552-89-6

Basic information

• Product Name: 2-Nitrobenzaldehyde
• Synonyms: 2-nitro-benzaldehyd;Benzaldehyde, o-nitro-;Benzaldehyde,2-nitro-;o-nitro-benzaldehyd;2-NITROBENZALDEHYDE;2-FORMYLNITROBENZENE;AKOS BBS-00003153;AKOS 93864
• CAS NO: 552-89-6
• Molecular Formula: C₇H₅NO₃
• Molecular Weight: 151.12
• EINECS: 209-025-3
• Product Categories: Benzaldehyde;Nifedipine;Aldehydes;C7;Carbonyl Compounds;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Pharmaceutical intermediates
• Mol File: 552-89-6.mol
• Article Data: 368

Chemical Properties

• Melting Point: 42-44 °C(lit.)
• Boiling Point: 153 °C23 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Yellow/Crystalline Powder, Needles and/or Chunks
• Density: 1,284 g/cm3
• Vapor Density: 5.2 (vs air)
• Vapor Pressure: 0.0078mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• Merck: 14,6586
• BRN: 742624
• CAS DataBase Reference: 2-Nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrobenzaldehyde(552-89-6)
• EPA Substance Registry System: 2-Nitrobenzaldehyde(552-89-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-68
• Safety Statements: 26-24/25-36/37/39-36
• WGK Germany: 2
• RTECS: CU7300000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 552-89-6(Hazardous Substances Data)

Usage

Chemical Properties

yellow or bright yellow needle-like crystals. It can volatilize with water vapor and has the fragrance of benzaldehyde. Soluble in ethanol, ether, benzene, slightly soluble in water, flash point>110℃, reacts violently with pyrrole.

Uses

2-Nitrobenzaldehyde is a benzaldhyde with a nitro group substituted in the ortho position. 2-Nitrobenzaldehyde is used in the preparation of dyes and colorants such as Indigo carmine. 2-Nitrobenzaldehyde gas been shown to be a useful photoremovable protecting group as well as in the preparation of more effective ones such as o-Nitrophenylethylene glycol.

Definition

ChEBI: 2-nitrobenzaldehyde is benzaldehyde substituted at the ortho-position with a nitro group. It is a C-nitro compound and a member of benzaldehydes.

Application

2-Nitrobenzaldehyde can react with chitosan to form 2-nitrobenzyl-chitosan, which is soluble in trifluoroacetic acid and can also be electrospun into nanofiber matrices. On photolysis, the nitrobenzyl group is cleaved to form neat chitosan nanofiber matrices. The same principle has been applied for the preparation of gelatin nanofiber matrices. The condensation of o-NBA with 2-aminobenzothiazole forms o-nitrobenzylidene 2-aminobenzothiazole, a Schiff′s base that can react with metal ions to form complexes.

Preparation

2-Nitrobenzaldehyde is synthesized from 2-Nitrotoluene by nitration and oxidation.Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene

Synthesis Reference(s)

Synthetic Communications, 19, p. 3385, 1989 DOI: 10.1080/00397918908052745

General Description

The 2-Nitrobenzyl group of 2-nitrobenzaldehyde is photolabile that can be cleaved when exposed to UV-light.

Purification Methods

Crystallise the aldehyde from toluene (2-2.5mL/g) by addition of 7mL pet ether (b 40-60o) for 1mL of solution. It can also be distilled under reduced pressures. [Beilstein 7 IV 584.]

InChI:InChI=1/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H

Synthetic route

1-diacetoxymethyl-2-nitro-benzene (6345-63-7) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;	100%
With beta zeolite modified with chlorosulphonic acid (28 wtpercent) In ethanol at 50℃; for 0.5h;	100%
With poly(4-vinylpyridine)-supported sulfuric acid In acetonitrile at 50℃; for 1h; Green chemistry;	100%

2-Nitrobenzyl alcohol (612-25-9) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 3h; Oxidation;	100%
With butyltriphenylphosphonium chlorochromate In acetonitrile for 2.5h; Heating;	100%
With 1H-imidazole; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 2h;	100%

Sodium; 6-{[1-(2-nitro-phenyl)-meth-(E)-ylidene]-amino}-hexanoate → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;	100%

o-Nitrobenzyloxytrimethylsilane (62673-13-6) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With nitrogen dioxide at 20℃; for 1h;	100%
With potassium permanganate; tetrachlorosilane In acetonitrile at 20℃; for 0.416667h;	89%
With zinc dichromate(VI) at 20℃;	89%

1-(2-nitrophenyl)ethane-1,2-diol (51673-59-7) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane at 25℃; for 8h; Inert atmosphere;	99%
With tert-butylhypochlorite; lead acetate; dibenzoyl peroxide In toluene at 20℃; for 0.75h;	90%

acetic acid 2-nitro-benzyl ester (77376-01-3) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With methanol; potassium permanganate In ethyl acetate at 25℃; for 30h;	99%

2-(2-nitrophenyl)-1,3-dithiane (35531-58-9) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide In methanol; dichloromethane at 20℃; for 0.05h;	98%
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 4h; Micellar solution;	98%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 4.5h;	98%

((2-nitrophenyl)methylene)bis(phenylsulfane) (93304-97-3) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With ammonium iodide; dihydrogen peroxide; acetic acid In water at 20℃; for 1.5h;	98%

2,2'-dinitrobibenzyl (16968-19-7) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With p-benzoquinone at 120℃; for 8h; Concentration; Temperature;	97.6%
With p-benzoquinone at 140℃; for 5h; Temperature;	91%

ortho-nitrobenzoic acid (552-16-9) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With manganese(IV) oxide In dichloromethane at 20℃; for 18h;	97%
With (CH3)2NCH2NpSiH2Ph at 110 - 140℃;	50%
With carboxylic acid reductase Kinetics; Green chemistry; Enzymatic reaction;
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C 3: pyridinium chlorochromate / dichloromethane / 20 °C View Scheme

1,2-bis(o-nitrophenyl)ethylene (6275-02-1) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With ozone In tetrachloromethane at -50℃; for 2h; Solvent;	96.5%
With ozone In chloroform at -10℃; Temperature; Solvent;	96.6%

2-(2-nitrophenyl)-1,3-dioxolane (48140-35-8) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 2.5h; Heating;	96%
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.266667h;	95%
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate for 0.0152778h;	93%

2-nitrobenzaldehyde-(O-methyl oxime) (135436-97-4) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With formaldehyd; toluene-4-sulfonic acid In tetrahydrofuran; water at 110℃; for 8h; Sealed tube;	95%

1-methyl-2-nitrobenzene (88-72-2) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;	94%
Stage #1: 1-methyl-2-nitrobenzene With bromine In propan-1-ol at 20℃; for 0.25h; UV-irradiation; Stage #2: With sodium hydrogencarbonate In propan-1-ol for 2h; Solvent; Reflux; UV-irradiation;	89%
With oxygen In acetonitrile at 20℃; for 12h; Irradiation;	80%

2-Nitrobenzaldehyde N,N-dimethylhydrazone (10424-94-9) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With triethylene diamine nickel thiosulfate; water In chloroform at 20℃; for 0.166667h; Hydrolysis;	94%
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile for 0.0333333h; deprotection;	93%
With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In chloroform at 20℃; for 1h; oxidative cleavage;	93%
With iron(II) sulfate In chloroform at 20℃; for 0.416667h; Hydrolysis;	90%

2-Nitrobenzyl alcohol (612-25-9) → ortho-nitrobenzoic acid (552-16-9) + 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In decane; acetonitrile at 20℃; for 2h;	A 92% B 5%
With peracetic acid; C24H29INO5 In acetic acid at 30℃; for 48h;	A 92% B 5%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique;	A 46% B 46%

dimethylsulfide (75-18-3) + 2-nitrostyrene (579-71-5) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With ozone In dichloromethane; ethyl acetate; benzene	91.5%

2-formylbenzene boronic acid (40138-16-7) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction;	91%

2-nitrobenzyl chloride (610-14-0) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In hexane; dichloromethane for 0.13h; Ambient temperature;	90%
With diethylene glycol dimethyl ether; lithium tri-t-butoxyaluminum hydride
Multi-step reaction with 2 steps 1: benzene; pyridine 2: LiAlH4; diethyl ether View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 20 °C View Scheme

1-(2-nitrobenzylidene)-2-phenylhydrazine (610-64-0) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With iron(II) sulfate In chloroform at 20℃; for 0.75h; Hydrolysis;	90%
With magnesium hydrogen sulfate; water; silica gel In hexane for 0.333333h; Heating;	90%
With citric acid In water for 0.133333h; Microwave irradiation; Green chemistry;	89%

o-(NO2)C6H4CH2OTHP (18483-88-0) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.333333h;	90%
With potassium permanganate; tetrachlorosilane In acetonitrile at 20℃; for 0.166667h;	88%
With 1-n-butylpyridinium tetrachloroferrate; pyridinium chlorochromate at 50℃; for 0.333333h;	88%

2-nitrobenzaldehyde diethylthioacetal (496045-96-6) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In dichloromethane; water at 20℃; for 0.166667h;	90%
With sodium hydrogen sulfate; water; silica gel In dichloromethane at 20℃; for 0.166667h;	90%

4,5-dihydro-2-(2-nitrophenyl)oxazole (88186-34-9) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol at -10 - 10℃;	90%

1-(dimethoxymethyl)-2-nitrobenzene (20627-73-0) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
perchloric acid In methanol; water at 25 - 30℃; for 0.333333h;	90%
With water In methanol at 25 - 30℃; for 0.416667h;	90%

benzaldehyde (100-52-7) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 15℃; for 0.666667h;	90%
Multi-step reaction with 3 steps 1: sodium acetate / ethanol; water / 2 h / 70 °C 2: palladium(II) trifluoroacetate; silver(I) nitrite; dipotassium peroxodisulfate / 1,2-dichloro-ethane / 48 h / 110 °C / Sealed tube; Schlenk technique 3: toluene-4-sulfonic acid; formaldehyd / tetrahydrofuran; water / 8 h / 100 °C / Sealed tube View Scheme
Multi-step reaction with 3 steps 1: sodium acetate / ethanol; water / 3 h / Reflux 2: palladium diacetate; silver(I) nitrite; dipotassium peroxodisulfate / 1,2-dichloro-ethane / 48 h / 110 °C / Sealed tube 3: toluene-4-sulfonic acid; formaldehyd / water; tetrahydrofuran / 8 h / 110 °C / Sealed tube View Scheme
With sulfuric acid at 0℃;

2-nitrophenylmethyl bromide (3958-60-9) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
With water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione at 50℃; for 0.583333h; Ionic liquid; Inert atmosphere;	89%
With dihydrogen peroxide In ethanol for 8h; Reflux; Green chemistry;	87%
With hexamethylenetetramine; water; sodium dodecyl-sulfate; lanthanum(lll) triflate at 100℃; for 2.5h; Sommelet Aldehyde Synthesis; Green chemistry;	61%

1-methyl-2-nitrobenzene (88-72-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
Stage #1: 1-methyl-2-nitrobenzene; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 135℃; Stage #2: With sodium periodate In water; N,N-dimethyl-formamide at 0℃;	89%

acetic anhydride (108-24-7) + 2-nitro-benzaldehyde (552-89-6) → 1-diacetoxymethyl-2-nitro-benzene (6345-63-7)

Conditions	Yield
With poly(4-vinylpyridine)-supported sulfuric acid In dichloromethane at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;	100%
With Envirocat EPZGR at 60 - 65℃; for 1.5h;	99%
copper(II) sulfate at 20℃; for 2h;	99%

p-toluidine (106-49-0) + 2-nitro-benzaldehyde (552-89-6) → 4-methyl-(2-nitrobenzylidene)aniline (17064-82-3)

Conditions	Yield
	100%
In ethanol for 3h; Reflux;	77.2%
In ethanol for 3h; Reflux;	77.2%

phosphonic acid diethyl ester (762-04-9) + 2-nitro-benzaldehyde (552-89-6) → diethyl (hydroxy)(2-nitrophenyl)methylphosphonate (79202-15-6)

Conditions	Yield
With triethylamine In neat (no solvent) at 20℃; for 24h; Pudovik Reaction; Inert atmosphere;	100%
With triethylamine at 50℃; Pudovik Reaction; Inert atmosphere; Sealed tube;	100%
With C42H74LiN6Si4Yb at 20℃; for 0.333333h; Neat (no solvent); Inert atmosphere;	98%

methanol (67-56-1) + 2-nitro-benzaldehyde (552-89-6) → 1-(dimethoxymethyl)-2-nitrobenzene (20627-73-0)

Conditions	Yield
With methanesulfonic acid; 3 A molecular sieve In chloroform for 24h; Heating;	100%
With ammonium cerium(IV) nitrate; sodium carbonate for 0.75h; Heating;	97%
With Br(1-)*C19H14Br3O3PS*Na(1+) at 20℃;	96%

N-methylhydroxyamine hydrochloride (4229-44-1) + 2-nitro-benzaldehyde (552-89-6) → α-(2-nitrophenyl)-N-methylnitrone (41106-02-9)

Conditions	Yield
With 3 A molecular sieve at 20℃; for 0.25h;	100%
With sodium hydroxide; silica gel at 20℃; for 0.166667h;	98%
With potassium carbonate In methanol Reflux;	96.5%
With ethanol; potassium acetate

2-nitro-benzaldehyde (552-89-6) + malononitrile (109-77-3) → 2-(2-nitrobenzylidene)malononitrile (2826-30-4)

Conditions	Yield
With Fe3O4(at)SiO2-N1-(3-trimethoxysilylpropyl)diethylenetriamine nanoparticles catalyst In toluene at 75℃; for 0.75h; Solvent; Knoevenagel Condensation;	100%
With hydroquinone; p-benzoquinone In water at 20℃; for 3h; Knoevenagel Condensation; Inert atmosphere; Sealed tube;	100%
With Zr(IV)-salen-MCM-41 In water at 35℃; for 0.5h; Catalytic behavior; Solvent; Knoevenagel Condensation;	99%

2-nitro-benzaldehyde (552-89-6) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-[(2-nitrophenyl)methylidene]malonate (65974-52-9)

Conditions	Yield
With piperidine; acetic acid In benzene at 80℃; for 15h; Knoevenagel Condensation; Microwave irradiation;	100%
With piperidin-1-ium piperidine-1-carboxylate In neat (no solvent) at 25℃; Knoevenagel Condensation;	87%
With potassium carbonate In acetic anhydride at 80℃; for 4h;	86%

2-nitro-benzaldehyde (552-89-6) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With sodium tetrahydroborate In water at 50℃; Green chemistry;	100%
With sodium tetrahydroborate; copper In water at 80℃; for 0.0833333h; Green chemistry;	97%
With sodium tetrahydroborate In tetrahydrofuran; water at 26℃; for 0.0833333h;	96%

2-nitro-benzaldehyde (552-89-6) → 2-Nitrobenzyl alcohol (612-25-9)

Conditions	Yield
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;	100%
With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃;	100%
With zirconium dioxide hydrate; isopropyl alcohol at 60℃; for 0.1h; Meerwein-Ponndorf-Verley Reduction;	100%

2-nitro-benzaldehyde (552-89-6) → anthranil (271-58-9)

Conditions	Yield
With hydrogen In toluene at 30℃; under 6750.68 Torr; for 1h; Autoclave; chemoselective reaction;	100%
With tin(ll) chloride In methanol; ethyl acetate at 20℃;	96%
With 2-bromo-2-nitropropane; indium In methanol; water at 50℃; for 0.166667h; Reduction; cyclisation;	93%

2-nitro-benzaldehyde (552-89-6) → 2-aminobenzaldehyde (529-23-7)

Conditions	Yield
With formic acid; 2,5-hexanedione for 12h; Autoclave; Inert atmosphere; Green chemistry;	100%
With iron; acetic acid In ethanol; water for 0.25h; pH=4.5;	100%
With iron; ammonium chloride In ethanol; water for 1 - 4h; Heating / reflux;	99%

ethyl 2-cyanoacetate (105-56-6) + 2-nitro-benzaldehyde (552-89-6) → ethyl (E)‐2‐cyano‐3‐(2‐nitrophenyl) acrylate (68792-18-7)

Conditions	Yield
With L-proline for 0.05h; Knoevenagel condensation; microwave irradiation;	100%
With 1H-imidazole In dichloromethane for 0.5h; Knoevenagel condensation; Heating;	98%
With Na8H[PW9O34]*7H2O In methanol at 25℃; for 6h; Knoevenagel Condensation;	98%

methylamine (74-89-5) + 2-nitro-benzaldehyde (552-89-6) → Methyl-[1-(2-nitro-phenyl)-meth-(Z)-ylidene]-amine (57707-11-6)

Conditions	Yield
With magnesium sulfate In dichloromethane for 2h; Reflux;	100%
In water for 0.25h;	15.35 g

2-Methoxypropene (116-11-0) + 2-nitro-benzaldehyde (552-89-6) → 1-[3-Methoxy-1-(1-methoxy-1-methyl-ethoxy)-but-3-enyl]-2-nitro-benzene

Conditions	Yield
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; silica gel; acetic acid at 25℃;	100%
With silica gel; acetic acid; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium In dichloromethane at 25℃; Addition;	99%

sodium 6-aminohexanoate (7234-49-3) + 2-nitro-benzaldehyde (552-89-6) → Sodium; 6-{[1-(2-nitro-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

Conditions	Yield
In di-isopropyl ether; water for 0.0416667h; Product distribution; Ambient temperature; separation of aldehyde;	100%

4,6-dimethoxy-2,3-diphenyl-1H-indole (91107-10-7) + 2-nitro-benzaldehyde (552-89-6) → di-(4,6-dimethoxy-2,3-diphenylindol-7-yl)(2-nitrophenyl)methane

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 3h;	100%

2-nitro-benzaldehyde (552-89-6) → sodium hydroxy(2-nitrophenyl)methanesulfonate (133721-90-1)

Conditions	Yield
With sodium hydrogensulfite In di-isopropyl ether; water for 0.0833333h; Product distribution; Ambient temperature; separation of aldehyde;	100%
With sodium metabisulfite In ethanol; water
With sodium hydrogensulfite In ethanol; water at 20℃; for 0.25h;

2-nitro-benzaldehyde (552-89-6) → 2-azidobenzaldehyde (16714-25-3)

Conditions	Yield
With sodium azide In N,N,N,N,N,N-hexamethylphosphoric triamide for 8h; Ambient temperature;	100%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide at 25℃; for 36h;	100%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide at 20℃; for 15h;	99%

methyl vinyl ketone (78-94-4) + 2-nitro-benzaldehyde (552-89-6) → 3-[hydroxy-(2-nitrophenyl)methyl]but-3-en-2-one (219982-00-0)

Conditions	Yield
With octanol; 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 12h; Baylis-Hillman reaction;	100%
With 4-nitro-phenol; triphenylphosphine In tetrahydrofuran at 20℃; for 18h; Morita-Baylis-Hillman reaction;	98%
With (1,3,5-triaza-7-phosphaadamantane) In tetrahydrofuran at 20℃; for 4h; Baylis-Hillman reaction;	91%

acrylonitrile (107-13-1) + 2-nitro-benzaldehyde (552-89-6) → 2-(hydroxy(2-nitrophenyl)methyl)acrylonitrile (225237-20-7)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane at 0℃; for 0.666667h; Morita-Baylis-Hillman reaction;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 0℃; for 0.25h; Catalytic behavior; Solvent; Time; Temperature; Morita-Baylis-Hillman Alkylation;	100%
With hexamethylenetetramine In 1,4-dioxane; water at 20℃; for 24h; Baylis-Hillman reaction;	99%

benzyltriphenylphosphonium bromide (1449-46-3) + 2-nitro-benzaldehyde (552-89-6) → 2-nitrostilbene (4714-25-4)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dichloromethane for 6h; Wittig Olefination; Reflux;	100%
With sodium hydroxide; tetrabutyl-ammonium chloride In tetrahydrofuran	96%
With sodium hydroxide In tetrahydrofuran at 20℃;	76%

formaldehyd (50-00-0) + sarcosine (107-97-1) + 2-nitro-benzaldehyde (552-89-6) → 3-methyl-5-(2'-nitrophenyl)oxazolidine (365275-13-4)

Conditions	Yield
In toluene for 1h; Heating;	100%
In benzene for 1h; Heating;	95%

2-nitro-benzaldehyde (552-89-6) + 6,7-dimethoxy-2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinoline → 6,7-dimethoxy-2-[1-(2-nitrobenzyl)-3-piperidyl]-1,2,3,4-tetrahydroisoquinoline

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 13h;	100%

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one (83-07-8) + 2-nitro-benzaldehyde (552-89-6) → 4-(2-nitrobenzylideneamino)-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one (93874-58-9)

Conditions	Yield
at 20℃; for 1h;	100%
Stage #1: 2-nitro-benzaldehyde With magnetite(at)citric acid nanoparticles In ethanol for 0.0333333h; Sonication; Green chemistry; Stage #2: 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one In ethanol at 80℃; for 0.25h; Green chemistry;	96%
In neat (no solvent) at 140℃; Microwave irradiation; Green chemistry;	95%
In ethanol at 20℃; for 0.0111111h;	88%

3-amino-4,6-dimethylpyrazolo[3,4-b]pyridine (41601-44-9) + 2-nitro-benzaldehyde (552-89-6) → N-(2-nitrobenzylidene)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-amine

Conditions	Yield
at 60℃; for 0.5h;	100%
With piperidine In ethanol for 2h; Reflux;	80%

acetone (67-64-1) + 2-nitro-benzaldehyde (552-89-6) → (R)-4-hydroxy-4-(2-nitrophenyl)butan-2-one

Conditions	Yield
With (S)-N-((1S,2S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-1,2-diphenylethyl)pyrrolidine-2-carboxamide; 4-nitro-benzoic acid In toluene at -20℃; for 24h; asymmetric aldol reaction; optical yield given as %ee; enantioselective reaction;	100%
With (S)-di-tert-butyl 2-{3-[(1S,2S)-1,2-diphenyl-2-[(S)-(pyrrolidine-2-carboxamido)]ethyl]thioureido}succinate; 4-nitro-benzoic acid In toluene at -20℃; for 24h; Aldol reaction; optical yield given as %ee; enantioselective reaction;	100%
With C29H39N3O3S In chloroform at 0℃; for 36h; optical yield given as %ee; enantioselective reaction;	98%

Upstream product

• 612-25-9 2-Nitrobenzyl alcohol 
• 355-43-1 n-perfluorohexyl iodide 
• 100-52-7 benzaldehyde 
• 88-72-2 1-methyl-2-nitrobenzene 
• 80-16-0 N-chlorobenzenesulfonamide 
• 7732-18-5 water 
• 7697-37-2 nitric acid 
• 7782-77-6 cis-nitrous acid 
• 4836-00-4 (E)-2-nitrobenzaldehyde oxime 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 13312-81-7 2-hydroxy-2-[2-nitrophenyl]acetonitrile 
• 3284-77-3 1-(dichloromethyl)-2-nitrobenzene 
• 5461-32-5 o-nitrophenylpyruvic acid 

Downstream Products

• 124525-52-6 2-methyl-3t-(2-nitro-phenyl)-acrylic acid 
• 71972-83-3 o-nitrophenyldi(2-thienyl)methane 
• 77340-84-2 2-(o-nitrostyryl)-pyridine 
• 5455-70-9 1-(2-nitro-phenyl)-2-[2]pyridyl-ethanol 
• 138457-93-9 4-(o-nitrostyryl)pyridine 
• 66385-94-2 2-<(o-nitrobenzylidene)amino>pyridine 
• 35548-91-5 (E)-N-(2-nitrobenzylidene)-4H-1,2,4-triazol-4-amine 
• 36140-65-5 (Z)-5-(2-nitrobenzylidene)thiazolidine-2,4-dione 
• 6308-22-1 5-(2-nitrobenzylidene)-4-thiazolidinone-2-thioxo 
• 951328-41-9 4-(2-nitro-trans-styryl)-quinoline 
• 7670-65-7 3,6-di(2-nitrobenzylidene)piperazine-2,5-dione 
• 114659-72-2 (E)-N’-(2'-nitrobenzylidene) nicotinohydrazide 
• 26908-37-2 5-(2-nitrobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 60045-65-0 5-[(2'-nitrophenyl)methylidene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 

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