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Formic acid 85%
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Formic acid
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Formic acid CAS: 64-18-6
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64-18-6 Usage

General Description

Formic acid (HCO2H), also called methanoic acid, is the simplest carboxylic acid. Formic acid was first isolated by the distillation of ant bodies and was named after the Latin formica, meaning “ant.” Its proper IUPAC name is now methanoic acid. Industrially, formic acid is produced by treatment of carbon monoxide with an alcohol such as methanol (methyl alcohol) in the presence of a catalyst.
Formic acid is found both naturally occurring and frequently synthesized in laboratories. It is most naturally found in the stings and bites of many insects, including bees and ants, as a chemical defense mechanism.

Reactivity Profile

Formic acid reacts exothmerically with all bases, both organic (for example, the amines) and inorganic. Reacts with active metals to form gaseous hydrogen and a metal salt. Reacts with cyanide salts to generate gaseous hydrogen cyanide. Reacts with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides to generate flammable or toxic gases. Reacts with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate carbon dioxide but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions or catalyze other chemical reactions. A mixture with furfuryl alcohol exploded [Chem. Eng. News 18:72(1940)].

Properties

FORMIC ACID is a colorless liquid with a pungent odor. It is a stable corrosive, combustible, and hygroscopic chemical substance. It is incompatible with H2SO4, strong caustics, furfuryl alcohol, hydrogen peroxide, strong oxidisers, and bases and reacts with strong explosion on contact with oxidising agents.
Due to the −CHO group, Formic acid imparts some of the character of an aldehyde. It can form salt and ester; can react with amine to form amide and to form ester by addition reaction with unsaturated hydrocarbon addition. It can reduce the silver ammonia solution to produce a silver mirror, and make the potassium permanganate solution fade, which can be used for the qualitative identification of formic acid.
As a carboxylic acid, formic acid shares most of the same chemical properties in reacting with alkalis to form water soluble formate. But formic acid is not a typical carboxylic acid as it can react with alkenes to form formate esters.

Air & Water Reactions

Fumes in air. Soluble in water with release of heat.

General Description

Formic acid,HCOOH, also known as methanoic acid, is a colorless, pungent, toxic,corrosive liquid that is soluble in water, ether,and alcohol.It is the most highly ionized of the common organic acids and therefore the most corrosive, It reacts readily with many oxidizing and reducing compounds and is somewhat unstable as the concentration approaches 100%, decomposing to carbon monoxide and water.
Formic acid is used as a chemical intermediate and solvent, in dyeing and electroplating processes, and in fumigants. In a reaction with glycerol at 220°C (430 OF), it is a source of allyl alcohol Formic acid has also been employed in brewing(to assist fermentation), as a food preservative, and in the preparation of metallic formates and esters.

Purification Methods

Anhydrous formic acid can be obtained by direct fractional distillation under reduced pressure, the receiver being cooled in ice-water. The use of P2O5 or CaCl2 as dehydrating agents is unsatisfactory. Reagent grade 88% formic acid can be satisfactorily dried by refluxing with phthalic anhydride for 6hours and then distilling it. Alternatively, if it is left in contact with freshly prepared anhydrous CuSO4 for several days about one half of the water is removed from 88% formic acid; distillation then removes the remainder. Boric anhydride (prepared by melting boric acid in an oven at a high temperature, cooling in a desiccator, and powdering) is a suitable dehydrating agent for 98% formic acid; after prolonged stirring with the anhydride the formic acid is distilled under vacuum. Formic acid can be further purified by fractional crystallisation using partial freezing. [Beilstein 2 IV 3.]

Fire Hazard

Special Hazards of Combustion Products: Toxic vapor generated in fires

Health Hazard

Liquid causes skin and eye burns. Vapors are irritating and painful to breath. Vapor exposure may cause nausea and vomiting.

Definition

ChEBI: The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed Induces severe metabolic acidosis and ocular injury in human subjects.

Production

  • Since 1896, formic aid is made in European countries by the action of sulfuric acid upon sodium formate, which is produced from carbon monoxide and sodium hydroxide.
  • In 1980, the United States Science and Design Corporation developed a carbonylation of methanol to produce formic acid with an annual output of 20,000 tons. The reaction formula is:
  • The mixture of liquid ammonia and methanol is used to absorb carbon monoxide at 70 ° C and 32.5 MPa to form formamide, which is then hydrolyzed in an aqueous acid solution.
  • Use oxalic acid and glycerol as raw materials being co-heated at 110 ° C to generate oxalic acid monoglyceride. Heat it to decarboxylate and form Monoglycerides formate, then hydrolyze it to obtain formic acid.
  • After the formic acid aqueous solution is obtained, a dehydrating agent (for anhydrous magnesium sulfate, anhydrous copper sulfate, etc.), extractive distillation (extracting agent may be trimethylamine, picoline, etc.) may be used for dehydration and purification, and anhydrous formic aic can be obtained.
InChI:InChI=1/CH2O2/c2-1-3/h1H,(H,2,3)

64-18-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Fluka (56302)  Formicacid  eluent additive for LC-MS 64-18-6 56302-1L-GL-F 11,161.80CNY Detail
Fluka (56302)  Formicacid  eluent additive for LC-MS 64-18-6 56302-1L-F 11,161.80CNY Detail
Fluka (56302)  Formicacid  eluent additive for LC-MS 64-18-6 56302-50ML-GL 2,500.29CNY Detail
Fluka (56302)  Formicacid  eluent additive for LC-MS 64-18-6 56302-50ML-F 2,500.29CNY Detail
Fluka (56302)  Formicacid  eluent additive for LC-MS 64-18-6 56302-10X1ML-F 858.78CNY Detail
Fluka (14265)  Formicacid  LC-MS Ultra, eluent additive for UHPLC-MS 64-18-6 14265-2ML 1,477.71CNY Detail
Fluka (14265)  Formicacid  LC-MS Ultra, eluent additive for UHPLC-MS 64-18-6 14265-1ML 817.83CNY Detail
Vetec (V900803)  Formicacid  Vetec reagent grade, 95% 64-18-6 V900803-250ML 81.95CNY Detail
Sigma-Aldrich (695076)  Formicacid  ACS reagent, ≥96% 64-18-6 695076-500ML 746.46CNY Detail
Sigma-Aldrich (695076)  Formicacid  ACS reagent, ≥96% 64-18-6 695076-100ML 462.15CNY Detail
Sigma-Aldrich (399388)  Formicacid  ACS reagent, 88-91% 64-18-6 399388-4X100ML 1,863.81CNY Detail
USP (1283200)  Formicacid  United States Pharmacopeia (USP) Reference Standard 64-18-6 1283200-3X1.2ML 4,326.66CNY Detail

64-18-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name formic acid

1.2 Other means of identification

Product number -
Other names formic

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Preservatives and Antioxidants;Processing Aids and Additives
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:64-18-6 SDS

64-18-6Synthetic route

carbon dioxide
124-38-9

carbon dioxide

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With chlorotris(sodium 3-sulfonatophenyldiphenylphosphine)rhodium(I); hydrogen; sodium formate In water at 50℃; under 75007.5 Torr; for 20h; Inert atmosphere;100%
With sodium hydrogencarbonate In water for 18h; Reagent/catalyst; Electrochemical reaction;93.6%
Stage #1: carbon dioxide With phenylsilane In N,N-dimethyl acetamide at 50℃; under 22502.3 Torr; for 4h; pH=Ca. 1.2; Autoclave; Green chemistry;
Stage #2: With water In N,N-dimethyl acetamide at 100℃; for 0.25h; Pressure; Temperature; Reagent/catalyst; Time; Green chemistry;
91%
methanol
67-56-1

methanol

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
Stage #1: methanol With oxygen; nickel dichloride In water at 20℃; for 0.166667h; Flow reactor;
Stage #2: With copper(II) sulfate In water at 55℃; for 0.166667h; Flow reactor;
98%
With sodium hydroxide; potassium hexacyanoferrate(III); iridium(III) chloride at 35℃; Rate constant; Thermodynamic data; ΔE, ΔS(excit.), ΔF(excit.);
With dipotassium peroxodisulfate In water at 45℃; Kinetics; Rate constant; Thermodynamic data; mechanism, concentration, temperature, overall energy of activation;
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

A

formic acid
64-18-6

formic acid

B

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen at 70℃; under 760.051 Torr; for 6h; Solvent; Green chemistry;A n/a
B 96%
2-((tert-butyl-diphenyl-silanyloxy)methyl)-2-methyl-malonaldehyde

2-((tert-butyl-diphenyl-silanyloxy)methyl)-2-methyl-malonaldehyde

A

formic acid
64-18-6

formic acid

B

3-(tert-butyldiphenylsilanyloxy)-2-methylpropionic acid
820963-51-7

3-(tert-butyldiphenylsilanyloxy)-2-methylpropionic acid

Conditions
ConditionsYield
With camphor-10-sulfonic acid; dihydrogen peroxide In chloroform-d1A 50%
B 96%
formic acid 2-formyloxy-1-methylpropyl ester
56153-29-8

formic acid 2-formyloxy-1-methylpropyl ester

A

formic acid
64-18-6

formic acid

B

trans-2-Butene
624-64-6

trans-2-Butene

C

buta-1,3-diene
106-99-0

buta-1,3-diene

D

butanone
78-93-3

butanone

Conditions
ConditionsYield
at 500℃; for 5h; Mechanism; Inert atmosphere; Flow reactor; Pyrolysis; chemoselective reaction;A 20%
B n/a
C 94%
D n/a
styrene
292638-84-7

styrene

A

formaldehyd
50-00-0

formaldehyd

B

formic acid
64-18-6

formic acid

C

benzaldehyde
100-52-7

benzaldehyde

D

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With pyridine; ozone at 20℃; for 1.16667h; Oxidation; ozonolysis;A 2%
B 2.4%
C 2.6%
D 93%
2 HCOOH/NHex3 adduct

2 HCOOH/NHex3 adduct

A

formic acid
64-18-6

formic acid

B

tri-n-hexylamine
102-86-3

tri-n-hexylamine

Conditions
ConditionsYield
at 160℃; under 99.76 Torr;A 92%
B n/a
cerium (IV) ammonium nitrate

cerium (IV) ammonium nitrate

pentamine methylmalonatocobalt(III)

pentamine methylmalonatocobalt(III)

A

formic acid
64-18-6

formic acid

B

carbon dioxide
124-38-9

carbon dioxide

C

cobalt(II)

cobalt(II)

D

cerium(III) ion

cerium(III) ion

Conditions
ConditionsYield
In perchloric acid; water Kinetics; react. at 30 +/- 0.2°C; detection by spectrophotometry;A 90%
B n/a
C >99
D n/a
cerium (IV) ammonium nitrate

cerium (IV) ammonium nitrate

pentamine malonatocobalt(III)

pentamine malonatocobalt(III)

A

formic acid
64-18-6

formic acid

B

carbon dioxide
124-38-9

carbon dioxide

C

cobalt(II)

cobalt(II)

D

cerium(III) ion

cerium(III) ion

Conditions
ConditionsYield
In perchloric acid; water Kinetics; react. at 30 +/- 0.2°C; detection by spectrophotometry;A 90%
B n/a
C >99
D n/a
dimethyl(phenyl)silyl formate

dimethyl(phenyl)silyl formate

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With water at 20℃; for 0.5h;90%
syringic aldehyde
134-96-3

syringic aldehyde

A

formic acid
64-18-6

formic acid

B

2,6-dimethoxy-1,4-hydroquinone
15233-65-5

2,6-dimethoxy-1,4-hydroquinone

Conditions
ConditionsYield
Stage #1: syringic aldehyde With sodium percarbonate In tetrahydrofuran; water at 25℃; Dakin Phenol Oxidation; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; Inert atmosphere;
A n/a
B 90%
6-methyl-6-phenyl-3-(1-phenylethyl)-5-(m-toluidino)-1,2,4-trioxan
76182-15-5

6-methyl-6-phenyl-3-(1-phenylethyl)-5-(m-toluidino)-1,2,4-trioxan

A

formic acid
64-18-6

formic acid

B

2-Phenylpropanal
34713-70-7

2-Phenylpropanal

C

acetophenone
98-86-2

acetophenone

D

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 0.0833333h; Ambient temperature; Further byproducts given;A 58%
B 69%
C 89%
D 75%
triethylsilyl formate
18296-01-0

triethylsilyl formate

A

formic acid
64-18-6

formic acid

B

Triethylsilanol
597-52-4

Triethylsilanol

Conditions
ConditionsYield
In water at 20℃; for 0.333333h; Schlenk technique; Inert atmosphere; Glovebox;A 88%
B n/a
sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
Stage #1: sodium hydrogencarbonate With hydrogen In water at 200℃; under 45004.5 Torr; for 4h; Autoclave;
Stage #2: Pressure; Reagent/catalyst;
86.1%
With nickel; hydrazine hydrate In water at 300℃; for 2h; Reagent/catalyst; Green chemistry;50%
With sodium chloride at 40℃; for 2h; Irradiation; Halobacterium halobium MMT22; Yield given;
glycolic Acid
79-14-1

glycolic Acid

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With potassium bromate; ruthenium trichloride; perchloric acid at 39.85℃; Kinetics; Further Variations:; Reagents; Temperatures; Oxidation;86%
With phosphovanadomolybdic acid; oxygen In water at 150℃; under 15001.5 Torr; for 3h;73.9%
With aluminium(III) triflate; dihydrogen peroxide In acetonitrile at 70℃; for 12h;63.1%
dihydroxyacetone
96-26-4

dihydroxyacetone

A

formic acid
64-18-6

formic acid

B

glycolic Acid
79-14-1

glycolic Acid

Conditions
ConditionsYield
With dihydrogen peroxide In neat (no solvent) at 25℃; for 24h; Catalytic behavior; Reagent/catalyst;A n/a
B 86%
With oxygen; vanadia In water at 79.84℃; under 2250.23 Torr; for 1h; Autoclave;A 14 %Chromat.
B 13 %Chromat.
Methyl formate
107-31-3

Methyl formate

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With 2,6-dimethylpyridine; water at 120℃; under 9000.9 Torr;85%
With sulfuric acid Hydrolysis;
With water; N-cyclohexyl-cyclohexanamine at 130℃; Equilibrium constant; Reagent/catalyst;
Glyoxal
131543-46-9

Glyoxal

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With phosphovanadomolybdic acid; oxygen In water at 150℃; under 15001.5 Torr; for 3h;84.3%
With dihydrogen peroxide; sodium molybdate; mercury(II) diacetate In 1,4-dioxane; water at 25℃; for 0.5h; Yield given;
With TiClO4 at 39.9℃; Rate constant; Kinetics; Thermodynamic data; E(excit.), ΔH(excit.), ΔS(excit.); var. temp.;
With sodium vanadate; sulfuric acid; oxygen In water at 160℃; under 22502.3 Torr; for 0.0166667h; Autoclave;
With H(1+)*Mo11O40PV(4-)*3C7H13N2O3S(1+); oxygen In water at 180℃; under 7500.75 Torr; for 1h; Autoclave;74.2 %Chromat.
potassium hydrogencarbonate
298-14-6

potassium hydrogencarbonate

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With hydrogen In water at 200℃; under 45004.5 Torr; for 4h; Autoclave;83.7%
With [{Ir(pentamethylcyclopentadienyl)(Cl)}2(4,4',6,6'-tetrahydroxybipyrimidine)](Cl2); hydrogen In water at 50℃; under 30003 Torr; for 8h; Catalytic behavior; Reagent/catalyst; Pressure; Time; Temperature;
With hydrogen carbonate reductase; hydrogen under 750.075 Torr; Kinetics; Reagent/catalyst; Enzymatic reaction;
dihydroxyacetone
96-26-4

dihydroxyacetone

A

formic acid
64-18-6

formic acid

B

glycolic Acid
79-14-1

glycolic Acid

Conditions
ConditionsYield
With dihydrogen peroxide In neat (no solvent) at 25℃; for 24h; Catalytic behavior; Reagent/catalyst;A n/a
B 86%
With oxygen; vanadia In water at 79.84℃; under 2250.23 Torr; for 1h; Autoclave;A 14 %Chromat.
B 13 %Chromat.
With iron hydroxide oxide; manganese(IV) oxide; dihydrogen peroxide In water at 25℃; for 24h; Reagent/catalyst; Autoclave;
cellulose

cellulose

A

formic acid
64-18-6

formic acid

B

levulinic acid
123-76-2

levulinic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 199.84℃; for 0.166667h; Concentration; Temperature; Time;A 83%
B 43%
With water at 185 - 205℃; for 0.420833h; Product distribution / selectivity; Acidic conditions;A 82%
B n/a
With 5-methyl-dihydro-furan-2-one at 159.84℃; for 16h;A 20%
B 69%
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

A

formic acid
64-18-6

formic acid

B

isobutyric Acid
79-31-2

isobutyric Acid

Conditions
ConditionsYield
With perchloric acid; bromamine T In water at 35 - 40℃; Kinetics; Mechanism; Thermodynamic data; ΔH and ΔS; var. solv.: D2O;A 82%
B 82%
With perchloric acid; mercury(II) diacetate; N-bromoacetamide In water at 30℃; Kinetics; Mechanism; effect of the concentrations of NBA, MIK, acid and Hg(OAc)2; effect of the ionic strength; D2O isotopic effect; further temperatures;
D-Glucose
2280-44-6

D-Glucose

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With phosphoric acid immobilized anatase TiO2 In tetrahydrofuran; water at 119.84℃; for 2h; Sealed tube; Green chemistry;A 81.2%
B 10.5%
With dihydrogen peroxide In water at 200℃; for 1h; pH=5.4;A 11.55%
B 5.68%
alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

formic acid
64-18-6

formic acid

C

levulinic acid
123-76-2

levulinic acid

D

levoglucosan
498-07-7

levoglucosan

Conditions
ConditionsYield
With 15 wtpercent phosphate impregnated titania In water; butan-1-ol at 175℃; under 22502.3 Torr; for 3h; Catalytic behavior; Temperature; Inert atmosphere; Autoclave;A 81%
B n/a
C n/a
D n/a
Glycolaldehyde
141-46-8

Glycolaldehyde

A

formic acid
64-18-6

formic acid

B

glycolic Acid
79-14-1

glycolic Acid

C

Glyoxal
131543-46-9

Glyoxal

D

carbon dioxide
124-38-9

carbon dioxide

E

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With water; oxygen at 90℃; under 7500.75 Torr; for 8h; Catalytic behavior; Mechanism; Temperature; Pressure; Time; Reagent/catalyst;A 80.5%
B 4.2%
C 6.2%
D 2.6%
E 0.3%
D-Arabinose
10323-20-3

D-Arabinose

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol; water at 69.84℃; for 5h; Inert atmosphere; Schlenk technique; chemoselective reaction;79.7%
D-xylose
58-86-6

D-xylose

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol; water at 69.84℃; for 5h; Inert atmosphere; Schlenk technique; chemoselective reaction;79.6%
With phosphovanadomolybdic acid; oxygen In water at 180℃; under 15001.5 Torr; for 3h;33.1%
With sodium chloride In water at 189.84℃; under 15001.5 Torr; for 2h; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;9.6%
With sodium vanadate; sulfuric acid; oxygen In water at 160℃; under 22502.3 Torr; for 0.0166667h; Autoclave;
With C13H16ClN3O2Pd; dihydrogen peroxide; sodium hydroxide In water at 25℃; for 16h; Catalytic behavior;
sodium formate
141-53-7

sodium formate

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With sulfuric acid79%
With water Electrolysis.Mehrkammersystem mit Kammerwaenden aus semipermeablen Ionenaustauschern;
With sulfuric acid; sulfur trioxide
1-octen-3-ol
3391-86-4

1-octen-3-ol

A

formic acid
64-18-6

formic acid

B

hexanoic acid
142-62-1

hexanoic acid

C

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; bis(acetylacetonato)dioxidomolybdenum(VI) In benzene at 70℃; for 48h; Product distribution; other reaction times, other catalysts, other allylic alcohols and olefins as substrates;A n/a
B 79%
C 6%
3β-formyloxy-5αH-cholestane
10437-24-8

3β-formyloxy-5αH-cholestane

A

formic acid
64-18-6

formic acid

B

cholestane
481-21-0

cholestane

C

Cholestanol
80-97-7

Cholestanol

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide; water for 5h; Irradiation;A n/a
B 79%
C 19%
phenylacetylene
536-74-3

phenylacetylene

A

formic acid
64-18-6

formic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With iodopentafluorobenzene bis(trifluoroacetate); water In benzene Product distribution; Heating; other alkynes or α-hydroxy-p-nitroacetophenone;A n/a
B 79%
piperidine
110-89-4

piperidine

formic acid
64-18-6

formic acid

N-Formylpiperidine
2591-86-8

N-Formylpiperidine

Conditions
ConditionsYield
With cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 3h; Reagent/catalyst; Solvent;100%
With aminoproplylated mesoporous SBA-15 silica at 40℃; for 0.25h; Neat (no solvent); chemoselective reaction;95%
With NH2-MIL-53 at 50℃; for 0.333333h;95%
morpholine
110-91-8

morpholine

formic acid
64-18-6

formic acid

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 3h; Reagent/catalyst; Solvent;100%
In butan-1-ol at 120℃; Solvent; Temperature;99.35%
In ethanol at 140℃; for 24h; Solvent; Autoclave;98%
formic acid
64-18-6

formic acid

n-Octylamine
111-86-4

n-Octylamine

N-octylformamide
6282-06-0

N-octylformamide

Conditions
ConditionsYield
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide at 20℃; for 3h; Reagent/catalyst; Solvent;100%
formic acid
64-18-6

formic acid

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

1-dodecanyl formate
28303-42-6

1-dodecanyl formate

Conditions
ConditionsYield
toluene-4-sulfonic acid at 85℃; for 4h; Esterification;100%
With 2-methyl-1-butylimidazolium trifluoroacetate In neat (no solvent) at 70℃; for 1h;96%
Stage #1: formic acid With acetic anhydride at 40℃; for 2h;
Stage #2: 1-dodecyl alcohol at 0 - 20℃; for 15.25h;
94%
With hydrogenchloride
formic acid
64-18-6

formic acid

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

3β-formyl-oxy-5-androsten-17-one
29163-23-3

3β-formyl-oxy-5-androsten-17-one

Conditions
ConditionsYield
In water for 19h;100%
at 20 - 25℃; for 4h;100%
for 5h; Reflux;89.3%
for 5h; Reflux;
formic acid
64-18-6

formic acid

2,3-diaminochlorobenzene
21745-41-5

2,3-diaminochlorobenzene

4-chloro-1H-1,3-benzodiazole
16931-35-4

4-chloro-1H-1,3-benzodiazole

Conditions
ConditionsYield
In water at 100℃; for 3h; Phillips cyclization;100%
In water at 100℃; for 3h;84.1%
formic acid
64-18-6

formic acid

Phenylalanine
150-30-1

Phenylalanine

N-formyl-phenylalanine
4289-95-6

N-formyl-phenylalanine

Conditions
ConditionsYield
With acetic anhydride at 20℃; for 1h;100%
With acetic anhydride at 20℃; for 19h;87%
In N,N-dimethyl-formamide for 0.166667h; Heating;81%
formic acid
64-18-6

formic acid

methanol
67-56-1

methanol

Conditions
ConditionsYield
With water In aq. phosphate buffer at 20℃; for 1h; pH=7.4; Catalytic behavior; Reagent/catalyst; Electrolysis; Inert atmosphere; Enzymatic reaction;100%
With cobalt(III) acetylacetonate; hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran; ethanol at 100℃; under 52505.3 Torr; for 24h; Autoclave; Inert atmosphere;59%
With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride In ethanol; toluene at 180℃; under 7500.75 - 45004.5 Torr; for 18h; Autoclave;31%
formic acid
64-18-6

formic acid

acetic anhydride
108-24-7

acetic anhydride

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

Conditions
ConditionsYield
at 60℃; for 1h; Inert atmosphere;100%
at 0 - 60℃; for 3.5h;78%
at 50℃; Fraktionierung im Vakuum;
formic acid
64-18-6

formic acid

4-chloro-aniline
106-47-8

4-chloro-aniline

N-(4-chlorophenyl)formamide
2617-79-0

N-(4-chlorophenyl)formamide

Conditions
ConditionsYield
In toluene Reflux;100%
With sodium formate at 20℃; for 2h; Neat (no solvent);98%
With TiO2-SO4(2-) In acetonitrile at 20℃; for 6h;98.3%
formic acid
64-18-6

formic acid

4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-methoxyformanilide
5470-34-8

4-methoxyformanilide

Conditions
ConditionsYield
In toluene Reflux;100%
With sodium formate at 20℃; for 3h; Neat (no solvent);99%
With TiO2-SO4(2-) In acetonitrile at 20℃; for 4h;99%
formic acid
64-18-6

formic acid

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
14301-36-1

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide

Conditions
ConditionsYield
With acetic anhydride 1.) 60 deg C, 30 min, 2.) 20 deg C, overnight;100%
With 4-methyl-morpholine; dmap; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 35℃; for 0.05h; microwave irradiation;98%
In dichloromethane at 80℃; for 8h;95%
formic acid
64-18-6

formic acid

phenethylamine
64-04-0

phenethylamine

N-(2-phenylethyl)formamide
23069-99-0

N-(2-phenylethyl)formamide

Conditions
ConditionsYield
Stage #1: formic acid With acetic acid at 25℃; for 1h;
Stage #2: phenethylamine at 0 - 25℃;
100%
With sulfated tungstate at 70℃; for 0.166667h; Neat (no solvent);98%
With pyridine; diisopropyl-carbodiimide at 20℃; for 72h;15%
formic acid
64-18-6

formic acid

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-chloro-1H-benzimidazole
4887-82-5

5-chloro-1H-benzimidazole

Conditions
ConditionsYield
With hydrogenchloride In water for 3h; Reflux;100%
at 110℃; for 4h;95%
With tetrabutyl-ammonium chloride In water; toluene at 160℃; for 0.25h; Microwave irradiation;89%
formic acid
64-18-6

formic acid

aniline
62-53-3

aniline

Formanilid
103-70-8

Formanilid

Conditions
ConditionsYield
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide at 20℃; for 3h; Reagent/catalyst; Solvent;100%
With zinc(II) oxide at 70℃; for 0.166667h;99%
Stage #1: formic acid With silica gel at 20℃; for 0.0166667h;
Stage #2: aniline With silica gel at 110℃; for 0.05h;
99%
formic acid
64-18-6

formic acid

4-Nitrophenylene-1,2-diamine
99-56-9

4-Nitrophenylene-1,2-diamine

5-nitrobenzimidazole
94-52-0

5-nitrobenzimidazole

Conditions
ConditionsYield
With hydrogenchloride In water for 8h; Reflux;100%
With tetrabutyl-ammonium chloride In water; toluene at 160℃; for 0.2h; Microwave irradiation;90%
With chloro-trimethyl-silane In water; N,N-dimethyl-formamide at 120℃; for 0.2h; Microwave irradiation;90%
formic acid
64-18-6

formic acid

glycine
56-40-6

glycine

formylglycine
2491-15-8

formylglycine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 110℃; for 0.666667h;100%
In N,N-dimethyl-formamide at 153℃; for 0.333333h; futher solvents, further temperatures, further reaction times;97%
Stage #1: formic acid With acetic anhydride at 45℃; for 1h; Inert atmosphere;
Stage #2: glycine at 20℃; for 72h; Inert atmosphere;
93%
formic acid
64-18-6

formic acid

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

2,6-dimethylformanilide
607-92-1

2,6-dimethylformanilide

Conditions
ConditionsYield
In toluene Reflux;100%
In toluene Reflux;100%
In toluene Reflux;100%
formic acid
64-18-6

formic acid

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

4-methoxy-, benzenemethanol, formate
122-91-8

4-methoxy-, benzenemethanol, formate

Conditions
ConditionsYield
Stage #1: formic acid With silica gel at 20℃; for 0.0166667h;
Stage #2: 4-Methoxybenzyl alcohol With silica gel at 110℃; for 0.0166667h;
100%
With aminopropylated mesoporous SBA-15 silica at 40℃; for 0.0833333h; Neat (no solvent); chemoselective reaction;95%
With iodine at 20℃; for 0.116667h; neat (no solvent);94%
formic acid
64-18-6

formic acid

benzylamine
100-46-9

benzylamine

N-benzylformamide
6343-54-0

N-benzylformamide

Conditions
ConditionsYield
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide at 20℃; for 3h; Reagent/catalyst; Solvent;100%
With 4-methyl-morpholine; dmap; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 35℃; for 0.1h; microwave irradiation;99%
With sulfated tungstate at 70℃; for 0.166667h; Neat (no solvent);99%
formic acid
64-18-6

formic acid

4-bromo-aniline
106-40-1

4-bromo-aniline

N-(4-bromophenyl)formamide
2617-78-9

N-(4-bromophenyl)formamide

Conditions
ConditionsYield
In toluene Reflux;100%
With sodium formate at 20℃; for 2.75h; Neat (no solvent);99%
With zinc(II) oxide at 70℃; for 0.333333h;98%
formic acid
64-18-6

formic acid

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
at 100℃;100%
With hydrogenchloride In water for 3h; Reflux;97.5%
for 2h; Reflux;85%
With hydrogenchloride
Stage #1: formic acid; 4-Bromo-benzene-1,2-diamine for 2h; Reflux;
Stage #2: With sodium hydroxide In water at 20℃;
formic acid
64-18-6

formic acid

methyl α-chloro-α-phenylbenzeneacetate
54311-64-7

methyl α-chloro-α-phenylbenzeneacetate

methyl (formyloxy)diphenylacetate
133217-21-7

methyl (formyloxy)diphenylacetate

Conditions
ConditionsYield
With sodium formate for 4h; Ambient temperature;100%
With sodium formate In N,N-dimethyl-formamide for 3h; Ambient temperature;96%
formic acid
64-18-6

formic acid

2-iodophenylamine
615-43-0

2-iodophenylamine

N-formyl-2-iodoaniline
10113-39-0

N-formyl-2-iodoaniline

Conditions
ConditionsYield
Stage #1: formic acid With acetic anhydride In dichloromethane at 20℃; for 0.166667h;
Stage #2: 2-iodophenylamine In dichloromethane at 20℃;
100%
In water; toluene at 110℃; for 4h;99%
Stage #1: formic acid With acetic anhydride at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 2-iodophenylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;
98%
formic acid
64-18-6

formic acid

tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

tetra(n-butyl)ammonium formate
35733-58-5

tetra(n-butyl)ammonium formate

Conditions
ConditionsYield
In water pH=Ca. 8.45; Glovebox;100%
In methanol; water at 20 - 60℃;99%
In methanol at 20℃; for 2h; Inert atmosphere;85%
formic acid
64-18-6

formic acid

4-(2-aminoethyl)-1-(phenylmethyl)piperidine
86945-25-7

4-(2-aminoethyl)-1-(phenylmethyl)piperidine

1-benzyl-4-<2-(N-formylamino)ethyl>piperidine
144319-70-0

1-benzyl-4-<2-(N-formylamino)ethyl>piperidine

Conditions
ConditionsYield
With acetic anhydride100%
at 100℃; for 6h;38%
formic acid
64-18-6

formic acid

1-(4-hydroxy-phenyl)-piperazine dihydrobromide
38869-37-3

1-(4-hydroxy-phenyl)-piperazine dihydrobromide

1-Formyl-4-(4-hydroxyphenyl)piperazine
112190-13-3

1-Formyl-4-(4-hydroxyphenyl)piperazine

Conditions
ConditionsYield
With sodium carbonate In water; toluene for 18h; Heating;100%
formic acid
64-18-6

formic acid

1-(2,2-dimethyl-3-but-enyl)-5-hydroxy-2-pyrrolid-one
84665-97-4

1-(2,2-dimethyl-3-but-enyl)-5-hydroxy-2-pyrrolid-one

rel-(6R,7aS)-6-<2-(formyloxy)prop-2-yl>hexahydro-3H-pyrrolizin-3-one
84665-98-5, 94162-37-5

rel-(6R,7aS)-6-<2-(formyloxy)prop-2-yl>hexahydro-3H-pyrrolizin-3-one

Conditions
ConditionsYield
for 0.0833333h; Ambient temperature;100%
at 40℃; for 0.0833333h;0.462 g
formic acid
64-18-6

formic acid

shinjulactone C
82470-74-4, 130195-55-0

shinjulactone C

20-O-formylshinjulactone

20-O-formylshinjulactone

Conditions
ConditionsYield
for 2h; Ambient temperature;100%

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