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Nitromethane is a versatile organic compound widely used as a solvent and reactant in various chemical reactions, including C-C bond-forming processes like Michael additions, cross-dehydrogenative couplings, and asymmetric conjugate additions. It serves as a carbon nucleophile in reactions catalyzed by iodine, amines, or metal complexes, enabling the synthesis of diverse products such as aza-Henry adducts, 1,3-dinitroalkanes, and enantioselective Michael adducts. Its reactivity is leveraged in cooperative catalysis, photooxidative transformations, and organocatalysis, often under mild conditions with high selectivity. Nitromethane's utility extends to diversity-oriented synthesis, where it contributes to the construction of complex alkaloid scaffolds and other bioactive molecules.

75-52-5 Suppliers

This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn't provide relevant sales information.
  • 75-52-5 Structure
  • Basic information

    1. Product Name: Nitromethane
    2. Synonyms: methane,-nitro-;Methane,nitro-;Nitrofuel;Nitrometan;nitrometan(polish);nitro-methan;NM-55;NITROMETHAN 96%
    3. CAS NO:75-52-5
    4. Molecular Formula: CH3NO2
    5. Molecular Weight: 61.04
    6. EINECS: 200-876-6
    7. Product Categories: Organics;Analytical Chemistry;Solvents for HPLC & Spectrophotometry;Solvents for Spectrophotometry;Analytical Reagents for General Use;I-N, Puriss p.a.;Puriss p.a.;Reagent Grade Solvents;ReagentSemi-Bulk Solvents;ReagentSolvents;Spectrophotometric Grade Solvents;Spectrophotometric GradeSolvents;ReagentPlus(R) Solvent Grade Products;ReagentPlus(R)Solvents;CHROMASOLV for HPLCSolvents;CHROMASOLV Solvents (HPLC, LC-MS);CHROMASOLV(R) HPLC Grade Solvents;Alpha Sort;N-O;Volatiles/ Semivolatiles;ACS Grade Solvents;ACS GradeSemi-Bulk Solvents;ACS GradeSolvents;Amber Glass Bottles;Carbon Steel Cans with NPT Threads;Solvent Bottles;ACS and Reagent Grade Solvents;Amber Glass Bottles;ReagentPlus;ReagentPlus Solvent Grade Products;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;ACS Grade;ACS Grade Solvents;Carbon Steel Cans with NPT Threads;Semi-Bulk Solvents;Anhydrous Solvents;Reagent;Analytical Reagents;Analytical/Chromatography;CHROMASOLV for HPLC;Chromato
    8. Mol File: 75-52-5.mol
  • Chemical Properties

    1. Melting Point: -29 °C
    2. Boiling Point: 101.2 °C(lit.)
    3. Flash Point: 95 °F
    4. Appearance: APHA: ≤10/Liquid
    5. Density: 1.127 g/mL at 25 °C(lit.)
    6. Vapor Density: 2.1 (vs air)
    7. Vapor Pressure: 27.3 mm Hg ( 20 °C)
    8. Refractive Index: n20/D 1.382(lit.)
    9. Storage Temp.: Flammables area
    10. Solubility: 105g/l
    11. PKA: 10.2(at 25℃)
    12. Explosive Limit: 7.3-63.0%(V)
    13. Water Solubility: 9.5 g/100 mL (20 ºC)
    14. Merck: 14,6611
    15. BRN: 1698205
    16. CAS DataBase Reference: Nitromethane(CAS DataBase Reference)
    17. NIST Chemistry Reference: Nitromethane(75-52-5)
    18. EPA Substance Registry System: Nitromethane(75-52-5)
  • Safety Data

    1. Hazard Codes: Xn,F,Xi
    2. Statements: 5-10-22
    3. Safety Statements: 41
    4. RIDADR: UN 1261 3/PG 2
    5. WGK Germany: 2
    6. RTECS: PA9800000
    7. F: 3-10
    8. TSCA: Yes
    9. HazardClass: 3
    10. PackingGroup: II
    11. Hazardous Substances Data: 75-52-5(Hazardous Substances Data)

75-52-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 75-52-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 75-52:
(4*7)+(3*5)+(2*5)+(1*2)=55
55 % 10 = 5
So 75-52-5 is a valid CAS Registry Number.
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%

75-52-5Relevant articles and documents

AN ESR STUDY OF THE PHOTOREACTION OF NITROALKANES WITH TETRAPHENYLBIPHOSPHINE AND TETRAETHYLPYROPHOSPHITE

Alberti, Angelo,Hudson, Andrew,Pedulli, Gian Franco

, p. 4955 - 4958 (1984)

Some paramagnetic species formed in the photoreactions of nitroalkanes with P-compounds have been characterized by ESR.The observed radicals are mostly nitroxides whose structures are consistent with the trapping of P-centred radicals by intermediate nitroso compounds.

Kinetics of the CH3O2 + NO Reaction: Temperature Dependence of the Overall Rate Constant and an Improved Upper Limit for the CH3ONO2 Branching Channel

Scholtens, Kurtis W.,Messer, Banjamin M.,Cappa, Christopher D.,Elrod, Matthew J.

, p. 4378 - 4384 (1999)

The overall rate constant and an upper limit for the CH3ONO2 product channel for the CH3O2 + NO reaction have been measured using the turbulent flow technique with high-pressure chemical ionization mass spectrometry for the detection of reactants and products. At room temperature and 100 Torr pressure, the rate constant (and the two standard deviation error limit) was determined to be (7.8 +/- 2.2)E-12 cm3 molecule-1 s-1. The temperature dependence of the rate constant was investigated between 295 and 203 K at pressures of either 100 or 200 Torr, and the data was fit to the following Arrhenius expression: (9.2+6.0-3.9E-13) exp cm3 molecule-1 s-1. Although the room-temperature rate constant value agrees well with the current recommendation for atmospheric modeling, our values for the rate constant at the lowest temperatures accessed in this study (203 K) are about 50 percent higher than the same recommendation. No CH3-ONO2 product was detected from the CH3O2 + NO reaction (using direct CH3ONO2 detection methods for the first time), but an improved upper limit of 0.03 (at 295 K and 100 torr) for this branching channel was determined.

Deprotonation of organic compounds bearing acid protons promoted by metal amido complexes with chiral diamine ligands leading to new organometallic compounds

Murata, Kunihiko,Konishi, Hirokazu,Ito, Masato,Ikariya, Takao

, p. 253 - 255 (2002)

Well-defined 16-electron metal amido complexes bearing chiral Ts-diamine ligands readily react with nitromethane, acetone, or phenylacetylene to give new organometallic compounds in almost quantitative yields. For example, an Ir amido complex, Cp*Ir[(R,R)Tscydn], reacts with nitromethane at room temperature to give quantitatively a nitromethyl Ir complex, Cp*Ir(CH2NO2)[(R,R)-Tscydn], as a single diastereomer. The isolable organometallic compounds with chiral amine ligands are relevant to active catalysts for asymmetric C-C bond formation.

Synthesis of nitromethane from acetic acid by radiation-induced nitration in aqueous solution

Ershov, Boris G.,Gordeev, Andrei V.,Bykov, Gennady L.,Zubkov, Andrei A.,Kosareva, Inessa M.

, p. 289 - 290 (2007)

The γ-irradiation of solutions containing acetic acid, nitric acid and/or their salts produces nitromethane.

Phase Effects on Conformational Equilibria. Nuclear Magnetic Resonance Studies of Methyl Nitrite

Chauvel, J. Paul,True, Nancy S.

, p. 1622 - 1625 (1983)

Gas-phase 1H NMR spectra of methyl nitrite are consistent with the following thermodynamic parameters for the syn anti conformational equilibrium: ΔHanti-syn, 998 (50) cal mol-1; ΔGanti-syn, 520 (5) cal mol-1 (at 205 K); and ΔSanti-syn 2.3(3) eu.These results agree well with values obtained from a statistical mechanical calculation.The large entropy difference between the conformers is due to a very low methyl top internal rotation barrier for the anti conformer.Neat liquid methyl nitrite and 1 percent solutions of methyl nitrite is carbon disulfide, acetone-d6, and n-pentane all produce temperature-dependent NMR spectra which are consistent with the following ranges of thermodynamic parameters: ΔHanti-syn, 803-866 cal mol-1; ΔGanti-syn, 440-460 cal mol-1 (at 205 K); ΔSanti-syn, 1.8-2.0 eu, demonstrating that in liquids the anti/syn partition function ratio is smaller and the equilibrium constant between the conformers is closer to 1.

Using Postsynthetic X-Type Ligand Exchange to Enhance CO2Adsorption in Metal-Organic Frameworks with Kuratowski-Type Building Units

Bien, Caitlin E.,Cai, Zhongzheng,Wade, Casey R.

, p. 11784 - 11794 (2021/07/26)

Postsynthetic modification methods have emerged as indispensable tools for tuning the properties and reactivity of metal-organic frameworks (MOFs). In particular, postsynthetic X-type ligand exchange (PXLE) at metal building units has gained increasing attention as a means of immobilizing guest species, modulating the reactivity of framework metal ions, and introducing new functional groups. The reaction of a Zn-OH functionalized analogue of CFA-1 (1-OH, Zn(ZnOH)4(bibta)3, where bibta2- = 5,5′-bibenzotriazolate) with organic substrates containing mildly acidic E-H groups (E = C, O, N) results in the formation of Zn-E species and water as a byproduct. This Br?nsted acid-base PXLE reaction is compatible with substrates with pKa(DMSO) values as high as 30 and offers a rapid and convenient means of introducing new functional groups at Kuratwoski-type metal nodes. Gas adsorption and diffuse reflectance infrared Fourier transform spectroscopy experiments reveal that the anilide-exchanged MOFs 1-NHPh0.9 and 1-NHPh2.5 exhibit enhanced low-pressure CO2 adsorption compared to 1-OH as a result of a Zn-NHPh + CO2 ? Zn-O2CNHPh chemisorption mechanism. The MFU-4l analogue 2-NHPh ([Zn5(OH)2.1(NHPh)1.9(btdd)3], where btdd2- = bis(1,2,3-triazolo)dibenzodioxin), shows a similar improvement in CO2 adsorption in comparison to the parent MOF containing only Zn-OH groups.

Transesterification of Methyl 2-Nitroacetate to Superior Esters

Corsi, Massimo,Machetti, Fabrizio,Magnolfi, Stefano

, (2020/03/19)

Methyl 2-nitroacetate and methyl acetoacetate have in common the presence of an electron-withdrawing substituent geminal to the methyl ester function but the well-known ease of thermal transesterification of methyl acetoacetate has not been found in methyl 2-nitroacetate. The latter gives uncatalysed thermal transesterification only in low yield and at a temperature higher than that of methyl acetoacetate. Comparative experiments provided further insight into the reactions; protic and Lewis acid catalysts promoted the smooth exchange of the alkanoyl groups, observing first the transesterification of methyl 2-nitroacetate with ethanol, already proved difficult to proceed. Dibutyltin(IV)oxide (DBTO) catalyst offered the spur to set up a convenient synthetic methodology from methyl 2-nitroacetate, encompassing higher molecular weight and functionalised alcohols: aliphatic, unsaturated and oxidation sensitive species were suited to react, delivering the corresponding 2-nitroacetate esters in good yields in most cases.

Accessing the Nitromethane (CH3NO2) Potential Energy Surface in Methanol (CH3OH)-Nitrogen Monoxide (NO) Ices Exposed to Ionizing Radiation: An FTIR and PI-ReTOF-MS Investigation

Góbi, Sándor,Crandall, Parker B.,Maksyutenko, Pavlo,F?rstel, Marko,Kaiser, Ralf I.

, p. 2329 - 2343 (2018/03/21)

(D3-)Methanol-nitrogen monoxide (CH3OH/CD3OH-NO) ices were exposed to ionizing radiation to facilitate the eventual determination of the CH3NO2 potential energy surface (PES) in the condensed phase. R

Preparation method of nitromethane and application of poly(4-vinylpyridine)

-

Paragraph 0039-0063, (2019/01/14)

The invention relates to a preparation method of nitromethane, and relates to the field of organic synthesis. The preparation method comprises the following step of mixing dimethyl sulfate, nitrite, alkali and poly(4-vinylpyridine) to react. The preparation method has the advantages that by adding the poly(4-vinylpyridine), the amount of harmful gas in the production process is reduced, and the yield rate and purity of the product are greatly improved; the poly(4-vinylpyridine) is easy to separate, and the poly(4-vinylpyridine) is suitable for the recycling of byproduct (sulfate); the conditions are mild, the operation is simple, and the production method is suitable for industrialized large-scale production. The application of the poly(4-vinylpyridine) is characterized in that the poly(4-vinylpyridine) is applied into the synthesis reaction of the nitromethane, the yield rate and purity of the nitromethane are improved, and the influence to the recycling of the byproduct is avoided.

A reactor for continuous production of nitromethane

-

Paragraph 0029-0038, (2018/07/30)

The utility model provides a for continuous production of nitromethane in the reactor, which comprises a series of n reaction zone, wherein the reaction region comprises a: housing, is arranged in the casing of the mixing chamber and the mixing chamber is connected to the reaction tube, the shell is provided with a mixing chamber connected to the dimethyl sulfate sodium nitrite inlet and inlet, with said reaction tube connected to the outlet of the reaction product, and heat transfer medium inlet and outlet; the reaction zone b to reaction zone n the reaction areas of the respective includes: shell, is arranged in the casing of the mixing chamber and the mixing chamber is connected to the reaction tube, the shell is provided with a connected on the mixing chamber of the reaction product of a reaction zone inlet and dimethyl sulfate inlet, with said reaction tube connected to the outlet of the reaction product, and heat transfer medium inlet and outlet; in addition to the last reaction zone other than the reaction zone of the reaction product outlet and the next reaction zone of the product inlet connected by pipelines.