-N-methylmethanimine (95547-10-7)

Conditions	Yield
In methanol; water	100%
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) + ortho-bromobenzaldehyde (6630-33-7) → N-[(2-bromophenyl)methylidene]-N-(2-propenyl)amine (183864-20-2)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 2-(2-cyclopropylethynyl)benzaldehyde (914220-97-6)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 2-Brom-benzaldehyd-phenylhydrazon (10407-11-1)

Conditions	Yield
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) + 7-chloro-4-piperazinylquinoline (837-52-5) → 4-[4-(2-bromo-benzyl)-piperazin-1-yl]-7-chloro-quinoline

Conditions	Yield
With sodium cyanoborohydride In methanol at 25℃; for 6h;	100%

ortho-bromobenzaldehyde (6630-33-7) + 1,4-dimethoxy-3-methyl-2-naphthylboronic acid (590401-48-2) → 2-(1,4-dimethoxy-3-methyl-2-naphthyl)benzaldehyde (827347-02-4)

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

phenylmagnesium bromide + ortho-bromobenzaldehyde (6630-33-7) → 2-Phenylbenzaldehyde (1203-68-5)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 1-bromo-2-(2-methylprop-1-en-1-yl)benzene (91388-25-9)

Conditions	Yield
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;

Upstream product

• 6630-31-5 ethyl (6-methoxy-2-methyl-4-oxoquinolin-1(4H)-yl)acetate 
• 6630-30-4 6-Chloro-5-Nitropyrimidine-2,4-Diol 
• 6630-29-1 4-[(1H-naphtho[2,3-d]imidazol-2-ylmethyl)amino]benzoic acid 
• 6630-28-0 4-[(1H-benzimidazol-2-ylmethyl)amino]phenol 
• 6630-26-8 1,6-Bis(morpholino)-2,4-hexadiyne 
• 66302-66-7 methyl (5E)-5-ethylidene-8-ibogamin-13-yl-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazecino[5,4-b]indole-14-carboxylate 
• 66302-50-9 (1R,10aR)-7-[(S)-2-(3-Furyl)-2-hydroxyethyl]-6,6aβ,7,8-tetrahydro-5β,8α-dihydroxy-11-methylene-1β,7β-ethanofuro[3,4-i][2]benzopyran-3(5H)-one 
• 6630-24-6 2H-1-Benzopyran-6-carboxylic acid, 3,4-dihydro-2,2-diMethyl-, ethyl ester 
• 66302-37-2 2-(4-chlorophenyl)-4,5-diphenyl-1,3-oxazole 
• 6630-23-5 methyl 4-{[(8-methoxy-6-oxo-6H-benzo[c]chromen-3-yl)oxy]methyl}benzoate 
• 6630-20-2 1,2-bis(6-methyl-2-pyridyl)ethanediol 
• 6630-18-8 4-BENZYLOXYANISOLE 
• 6630-15-5 Di-p-tolyl Phosphorochloridate 
• 6630-14-4 3,4-dichloro-N-{2-[2-({4-[(4-chlorobenzyl)oxy]phenyl}methylidene)hydrazino]-2-oxoethyl}benzamide (non-preferred name) 

Downstream Products

• 75416-51-2 8-bromo-1,2,3,4-tetrahydroisoquinoline 
• 63927-22-0 8-Bromoisoquinoline 

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