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126-11-4

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126-11-4 Usage

Chemical Properties

Off-white to orange solid. It crystallizes as white crystals in the mixed solution of ethyl acetate and benzene. Soluble in alcohol, slightly soluble in benzene and other hydrocarbons. Solubility in water (20°C) 220g/100ml.

Uses

Tris(hydroxymethyl)nitromethane, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is used as a primary and secondary intermediate.

Preparation

Tris(hydroxymethyl)nitromethane is prepared by the condensation of nitromethane and formaldehyde under basic conditions.

Application

Tris(hydroxymethyl)nitromethane is a bactericide and slimicide for use in cooling fluids, paper and pulp industry; as a curing agent for certain adhesives; viscositycontrolling agent in cosmetics.To inhibit bacterial growth in circulating industrial water systems, cutting oils, nonprotein glues and sizings.

General Description

Tris(hydroxymethyl)nitromethane undergoes crosslinking with hexamethylene diisocyanate to form monolithic energetic gels. It is an effective hardener for variety of tannin-based adhesives.

Purification Methods

Crystallise it from CHCl3/ethyl acetate or ethyl acetate/*benzene. It is an acid and a 0.1M solution in H2O has pH 4.5. IRRITANT. [Beilstein 1 H 520.]

Check Digit Verification of cas no

The CAS Registry Mumber 126-11-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 6 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 126-11:
(5*1)+(4*2)+(3*6)+(2*1)+(1*1)=34
34 % 10 = 4
So 126-11-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H9NO5/c6-1-4(2-7,3-8)5(9)10/h6-8H,1-3H2

126-11-4 Well-known Company Product Price

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  • Alfa Aesar

  • (L13349)  Tris(hydroxymethyl)nitromethane, 95%   

  • 126-11-4

  • 100g

  • 302.0CNY

  • Detail
  • Alfa Aesar

  • (L13349)  Tris(hydroxymethyl)nitromethane, 95%   

  • 126-11-4

  • 500g

  • 1145.0CNY

  • Detail
  • Aldrich

  • (108189)  Tris(hydroxymethyl)nitromethane  98%

  • 126-11-4

  • 108189-100G

  • 410.67CNY

  • Detail
  • Aldrich

  • (108189)  Tris(hydroxymethyl)nitromethane  98%

  • 126-11-4

  • 108189-500G

  • 1,904.76CNY

  • Detail

126-11-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Tris(hydroxymethyl)nitromethane

1.2 Other means of identification

Product number -
Other names Trimethylolnitromethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. 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:126-11-4 SDS

126-11-4Synthetic route

formaldehyd
50-00-0

formaldehyd

nitromethane
75-52-5

nitromethane

A

2-nitropropane-1,3-diol
1794-90-7

2-nitropropane-1,3-diol

B

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With potassium fluoride; tetrabutylammomium bromide In isopropyl alcohol at 18 - 22℃; for 72h;A 8%
B 83%
tetrachloromethane
56-23-5

tetrachloromethane

formaldehyd
50-00-0

formaldehyd

2,4,4-trimethyl-1-nitro-pentan-2-ol
35223-67-7

2,4,4-trimethyl-1-nitro-pentan-2-ol

ethanol
64-17-5

ethanol

A

4,4-dimethyl-pentan-2-one
590-50-1

4,4-dimethyl-pentan-2-one

B

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

nitromethane
75-52-5

nitromethane

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

nitromethane
75-52-5

nitromethane

A

2-nitro-1-ethanol
625-48-9

2-nitro-1-ethanol

B

2-nitropropane-1,3-diol
1794-90-7

2-nitropropane-1,3-diol

C

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

dl-2-hydroxy-3-nitropropanoic acid
74612-09-2

dl-2-hydroxy-3-nitropropanoic acid

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With potassium carbonate at 25℃;
With sodium hydroxide; ethyl acetate
formaldehyd
50-00-0

formaldehyd

2-hydroxy-1-nitropropane
3156-73-8

2-hydroxy-1-nitropropane

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With potassium carbonate at 25℃;
With sodium hydroxide; ethyl acetate
formaldehyd
50-00-0

formaldehyd

2-nitropropane-1,3-diol
1794-90-7

2-nitropropane-1,3-diol

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With alkali
formaldehyd
50-00-0

formaldehyd

1-ethoxy-3-nitro-propan-2-ol

1-ethoxy-3-nitro-propan-2-ol

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With potassium carbonate at 25℃;
With sodium hydroxide; ethyl acetate
formaldehyd
50-00-0

formaldehyd

1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

1-nitromethylcyclohexanol
3164-73-6

1-nitromethylcyclohexanol

A

cyclohexanone
108-94-1

cyclohexanone

B

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

1-nitromethylcyclohexanol
3164-73-6

1-nitromethylcyclohexanol

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With sodium hydroxide; water
2-bromo-2-nitro-1,3-propanediol
52-51-7

2-bromo-2-nitro-1,3-propanediol

A

2,2-dinitroethanol
29609-98-1

2,2-dinitroethanol

B

methanol
67-56-1

methanol

C

formic acid
64-18-6

formic acid

D

glycolic Acid
79-14-1

glycolic Acid

E

2-bromo-2-nitro-1-ethanol
5437-60-5

2-bromo-2-nitro-1-ethanol

F

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With borax buffer In tert-butyl alcohol Rate constant; pH 8.98;
formaldehyd
50-00-0

formaldehyd

nitroethanol

nitroethanol

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With potassium carbonate
formaldehyd
50-00-0

formaldehyd

2-nitropropane-1,3-diol
1794-90-7

2-nitropropane-1,3-diol

alkali

alkali

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

nitromethane
75-52-5

nitromethane

calcium carbonate

calcium carbonate

A

2-nitro-1-ethanol
625-48-9

2-nitro-1-ethanol

B

2-nitropropane-1,3-diol
1794-90-7

2-nitropropane-1,3-diol

C

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

2-hydroxy-1-nitropropane
3156-73-8

2-hydroxy-1-nitropropane

K2CO3

K2CO3

A

acetaldehyde
75-07-0

acetaldehyde

B

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

3-nitromethyl-pentan-3-ol
156544-56-8

3-nitromethyl-pentan-3-ol

aq.-ethanolic KOH-solution

aq.-ethanolic KOH-solution

A

pentan-3-one
96-22-0

pentan-3-one

B

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

formaldehyd
50-00-0

formaldehyd

dl-2-hydroxy-3-nitropropanoic acid
74612-09-2

dl-2-hydroxy-3-nitropropanoic acid

dil.K2CO3

dil.K2CO3

A

Glyoxilic acid
298-12-4

Glyoxilic acid

B

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-bromo-2-nitro-1,3-propanediol
52-51-7

2-bromo-2-nitro-1,3-propanediol

A

methanol
67-56-1

methanol

B

formaldehyd
50-00-0

formaldehyd

C

formic acid
64-18-6

formic acid

D

glycolic Acid
79-14-1

glycolic Acid

E

2-bromo-2-nitro-1-ethanol
5437-60-5

2-bromo-2-nitro-1-ethanol

F

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

G

NO2-, Br-

NO2-, Br-

Conditions
ConditionsYield
With potassium hydroxide Mechanism;
2-nitro-2-phosphonooxymethyl-propane-1,3-diol; barium salt

2-nitro-2-phosphonooxymethyl-propane-1,3-diol; barium salt

alkaline solution

alkaline solution

A

phosphoric acid
86119-84-8, 7664-38-2

phosphoric acid

B

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

nitromethane
75-52-5

nitromethane

formaldehyde(methanol 44%, water 10%)
71481-64-6

formaldehyde(methanol 44%, water 10%)

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

Conditions
ConditionsYield
With triethylamine at 45 - 50℃; for 1h;
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane
4728-14-7

2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;99%
With hydrogenchloride In acetonitrile82%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

tris(tert-butyldimethylsilyloxymethyl)nitromethane
194284-20-3

tris(tert-butyldimethylsilyloxymethyl)nitromethane

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Ambient temperature;97%
benzoyl chloride
98-88-4

benzoyl chloride

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-Benzoyloxymethyl-2-nitro-1,3-propanediol dibenzoate
65102-57-0

2-Benzoyloxymethyl-2-nitro-1,3-propanediol dibenzoate

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at 60℃; for 10h; Temperature;94%
In pyridine at 70℃; for 15h;90%
With pyridine In benzene
2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

1',2',3',4'-tetrahydro-5-hydroxymethyl-6'-methoxy-5-nitrospiro[1,3-dioxane-2,1'-naphthaline]
1580372-25-3

1',2',3',4'-tetrahydro-5-hydroxymethyl-6'-methoxy-5-nitrospiro[1,3-dioxane-2,1'-naphthaline]

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide; orthoformic acid triethyl ester In neat (no solvent) at 20℃; for 48h;89%
cyclohexanone
108-94-1

cyclohexanone

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

3-hydroxymethyl-3-nitro-1,5-dioxaspiro<5.5>undecane
51430-72-9

3-hydroxymethyl-3-nitro-1,5-dioxaspiro<5.5>undecane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran at 20℃;88%
With toluene-4-sulfonic acid In chloroform Heating;63.6%
With toluene-4-sulfonic acid; benzene
trifluoroborane diethyl ether
109-63-7

trifluoroborane diethyl ether

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane
4728-14-7

2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With nitrogen In acetone88%
With nitrogen In acetone
1,3,5-triethyl-1,3,5-triazacyclohexane
7779-27-3

1,3,5-triethyl-1,3,5-triazacyclohexane

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

3-ethyl-5-hydroxymethyl-5-nitrotetrahydro-1,3-oxazine
96286-41-8

3-ethyl-5-hydroxymethyl-5-nitrotetrahydro-1,3-oxazine

Conditions
ConditionsYield
87%
Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-ethoxy-2-methyl-5-nitro-5-(hydroxymethyl)-1,3-dioxane
95798-40-6

2-ethoxy-2-methyl-5-nitro-5-(hydroxymethyl)-1,3-dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 25℃; for 22h;87%
benzaldehyde
100-52-7

benzaldehyde

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-phenyl-5-(hydroxymethyl)-5-nitro-1,3-dioxane
51430-71-8

2-phenyl-5-(hydroxymethyl)-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran at 20℃;86%
With sulfuric acid
With hydrogenchloride; 2-methoxy-ethanol
With BF3•Et2O or p-toluenesulfonic acid
ethyl-vinyl ether

ethyl-vinyl ether

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

(2-methyl-5-nitro-1,3-dioxan-5-yl)methanol
60766-67-8

(2-methyl-5-nitro-1,3-dioxan-5-yl)methanol

Conditions
ConditionsYield
With hydrogenchloride; nitrogen In acetonitrile86%
acetic anhydride
108-24-7

acetic anhydride

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

1,3-Diacetoxy-2-(acetoxymethyl)-2-nitropropane
7344-23-2

1,3-Diacetoxy-2-(acetoxymethyl)-2-nitropropane

Conditions
ConditionsYield
With sulfuric acid Cooling with ice;85%
With dmap; triethylamine In dichloromethane Ambient temperature;76%
With pyridine
formaldehyd
50-00-0

formaldehyd

tert-butylamine
75-64-9

tert-butylamine

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

N-((3-(tert-butyl)-5-nitro-1,3-oxazinan-5-yl)methyl)-2-methylpropan-2-amine

N-((3-(tert-butyl)-5-nitro-1,3-oxazinan-5-yl)methyl)-2-methylpropan-2-amine

Conditions
ConditionsYield
Stage #1: tert-butylamine; 2-hydroxymethyl-2-nitro-propane-1,3-diol In methanol at 0℃; for 0.5h;
Stage #2: formaldehyd In methanol at 0 - 25℃; for 48h;
83%
tert-butoxycarbonylglycine p-nitrophenylester
3655-05-8

tert-butoxycarbonylglycine p-nitrophenylester

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

3'-hydroxy-2'-hydroxymethyl-2'-nitropropyl 2-N-(tert-butoxycarbonylamino)acetate
1228443-32-0

3'-hydroxy-2'-hydroxymethyl-2'-nitropropyl 2-N-(tert-butoxycarbonylamino)acetate

Conditions
ConditionsYield
With Theremomyces lanuginosus lipase immobilized on silica In 1,4-dioxane at 50℃; for 72h; Molecular sieve; Enzymatic reaction; regioselective reaction;80%
cyclopentanone
120-92-3

cyclopentanone

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

(8-nitro-6,10-dioxaspiro[4.5]dec-8-yl)methanol
1256364-04-1

(8-nitro-6,10-dioxaspiro[4.5]dec-8-yl)methanol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran at 20℃;80%
With BF3•Et2O or p-toluenesulfonic acid
formaldehyd
50-00-0

formaldehyd

tert-butylamine
75-64-9

tert-butylamine

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

3-tert-butyl-5-hydroxymethyl-5-nitrotetrahydro-1,3-oxazine
32051-21-1

3-tert-butyl-5-hydroxymethyl-5-nitrotetrahydro-1,3-oxazine

Conditions
ConditionsYield
In methanol at 0℃;78%
(i) NaHCO3, (ii) /BRN= 605267/; Multistep reaction;
Mannich Aminomethylation;
acetone
67-64-1

acetone

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane
4728-14-7

2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;77%
With boron trifluoride diethyl etherate In tetrahydrofuran at 20℃;73%
With boron trifluoride diethyl etherate at 55℃; for 0.0833333h;72%
3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

1',2',3',4'-tetrahydro-5-hydroxymethyl-5-nitrospiro[1,3-dioxane-2,1'-naphthaline]
1580372-21-9

1',2',3',4'-tetrahydro-5-hydroxymethyl-5-nitrospiro[1,3-dioxane-2,1'-naphthaline]

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide; orthoformic acid triethyl ester In neat (no solvent) at 20℃; for 48h;77%
acetophenone
98-86-2

acetophenone

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

(2-methyl-5-nitro-2-phenyl-[1,3]dioxan-5-yl)-methanol
173376-22-2

(2-methyl-5-nitro-2-phenyl-[1,3]dioxan-5-yl)-methanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 87h; Heating;76%
With toluene-4-sulfonic acid; benzene
benzaldehyde
100-52-7

benzaldehyde

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

C11H15NO4
65102-45-6

C11H15NO4

Conditions
ConditionsYield
With acetic acid; zinc In ethanol at 0 - 60℃; for 10h; Inert atmosphere; Darkness; Molecular sieve;72%
(i) NH4Cl, Zn, (ii) /BRN= 471223/; Multistep reaction;
tetrabutylammonium octamolybdate

tetrabutylammonium octamolybdate

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

acetonitrile
75-05-8

acetonitrile

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

(tetrabutylammonium)3{CoMo6O18[O2NC(CH2O)3]2}*2(CH3CN)

(tetrabutylammonium)3{CoMo6O18[O2NC(CH2O)3]2}*2(CH3CN)

Conditions
ConditionsYield
for 12h; Reflux;71.6%
formaldehyd
50-00-0

formaldehyd

cyclohexylamine
108-91-8

cyclohexylamine

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

1,3-dicyclohexyl 5-hydroxymethyl 5-nitrohexahydropyrimidine
139177-61-0

1,3-dicyclohexyl 5-hydroxymethyl 5-nitrohexahydropyrimidine

Conditions
ConditionsYield
In water for 8h; Heating;71%
1,1-Dichloroacetone
513-88-2

1,1-Dichloroacetone

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-(dichloromethyl)-2-methyl-5,5-dinitro-1,3-dioxane
1438289-49-6

2-(dichloromethyl)-2-methyl-5,5-dinitro-1,3-dioxane

Conditions
ConditionsYield
Stage #1: 1,1-Dichloroacetone; 2-hydroxymethyl-2-nitro-propane-1,3-diol With trifluoroborane diethyl ether In acetonitrile at 20 - 35℃; for 12h;
Stage #2: With potassium hexacyanoferrate(III); sodium nitrite In water for 4h;
70%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-Methylsulfonyloxymethyl-2-nitro-1,3-propanediol dimethanesulfonate
113967-51-4

2-Methylsulfonyloxymethyl-2-nitro-1,3-propanediol dimethanesulfonate

Conditions
ConditionsYield
In pyridine at 0℃; for 14h;68%
With pyridine
N-methyl-2-(benzylamino)ethylamine
56904-09-7

N-methyl-2-(benzylamino)ethylamine

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

1-benzyl-6-hydroxymethyl-4-methyl-6-nitrohexahydro-1H-1,4-diazepine
129295-40-5

1-benzyl-6-hydroxymethyl-4-methyl-6-nitrohexahydro-1H-1,4-diazepine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 50℃; for 2h;68%
With sodium hydrogencarbonate In water
chloroacetone
78-95-5

chloroacetone

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-chloromethyl-2-methyl-5,5-dinitro-1,3-dioxane
1438289-48-5

2-chloromethyl-2-methyl-5,5-dinitro-1,3-dioxane

Conditions
ConditionsYield
Stage #1: chloroacetone; 2-hydroxymethyl-2-nitro-propane-1,3-diol With trifluoroborane diethyl ether In acetonitrile at 20 - 35℃; for 1.5h;
Stage #2: With potassium hexacyanoferrate(III); sodium nitrite In water for 2h;
66%
Dimethoxymethane
109-87-5

Dimethoxymethane

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

(5-nitro-1,3-dioxan-5-yl)methanol
115430-84-7

(5-nitro-1,3-dioxan-5-yl)methanol

Conditions
ConditionsYield
Acidic conditions;63%
With toluene-4-sulfonic acid; lithium bromide 1.) 21 deg C, 40 min, 2.) 60 deg C, 10 min;51%
benzaldehyde
100-52-7

benzaldehyde

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

2-(hydroxymethyl)-2-[(phenylmethylene)amino]propane-1,3-diol N-oxide

2-(hydroxymethyl)-2-[(phenylmethylene)amino]propane-1,3-diol N-oxide

Conditions
ConditionsYield
With acetic acid; zinc In ethanol for 92h;62%
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

nitroisobutylglycerol tricarbamate

nitroisobutylglycerol tricarbamate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1.5h;62%
benzyl bromide
100-39-0

benzyl bromide

2-hydroxymethyl-2-nitro-propane-1,3-diol
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

C18H21NO5

C18H21NO5

Conditions
ConditionsYield
Stage #1: 2-hydroxymethyl-2-nitro-propane-1,3-diol With sodium hydride In N,N-dimethyl-formamide; mineral oil at -5 - 10℃; for 1h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃;
61.3%
Stage #1: 2-hydroxymethyl-2-nitro-propane-1,3-diol With sodium hydride In N,N-dimethyl-formamide; mineral oil at -5 - 10℃; for 1h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃;
61.3%

126-11-4Relevant articles and documents

Formation and Out-of-Equilibrium, High/Low State Switching of a Nitroaldol Dynamer in Neutral Aqueous Media

Elofsson, Ulla,Karalius, Antanas,Kravchenko, Oleksandr,Ramstr?m, Olof,Szabó, Zoltán,Yan, Mingdi,Zhang, Yang

, p. 3434 - 3438 (2020)

The nitroaldol reaction is demonstrated as an efficient dynamic covalent reaction in phosphate buffers at neutral pH. Rapid equilibration was recorded with pyridine-based aldehydes, and dynamic oligomerization could be achieved, leading to nitroaldol dynamers of up to 17 repeating units. The dynamers were applied in a coherent stimuli-responsive molecular system in which larger dynamers transiently existed out-of-equilibrium in a neutral aqueous system rich in formaldehyde, controlled by nitromethane.

IS 1,3-DIHYDROXYPROPANENITRONIC ACID REALLY STABLE?

Eremenko, L. T.,Oreshko, G. V.,Lagodzinskaya, G. V.,Zabrodin, V. A.

, p. 555 - 557 (1990)

The condensation of nitromethane with paraformaldehyde in the presence of catalytic amounts of KF and tetra-n-butylammonium bromide in a medium of isopropanol does not afford stable 1,3-dihydroxypropanenitronic acid.In the neutralization of 2-nitro-1,3-propanediol sodium salt by anhydrous CF3COOH, 2-nitro-1,3-propanediol and 2-nitro-1-propen-3-ol were identified.

PROCESS FOR THE PREPARATION OF NITROALCOHOLS

-

Paragraph 0018, (2013/09/26)

A process of preparing a nitroalcohol, e.g., 2-nitro-2-methyl-1-propane, from a nitropolyol, e.g., 2-nitro-2 -methyl-1,3-propanediol, the process comprising the step of contacting under hydrogenation conditions the nitropolyol with hydrogen, a hydrogenation catalyst and, optionally, a chelating agent.

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