6125-24-2

Basic information

• Product Name: 1-(PHENYL) 2-NITROETHANE
• Synonyms: 1-(PHENYL) 2-NITROETHANE;PHENYLNITROETHANE;Benzene, (2-nitroethyl)-;3-Nitroethylbenzene;nitro-phenylethane,1-nitro-2-phenylethane;1-Nitro-2-phenylethane;Nsc23854;1-(2-Nitroethyl)benzene
• CAS NO: 6125-24-2
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 228-094-0
• Product Categories: Ethanes/ethenes
• Mol File: 6125-24-2.mol
• Article Data: 129

Chemical Properties

• Melting Point: 56-58℃
• Boiling Point: 250℃
• Flash Point: 118.8 °C
• Appearance: /
• Density: 1.122 g/cm3 (25℃)
• Vapor Pressure: 0.0122mmHg at 25°C
• Refractive Index: 1.5270 (589.3 nm 20℃)
• Storage Temp.: 2-8°C
• PKA: 8.13±0.10(Predicted)
• CAS DataBase Reference: 1-(PHENYL) 2-NITROETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(PHENYL) 2-NITROETHANE(6125-24-2)
• EPA Substance Registry System: 1-(PHENYL) 2-NITROETHANE(6125-24-2)

Safety Data

• Hazardous Substances Data: 6125-24-2(Hazardous Substances Data)

Usage

General Description

1-(Phenyl) 2-nitroethane is a chemical compound with the molecular formula C8H9NO2. It is an organic nitro compound that consists of a phenyl group attached to a 2-nitro ethane moiety. This chemical is commonly used in the field of organic synthesis and pharmaceutical research as a precursor and intermediate for the synthesis of various compounds including drugs, agrochemicals, and other organic molecules. It is important to handle 1-(phenyl) 2-nitroethane with care as it is a potentially hazardous chemical and should only be used by trained professionals in a controlled laboratory setting.

InChI:InChI=1/C8H9NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

Synthetic route

(2-nitroethenyl)benzene (102-96-5) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With polymer-bound NADH (2a)	100%
With magnesium(II) perchlorate; "grafted NADH model" reagent In acetonitrile; benzene at 80℃; for 120h;	100%
With tri(1-naphthyl)phosphonium tris(pentafluorophenyl)borohydride In dichloromethane-d2 for 12h; Reagent/catalyst; Glovebox; Sealed tube;	100%

nitrostyrene (5153-67-3) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With magnesium(II) perchlorate; model of NADH grafted on silica matrix In acetonitrile at 65℃; for 120h;	100%
With sodium tetrahydroborate; silica gel In chloroform; isopropyl alcohol at 0 - 23℃; for 1.33333h; Inert atmosphere;	99%
With hydrogen; tris(triphenylphosphine)rhodium(l) chloride In benzene at 50℃; under 2585.81 Torr; for 14h;	98%

nitrostyrene (5153-67-3) + 5-carbamoyl thieno<2,3-b>pyridine (117390-40-6) + bromo-8 octyl dimethylchlorosilane (125056-17-9) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With magnesium(II) perchlorate; silice (Merck Kieselgel Art.:7734) Product distribution; multistep reaction; 1.) grafting on a silica matrix, reflux, in toluene, 12 h, 2.) reflux, toluene, 5 days. 3.) acetonitrile, 65 deg C, 5 days; reagent quqntity, reaction time varied;	100%

2-nitro-1-phenylethan-1-ol (141377-54-0, 145920-96-3, 149495-00-1, 15990-45-1) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With tri-n-butyl-tin hydride In water at 80℃; for 0.166667h; Microwave irradiation; Green chemistry;	96%
(i) Ac2O, H2SO4, (ii) NaBH4, DMSO; Multistep reaction;
Multi-step reaction with 3 steps 1: pyridine / 2 h / Ambient temperature 2: sodium carbonate / benzene / 5 h / Heating 3: 84 percent / 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine, silica gel / benzene / 0.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water 2: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol View Scheme

nitrostyrene (5153-67-3) + 1,2-diamino-benzene (95-54-5) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With benzaldehyde	95%
With benzaldehyde	95%

nitrostyrene (5153-67-3) → 1,3-dinitro-2,4-diphenyl-butane (101280-71-1) + 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With methanol; sodium tetrahydroborate In water at 25℃; for 1h;	A 1.92 %Spectr. B 92.7%

C14H23NO2Si (1393099-04-1) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With sodium cyanide; magnesium(II) perchlorate In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;	72%

<2-nitro-2-(phenylsulfonyl)ethyl>-benzene (74737-94-3) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide In benzene for 42h; Irradiation;	62%
With sodium dithionite; potassium carbonate; 1,1′-dioctyl-4,4′-bipyridinium In dichloromethane; water at 35℃; for 3h;	62%
With sodium dithionite; potassium carbonate; 1,1′-dioctyl-4,4′-bipyridinium In dichloromethane; water at 35℃; for 3h; other α-nitro sulfones; other reaction conditions; also without viologen;	62%

2-phenethyl iodide (17376-04-4) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With silver(I) nitrite In water at 60℃; for 1.5h; Darkness;	60%
With silver(I) nitrite; diethyl ether

nitromethane (75-52-5) + N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate (66310-10-9) → 2-Phenylnitroethane (6125-24-2) + 2,4,6-triphenylpyridine (580-35-8)

Conditions	Yield
With sodium hydride In methanol; dimethyl sulfoxide at 25℃; for 2h;	A 58% B n/a

sodium nitromethane (25854-38-0) + N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate (66310-10-9) → 2-Phenylnitroethane (6125-24-2) + 2,4,6-triphenylpyridine (580-35-8)

Conditions	Yield
In dimethyl sulfoxide at 25℃; for 2h; Rate constant; Mechanism;	A 58% B n/a

nitromethane (75-52-5) + benzyl alcohol (100-51-6) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; caesium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride In toluene at 150℃; for 72h;	54%

2-nitroacetophenone (614-21-1) → 2-Phenylnitroethane (6125-24-2) + 2-nitro-1-phenylethan-1-ol (141377-54-0, 145920-96-3, 149495-00-1, 15990-45-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In hydrogenchloride; ethanol at 50℃; under 760 Torr;	A 37% B 14%

phenethylamine (64-04-0) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 3h; Heating;	30%
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane Heating;
With 3-chloro-benzenecarboperoxoic acid

(2-nitroprop-1-enyl)benzene (705-60-2) → 2-Phenylnitroethane (6125-24-2) + 1-phenyl-acetone (103-79-7)

Conditions	Yield
With tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid 1.) methylene chloride; Multistep reaction;	A 10% B n/a

(2-nitroethenyl)benzene (102-96-5) → 2-Phenylnitroethane (6125-24-2) + phenylacetaldehyde (122-78-1)

Conditions	Yield
With tri-n-butyl-tin hydride; ozone 1.) methylene chloride; Multistep reaction;	A 10% B n/a

(2-nitroethenyl)benzene (102-96-5) → 1,3-dinitro-2,4-diphenyl-butane (101280-71-1) + 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With sodium tetrahydroborate; ethanol
With tetrahydrofuran; diethyl ether; Trimethyl borate; sodium
With sodium hydroxide; sodium tetrahydroborate In ethanol at 0 - 5℃; for 2h;
With sodium hydroxide; sodium tetrahydroborate In water; acetonitrile at 0 - 5℃; for 2h;

nitromethane (75-52-5) + N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate (66310-10-9) → 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
(i) NaOEt, EtOH, (ii) /BRN= 4225599/, DMSO; Multistep reaction;

1-benzyl-2,4,6-triphenylpyridinium cation (56524-87-9) + nitromethane anion (18137-96-7) → 2-Phenylnitroethane (6125-24-2) + 2,4,6-triphenylpyridine (580-35-8)

Conditions	Yield
In pentan-1-ol at 25℃; also in DMSO;
In pentan-1-ol at 25℃; Kinetics; Rate constant; Mechanism; also in DMSO;

(2-nitroethenyl)benzene (102-96-5) → 1,3,5-triphenylbenzene (612-71-5) + 2-Phenylnitroethane (6125-24-2)

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide In acetonitrile at 80℃; Yield given;

acetic anhydride (108-24-7) + C8H8NO2(1-)*Li(1+) → 2-Phenylnitroethane (6125-24-2) + anhydride N-acetyl phenyl-acetohydroxamique-acetique (56523-74-1)

Conditions	Yield
In diethyl ether for 65h;	A 13 % Spectr. B 82 % Spectr.

2-Phenylnitroethane (6125-24-2) → phenethylamine (64-04-0)

Conditions	Yield
With samarium diiodide; water; isopropylamine In tetrahydrofuran	99%
With trichlorosilane; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 18h; Inert atmosphere;	98%
With poly(p-aminostyrene)-palladium(II); hydrogen In N,N-dimethyl-formamide at 70℃; under 760 Torr; for 6h;	91%

2-fluoro-ethane-1,1-diol (430-73-9) + 2-Phenylnitroethane (6125-24-2) → 1-Fluoro-2-hydroxy-3-nitro-4-phenylbutane (102195-94-8)

Conditions	Yield
potassium carbonate at 50℃; for 6h;	95%

2,2-difluoro-ethane-1,1-diol (431-12-9) + 2-Phenylnitroethane (6125-24-2) → 1,1-Difluoro-3-nitro-4-phenyl-butan-2-ol (102195-93-7)

Conditions	Yield
potassium carbonate at 50℃; for 6h;	95%

2,2,2-trifluoro-1,1-ethanediol (421-53-4) + 2-Phenylnitroethane (6125-24-2) → 3-nitro-4-phenyl-1,1,1-trifluorobutan-2-ol (102195-92-6)

Conditions	Yield
potassium carbonate at 50℃; for 6h;	95%

2-Phenylnitroethane (6125-24-2) → phenylacetic acid (103-82-2)

Conditions	Yield
With acetic acid; sodium nitrite In dimethyl sulfoxide at 35℃; for 6h;	95%
With acetic acid; sodium nitrite In water; dimethyl sulfoxide at 65℃;	75%
With (S)-1-phenyl-ethylamine; sodium nitrite; isopentyl nitrite In N,N-dimethyl-formamide for 48h;

2-Phenylnitroethane (6125-24-2) + N-benzylidenediphenylphosphinamide (98837-46-8) → N-(2-nitro-1,3-diphenylpropyl)diphenylphosphinic amide

Conditions	Yield
N,N,N',N'-tetramethylguanidine at 20℃; for 26h; aza-Henry reaction;	95%

2-Phenylnitroethane (6125-24-2) + benzaldehyde N-boc imine (150884-50-7) → tert-butyl (1R,2S)-2-nitro-1,3-diphenylpropylcarbamate

Conditions	Yield
With N-((1R,2R)-2-(3-((1R,2R)-2-(dimethylamino)cyclohexyl)thioureido)-1,2-diphenylethyl)-3,5-bis(trifluoromethyl)benzenesulfonamide In acetonitrile at -20℃; Mannich reaction; Molecular sieve;	95%

1-hexene (592-41-6) + 2-Phenylnitroethane (6125-24-2) → 3-Benzyl-5-butyl-4,5-dihydro-isoxazole

Conditions	Yield
With triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid In tetrahydrofuran at -30 - 50℃; for 2h; Product distribution; different dehydration reagents, solvents, reaction temperatures, times;	91%
With triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid In tetrahydrofuran at -30 - 50℃; for 2h;	91%
With acetic acid; sodium nitrite In dimethyl sulfoxide at 35℃;	72%

crotonic acid methyl ester (623-43-8) + 2-Phenylnitroethane (6125-24-2) → methyl b-methyl-g-nitrobenzenepentanoate (89706-87-6)

Conditions	Yield
With Aliquat 336; potassium carbonate Ambient temperature; Irradiation;	91%

2-Phenylnitroethane (6125-24-2) + N-[(4-methylbenzene-1-sulfonyl)(phenyl)methyl]formamide (37643-54-2) → N-(2-nitro-1,3-diphenyl-propyl)-formamide

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; aza-Henry reaction;	90%

2-Phenylnitroethane (6125-24-2) + 4-methoxy-benzaldehyde (123-11-5) → 1-methoxy-4-(2-nitro-3-phenyl-1-propenyl)benzene (1168207-82-6)

Conditions	Yield
With N-butylamine In toluene for 12h; Henry reaction; Reflux;	90%

2-hydrazinyl-4-methylquinoline (21703-52-6) + 2-Phenylnitroethane (6125-24-2) → 1-benzyl-5-methyl-[1,2,4]triazolo[4,3-a]quinoline

Conditions	Yield
Stage #1: 2-Phenylnitroethane With polyphosphoric acid at 130℃; Stage #2: 2-hydrazinyl-4-methylquinoline at 130℃;	90%

2-Phenylnitroethane (6125-24-2) → 1-fluoro-1-nitro-2-phenylethane (110683-92-6)

Conditions	Yield
Stage #1: 2-Phenylnitroethane With tetra(n-butyl)ammonium hydroxide In acetonitrile at 25℃; Stage #2: With Selectfluor In water; acetonitrile	89%
Stage #1: 2-Phenylnitroethane With potassium hydroxide In water; acetonitrile at -15 - -5℃; Stage #2: With Selectfluor In dichloromethane; water; acetonitrile at -15 - 10℃; Further stages.;	83%
Stage #1: 2-Phenylnitroethane With potassium hydroxide In water; acetonitrile at 0℃; for 1h; Stage #2: With Selectfluor In dichloromethane; water; acetonitrile at -17 - 10℃; for 0.166667h;	80%

2-Phenylnitroethane (6125-24-2) + N-[(4-nitro-phenyl)-(toluene-4-sulfonyl)-methyl]-formamide → N-[2-nitro-1-(4-nitro-phenyl)-3-phenyl-propyl]-formamide

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; aza-Henry reaction;	89%

(2-nitroethenyl)benzene (102-96-5) + 2-Phenylnitroethane (6125-24-2) → ((2R,3R)-1,3-dinitrobutane-1,3-diyl)dibenzene (1127388-74-2)

Conditions	Yield
With N-((1R,2R)-2-(3-((1R,2R)-2-(dimethylamino)cyclohexyl)thioureido)-1,2-diphenylethyl)-3,5-bis(trifluoromethyl)benzenesulfonamide In dichloromethane at -30℃; Michael condensation; optical yield given as %ee; enantioselective reaction;	89%

3,5-Dibromosalicylaldehyde (90-59-5) + 2-Phenylnitroethane (6125-24-2) → 2,4-dibromo-6-[(Z)-2-nitro-3-phenylprop-1-en-1-yl]phenol

Conditions	Yield
With potassium fluoride; N,N-dimethylammonium chloride In toluene at 110℃; for 12h;	89%

2-Phenylnitroethane (6125-24-2) + (2S)-N,N-dibenzylphenylalaninal (123054-12-6, 123808-74-2, 136370-73-5, 111060-64-1) → (S)-2-Dibenzylamino-4-nitro-1,5-diphenyl-pentan-3-ol (501668-70-8)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.333333h; Henry reaction;	87%

2-Phenylnitroethane (6125-24-2) + trans-4-decenal (65405-70-1) → (E)-2-nitro-1-phenyl-6-dodecen-3-ol

Conditions	Yield
With cetyltrimethylammonium hydroxide at 20℃; for 3h; Henry reaction;	86%

2-Phenylnitroethane (6125-24-2) + benzaldehyde (100-52-7) → (2-nitroprop-1-ene-1,3-diyl)dibenzene (58497-32-8)

Conditions	Yield
With N-butylamine In toluene for 9.5h; Reflux;	85%
With ammonium acetate In acetic acid
With methylamine hydrochloride; potassium acetate; trimethyl orthoformate In methanol for 16h; Heating;
With hydrogenchloride; potassium fluoride; dimethyl amine In water; toluene for 24h; Reflux; Dean-Stark;

methyl crotonate (623-43-8, 4358-59-2, 18707-60-3, 130981-57-6) + 2-Phenylnitroethane (6125-24-2) → methyl b-methyl-g-nitrobenzenepentanoate (89706-87-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 22h; Ambient temperature;	85%

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 75-52-5 nitromethane 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 102-96-5 (2-nitroethenyl)benzene 
• 5153-67-3 nitrostyrene 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 67-63-0 isopropyl alcohol 
• 95-54-5 1,2-diamino-benzene 
• 60-12-8 2-phenylethanol 
• 620-05-3 iodomethylbenzene 
• 141377-54-0 2-nitro-1-phenylethan-1-ol 
• 100-51-6 benzyl alcohol 
• 274-07-7 benzo[1,3,2]dioxaborole 

Downstream Products

• 53607-34-4 (2-bromo-2-nitroethyl)benzene 
• 102613-62-7 (E)-N,N-Bis(trimethylsiloxy)-2-phenylethen-1-amin 
• 102503-45-7 (Z)-2-Phenyl-2-(trimethylsiloxy)ethanaloxim-O-trimethylsilylether 
• 102503-44-6 (E)-2-Phenyl-2-(trimethylsiloxy)ethanaloxim-O-trimethylsilylether 
• 103-82-2 phenylacetic acid 
• 89706-87-6 methyl b-methyl-g-nitrobenzenepentanoate 
• 253140-21-5 4-Nitro-5-phenyl-3-trifluoromethyl-pentanoic acid methyl ester 
• 122-78-1 phenylacetaldehyde 
• 101-41-7 benzeneacetic acid methyl ester 
• 640279-63-6 O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol 

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