Welcome to LookChem.com Sign In|Join Free
  • or

75-52-5

Post Buying Request

75-52-5 Suppliers

Recommended suppliersmore

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

75-52-5 Usage

Reactivity Profile

Nitromethane may explode if heated or strongly shocked, especially if mixed with acids, bases [Handling Chemicals Safely 1980. p.687], acetone, aluminum powder, ammonium salts in the presence of organic solvents, haloforms (chloroform, bromoform), or hydrazine in methanol. Ignites on contact with alkyl aluminum or alkyl zinc halides. Reacts violently with strong bases (potassium hydroxide, calcium hydroxide), amines (1,2-diaminoethane, hydrazine), bromine, carbon disulfide, hydrocarbons, formaldehyde, metal oxides, lithium aluminum hydride, sodium hydride, strong oxidizing agents (lithium perchlorate, nitric acid, calcium hypochlorite). Reacts with aqueous silver nitrate to form explosive silver fulminate [Bretherick, 5th ed., 1995, p. 183]. Mixtures of Nitromethane and aluminum chloride may explode when organic matter is present [Chem. Eng. News 26:2257. 1948]. Nitromethane, either alone or in a mixture with methanol and castor oil, has a delayed but violent reaction with powdered calcium hypochlorite [Haz. Home Chem 1963]. Nitromethane reacts violently with hexamethylbenzene [Lewis 2544]. Nitromethane is strongly sensitized by hydrazine [Forshey, D. RR. et al, Explosivestoffe, 1969, 17(6), 125-129].

Uses

Solvent; chemical synthesis; fuel for professional and model racing cars; in explosive mixtures

Incompatibilities

May explode from heat, shock, friction, or concussion. Reacts with alkalis, strong acids; metallic oxides. Detonates or reacts violently with strong oxidizers, strong reducing agents such as hydrides; formaldehyde, copper, copper alloys; lead, lead alloys; hydrocarbons and other combustibles, causing fire and explosion hazard. Forms shock sensitive mixture when contaminated with acids, amines, bases, metal oxides; hydrocarbons, and other combustible materials.

Health Hazard

Liquid may dry out skin and cause irritation.

Metabolism

Nitromethane is converted to nitrite and formaldehyde in a 1:1 ratio by hepatic microsomes from phenobarbital-pretreated male Sprague-Dawley rats (Sakurai et al 1980), but no formaldehyde could be detected when microsomes from the nose or liver of untreated male Fischer-344 rats were incubated with nitromethane (Dahl and Hadley 1983). Whether a similar conversion occurs in vivo has not been determined, but the absence of nitromethane metabolism in microsomes from untreated rats suggests that its metabolism in vivo may be slow.

Chemical Properties

clear liquid

Carcinogenicity

Nitromethane is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Production Methods

Nitromethane and the other important nitroparaffins are synthesized commercially by the vapor-phase nitration of propane (Baker and Bollmeier 1978). At temperatures of 370-450°C and pressures of 8-12 atmospheres, nitromethane, nitroethane and 1- and 2-nitropropane are formed and then separated by distillation.

Hazard

Dangerous fire and explosion risk, lower explosion limit 7.3% in air. Toxic by ingestion and inhalation. Thyroid effects, upper respiratory tract irritant, and lung damage. Possible carcinogen.

Shipping

UN1261 Nitromethane, Hazard Class: 3; Labels: 3-Flammable liquid.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by intravenous route. Mildly toxic by inhalation. In humans it may cause anorexia, nausea, vomiting, darrhea, kidney injury, and liver damage. exposed to heat, oxidizers, or flame. May explode by detonation, heat, or shock. Its sensitivity is increased when mixed with acids, bases, acetone, aluminum powder, ammonium salts + organic solvents, bis(2- aminoethyl)amine, 1,2-daminoethane + N,2,4,6-tetranitro-N-methyl aniLtne, halo forms (e.g., chloroform, bromoform), hydrazine + methanol. Ignites when mixed with alkyl metal halides (e.g., diethylaluminum bromide, dimethylaluminum bromide, ethylaluminum bromide iodide, methyl zinc iodide, methylaluminum diiodide). Can react violently with AlCl3 + organic matter, Ca(OH)2, m-methyl aniline, Ca(OCl)2, hexamethylbenzene, hydrocarbons, inorganic bases, hydroxides, organic amines, KOH, formaldehyde, nitric acid, metal oxides, 1,2-diaminomethane, litlvum perchlorate, sodium hydride. Reacts with aqueous silver nitrate to form the explosive silver fuhnate. When heated to decomposition it emits toxic fumes of NOx. See also NITROALKANES. A very dangerous fire hazard when exposed to heat, oxidizers, or flame. May explode by detonation, heat, or shock. Its sensitivity is increased when mixed with acids, bases, acetone, aluminum powder, ammonium salts + organic solvents, bis(2- aminoethyl)amine, 1,2-daminoethane + N,2,4,6-tetranitro-N-methyl aniLtne, halo forms (e.g., chloroform, bromoform), hydrazine + methanol. Ignites when mixed with alkyl metal halides (e.g., diethylaluminum bromide, dimethylaluminum bromide, ethylaluminum bromide iodide, methyl zinc iodide, methylaluminum diiodide). Can react violently with AlCl3 + organic matter, Ca(OH)2, m-methyl aniline, Ca(OCl)2, hexamethylbenzene, hydrocarbons, inorganic bases, hydroxides, organic amines, KOH, formaldehyde, nitric acid, metal oxides, 1,2-diaminomethane, litlvum perchlorate, sodium hydride. Reacts with aqueous silver nitrate to form the explosive silver fuhnate. When heated to decomposition it emits toxic fumes of NOx. See also NITROALKANES. concentrated sulfuric acid. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS and AMINES.

Physical properties

Colorless liquid with a strong, disagreeable odor. Odor threshold concentration is 3.5 ppm (quoted, Amoore and Hautala, 1983).

Chemical Properties

Nitromethane is a highly flammable and explosive colorless liquid with a strong, disagreeable odor.

General Description

A colorless oily liquid. Flash point 95°F. May violently decompose if intensely heated when contaminated. Denser than water and slightly soluble in water. Hence sinks in water. Vapors are heavier than air. Moderately toxic. Produces toxic oxides of nitrogen during combustion.

Waste Disposal

Incineration: large quantities of material may require nitrogen oxide removal by catalytic or scrubbing processes.

Potential Exposure

Nitromethane is used in the production of the fumigant, chloropicrin. It is best known as racing car fuel. It is also used as a solvent and as an intermediate in the pharmaceutical industry.

Uses

Most of the nitromethane produced in the United States (85% to 90%) is used in the synthesis of nitromethane derivatives used as pharmaceuticals, agricultural soil fumigants, and industrial antimicrobials (Markofsky 1991, Angus 2001). Nitromethane also is used as a fuel or fuel additive with methanol in racing cars, boats, and model engines. It formerly was used in the explosives industry as a component in a binary explosive formulation with ammonium nitrate and in shaped charges, and it was used as a chemical stabilizer to prevent decomposition of various halogenated hydrocarbons (NTP 1997, IARC 2000, Angus 2001).

Purification Methods

Nitromethane is generally manufactured by gas-phase nitration of methane. The usual impurities include aldehydes, nitroethane, water and small amounts of alcohols. Most of these can be removed by drying with CaCl2 or by distillation to remove the water/nitromethane azeotrope, followed by drying with CaSO4. Phosphorus pentoxide is not suitable as a drying agent. [Wright et al. J Chem Soc 199 1936.] The purified material should be stored by dark bottles, away from strong light, in a cool place. Purifications using extraction are commonly used. For example, Van Looy and Hammett [J Am Chem Soc 81 3872 1959] mixed about 150mL of conc H2SO4 with 1L of nitromethane and allowed it to stand for 1 or 2days. The solvent was washed with water, aqueous Na2CO3, and again with water, then dried for several days with MgSO4, filtered again with CaSO4. It was fractionally distilled before use. Smith, Fainberg and Winstein [J Am Chem Soc 83 618 1961] washed it successively with aqueous NaHCO3, aqueous NaHSO3, water, 5% H2SO4, water and dilute NaHCO3. The solvent was dried with CaSO4, then percolated through a column of Linde type 4A molecular sieves, followed by distillation from some of this material (in powdered form). Buffagni and Dunn [J Chem Soc 5105 1961] refluxed it for 24hours with activated charcoal while bubbling a stream of nitrogen through the liquid. The suspension was filtered, dried (Na2SO4) and distilled, then passed through an alumina column and redistilled. It has also been refluxed over CaH2, distilled and kept under argon over 4A molecular sieves. It has been purified by zone melting at low temperature, or by distillation under vacuum at 0o, subjecting the middle fraction to several freeze-pump-thaw cycles. An impure sample containing higher nitroalkanes and traces of cyanoalkanes was purified (on the basis of its NMR spectrum) by crystallisation from diethyl ether at -60o (cooling in Dry-ice)[Parrett & Sun J Chem Educ 54 448 1977]. Fractional crystallisation is more effective than fractional distillation from Drierite in purifying nitromethane for conductivity measurements. [Coetzee & Cunningham J Am Chem Soc 87 2529 1965.] Specific conductivities around 5 x 10-9 ohm-1cm-1 were obtained. [Beilstein 1 IV 100.]

Industrial uses

Nitromethane is used as an intermediate in chemical syntheses, but more importantly it is used as a solvent for coatings and inks. It and the other nitroparaffins are excellent solvents for vinyls, epoxies, polyamides and acrylic polymers (Baker and Bollmeier 1978). It also is used as a military propellant and a racing fuel additive (HSDB 1988). Mixed with methanol and castor oil it is employed as a model airplane fuel.

Environmental fate

Chemical/Physical. Nitromethane will not hydrolyze because it does not contain a hydrolyzable functional group.

Uses

Rocket fuel; solvent for zein. Used in the coating industry.

Fire Hazard

Behavior in Fire: Containers may explode

Chemical Properties

Nitromethane is explosive and can be detonated by shock or heat (HSDB 1988) and the chemical can be made more sensitive to detonation through the presence of other chemicals, especially amines and acids. Nitromethane forms salts with inorganic bases and the dry salts are explosive.

Health Hazard

Nitromethane is mildly irritating to the skin and mucous membranes (Gosselin et al 1976). It produces narcosis, mucus membrane irritation and central nervous system excitation, and some liver damage. These effects are generally not as marked as after administration of nitroethane. One case of human poisoning has been reported (Kaiffer et al 1972). In that case, a handyman was exposed to high concentrations of nitrocellulose and nitromethane resulting in a 67% conversion of his hemoglobin to methemoglobin and sulfhemoglobin. Treatment with hyperbaric oxygen, transfusion, peritoneal dialysis and then 6 sessions of hemodialysis resulted in recovery.
InChI:InChI=1/CH3NO2/c1-2(3)4/h1H3

75-52-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name nitromethane

1.2 Other means of identification

Product number -
Other names nitro-methane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Agricultural chemicals (non-pesticidal),Fuels and fuel additives,Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:75-52-5 SDS

75-52-5Synthetic route

formaldoxime
75-17-2

formaldoxime

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
With dihydrogen peroxide; triethylamine In tert-butyl alcohol at 60℃; under 6000.6 Torr;96.5%
dimethyl sulfate
77-78-1

dimethyl sulfate

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
With sodium carbonate; sodium nitrite In water at 30℃; for 3h; Reagent/catalyst; Temperature;84%
With sodium nitrite In water at 60℃;75%
With water; sodium carbonate; sodium nitrite zuletzt bei 120grad;
tetramethylsilane
75-76-3

tetramethylsilane

A

nitromethane
75-52-5

nitromethane

B

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

Conditions
ConditionsYield
With nitronium tetrafluoborate In sulfolane at 80℃; for 2h; Product distribution; Mechanism; other alkyl- and allylsilanes; other temperature, var. solvents;A 80%
B n/a
6-chloro-1-hexanol
2009-83-8

6-chloro-1-hexanol

methyl 2-nitroacetate
2483-57-0

methyl 2-nitroacetate

A

nitromethane
75-52-5

nitromethane

B

carbon dioxide
124-38-9

carbon dioxide

C

6-chlorohexyl 2-nitroacetate

6-chlorohexyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Sealed tube; Inert atmosphere;A n/a
B n/a
C 76%
octanol
111-87-5

octanol

methyl 2-nitroacetate
2483-57-0

methyl 2-nitroacetate

A

nitromethane
75-52-5

nitromethane

B

carbon dioxide
124-38-9

carbon dioxide

C

octyl 2-nitroacetate

octyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;A n/a
B n/a
C 69%
methyl iodide
74-88-4

methyl iodide

A

nitromethane
75-52-5

nitromethane

B

methyl nitrite
624-91-9

methyl nitrite

Conditions
ConditionsYield
With tetrabutylammonium nitrite In chloroform-d1 at 20℃;A 67%
B 28 % Spectr.
With silver(I) nitrite
With silver nitrate
(+/-)-2-pentanol
6032-29-7

(+/-)-2-pentanol

methyl 2-nitroacetate
2483-57-0

methyl 2-nitroacetate

A

nitromethane
75-52-5

nitromethane

B

carbon dioxide
124-38-9

carbon dioxide

C

s-pentyl 2-nitroacetate

s-pentyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Sealed tube; Inert atmosphere;A n/a
B n/a
C 66%
methyl 2-nitroacetate
2483-57-0

methyl 2-nitroacetate

allyl alcohol
107-18-6

allyl alcohol

A

nitromethane
75-52-5

nitromethane

B

carbon dioxide
124-38-9

carbon dioxide

C

allyl 2-nitroacetate
221116-46-7

allyl 2-nitroacetate

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Sealed tube; Inert atmosphere;A n/a
B n/a
C 66%
ethanol
64-17-5

ethanol

methyl 2-nitroacetate
2483-57-0

methyl 2-nitroacetate

A

nitroacetic acid ethyl ester
626-35-7

nitroacetic acid ethyl ester

B

nitromethane
75-52-5

nitromethane

C

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
With di(n-butyl)tin oxide at 100℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;A 61%
B n/a
C n/a
Methyl methanesulfonate
66-27-3

Methyl methanesulfonate

A

nitromethane
75-52-5

nitromethane

B

methyl nitrite
624-91-9

methyl nitrite

Conditions
ConditionsYield
With tetrabutylammonium nitrite In chloroform-d1 at 20℃;A 60%
B 29 % Spectr.
sodium salt of nitromethane
22755-24-4

sodium salt of nitromethane

A

nitromethane
75-52-5

nitromethane

B

difluoro-nitro-methane
1493-05-6

difluoro-nitro-methane

C

fluorotrinitromethane
21824-10-2

fluorotrinitromethane

Conditions
ConditionsYield
With calcium fluoride; fluorine at -70 - -65℃;A 24%
B 20%
C 45%
trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

A

nitromethane
75-52-5

nitromethane

B

methyl nitrite
624-91-9

methyl nitrite

Conditions
ConditionsYield
With tetrabutylammonium nitrite In chloroform-d1 at 20℃;A 41%
B 41 % Spectr.
methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

A

nitromethane
75-52-5

nitromethane

B

methyl nitrite
624-91-9

methyl nitrite

Conditions
ConditionsYield
With tetrabutylammonium nitrite In chloroform-d1 at 20℃;A 38%
B 56 % Spectr.
sodium aci-nitroethane

sodium aci-nitroethane

A

nitromethane
75-52-5

nitromethane

B

difluoro-nitro-methane
1493-05-6

difluoro-nitro-methane

C

1-fluoro-1-nitro-ethane
17003-27-9

1-fluoro-1-nitro-ethane

Conditions
ConditionsYield
With calcium fluoride; fluorine at -80 - -75℃;A 24%
B 20%
C 23%
methanol
67-56-1

methanol

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
With Cu(MeNO2)2+ Thermodynamic data; free energie for exchange of both ligands;
With water; sodium hydrogencarbonate; iron(II) sulfate; sodium nitrite
With sulfuric acid; sodium nitrite
methyl bromide
74-83-9

methyl bromide

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
With sodium nitrite bei pH 6-10;
methylene chloride
74-87-3

methylene chloride

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
With sodium nitrite bei pH 6-10;
diethyl ether
60-29-7

diethyl ether

A

nitromethane
75-52-5

nitromethane

B

1-ethoxy-2-nitroethane
31890-52-5

1-ethoxy-2-nitroethane

Conditions
ConditionsYield
With nitric acid at 400℃; Nebenprod.2:Nitroaethan;
methyl nitrite
624-91-9

methyl nitrite

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
With magnesium hydrosilicate at 120 - 130℃;
ethyl nitrate
625-58-1

ethyl nitrate

A

nitromethane
75-52-5

nitromethane

B

methyl nitrite
624-91-9

methyl nitrite

C

ethyl nitrite
109-95-5

ethyl nitrite

Conditions
ConditionsYield
at 160 - 219℃; Kinetics; unter vermindertem Druck.Pyrolysis;
ethyl nitrate
625-58-1

ethyl nitrate

A

formaldehyd
50-00-0

formaldehyd

B

nitromethane
75-52-5

nitromethane

C

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
at 95℃; unter vermindertem Druck.Photolysis;
methane
34557-54-5

methane

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
With nitric acid at 475℃;
With nitric acid
With oxygen; nitric acid
ethane
74-84-0

ethane

A

Nitroethane
79-24-3

Nitroethane

B

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
at 420℃; beim Nitrieren in der Dampfphase;
ethane
74-84-0

ethane

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
bei der Nitrierung;
propane
74-98-6

propane

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
bei der Nitrierung;
With nitric acid
With oxygen; nitric acid
With nitric acid; acetic acid In water at 235℃; under 72402.6 Torr; for 0.05h;
Isobutane
75-28-5

Isobutane

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
bei der Nitrierung;
methylbutane
78-78-4

methylbutane

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
bei der Nitrierung;
2,3-dimethylbutane
79-29-8

2,3-dimethylbutane

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
bei der Nitrierung;
2-methyl-1-nitro-2-propanol
5447-98-3

2-methyl-1-nitro-2-propanol

A

nitromethane
75-52-5

nitromethane

B

acetone
67-64-1

acetone

Conditions
ConditionsYield
With water at 130 - 150℃;
at 245.6℃; under 55 Torr; Kinetics; Further Variations:; Pressures; Temperatures; also in the presence of free radical inhibitors;
nitroacetic acid
625-75-2

nitroacetic acid

A

nitromethane
75-52-5

nitromethane

B

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

Conditions
ConditionsYield
at 25℃; Geschwindigkeit in saurer Loesung bei verschiedenen pH und Einfluss von verschiedenen anorganischen und organischen Salzen;
at 15℃; Geschwindigkeit in saurer Loesung bei verschiedenen pH und Einfluss von verschiedenen anorganischen und organischen Salzen;
at 15℃; Geschwindigkeit in saurer Loesung bei verschiedenen pH und Einfluss von Glucose und Rohrzucker;
p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

nitromethane
75-52-5

nitromethane

(E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene
2982-55-0

(E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene

Conditions
ConditionsYield
Stage #1: p-benzyloxybenzaldehyde; nitromethane With sodium methylate In methanol at 0 - 20℃; for 0.166667h;
Stage #2: With hydrogenchloride; water In methanol at 0 - 20℃; for 0.25h;
100%
Stage #1: p-benzyloxybenzaldehyde; nitromethane With sodium methylate In methanol at 0 - 20℃; for 0.166667h;
Stage #2: With hydrogenchloride In methanol; water at 0 - 20℃; for 0.25h;
100%
Stage #1: p-benzyloxybenzaldehyde; nitromethane With sodium methylate In methanol at 0 - 20℃;
Stage #2: With hydrogenchloride In methanol; water at 0 - 20℃;
100%
nitromethane
75-52-5

nitromethane

crotonic acid methyl ester
623-43-8

crotonic acid methyl ester

methyl 3-methyl-4-nitro-butyrate
16507-06-5

methyl 3-methyl-4-nitro-butyrate

Conditions
ConditionsYield
With N,N,N',N'-tetramethylguanidine at 20℃; for 576h;100%
With DBN In methanol at 60℃; for 6h; Inert atmosphere;71.44%
With methanol; potassium carbonate
With N-benzyl-trimethylammonium hydroxide In methanol
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol Michael addition;
nitromethane
75-52-5

nitromethane

Octanal
124-13-0

Octanal

2-hydroxy-1-nitrononane
4013-87-0

2-hydroxy-1-nitrononane

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; butan-1-ol at 23℃; Inert atmosphere;100%
With silica gel; triethylamine at 20℃; for 3h; Henry Nitro Aldol Condensation;95%
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 20℃; for 18.5h; Henry reaction;94%
nitromethane
75-52-5

nitromethane

2-chloro-3,4-dimethoxybenzaldehyde
5417-17-4

2-chloro-3,4-dimethoxybenzaldehyde

(E)-2-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene
41122-35-4

(E)-2-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene

Conditions
ConditionsYield
With ammonium acetate; acetic acid for 4h; Inert atmosphere; Reflux;100%
With ammonium acetate In acetic acid for 3h; Heating;95%
With ammonium acetate; acetic acid
nitromethane
75-52-5

nitromethane

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-methyl-β-nitrostyrene
7559-36-6

4-methyl-β-nitrostyrene

Conditions
ConditionsYield
With C62H54N2O2; copper diacetate In ethanol at 10℃; for 48h; Henry Nitro Aldol Condensation; enantioselective reaction;100%
With C62H48CuN2O2; copper diacetate; benzaldehyde In ethanol at 10℃; for 48h; Reagent/catalyst; Henry Nitro Aldol Condensation;100%
With (2-hydroxyethyl)ammonium formate at 20℃; for 0.8h; Knoevenagel condensation; Ionic liquid;95%
nitromethane
75-52-5

nitromethane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-chloro-4-(2-nitrovinyl)benzene
706-07-0

1-chloro-4-(2-nitrovinyl)benzene

Conditions
ConditionsYield
With copper(II) ferrite In dimethyl sulfoxide at 120℃; for 0.0333333h; Microwave irradiation;100%
With bridged diamino-functionalized periodic mesoporous organosilicas with high nitrogen contents at 90℃; for 5h; Henry Nitro Aldol Condensation;99%
With acetic acid; benzylamine at 78 - 80℃; for 3.5h; Product distribution / selectivity;97.1%
nitromethane
75-52-5

nitromethane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-(4-chlorophenyl)-2-nitroethanol
89979-04-4

1-(4-chlorophenyl)-2-nitroethanol

Conditions
ConditionsYield
With polymer supported 4-DMAP at 20℃; for 0.416667h; Reagent/catalyst; Henry Nitro Aldol Condensation;100%
With triethylamine at 80℃; for 0.0166667h; Henry reaction; microwave irradiation;99%
With Musca acuminata (banana) peel ash In neat (no solvent) at 20℃; for 0.333333h; Henry Nitro Aldol Condensation; Green chemistry;98%
nitromethane
75-52-5

nitromethane

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1-(4-nitrophenyl)-2-nitroethanol
18731-47-0

1-(4-nitrophenyl)-2-nitroethanol

Conditions
ConditionsYield
With C57H78N12; copper(II) acetate monohydrate In methanol; dichloromethane for 72h; Henry reaction; Inert atmosphere;100%
With polymer supported 4-DMAP at 20℃; for 0.333333h; Reagent/catalyst; Henry Nitro Aldol Condensation;100%
With P(i-PrNCH2CH2)3N; magnesium sulfate for 0.0833333h; Ambient temperature;99%
nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
palladium/alumina at 60℃; for 1h;100%
With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane hydroxide In neat (no solvent) at 20℃; for 0.166667h; Reagent/catalyst; Henry Nitro Aldol Condensation; Green chemistry;99%
With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane hydroxide In neat (no solvent) at 20℃; for 0.166667h; Catalytic behavior; Reagent/catalyst; Henry Nitro Aldol Condensation; Ionic liquid; Green chemistry;99%
nitromethane
75-52-5

nitromethane

butyraldehyde
123-72-8

butyraldehyde

1-nitropentan-2-ol
2224-37-5

1-nitropentan-2-ol

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 0℃; for 0.166667h; Addition; Henry reaction;100%
With P(i-PrNCH2CH2)3N; magnesium sulfate for 0.666667h; Ambient temperature;98%
With rac-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline In tetrahydrofuran at 20℃; for 24h; Henry Nitro Aldol Condensation;98%
nitromethane
75-52-5

nitromethane

hexanal
66-25-1

hexanal

1-nitroheptan-2-ol
6302-74-5

1-nitroheptan-2-ol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 0 - 20℃; for 24h; Henry reaction;100%
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol Addition;99%
With (S,S)-1,2-diaminocyclohexane; copper(II) acetate monohydrate In ethanol at 20℃; for 12h; Henry reaction; Inert atmosphere; enantioselective reaction;99%
nitromethane
75-52-5

nitromethane

benzalacetophenone
94-41-7

benzalacetophenone

4-nitro-1,3-diphenyl-butan-1-one
6277-67-4

4-nitro-1,3-diphenyl-butan-1-one

Conditions
ConditionsYield
With potassium carbonate In ethanol Michael condensation; Reflux;100%
With alkaline hydroxide In ethanol at 60℃; for 12h; Michael addition;100%
With potassium fluoride In ethanol at 20℃; for 2h; Addition;98%
nitromethane
75-52-5

nitromethane

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

3-(nitromethyl)-isobenzofuran-1-(3H)-one
3598-68-3

3-(nitromethyl)-isobenzofuran-1-(3H)-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 15 - 30℃; for 1h;100%
With alkaline solution
nitromethane
75-52-5

nitromethane

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

Conditions
ConditionsYield
tris(bis(trimethylsilyl)amido)samarium(III) In tetrahydrofuran for 25h; Ambient temperature;100%
With potassium fluoride In isopropyl alcohol at 0 - 20℃; for 24h; Inert atmosphere;100%
With calcium oxide at 50℃; for 12h;99%
nitromethane
75-52-5

nitromethane

cyclohexanone
108-94-1

cyclohexanone

phenylmethanethiol
100-53-8

phenylmethanethiol

1-benzylthio-1-nitromethylcyclohexane
335458-24-7

1-benzylthio-1-nitromethylcyclohexane

Conditions
ConditionsYield
With piperidine In benzene100%
With piperidine In acetonitrile for 4h; Heating;96%
With piperidine In acetonitrile for 4h; Heating / reflux;22%
With piperidine In benzene Heating;
nitromethane
75-52-5

nitromethane

cyclopentanone
120-92-3

cyclopentanone

phenylmethanethiol
100-53-8

phenylmethanethiol

1-benzylthio-1-nitromethylcyclopentane
335458-23-6

1-benzylthio-1-nitromethylcyclopentane

Conditions
ConditionsYield
With piperidine In benzene100%
With piperidine In acetonitrile for 4h; Heating;94%
With piperidine In benzene Heating;
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

nitromethane
75-52-5

nitromethane

Conditions
ConditionsYield
(anthracenebisresorcinol(4-):2La(3+))polymer In benzene at 20℃; for 0.333333h; Addition; nitroaldol reaction;100%
With potassium fluoride In isopropyl alcohol at 0 - 20℃; for 24h; Inert atmosphere;100%
With silica gel; triethylamine at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Henry Nitro Aldol Condensation;99%
nitromethane
75-52-5

nitromethane

2-Formyl-2,3-dihydronaphtho<1,8-bc>pyran
133157-50-3

2-Formyl-2,3-dihydronaphtho<1,8-bc>pyran

1-(1-Hydroxy-2-nitroethyl)-2,3-dihydronaphtho<1,8-bc>pyran
133157-51-4

1-(1-Hydroxy-2-nitroethyl)-2,3-dihydronaphtho<1,8-bc>pyran

Conditions
ConditionsYield
With triethylamine 1) 15 min, cooling 2) 2 h, r.t.;100%
nitromethane
75-52-5

nitromethane

(+)-(4S,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone
127181-13-9

(+)-(4S,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

(-)-(2R,3S,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-3,4-O-isopropylidene-5-(nitromethyl)-3,4,5-piperidinetriol
141781-97-7

(-)-(2R,3S,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-3,4-O-isopropylidene-5-(nitromethyl)-3,4,5-piperidinetriol

Conditions
ConditionsYield
With sodium hydride In 1,2-dimethoxyethane for 2h; Ambient temperature;100%
nitromethane
75-52-5

nitromethane

benzalacetophenone
94-41-7

benzalacetophenone

A

(R)-1,3-diphenyl-4-nitrobutane-1-one
6277-67-4, 68047-61-0, 122348-60-1, 77670-36-1

(R)-1,3-diphenyl-4-nitrobutane-1-one

B

(S)-4-nitro-1,3-diphenylbutan-1-one
6277-67-4, 77670-36-1, 122348-60-1, 68047-61-0

(S)-4-nitro-1,3-diphenylbutan-1-one

Conditions
ConditionsYield
With (+)-quinidine-acrylonitrile copolymer In toluene under 661957 Torr; for 5h;A n/a
B 100%
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea In toluene at 20℃; for 192h; Kinetics; Reagent/catalyst; Michael addition; enantioselective reaction;
Stage #1: nitromethane With (1R,1'R,2S,2'S)-1,1'-(propane-1,3-diyl)bis(2-((2,6-diisopropylphenyl)carbamoyl)pyrrolidine-1-oxide); ytterbium(III) triflate In tetrahydrofuran at 30℃; for 0.5h; Asymmetric Michael addition; Inert atmosphere;
Stage #2: benzalacetophenone With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 30℃; for 48h; Asymmetric Michael addition; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
nitromethane
75-52-5

nitromethane

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

methyl-2 β-nitrostyrene
28638-59-7, 34222-71-4

methyl-2 β-nitrostyrene

Conditions
ConditionsYield
ammonium acetate at 90℃; for 2h;100%
With sodium hydroxide
nitromethane
75-52-5

nitromethane

phenylmethanethiol
100-53-8

phenylmethanethiol

acetone
67-64-1

acetone

benzyl(2-methyl-1-nitropropan-2-yl)sulfane
105780-12-9

benzyl(2-methyl-1-nitropropan-2-yl)sulfane

Conditions
ConditionsYield
With piperidine In benzene100%
With piperidine In tetrahydrofuran for 12h; Heating;96%
With piperidine for 15h; Heating;49%
In benzene at 100℃; for 22h; Dean-Stark;23%
With piperidine In benzene for 10h; Reflux; Inert atmosphere;
nitromethane
75-52-5

nitromethane

1-Phenylbut-1-en-3-one
122-57-6

1-Phenylbut-1-en-3-one

Conditions
ConditionsYield
With hydrotalcite for 0.1h; Michael addition; Microwave irradiation;100%
With potassium fluoride; 18-crown-6 ether In acetonitrile for 168h; Heating;93%
With C10H20NaO5*HO(1-); water In methanol at 25℃; for 0.833333h; Michael addition;90%
nitromethane
75-52-5

nitromethane

1-O-methyl-2,3-O-isopropylidene-α-D-mannopentoaldo-1,4-furanose
33985-40-9, 58056-24-9, 63029-10-7, 105368-48-7, 141610-28-8, 141724-46-1

1-O-methyl-2,3-O-isopropylidene-α-D-mannopentoaldo-1,4-furanose

6-Deoxy-2,3-O-isopropylidene-6-nitro-α-D-lyxo-hexofuranoside
85339-08-8, 85339-09-9, 118205-71-3, 118205-72-4, 124648-90-4, 129443-53-4

6-Deoxy-2,3-O-isopropylidene-6-nitro-α-D-lyxo-hexofuranoside

Conditions
ConditionsYield
With sodium methylate In methanol at 0℃; for 2h;100%
With sodium methylate In methanol at 0℃; for 2h;
nitromethane
75-52-5

nitromethane

benzyloxyacetoaldehyde
60656-87-3

benzyloxyacetoaldehyde

(+/-)-3-benzyloxy-1-nitropropan-2-ol
169139-89-3

(+/-)-3-benzyloxy-1-nitropropan-2-ol

Conditions
ConditionsYield
With potassium fluoride In isopropyl alcohol at 20℃; for 15h; Addition; Henry reaction;100%
With aluminum oxide at 21℃; for 24h;98%
With potassium hydroxide In methanol at 20℃; for 1.5h;88%
nitromethane
75-52-5

nitromethane

Toluene-4-sulfonic acid 5-bromo-3-formyl-1H-indol-7-yl ester
201684-34-6

Toluene-4-sulfonic acid 5-bromo-3-formyl-1H-indol-7-yl ester

(E)-5-bromo-3-nitrovinyl-7-(p-toluenesulfonyloxy)indole
126260-59-1

(E)-5-bromo-3-nitrovinyl-7-(p-toluenesulfonyloxy)indole

Conditions
ConditionsYield
With ammonium acetate for 3h; Heating;100%
nitromethane
75-52-5

nitromethane

Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

3-nitro-2-phenylpropane-1,1-dicarbonitrile

3-nitro-2-phenylpropane-1,1-dicarbonitrile

Conditions
ConditionsYield
aluminum oxide at 90℃; for 0.15h;100%
With piperazine-grafted reduced graphene oxide (rGO-NH) In ethanol at 60℃; for 8h; Reagent/catalyst; Michael Addition;72%
With aluminum oxide at 20 - 90℃; for 0.2h; microwave irradiation;63%
at 60℃; for 4h; Michael Addition;
With quinidine In toluene at 20℃;
nitromethane
75-52-5

nitromethane

methyl 2-(2-fluorobenzylidene)-2-cyanoacetate

methyl 2-(2-fluorobenzylidene)-2-cyanoacetate

methyl 2-cyano-4-nitro-3-(2-fluorophenyl)butanoate

methyl 2-cyano-4-nitro-3-(2-fluorophenyl)butanoate

Conditions
ConditionsYield
aluminum oxide at 90℃; for 0.15h;100%
With aluminum oxide at 20 - 90℃; for 0.2h; microwave irradiation;70%
nitromethane
75-52-5

nitromethane

2-(2-Benzyloxy-3-methoxyphenyl)acetaldehyde
211935-30-7

2-(2-Benzyloxy-3-methoxyphenyl)acetaldehyde

1-(2-Benzyloxy-3-methoxyphenyl)-3-nitropropan-2-ol
211935-31-8

1-(2-Benzyloxy-3-methoxyphenyl)-3-nitropropan-2-ol

Conditions
ConditionsYield
With cetyltrimethylammonim bromide In sodium hydroxide100%
With sodium hydroxide; cetyltrimethylammonim bromide Condensation; Henry condensation;100%
nitromethane
75-52-5

nitromethane

(1-Formyl-7-methoxy-naphthalen-2-yloxy)-acetic acid ethyl ester
209175-47-3

(1-Formyl-7-methoxy-naphthalen-2-yloxy)-acetic acid ethyl ester

[7-Methoxy-1-((E)-2-nitro-vinyl)-naphthalen-2-yloxy]-acetic acid ethyl ester
209175-48-4

[7-Methoxy-1-((E)-2-nitro-vinyl)-naphthalen-2-yloxy]-acetic acid ethyl ester

Conditions
ConditionsYield
With ammonium acetate for 3h; Heating;100%

75-52-5Downstream Products